diff --git a/api/api.go b/api/api.go
index 4adb589..1860e37 100644
--- a/api/api.go
+++ b/api/api.go
@@ -2,10 +2,10 @@ package api
 
 import (
 	"bytes"
+	"emperror.dev/errors"
 	"encoding/json"
 	"fmt"
 	"github.com/apex/log"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/config"
 	"github.com/pterodactyl/wings/system"
 	"io"
@@ -69,7 +69,7 @@ func (r *Request) Endpoint(endpoint string) string {
 func (r *Request) Make(method, url string, body io.Reader, opts ...func(r *http.Request)) (*Response, error) {
 	req, err := http.NewRequest(method, url, body)
 	if err != nil {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	}
 
 	req.Header.Set("User-Agent", fmt.Sprintf("Pterodactyl Wings/v%s (id:%s)", system.Version, config.Get().AuthenticationTokenId))
@@ -127,7 +127,7 @@ func (r *Request) Get(url string, data Q) (*Response, error) {
 func (r *Request) Post(url string, data interface{}) (*Response, error) {
 	b, err := json.Marshal(data)
 	if err != nil {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	}
 
 	return r.Make(http.MethodPost, r.Endpoint(url), bytes.NewBuffer(b))
@@ -167,10 +167,10 @@ func (r *Response) Read() ([]byte, error) {
 func (r *Response) Bind(v interface{}) error {
 	b, err := r.Read()
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
-	return errors.WithStack(json.Unmarshal(b, &v))
+	return errors.WithStackIf(json.Unmarshal(b, &v))
 }
 
 // Returns the error message from the API call as a string. The error message will be formatted
diff --git a/api/backup_endpoints.go b/api/backup_endpoints.go
index 6cd0617..87fe38c 100644
--- a/api/backup_endpoints.go
+++ b/api/backup_endpoints.go
@@ -1,8 +1,8 @@
 package api
 
 import (
+	"emperror.dev/errors"
 	"fmt"
-	"github.com/pkg/errors"
 	"strconv"
 )
 
@@ -16,7 +16,7 @@ type BackupRemoteUploadResponse struct {
 func (r *Request) GetBackupRemoteUploadURLs(backup string, size int64) (*BackupRemoteUploadResponse, error) {
 	resp, err := r.Get(fmt.Sprintf("/backups/%s", backup), Q{"size": strconv.FormatInt(size, 10)})
 	if err != nil {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	}
 	defer resp.Body.Close()
 
@@ -26,7 +26,7 @@ func (r *Request) GetBackupRemoteUploadURLs(backup string, size int64) (*BackupR
 
 	var res BackupRemoteUploadResponse
 	if err := resp.Bind(&res); err != nil {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	}
 
 	return &res, nil
@@ -44,7 +44,7 @@ type BackupRequest struct {
 func (r *Request) SendBackupStatus(backup string, data BackupRequest) error {
 	resp, err := r.Post(fmt.Sprintf("/backups/%s", backup), data)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 	defer resp.Body.Close()
 
diff --git a/api/server_endpoints.go b/api/server_endpoints.go
index 6b402be..db1abee 100644
--- a/api/server_endpoints.go
+++ b/api/server_endpoints.go
@@ -2,10 +2,10 @@ package api
 
 import (
 	"context"
+	"emperror.dev/errors"
 	"encoding/json"
 	"fmt"
 	"github.com/apex/log"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/config"
 	"golang.org/x/sync/errgroup"
 	"strconv"
@@ -57,7 +57,7 @@ type RawServerData struct {
 func (r *Request) GetServers() ([]RawServerData, error) {
 	resp, err := r.Get("/servers", Q{"per_page": strconv.Itoa(int(config.Get().RemoteQuery.BootServersPerPage))})
 	if err != nil {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	}
 	defer resp.Body.Close()
 
@@ -67,7 +67,7 @@ func (r *Request) GetServers() ([]RawServerData, error) {
 
 	var res allServerResponse
 	if err := resp.Bind(&res); err != nil {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	}
 
 	var mu sync.Mutex
@@ -117,7 +117,7 @@ func (r *Request) GetServers() ([]RawServerData, error) {
 		}
 
 		if err := g.Wait(); err != nil {
-			return nil, errors.WithStack(err)
+			return nil, errors.WithStackIf(err)
 		}
 	}
 
@@ -130,7 +130,7 @@ func (r *Request) GetServerConfiguration(uuid string) (ServerConfigurationRespon
 
 	resp, err := r.Get(fmt.Sprintf("/servers/%s", uuid), nil)
 	if err != nil {
-		return cfg, errors.WithStack(err)
+		return cfg, errors.WithStackIf(err)
 	}
 	defer resp.Body.Close()
 
@@ -139,7 +139,7 @@ func (r *Request) GetServerConfiguration(uuid string) (ServerConfigurationRespon
 	}
 
 	if err := resp.Bind(&cfg); err != nil {
-		return cfg, errors.WithStack(err)
+		return cfg, errors.WithStackIf(err)
 	}
 
 	return cfg, nil
@@ -150,7 +150,7 @@ func (r *Request) GetInstallationScript(uuid string) (InstallationScript, error)
 	var is InstallationScript
 	resp, err := r.Get(fmt.Sprintf("/servers/%s/install", uuid), nil)
 	if err != nil {
-		return is, errors.WithStack(err)
+		return is, errors.WithStackIf(err)
 	}
 	defer resp.Body.Close()
 
@@ -159,7 +159,7 @@ func (r *Request) GetInstallationScript(uuid string) (InstallationScript, error)
 	}
 
 	if err := resp.Bind(&is); err != nil {
-		return is, errors.WithStack(err)
+		return is, errors.WithStackIf(err)
 	}
 
 	return is, nil
@@ -169,7 +169,7 @@ func (r *Request) GetInstallationScript(uuid string) (InstallationScript, error)
 func (r *Request) SendInstallationStatus(uuid string, successful bool) error {
 	resp, err := r.Post(fmt.Sprintf("/servers/%s/install", uuid), D{"successful": successful})
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 	defer resp.Body.Close()
 
@@ -183,7 +183,7 @@ func (r *Request) SendInstallationStatus(uuid string, successful bool) error {
 func (r *Request) SendArchiveStatus(uuid string, successful bool) error {
 	resp, err := r.Post(fmt.Sprintf("/servers/%s/archive", uuid), D{"successful": successful})
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 	defer resp.Body.Close()
 
@@ -193,7 +193,7 @@ func (r *Request) SendArchiveStatus(uuid string, successful bool) error {
 func (r *Request) SendTransferFailure(uuid string) error {
 	resp, err := r.Get(fmt.Sprintf("/servers/%s/transfer/failure", uuid), nil)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 	defer resp.Body.Close()
 
@@ -203,7 +203,7 @@ func (r *Request) SendTransferFailure(uuid string) error {
 func (r *Request) SendTransferSuccess(uuid string) error {
 	resp, err := r.Get(fmt.Sprintf("/servers/%s/transfer/success", uuid), nil)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 	defer resp.Body.Close()
 
diff --git a/api/sftp_endpoints.go b/api/sftp_endpoints.go
index 5dbbfa6..bc480eb 100644
--- a/api/sftp_endpoints.go
+++ b/api/sftp_endpoints.go
@@ -1,8 +1,8 @@
 package api
 
 import (
+	"emperror.dev/errors"
 	"github.com/apex/log"
-	"github.com/pkg/errors"
 	"regexp"
 )
 
diff --git a/cmd/root.go b/cmd/root.go
index fe92e6e..61533b2 100644
--- a/cmd/root.go
+++ b/cmd/root.go
@@ -19,7 +19,7 @@ import (
 	"github.com/pterodactyl/wings/loggers/cli"
 	"golang.org/x/crypto/acme/autocert"
 
-	"github.com/pkg/errors"
+	"emperror.dev/errors"
 	"github.com/pkg/profile"
 	"github.com/pterodactyl/wings/config"
 	"github.com/pterodactyl/wings/environment"
@@ -77,7 +77,7 @@ func readConfiguration() (*config.Configuration, error) {
 	}
 
 	if s, err := os.Stat(p); err != nil {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	} else if s.IsDir() {
 		return nil, errors.New("cannot use directory as configuration file path")
 	}
@@ -199,7 +199,7 @@ func rootCmdRun(*cobra.Command, []string) {
 
 	states, err := server.CachedServerStates()
 	if err != nil {
-		log.WithField("error", errors.WithStack(err)).Error("failed to retrieve locally cached server states from disk, assuming all servers in offline state")
+		log.WithField("error", errors.WithStackIf(err)).Error("failed to retrieve locally cached server states from disk, assuming all servers in offline state")
 	}
 
 	// Create a new workerpool that limits us to 4 servers being bootstrapped at a time
@@ -235,7 +235,7 @@ func rootCmdRun(*cobra.Command, []string) {
 			// as a result will result in a slow boot.
 			if !r && (st == environment.ProcessRunningState || st == environment.ProcessStartingState) {
 				if err := s.HandlePowerAction(server.PowerActionStart); err != nil {
-					s.Log().WithField("error", errors.WithStack(err)).Warn("failed to return server to running state")
+					s.Log().WithField("error", errors.WithStackIf(err)).Warn("failed to return server to running state")
 				}
 			} else if r || (!r && s.IsRunning()) {
 				// If the server is currently running on Docker, mark the process as being in that state.
@@ -248,7 +248,7 @@ func rootCmdRun(*cobra.Command, []string) {
 
 				s.Environment.SetState(environment.ProcessRunningState)
 				if err := s.Environment.Attach(); err != nil {
-					s.Log().WithField("error", errors.WithStack(err)).Warn("failed to attach to running server environment")
+					s.Log().WithField("error", errors.WithStackIf(err)).Warn("failed to attach to running server environment")
 				}
 
 				return
@@ -369,13 +369,13 @@ func Execute() error {
 // in the code without having to pass around a logger instance.
 func configureLogging(logDir string, debug bool) error {
 	if err := os.MkdirAll(path.Join(logDir, "/install"), 0700); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	p := filepath.Join(logDir, "/wings.log")
 	w, err := logrotate.NewFile(p)
 	if err != nil {
-		panic(errors.Wrap(err, "failed to open process log file"))
+		panic(errors.WrapIf(err, "failed to open process log file"))
 	}
 
 	if debug {
diff --git a/config/config.go b/config/config.go
index 26b6e28..d2e2992 100644
--- a/config/config.go
+++ b/config/config.go
@@ -1,11 +1,11 @@
 package config
 
 import (
+	"emperror.dev/errors"
 	"fmt"
 	"github.com/cobaugh/osrelease"
 	"github.com/creasty/defaults"
 	"github.com/gbrlsnchs/jwt/v3"
-	"github.com/pkg/errors"
 	"gopkg.in/yaml.v2"
 	"io/ioutil"
 	"os"
@@ -198,7 +198,7 @@ func GetJwtAlgorithm() *jwt.HMACSHA {
 func NewFromPath(path string) (*Configuration, error) {
 	c := new(Configuration)
 	if err := defaults.Set(c); err != nil {
-		return c, errors.WithStack(err)
+		return c, errors.WithStackIf(err)
 	}
 
 	c.unsafeSetPath(path)
@@ -236,12 +236,12 @@ func (c *Configuration) EnsurePterodactylUser() (*user.User, error) {
 	if err == nil {
 		return u, c.setSystemUser(u)
 	} else if _, ok := err.(user.UnknownUserError); !ok {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	}
 
 	sysName, err := getSystemName()
 	if err != nil {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	}
 
 	var command = fmt.Sprintf("useradd --system --no-create-home --shell /bin/false %s", c.System.Username)
@@ -254,17 +254,17 @@ func (c *Configuration) EnsurePterodactylUser() (*user.User, error) {
 		// We have to create the group first on Alpine, so do that here before continuing on
 		// to the user creation process.
 		if _, err := exec.Command("addgroup", "-S", c.System.Username).Output(); err != nil {
-			return nil, errors.WithStack(err)
+			return nil, errors.WithStackIf(err)
 		}
 	}
 
 	split := strings.Split(command, " ")
 	if _, err := exec.Command(split[0], split[1:]...).Output(); err != nil {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	}
 
 	if u, err := user.Lookup(c.System.Username); err != nil {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	} else {
 		return u, c.setSystemUser(u)
 	}
@@ -306,11 +306,11 @@ func (c *Configuration) WriteToDisk() error {
 
 	b, err := yaml.Marshal(&ccopy)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	if err := ioutil.WriteFile(c.GetPath(), b, 0644); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	return nil
@@ -320,7 +320,7 @@ func (c *Configuration) WriteToDisk() error {
 func getSystemName() (string, error) {
 	// use osrelease to get release version and ID
 	if release, err := osrelease.Read(); err != nil {
-		return "", errors.WithStack(err)
+		return "", errors.WithStackIf(err)
 	} else {
 		return release["ID"], nil
 	}
diff --git a/config/config_docker.go b/config/config_docker.go
index 3d561df..53b3908 100644
--- a/config/config_docker.go
+++ b/config/config_docker.go
@@ -1,10 +1,10 @@
 package config
 
 import (
+	"emperror.dev/errors"
 	"encoding/base64"
 	"encoding/json"
 	"github.com/docker/docker/api/types"
-	"github.com/pkg/errors"
 )
 
 type dockerNetworkInterfaces struct {
@@ -73,7 +73,7 @@ func (c RegistryConfiguration) Base64() (string, error) {
 
 	b, err := json.Marshal(authConfig)
 	if err != nil {
-		return "", errors.WithStack(err)
+		return "", errors.WithStackIf(err)
 	}
 
 	return base64.URLEncoding.EncodeToString(b), nil
diff --git a/config/config_system.go b/config/config_system.go
index 8538645..9176403 100644
--- a/config/config_system.go
+++ b/config/config_system.go
@@ -2,9 +2,9 @@ package config
 
 import (
 	"context"
+	"emperror.dev/errors"
 	"fmt"
 	"github.com/apex/log"
-	"github.com/pkg/errors"
 	"html/template"
 	"io/ioutil"
 	"os"
@@ -94,7 +94,7 @@ func (sc *SystemConfiguration) ConfigureDirectories() error {
 	// that.
 	if d, err := filepath.EvalSymlinks(sc.Data); err != nil {
 		if !os.IsNotExist(err) {
-			return errors.WithStack(err)
+			return errors.WithStackIf(err)
 		}
 	} else if d != sc.Data {
 		sc.Data = d
@@ -130,13 +130,13 @@ func (sc *SystemConfiguration) EnableLogRotation() error {
 	}
 
 	if st, err := os.Stat("/etc/logrotate.d"); err != nil && !os.IsNotExist(err) {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	} else if (err != nil && os.IsNotExist(err)) || !st.IsDir() {
 		return nil
 	}
 
 	if _, err := os.Stat("/etc/logrotate.d/wings"); err != nil && !os.IsNotExist(err) {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	} else if err == nil {
 		return nil
 	}
@@ -147,7 +147,7 @@ func (sc *SystemConfiguration) EnableLogRotation() error {
 	// it so files can be rotated easily.
 	f, err := os.Create("/etc/logrotate.d/wings")
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 	defer f.Close()
 
@@ -167,10 +167,10 @@ func (sc *SystemConfiguration) EnableLogRotation() error {
 }`)
 
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
-	return errors.Wrap(t.Execute(f, sc), "failed to write logrotate file to disk")
+	return errors.WrapIf(t.Execute(f, sc), "failed to write logrotate file to disk")
 }
 
 // Returns the location of the JSON file that tracks server states.
@@ -190,7 +190,7 @@ func (sc *SystemConfiguration) ConfigureTimezone() error {
 	if sc.Timezone == "" {
 		if b, err := ioutil.ReadFile("/etc/timezone"); err != nil {
 			if !os.IsNotExist(err) {
-				return errors.Wrap(err, "failed to open /etc/timezone for automatic server timezone calibration")
+				return errors.WrapIf(err, "failed to open /etc/timezone for automatic server timezone calibration")
 			}
 
 			ctx, _ := context.WithTimeout(context.Background(), time.Second*5)
@@ -224,5 +224,5 @@ func (sc *SystemConfiguration) ConfigureTimezone() error {
 
 	_, err := time.LoadLocation(sc.Timezone)
 
-	return errors.Wrap(err, fmt.Sprintf("the supplied timezone %s is invalid", sc.Timezone))
+	return errors.WrapIf(err, fmt.Sprintf("the supplied timezone %s is invalid", sc.Timezone))
 }
diff --git a/environment/docker/container.go b/environment/docker/container.go
index 148180d..a45ff2f 100644
--- a/environment/docker/container.go
+++ b/environment/docker/container.go
@@ -4,6 +4,7 @@ import (
 	"bufio"
 	"bytes"
 	"context"
+	"emperror.dev/errors"
 	"encoding/json"
 	"fmt"
 	"github.com/apex/log"
@@ -12,7 +13,6 @@ import (
 	"github.com/docker/docker/api/types/mount"
 	"github.com/docker/docker/client"
 	"github.com/docker/docker/daemon/logger/jsonfilelog"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/config"
 	"github.com/pterodactyl/wings/environment"
 	"io"
@@ -36,7 +36,7 @@ func (e *Environment) Attach() error {
 	}
 
 	if err := e.followOutput(); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	opts := types.ContainerAttachOptions{
@@ -48,7 +48,7 @@ func (e *Environment) Attach() error {
 
 	// Set the stream again with the container.
 	if st, err := e.client.ContainerAttach(context.Background(), e.Id, opts); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	} else {
 		e.SetStream(&st)
 	}
@@ -70,14 +70,14 @@ func (e *Environment) Attach() error {
 		// indicates that the container is no longer running.
 		go func(ctx context.Context) {
 			if err := e.pollResources(ctx); err != nil {
-				log.WithField("environment_id", e.Id).WithField("error", errors.WithStack(err)).Error("error during environment resource polling")
+				log.WithField("environment_id", e.Id).WithField("error", errors.WithStackIf(err)).Error("error during environment resource polling")
 			}
 		}(ctx)
 
 		// Stream the reader output to the console which will then fire off events and handle console
 		// throttling and sending the output to the user.
 		if _, err := io.Copy(console, e.stream.Reader); err != nil {
-			log.WithField("environment_id", e.Id).WithField("error", errors.WithStack(err)).Error("error while copying environment output to console")
+			log.WithField("environment_id", e.Id).WithField("error", errors.WithStackIf(err)).Error("error while copying environment output to console")
 		}
 	}(c)
 
@@ -115,7 +115,7 @@ func (e *Environment) InSituUpdate() error {
 			return nil
 		}
 
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	u := container.UpdateConfig{
@@ -125,7 +125,7 @@ func (e *Environment) InSituUpdate() error {
 	ctx, cancel := context.WithTimeout(context.Background(), time.Second*10)
 	defer cancel()
 	if _, err := e.client.ContainerUpdate(ctx, e.Id, u); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	return nil
@@ -140,12 +140,12 @@ func (e *Environment) Create() error {
 	if _, err := e.client.ContainerInspect(context.Background(), e.Id); err == nil {
 		return nil
 	} else if !client.IsErrNotFound(err) {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	// Try to pull the requested image before creating the container.
 	if err := e.ensureImageExists(e.meta.Image); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	a := e.Configuration.Allocations()
@@ -220,7 +220,7 @@ func (e *Environment) Create() error {
 	}
 
 	if _, err := e.client.ContainerCreate(context.Background(), conf, hostConf, nil, e.Id); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	return nil
@@ -272,7 +272,7 @@ func (e *Environment) Destroy() error {
 func (e *Environment) followOutput() error {
 	if exists, err := e.Exists(); !exists {
 		if err != nil {
-			return errors.WithStack(err)
+			return errors.WithStackIf(err)
 		}
 
 		return errors.New(fmt.Sprintf("no such container: %s", e.Id))
@@ -338,7 +338,7 @@ func (e *Environment) followOutput() error {
 		}
 	}(reader)
 
-	return errors.WithStack(err)
+	return errors.WithStackIf(err)
 }
 
 // Pulls the image from Docker. If there is an error while pulling the image from the source
diff --git a/environment/docker/environment.go b/environment/docker/environment.go
index d4aaf1c..1597b65 100644
--- a/environment/docker/environment.go
+++ b/environment/docker/environment.go
@@ -2,9 +2,9 @@ package docker
 
 import (
 	"context"
+	"emperror.dev/errors"
 	"github.com/docker/docker/api/types"
 	"github.com/docker/docker/client"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/api"
 	"github.com/pterodactyl/wings/environment"
 	"github.com/pterodactyl/wings/events"
@@ -156,7 +156,7 @@ func (e *Environment) ExitState() (uint32, bool, error) {
 			return 1, false, nil
 		}
 
-		return 0, false, errors.WithStack(err)
+		return 0, false, errors.WithStackIf(err)
 	}
 
 	return uint32(c.State.ExitCode), c.State.OOMKilled, nil
diff --git a/environment/docker/power.go b/environment/docker/power.go
index 6544fef..a6305cc 100644
--- a/environment/docker/power.go
+++ b/environment/docker/power.go
@@ -2,11 +2,11 @@ package docker
 
 import (
 	"context"
+	"emperror.dev/errors"
 	"github.com/apex/log"
 	"github.com/docker/docker/api/types"
 	"github.com/docker/docker/api/types/container"
 	"github.com/docker/docker/client"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/api"
 	"github.com/pterodactyl/wings/environment"
 	"os"
@@ -26,7 +26,7 @@ func (e *Environment) OnBeforeStart() error {
 	// the Panel is usee.
 	if err := e.client.ContainerRemove(context.Background(), e.Id, types.ContainerRemoveOptions{RemoveVolumes: true}); err != nil {
 		if !client.IsErrNotFound(err) {
-			return errors.Wrap(err, "failed to remove server docker container during pre-boot")
+			return errors.WrapIf(err, "failed to remove server docker container during pre-boot")
 		}
 	}
 
@@ -69,7 +69,7 @@ func (e *Environment) Start() error {
 		//
 		// @see https://github.com/pterodactyl/panel/issues/2000
 		if !client.IsErrNotFound(err) {
-			return errors.WithStack(err)
+			return errors.WithStackIf(err)
 		}
 	} else {
 		// If the server is running update our internal state and continue on with the attach.
@@ -84,7 +84,7 @@ func (e *Environment) Start() error {
 		// to truncate them.
 		if _, err := os.Stat(c.LogPath); err == nil {
 			if err := os.Truncate(c.LogPath, 0); err != nil {
-				return errors.WithStack(err)
+				return errors.WithStackIf(err)
 			}
 		}
 	}
@@ -99,14 +99,14 @@ func (e *Environment) Start() error {
 	// exists on the system, and rebuild the container if that is required for server booting to
 	// occur.
 	if err := e.OnBeforeStart(); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	ctx, cancel := context.WithTimeout(context.Background(), time.Second*10)
 	defer cancel()
 
 	if err := e.client.ContainerStart(ctx, e.Id, types.ContainerStartOptions{}); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	// No errors, good to continue through.
@@ -169,7 +169,7 @@ func (e *Environment) Stop() error {
 // will be terminated forcefully depending on the value of the second argument.
 func (e *Environment) WaitForStop(seconds uint, terminate bool) error {
 	if err := e.Stop(); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	ctx, cancel := context.WithTimeout(context.Background(), time.Duration(seconds)*time.Second)
@@ -185,20 +185,20 @@ func (e *Environment) WaitForStop(seconds uint, terminate bool) error {
 			if terminate {
 				log.WithField("container_id", e.Id).Debug("server did not stop in time, executing process termination")
 
-				return errors.WithStack(e.Terminate(os.Kill))
+				return errors.WithStackIf(e.Terminate(os.Kill))
 			}
 
-			return errors.WithStack(ctxErr)
+			return errors.WithStackIf(ctxErr)
 		}
 	case err := <-errChan:
 		if err != nil {
 			if terminate {
-				log.WithField("container_id", e.Id).WithField("error", errors.WithStack(err)).Warn("error while waiting for container stop, attempting process termination")
+				log.WithField("container_id", e.Id).WithField("error", errors.WithStackIf(err)).Warn("error while waiting for container stop, attempting process termination")
 
-				return errors.WithStack(e.Terminate(os.Kill))
+				return errors.WithStackIf(e.Terminate(os.Kill))
 			}
 
-			return errors.WithStack(err)
+			return errors.WithStackIf(err)
 		}
 	case <-ok:
 	}
@@ -210,7 +210,7 @@ func (e *Environment) WaitForStop(seconds uint, terminate bool) error {
 func (e *Environment) Terminate(signal os.Signal) error {
 	c, err := e.client.ContainerInspect(context.Background(), e.Id)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	if !c.State.Running {
diff --git a/environment/docker/state.go b/environment/docker/state.go
index 240eec5..ee03443 100644
--- a/environment/docker/state.go
+++ b/environment/docker/state.go
@@ -1,8 +1,8 @@
 package docker
 
 import (
+	"emperror.dev/errors"
 	"fmt"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/environment"
 )
 
diff --git a/environment/docker/stats.go b/environment/docker/stats.go
index ba4b367..c98f65e 100644
--- a/environment/docker/stats.go
+++ b/environment/docker/stats.go
@@ -2,10 +2,10 @@ package docker
 
 import (
 	"context"
+	"emperror.dev/errors"
 	"encoding/json"
 	"github.com/apex/log"
 	"github.com/docker/docker/api/types"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/environment"
 	"io"
 	"math"
@@ -26,7 +26,7 @@ func (e *Environment) pollResources(ctx context.Context) error {
 
 	stats, err := e.client.ContainerStats(context.Background(), e.Id, true)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 	defer stats.Body.Close()
 
@@ -41,7 +41,7 @@ func (e *Environment) pollResources(ctx context.Context) error {
 
 			if err := dec.Decode(&v); err != nil {
 				if err != io.EOF {
-					l.WithField("error", errors.WithStack(err)).Warn("error while processing Docker stats output for container")
+					l.WithField("error", errors.WithStackIf(err)).Warn("error while processing Docker stats output for container")
 				} else {
 					l.Debug("io.EOF encountered during stats decode, stopping polling...")
 				}
@@ -76,7 +76,7 @@ func (e *Environment) pollResources(ctx context.Context) error {
 			}
 
 			if b, err := json.Marshal(st); err != nil {
-				l.WithField("error", errors.WithStack(err)).Warn("error while marshaling stats object for environment")
+				l.WithField("error", errors.WithStackIf(err)).Warn("error while marshaling stats object for environment")
 			} else {
 				e.Events().Publish(environment.ResourceEvent, string(b))
 			}
diff --git a/environment/docker/stream.go b/environment/docker/stream.go
index af02362..984eafd 100644
--- a/environment/docker/stream.go
+++ b/environment/docker/stream.go
@@ -4,9 +4,9 @@ import (
 	"bufio"
 	"bytes"
 	"context"
+	"emperror.dev/errors"
 	"encoding/json"
 	"github.com/docker/docker/api/types"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/environment"
 	"strconv"
 )
@@ -15,7 +15,7 @@ type dockerLogLine struct {
 	Log string `json:"log"`
 }
 
-var ErrNotAttached = errors.New("not attached to instance")
+var ErrNotAttached = errors.Sentinel("not attached to instance")
 
 func (e *Environment) setStream(s *types.HijackedResponse) {
 	e.mu.Lock()
@@ -42,7 +42,7 @@ func (e *Environment) SendCommand(c string) error {
 
 	_, err := e.stream.Conn.Write([]byte(c + "\n"))
 
-	return errors.WithStack(err)
+	return errors.WithStackIf(err)
 }
 
 // Reads the log file for the server. This does not care if the server is running or not, it will
@@ -54,7 +54,7 @@ func (e *Environment) Readlog(lines int) ([]string, error) {
 		Tail:       strconv.Itoa(lines),
 	})
 	if err != nil {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	}
 	defer r.Close()
 
diff --git a/events/events.go b/events/events.go
index 3b5cc63..f8c3ffe 100644
--- a/events/events.go
+++ b/events/events.go
@@ -1,9 +1,9 @@
 package events
 
 import (
+	"emperror.dev/errors"
 	"encoding/json"
 	"github.com/gammazero/workerpool"
-	"github.com/pkg/errors"
 	"strings"
 	"sync"
 )
@@ -69,7 +69,7 @@ func (e *EventBus) Publish(topic string, data string) {
 func (e *EventBus) PublishJson(topic string, data interface{}) error {
 	b, err := json.Marshal(data)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	e.Publish(topic, string(b))
diff --git a/go.mod b/go.mod
index cecb97c..c09c340 100644
--- a/go.mod
+++ b/go.mod
@@ -3,6 +3,7 @@ module github.com/pterodactyl/wings
 go 1.13
 
 require (
+	emperror.dev/errors v0.8.0
 	github.com/AlecAivazis/survey/v2 v2.1.0
 	github.com/Azure/go-ansiterm v0.0.0-20170929234023-d6e3b3328b78 // indirect
 	github.com/Jeffail/gabs/v2 v2.5.1
@@ -57,7 +58,6 @@ require (
 	github.com/opencontainers/image-spec v1.0.1 // indirect
 	github.com/patrickmn/go-cache v2.1.0+incompatible
 	github.com/pierrec/lz4 v2.5.2+incompatible // indirect
-	github.com/pkg/errors v0.9.1
 	github.com/pkg/profile v1.5.0
 	github.com/pkg/sftp v1.11.0
 	github.com/prometheus/common v0.11.1 // indirect
diff --git a/go.sum b/go.sum
index 5c762cc..5c5eddc 100644
--- a/go.sum
+++ b/go.sum
@@ -1,5 +1,7 @@
 cloud.google.com/go v0.26.0/go.mod h1:aQUYkXzVsufM+DwF1aE+0xfcU+56JwCaLick0ClmMTw=
 cloud.google.com/go v0.34.0/go.mod h1:aQUYkXzVsufM+DwF1aE+0xfcU+56JwCaLick0ClmMTw=
+emperror.dev/errors v0.8.0 h1:4lycVEx0sdJkwDUfQ9pdu6SR0x7rgympt5f4+ok8jDk=
+emperror.dev/errors v0.8.0/go.mod h1:YcRvLPh626Ubn2xqtoprejnA5nFha+TJ+2vew48kWuE=
 github.com/AlecAivazis/survey/v2 v2.1.0 h1:AT4+23hOFopXYZaNGugbk7MWItkz0SfTmH/Hk92KeeE=
 github.com/AlecAivazis/survey/v2 v2.1.0/go.mod h1:9FJRdMdDm8rnT+zHVbvQT2RTSTLq0Ttd6q3Vl2fahjk=
 github.com/Azure/go-ansiterm v0.0.0-20170929234023-d6e3b3328b78 h1:w+iIsaOQNcT7OZ575w+acHgRric5iCyQh+xv+KJ4HB8=
@@ -561,9 +563,13 @@ go.uber.org/atomic v1.3.2 h1:2Oa65PReHzfn29GpvgsYwloV9AVFHPDk8tYxt2c2tr4=
 go.uber.org/atomic v1.3.2/go.mod h1:gD2HeocX3+yG+ygLZcrzQJaqmWj9AIm7n08wl/qW/PE=
 go.uber.org/atomic v1.4.0/go.mod h1:gD2HeocX3+yG+ygLZcrzQJaqmWj9AIm7n08wl/qW/PE=
 go.uber.org/atomic v1.5.0/go.mod h1:sABNBOSYdrvTF6hTgEIbc7YasKWGhgEQZyfxyTvoXHQ=
+go.uber.org/atomic v1.7.0 h1:ADUqmZGgLDDfbSL9ZmPxKTybcoEYHgpYfELNoN+7hsw=
+go.uber.org/atomic v1.7.0/go.mod h1:fEN4uk6kAWBTFdckzkM89CLk9XfWZrxpCo0nPH17wJc=
 go.uber.org/multierr v1.1.0 h1:HoEmRHQPVSqub6w2z2d2EOVs2fjyFRGyofhKuyDq0QI=
 go.uber.org/multierr v1.1.0/go.mod h1:wR5kodmAFQ0UK8QlbwjlSNy0Z68gJhDJUG5sjR94q/0=
 go.uber.org/multierr v1.3.0/go.mod h1:VgVr7evmIr6uPjLBxg28wmKNXyqE9akIJ5XnfpiKl+4=
+go.uber.org/multierr v1.6.0 h1:y6IPFStTAIT5Ytl7/XYmHvzXQ7S3g/IeZW9hyZ5thw4=
+go.uber.org/multierr v1.6.0/go.mod h1:cdWPpRnG4AhwMwsgIHip0KRBQjJy5kYEpYjJxpXp9iU=
 go.uber.org/tools v0.0.0-20190618225709-2cfd321de3ee h1:0mgffUl7nfd+FpvXMVz4IDEaUSmT1ysygQC7qYo7sG4=
 go.uber.org/tools v0.0.0-20190618225709-2cfd321de3ee/go.mod h1:vJERXedbb3MVM5f9Ejo0C68/HhF8uaILCdgjnY+goOA=
 go.uber.org/zap v1.10.0/go.mod h1:vwi/ZaCAaUcBkycHslxD9B2zi4UTXhF60s6SWpuDF0Q=
diff --git a/installer/installer.go b/installer/installer.go
index 4910e68..f400091 100644
--- a/installer/installer.go
+++ b/installer/installer.go
@@ -1,10 +1,10 @@
 package installer
 
 import (
+	"emperror.dev/errors"
 	"encoding/json"
 	"github.com/asaskevich/govalidator"
 	"github.com/buger/jsonparser"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/api"
 	"github.com/pterodactyl/wings/environment"
 	"github.com/pterodactyl/wings/server"
@@ -43,21 +43,21 @@ func New(data []byte) (*Installer, error) {
 
 	// Unmarshal the environment variables from the request into the server struct.
 	if b, _, _, err := jsonparser.Get(data, "environment"); err != nil {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	} else {
 		cfg.EnvVars = make(environment.Variables)
 		if err := json.Unmarshal(b, &cfg.EnvVars); err != nil {
-			return nil, errors.WithStack(err)
+			return nil, errors.WithStackIf(err)
 		}
 	}
 
 	// Unmarshal the allocation mappings from the request into the server struct.
 	if b, _, _, err := jsonparser.Get(data, "allocations", "mappings"); err != nil {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	} else {
 		cfg.Allocations.Mappings = make(map[string][]int)
 		if err := json.Unmarshal(b, &cfg.Allocations.Mappings); err != nil {
-			return nil, errors.WithStack(err)
+			return nil, errors.WithStackIf(err)
 		}
 	}
 
@@ -66,7 +66,7 @@ func New(data []byte) (*Installer, error) {
 	c, err := api.New().GetServerConfiguration(cfg.Uuid)
 	if err != nil {
 		if !api.IsRequestError(err) {
-			return nil, errors.WithStack(err)
+			return nil, errors.WithStackIf(err)
 		}
 
 		return nil, errors.New(err.Error())
diff --git a/loggers/cli/cli.go b/loggers/cli/cli.go
index fab7368..e2d8b44 100644
--- a/loggers/cli/cli.go
+++ b/loggers/cli/cli.go
@@ -6,7 +6,7 @@ import (
 	"github.com/apex/log/handlers/cli"
 	color2 "github.com/fatih/color"
 	"github.com/mattn/go-colorable"
-	"github.com/pkg/errors"
+	"emperror.dev/errors"
 	"io"
 	"os"
 	"sync"
@@ -88,10 +88,10 @@ func getErrorStack(err error, i bool) errors.StackTrace {
 		if i {
 			// Just abort out of this and return a stacktrace leading up to this point. It isn't perfect
 			// but it'll at least include what function lead to this being called which we can then handle.
-			return errors.Wrap(err, "failed to generate stacktrace for caught error").(tracer).StackTrace()
+			return errors.WrapIf(err, "failed to generate stacktrace for caught error").(tracer).StackTrace()
 		}
 
-		return getErrorStack(errors.Wrap(err, err.Error()), true)
+		return getErrorStack(errors.WrapIf(err, err.Error()), true)
 	}
 
 	st := e.StackTrace()
@@ -101,7 +101,7 @@ func getErrorStack(err error, i bool) errors.StackTrace {
 	// trace since they'll point to the error that was generated by this function.
 	f := 0
 	if i {
-		f = 4
+		f = 5
 	}
 
 	if i && l > 9 {
diff --git a/parser/helpers.go b/parser/helpers.go
index 9b6708e..b410e8b 100644
--- a/parser/helpers.go
+++ b/parser/helpers.go
@@ -2,11 +2,11 @@ package parser
 
 import (
 	"bytes"
+	"emperror.dev/errors"
 	"github.com/Jeffail/gabs/v2"
 	"github.com/apex/log"
 	"github.com/buger/jsonparser"
 	"github.com/iancoleman/strcase"
-	"github.com/pkg/errors"
 	"io/ioutil"
 	"os"
 	"regexp"
@@ -76,13 +76,13 @@ func (cfr *ConfigurationFileReplacement) getKeyValue(value []byte) interface{} {
 func (f *ConfigurationFile) IterateOverJson(data []byte) (*gabs.Container, error) {
 	parsed, err := gabs.ParseJSON(data)
 	if err != nil {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	}
 
 	for _, v := range f.Replace {
 		value, err := f.LookupConfigurationValue(v)
 		if err != nil {
-			return nil, errors.WithStack(err)
+			return nil, errors.WithStackIf(err)
 		}
 
 		// Check for a wildcard character, and if found split the key on that value to
@@ -101,7 +101,7 @@ func (f *ConfigurationFile) IterateOverJson(data []byte) (*gabs.Container, error
 						continue
 					}
 
-					return nil, errors.Wrap(err, "failed to set config value of array child")
+					return nil, errors.WrapIf(err, "failed to set config value of array child")
 				}
 			}
 		} else {
@@ -110,7 +110,7 @@ func (f *ConfigurationFile) IterateOverJson(data []byte) (*gabs.Container, error
 					continue
 				}
 
-				return nil, errors.Wrap(err, "unable to set config value at pathway: "+v.Match)
+				return nil, errors.WrapIf(err, "unable to set config value at pathway: "+v.Match)
 			}
 		}
 	}
@@ -138,7 +138,7 @@ func setValueAtPath(c *gabs.Container, path string, value interface{}) error {
 			_, err = c.SetP(value, path)
 		}
 
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	i, _ := strconv.Atoi(matches[2])
@@ -147,7 +147,7 @@ func setValueAtPath(c *gabs.Container, path string, value interface{}) error {
 	ct, err := c.ArrayElementP(i, matches[1])
 	if err != nil {
 		if i != 0 || (!errors.Is(err, gabs.ErrNotArray) && !errors.Is(err, gabs.ErrNotFound)) {
-			return errors.Wrap(err, "error while parsing array element at path")
+			return errors.WrapIf(err, "error while parsing array element at path")
 		}
 
 		var t = make([]interface{}, 1)
@@ -162,7 +162,7 @@ func setValueAtPath(c *gabs.Container, path string, value interface{}) error {
 		// an empty object if we have additional things to set on the array, or just an empty array type
 		// if there is not an object structure detected (no matches[3] available).
 		if _, err = c.SetP(t, matches[1]); err != nil {
-			return errors.Wrap(err, "failed to create empty array for missing element")
+			return errors.WrapIf(err, "failed to create empty array for missing element")
 		}
 
 		// Set our cursor to be the array element we expect, which in this case is just the first element
@@ -170,7 +170,7 @@ func setValueAtPath(c *gabs.Container, path string, value interface{}) error {
 		// to match additional elements. In those cases the server will just have to be rebooted or something.
 		ct, err = c.ArrayElementP(0, matches[1])
 		if err != nil {
-			return errors.Wrap(err, "failed to find array element at path")
+			return errors.WrapIf(err, "failed to find array element at path")
 		}
 	}
 
@@ -187,7 +187,7 @@ func setValueAtPath(c *gabs.Container, path string, value interface{}) error {
 	}
 
 	if err != nil {
-		return errors.Wrap(err, "failed to set value at config path: "+path)
+		return errors.WrapIf(err, "failed to set value at config path: "+path)
 	}
 
 	return nil
@@ -253,7 +253,7 @@ func (f *ConfigurationFile) LookupConfigurationValue(cfr ConfigurationFileReplac
 	match, _, _, err := jsonparser.Get(f.configuration, path...)
 	if err != nil {
 		if err != jsonparser.KeyPathNotFoundError {
-			return string(match), errors.WithStack(err)
+			return string(match), errors.WithStackIf(err)
 		}
 
 		log.WithFields(log.Fields{"path": path, "filename": f.FileName}).Debug("attempted to load a configuration value that does not exist")
diff --git a/parser/parser.go b/parser/parser.go
index 8e0e5bd..ec4888e 100644
--- a/parser/parser.go
+++ b/parser/parser.go
@@ -2,13 +2,13 @@ package parser
 
 import (
 	"bufio"
+	"emperror.dev/errors"
 	"encoding/json"
 	"github.com/apex/log"
 	"github.com/beevik/etree"
 	"github.com/buger/jsonparser"
 	"github.com/icza/dyno"
 	"github.com/magiconair/properties"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/config"
 	"gopkg.in/ini.v1"
 	"gopkg.in/yaml.v2"
@@ -166,17 +166,17 @@ func (f *ConfigurationFile) Parse(path string, internal bool) error {
 
 		b := strings.TrimSuffix(path, filepath.Base(path))
 		if err := os.MkdirAll(b, 0755); err != nil {
-			return errors.Wrap(err, "failed to create base directory for missing configuration file")
+			return errors.WrapIf(err, "failed to create base directory for missing configuration file")
 		} else {
 			if _, err := os.Create(path); err != nil {
-				return errors.Wrap(err, "failed to create missing configuration file")
+				return errors.WrapIf(err, "failed to create missing configuration file")
 			}
 		}
 
 		return f.Parse(path, true)
 	}
 
-	return errors.WithStack(err)
+	return errors.WithStackIf(err)
 }
 
 // Parses an xml file.
@@ -348,12 +348,12 @@ func (f *ConfigurationFile) parseJsonFile(path string) error {
 func (f *ConfigurationFile) parseYamlFile(path string) error {
 	b, err := readFileBytes(path)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	i := make(map[string]interface{})
 	if err := yaml.Unmarshal(b, &i); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	// Unmarshal the yaml data into a JSON interface such that we can work with
@@ -361,20 +361,20 @@ func (f *ConfigurationFile) parseYamlFile(path string) error {
 	// makes working with unknown JSON significantly easier.
 	jsonBytes, err := json.Marshal(dyno.ConvertMapI2MapS(i))
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	// Now that the data is converted, treat it just like JSON and pass it to the
 	// iterator function to update values as necessary.
 	data, err := f.IterateOverJson(jsonBytes)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	// Remarshal the JSON into YAML format before saving it back to the disk.
 	marshaled, err := yaml.Marshal(data.Data())
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	return ioutil.WriteFile(path, marshaled, 0644)
@@ -386,7 +386,7 @@ func (f *ConfigurationFile) parseYamlFile(path string) error {
 func (f *ConfigurationFile) parseTextFile(path string) error {
 	input, err := ioutil.ReadFile(path)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	lines := strings.Split(string(input), "\n")
@@ -403,7 +403,7 @@ func (f *ConfigurationFile) parseTextFile(path string) error {
 	}
 
 	if err := ioutil.WriteFile(path, []byte(strings.Join(lines, "\n")), 0644); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	return nil
@@ -415,7 +415,7 @@ func (f *ConfigurationFile) parsePropertiesFile(path string) error {
 	// Open the file.
 	f2, err := os.Open(path)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	var s strings.Builder
@@ -437,20 +437,20 @@ func (f *ConfigurationFile) parsePropertiesFile(path string) error {
 
 	// Handle any scanner errors.
 	if err := scanner.Err(); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	// Decode the properties file.
 	p, err := properties.LoadFile(path, properties.UTF8)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	// Replace any values that need to be replaced.
 	for _, replace := range f.Replace {
 		data, err := f.LookupConfigurationValue(replace)
 		if err != nil {
-			return errors.WithStack(err)
+			return errors.WithStackIf(err)
 		}
 
 		v, ok := p.Get(replace.Match)
@@ -462,7 +462,7 @@ func (f *ConfigurationFile) parsePropertiesFile(path string) error {
 		}
 
 		if _, _, err := p.Set(replace.Match, data); err != nil {
-			return errors.WithStack(err)
+			return errors.WithStackIf(err)
 		}
 	}
 
@@ -482,7 +482,7 @@ func (f *ConfigurationFile) parsePropertiesFile(path string) error {
 	// Open the file for writing.
 	w, err := os.OpenFile(path, os.O_CREATE|os.O_WRONLY|os.O_TRUNC, 0644)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 	defer w.Close()
 
diff --git a/router/error.go b/router/error.go
index fdd90ea..63369de 100644
--- a/router/error.go
+++ b/router/error.go
@@ -1,11 +1,11 @@
 package router
 
 import (
+	"emperror.dev/errors"
 	"fmt"
 	"github.com/apex/log"
 	"github.com/gin-gonic/gin"
 	"github.com/google/uuid"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/server"
 	"github.com/pterodactyl/wings/server/filesystem"
 	"net/http"
@@ -75,7 +75,7 @@ func (e *RequestError) AbortWithStatus(status int, c *gin.Context) {
 	if status >= 500 {
 		e.logger().WithField("error", e.Err).Error("encountered HTTP/500 error while handling request")
 
-		c.Error(errors.WithStack(e))
+		c.Error(errors.WithStackIf(e))
 	} else {
 		e.logger().WithField("error", e.Err).Debug("encountered non-HTTP/500 error while handling request")
 	}
@@ -99,38 +99,32 @@ func (e *RequestError) AbortWithServerError(c *gin.Context) {
 
 // Handle specific filesystem errors for a server.
 func (e *RequestError) AbortFilesystemError(c *gin.Context) {
-	if errors.Is(e.Err, os.ErrNotExist) {
-		c.AbortWithStatusJSON(http.StatusNotFound, gin.H{
-			"error": "The requested resource was not found.",
-		})
+	if errors.Is(e.Err, os.ErrNotExist) || filesystem.IsBadPathResolutionError(e.Err) {
+		if filesystem.IsBadPathResolutionError(e.Err) {
+			e.logger().Warn(e.Err.Error())
+		}
+
+		c.AbortWithStatusJSON(http.StatusNotFound, gin.H{"error": "The requested resource was not found."})
 		return
 	}
 
 	if errors.Is(e.Err, filesystem.ErrNotEnoughDiskSpace) {
-		c.AbortWithStatusJSON(http.StatusConflict, gin.H{
-			"error": "There is not enough disk space available to perform that action.",
-		})
+		c.AbortWithStatusJSON(http.StatusConflict, gin.H{"error": "There is not enough disk space available to perform that action."})
 		return
 	}
 
 	if strings.HasSuffix(e.Err.Error(), "file name too long") {
-		c.AbortWithStatusJSON(http.StatusBadRequest, gin.H{
-			"error": "File name is too long.",
-		})
+		c.AbortWithStatusJSON(http.StatusBadRequest, gin.H{"error": "File name is too long."})
 		return
 	}
 
 	if e, ok := e.Err.(*os.SyscallError); ok && e.Syscall == "readdirent" {
-		c.AbortWithStatusJSON(http.StatusNotFound, gin.H{
-			"error": "The requested directory does not exist.",
-		})
+		c.AbortWithStatusJSON(http.StatusNotFound, gin.H{"error": "The requested directory does not exist."})
 		return
 	}
 
 	if strings.HasSuffix(e.Err.Error(), "file name too long") {
-		c.AbortWithStatusJSON(http.StatusBadRequest, gin.H{
-			"error": "Cannot perform that action: file name is too long.",
-		})
+		c.AbortWithStatusJSON(http.StatusBadRequest, gin.H{"error": "Cannot perform that action: file name is too long."})
 		return
 	}
 
diff --git a/router/router_server.go b/router/router_server.go
index 8b7669b..12d83a9 100644
--- a/router/router_server.go
+++ b/router/router_server.go
@@ -3,9 +3,9 @@ package router
 import (
 	"bytes"
 	"context"
+	"emperror.dev/errors"
 	"github.com/apex/log"
 	"github.com/gin-gonic/gin"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/router/tokens"
 	"github.com/pterodactyl/wings/server"
 	"net/http"
@@ -227,7 +227,7 @@ func deleteServer(c *gin.Context) {
 		if err := os.RemoveAll(p); err != nil {
 			log.WithFields(log.Fields{
 				"path":  p,
-				"error": errors.WithStack(err),
+				"error": errors.WithStackIf(err),
 			}).Warn("failed to remove server files during deletion process")
 		}
 	}(s.Filesystem().Path())
diff --git a/router/router_server_files.go b/router/router_server_files.go
index 7fd19e1..07e1d43 100644
--- a/router/router_server_files.go
+++ b/router/router_server_files.go
@@ -2,8 +2,8 @@ package router
 
 import (
 	"context"
+	"emperror.dev/errors"
 	"github.com/gin-gonic/gin"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/router/tokens"
 	"github.com/pterodactyl/wings/server"
 	"github.com/pterodactyl/wings/server/filesystem"
@@ -35,19 +35,19 @@ func getServerFileContents(c *gin.Context) {
 		return
 	}
 
-	c.Header("X-Mime-Type", st.Mimetype)
-	c.Header("Content-Length", strconv.Itoa(int(st.Info.Size())))
-
-	// If a download parameter is included in the URL go ahead and attach the necessary headers
-	// so that the file can be downloaded.
-	if c.Query("download") != "" {
-		c.Header("Content-Disposition", "attachment; filename="+st.Info.Name())
-		c.Header("Content-Type", "application/octet-stream")
-	}
-
 	if err := s.Filesystem().Readfile(p, c.Writer); err != nil {
 		TrackedServerError(err, s).AbortFilesystemError(c)
 		return
+	} else {
+		c.Header("X-Mime-Type", st.Mimetype)
+		c.Header("Content-Length", strconv.Itoa(int(st.Info.Size())))
+
+		// If a download parameter is included in the URL go ahead and attach the necessary headers
+		// so that the file can be downloaded.
+		if c.Query("download") != "" {
+			c.Header("Content-Disposition", "attachment; filename="+st.Info.Name())
+			c.Header("Content-Type", "application/octet-stream")
+		}
 	}
 }
 
@@ -413,12 +413,12 @@ func postServerUploadFiles(c *gin.Context) {
 func handleFileUpload(p string, s *server.Server, header *multipart.FileHeader) error {
 	file, err := header.Open()
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 	defer file.Close()
 
 	if err := s.Filesystem().Writefile(p, file); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	return nil
diff --git a/router/router_transfer.go b/router/router_transfer.go
index 3584a30..f2df212 100644
--- a/router/router_transfer.go
+++ b/router/router_transfer.go
@@ -4,12 +4,12 @@ import (
 	"bufio"
 	"bytes"
 	"crypto/sha256"
+	"emperror.dev/errors"
 	"encoding/hex"
 	"github.com/apex/log"
 	"github.com/buger/jsonparser"
 	"github.com/gin-gonic/gin"
 	"github.com/mholt/archiver/v3"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/api"
 	"github.com/pterodactyl/wings/config"
 	"github.com/pterodactyl/wings/installer"
@@ -157,7 +157,7 @@ func postTransfer(c *gin.Context) {
 		// Make a new GET request to the URL the panel gave us.
 		req, err := http.NewRequest("GET", url, nil)
 		if err != nil {
-			log.WithField("error", errors.WithStack(err)).Error("failed to create http request for archive transfer")
+			log.WithField("error", errors.WithStackIf(err)).Error("failed to create http request for archive transfer")
 			return
 		}
 
@@ -167,7 +167,7 @@ func postTransfer(c *gin.Context) {
 		// Execute the http request.
 		res, err := client.Do(req)
 		if err != nil {
-			l.WithField("error", errors.WithStack(err)).Error("failed to send archive http request")
+			l.WithField("error", errors.WithStackIf(err)).Error("failed to send archive http request")
 			return
 		}
 		defer res.Body.Close()
@@ -176,12 +176,12 @@ func postTransfer(c *gin.Context) {
 		if res.StatusCode != 200 {
 			_, err := ioutil.ReadAll(res.Body)
 			if err != nil {
-				l.WithField("error", errors.WithStack(err)).WithField("status", res.StatusCode).Error("failed read transfer response body")
+				l.WithField("error", errors.WithStackIf(err)).WithField("status", res.StatusCode).Error("failed read transfer response body")
 
 				return
 			}
 
-			l.WithField("error", errors.WithStack(err)).WithField("status", res.StatusCode).Error("failed to request server archive")
+			l.WithField("error", errors.WithStackIf(err)).WithField("status", res.StatusCode).Error("failed to request server archive")
 
 			return
 		}
@@ -193,12 +193,12 @@ func postTransfer(c *gin.Context) {
 		_, err = os.Stat(archivePath)
 		if err != nil {
 			if !os.IsNotExist(err) {
-				l.WithField("error", errors.WithStack(err)).Error("failed to stat archive file")
+				l.WithField("error", errors.WithStackIf(err)).Error("failed to stat archive file")
 				return
 			}
 		} else {
 			if err := os.Remove(archivePath); err != nil {
-				l.WithField("error", errors.WithStack(err)).Warn("failed to remove old archive file")
+				l.WithField("error", errors.WithStackIf(err)).Warn("failed to remove old archive file")
 
 				return
 			}
@@ -207,7 +207,7 @@ func postTransfer(c *gin.Context) {
 		// Create the file.
 		file, err := os.Create(archivePath)
 		if err != nil {
-			l.WithField("error", errors.WithStack(err)).Error("failed to open archive on disk")
+			l.WithField("error", errors.WithStackIf(err)).Error("failed to open archive on disk")
 
 			return
 		}
@@ -216,14 +216,14 @@ func postTransfer(c *gin.Context) {
 		buf := make([]byte, 1024*4)
 		_, err = io.CopyBuffer(file, res.Body, buf)
 		if err != nil {
-			l.WithField("error", errors.WithStack(err)).Error("failed to copy archive file to disk")
+			l.WithField("error", errors.WithStackIf(err)).Error("failed to copy archive file to disk")
 
 			return
 		}
 
 		// Close the file so it can be opened to verify the checksum.
 		if err := file.Close(); err != nil {
-			l.WithField("error", errors.WithStack(err)).Error("failed to close archive file")
+			l.WithField("error", errors.WithStackIf(err)).Error("failed to close archive file")
 
 			return
 		}
@@ -233,7 +233,7 @@ func postTransfer(c *gin.Context) {
 		// Open the archive file for computing a checksum.
 		file, err = os.Open(archivePath)
 		if err != nil {
-			l.WithField("error", errors.WithStack(err)).Error("failed to open archive on disk")
+			l.WithField("error", errors.WithStackIf(err)).Error("failed to open archive on disk")
 			return
 		}
 
@@ -241,7 +241,7 @@ func postTransfer(c *gin.Context) {
 		hash := sha256.New()
 		buf = make([]byte, 1024*4)
 		if _, err := io.CopyBuffer(hash, file, buf); err != nil {
-			l.WithField("error", errors.WithStack(err)).Error("failed to copy archive file for checksum verification")
+			l.WithField("error", errors.WithStackIf(err)).Error("failed to copy archive file for checksum verification")
 			return
 		}
 
@@ -253,7 +253,7 @@ func postTransfer(c *gin.Context) {
 
 		// Close the file.
 		if err := file.Close(); err != nil {
-			l.WithField("error", errors.WithStack(err)).Error("failed to close archive file after calculating checksum")
+			l.WithField("error", errors.WithStackIf(err)).Error("failed to close archive file after calculating checksum")
 			return
 		}
 
@@ -269,7 +269,7 @@ func postTransfer(c *gin.Context) {
 		// Create a new server installer (note this does not execute the install script)
 		i, err := installer.New(serverData)
 		if err != nil {
-			l.WithField("error", errors.WithStack(err)).Error("failed to validate received server data")
+			l.WithField("error", errors.WithStackIf(err)).Error("failed to validate received server data")
 			return
 		}
 
@@ -284,7 +284,7 @@ func postTransfer(c *gin.Context) {
 
 		// Un-archive the archive. That sounds weird..
 		if err := archiver.NewTarGz().Unarchive(archivePath, i.Server().Filesystem().Path()); err != nil {
-			l.WithField("error", errors.WithStack(err)).Error("failed to extract server archive")
+			l.WithField("error", errors.WithStackIf(err)).Error("failed to extract server archive")
 			return
 		}
 
@@ -299,7 +299,7 @@ func postTransfer(c *gin.Context) {
 		err = api.New().SendTransferSuccess(serverID)
 		if err != nil {
 			if !api.IsRequestError(err) {
-				l.WithField("error", errors.WithStack(err)).Error("failed to notify panel of transfer success")
+				l.WithField("error", errors.WithStackIf(err)).Error("failed to notify panel of transfer success")
 				return
 			}
 
diff --git a/router/websocket/websocket.go b/router/websocket/websocket.go
index c764be3..3a4620c 100644
--- a/router/websocket/websocket.go
+++ b/router/websocket/websocket.go
@@ -2,13 +2,13 @@ package websocket
 
 import (
 	"context"
+	"emperror.dev/errors"
 	"encoding/json"
 	"fmt"
 	"github.com/apex/log"
 	"github.com/gbrlsnchs/jwt/v3"
 	"github.com/google/uuid"
 	"github.com/gorilla/websocket"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/config"
 	"github.com/pterodactyl/wings/environment"
 	"github.com/pterodactyl/wings/environment/docker"
@@ -41,10 +41,10 @@ type Handler struct {
 }
 
 var (
-	ErrJwtNotPresent    = errors.New("jwt: no jwt present")
-	ErrJwtNoConnectPerm = errors.New("jwt: missing connect permission")
-	ErrJwtUuidMismatch  = errors.New("jwt: server uuid mismatch")
-	ErrJwtOnDenylist    = errors.New("jwt: created too far in past (denylist)")
+	ErrJwtNotPresent    = errors.Sentinel("jwt: no jwt present")
+	ErrJwtNoConnectPerm = errors.Sentinel("jwt: missing connect permission")
+	ErrJwtUuidMismatch  = errors.Sentinel("jwt: server uuid mismatch")
+	ErrJwtOnDenylist    = errors.Sentinel("jwt: created too far in past (denylist)")
 )
 
 func IsJwtError(err error) bool {
@@ -108,7 +108,7 @@ func GetHandler(s *server.Server, w http.ResponseWriter, r *http.Request) (*Hand
 
 	u, err := uuid.NewRandom()
 	if err != nil {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	}
 
 	return &Handler{
diff --git a/server/archiver.go b/server/archiver.go
index 35e6f05..951c6c9 100644
--- a/server/archiver.go
+++ b/server/archiver.go
@@ -2,9 +2,9 @@ package server
 
 import (
 	"crypto/sha256"
+	"emperror.dev/errors"
 	"encoding/hex"
 	"github.com/mholt/archiver/v3"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/config"
 	"github.com/pterodactyl/wings/server/filesystem"
 	"io"
@@ -41,7 +41,7 @@ func (a *Archiver) Exists() bool {
 func (a *Archiver) Stat() (*filesystem.Stat, error) {
 	s, err := os.Stat(a.Path())
 	if err != nil {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	}
 
 	return &filesystem.Stat{
@@ -99,7 +99,7 @@ func (a *Archiver) DeleteIfExists() error {
 	}
 
 	if err := os.Remove(a.Path()); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	return nil
diff --git a/server/backup.go b/server/backup.go
index 9d8cd1f..c50003e 100644
--- a/server/backup.go
+++ b/server/backup.go
@@ -2,8 +2,8 @@ package server
 
 import (
 	"bufio"
+	"emperror.dev/errors"
 	"github.com/apex/log"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/api"
 	"github.com/pterodactyl/wings/server/backup"
 	"os"
@@ -80,7 +80,7 @@ func (s *Server) Backup(b backup.BackupInterface) error {
 	// Get the included files based on the root path and the ignored files provided.
 	inc, err := s.GetIncludedBackupFiles(b.Ignored())
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	ad, err := b.Generate(inc, s.Filesystem().Path())
@@ -100,7 +100,7 @@ func (s *Server) Backup(b backup.BackupInterface) error {
 			"file_size":     0,
 		})
 
-		return errors.Wrap(err, "error while generating server backup")
+		return errors.WrapIf(err, "error while generating server backup")
 	}
 
 	// Try to notify the panel about the status of this backup. If for some reason this request
diff --git a/server/backup/archiver.go b/server/backup/archiver.go
index 4dedccb..03d9db1 100644
--- a/server/backup/archiver.go
+++ b/server/backup/archiver.go
@@ -3,9 +3,9 @@ package backup
 import (
 	"archive/tar"
 	"context"
+	"emperror.dev/errors"
 	"github.com/apex/log"
 	gzip "github.com/klauspost/pgzip"
-	"github.com/pkg/errors"
 	"github.com/remeh/sizedwaitgroup"
 	"golang.org/x/sync/errgroup"
 	"io"
@@ -26,7 +26,7 @@ type Archive struct {
 func (a *Archive) Create(dst string, ctx context.Context) error {
 	f, err := os.OpenFile(dst, os.O_WRONLY|os.O_CREATE|os.O_TRUNC, 0600)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 	defer f.Close()
 
@@ -58,7 +58,7 @@ func (a *Archive) Create(dst string, ctx context.Context) error {
 
 			select {
 			case <-ctx.Done():
-				return errors.WithStack(ctx.Err())
+				return errors.WithStackIf(ctx.Err())
 			default:
 				return a.addToArchive(p, tw)
 			}
@@ -75,7 +75,7 @@ func (a *Archive) Create(dst string, ctx context.Context) error {
 			log.WithField("location", dst).Warn("failed to delete corrupted backup archive")
 		}
 
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	return nil
@@ -91,7 +91,7 @@ func (a *Archive) addToArchive(p string, w *tar.Writer) error {
 			return nil
 		}
 
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 	defer f.Close()
 
@@ -102,7 +102,7 @@ func (a *Archive) addToArchive(p string, w *tar.Writer) error {
 			return nil
 		}
 
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	header := &tar.Header{
@@ -120,12 +120,12 @@ func (a *Archive) addToArchive(p string, w *tar.Writer) error {
 	defer a.Unlock()
 
 	if err := w.WriteHeader(header); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	buf := make([]byte, 4*1024)
 	if _, err := io.CopyBuffer(w, f, buf); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	return nil
diff --git a/server/backup/backup.go b/server/backup/backup.go
index 67006ce..5ba270a 100644
--- a/server/backup/backup.go
+++ b/server/backup/backup.go
@@ -2,9 +2,9 @@ package backup
 
 import (
 	"crypto/sha1"
+	"emperror.dev/errors"
 	"encoding/hex"
 	"github.com/apex/log"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/api"
 	"github.com/pterodactyl/wings/config"
 	"io"
@@ -87,7 +87,7 @@ func (b *Backup) Path() string {
 func (b *Backup) Size() (int64, error) {
 	st, err := os.Stat(b.Path())
 	if err != nil {
-		return 0, errors.WithStack(err)
+		return 0, errors.WithStackIf(err)
 	}
 
 	return st.Size(), nil
@@ -99,7 +99,7 @@ func (b *Backup) Checksum() ([]byte, error) {
 
 	f, err := os.Open(b.Path())
 	if err != nil {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	}
 	defer f.Close()
 
diff --git a/server/backup/backup_local.go b/server/backup/backup_local.go
index bc07bfe..45cb8a9 100644
--- a/server/backup/backup_local.go
+++ b/server/backup/backup_local.go
@@ -2,7 +2,7 @@ package backup
 
 import (
 	"context"
-	"github.com/pkg/errors"
+	"emperror.dev/errors"
 	"os"
 )
 
@@ -24,7 +24,7 @@ func LocateLocal(uuid string) (*LocalBackup, os.FileInfo, error) {
 
 	st, err := os.Stat(b.Path())
 	if err != nil {
-		return nil, nil, errors.WithStack(err)
+		return nil, nil, errors.WithStackIf(err)
 	}
 
 	if st.IsDir() {
@@ -48,7 +48,7 @@ func (b *LocalBackup) Generate(included *IncludedFiles, prefix string) (*Archive
 	}
 
 	if err := a.Create(b.Path(), context.Background()); err != nil {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	}
 
 	return b.Details(), nil
diff --git a/server/backup/backup_request.go b/server/backup/backup_request.go
index a240596..ae14a1c 100644
--- a/server/backup/backup_request.go
+++ b/server/backup/backup_request.go
@@ -1,8 +1,8 @@
 package backup
 
 import (
+	"emperror.dev/errors"
 	"fmt"
-	"github.com/pkg/errors"
 )
 
 type Request struct {
diff --git a/server/backup/backup_s3.go b/server/backup/backup_s3.go
index 8dcf269..6476b72 100644
--- a/server/backup/backup_s3.go
+++ b/server/backup/backup_s3.go
@@ -3,9 +3,9 @@ package backup
 import (
 	"bytes"
 	"context"
+	"emperror.dev/errors"
 	"fmt"
 	"github.com/apex/log"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/api"
 	"io"
 	"net/http"
@@ -31,17 +31,17 @@ func (s *S3Backup) Generate(included *IncludedFiles, prefix string) (*ArchiveDet
 	}
 
 	if err := a.Create(s.Path(), context.Background()); err != nil {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	}
 
 	rc, err := os.Open(s.Path())
 	if err != nil {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	}
 	defer rc.Close()
 
 	if err := s.generateRemoteRequest(rc); err != nil {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	}
 
 	return s.Details(), err
diff --git a/server/console.go b/server/console.go
index e6637ea..8d1736e 100644
--- a/server/console.go
+++ b/server/console.go
@@ -2,9 +2,9 @@ package server
 
 import (
 	"context"
+	"emperror.dev/errors"
 	"fmt"
 	"github.com/mitchellh/colorstring"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/config"
 	"github.com/pterodactyl/wings/system"
 	"sync"
@@ -12,7 +12,7 @@ import (
 	"time"
 )
 
-var ErrTooMuchConsoleData = errors.New("console is outputting too much data")
+var ErrTooMuchConsoleData = errors.Sentinel("console is outputting too much data")
 
 type ConsoleThrottler struct {
 	mu sync.Mutex
diff --git a/server/crash.go b/server/crash.go
index 256d8bd..1200ff7 100644
--- a/server/crash.go
+++ b/server/crash.go
@@ -1,8 +1,8 @@
 package server
 
 import (
+	"emperror.dev/errors"
 	"fmt"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/config"
 	"github.com/pterodactyl/wings/environment"
 	"sync"
@@ -57,7 +57,7 @@ func (s *Server) handleServerCrash() error {
 
 	exitCode, oomKilled, err := s.Environment.ExitState()
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	// If the system is not configured to detect a clean exit code as a crash, and the
diff --git a/server/errors.go b/server/errors.go
index 80fdaa9..2e8f50b 100644
--- a/server/errors.go
+++ b/server/errors.go
@@ -1,9 +1,9 @@
 package server
 
-import "github.com/pkg/errors"
+import "emperror.dev/errors"
 
-var ErrIsRunning = errors.New("server is running")
-var ErrSuspended = errors.New("server is currently in a suspended state")
+var ErrIsRunning = errors.Sentinel("server is running")
+var ErrSuspended = errors.Sentinel("server is currently in a suspended state")
 
 type crashTooFrequent struct {
 }
diff --git a/server/filesystem.go b/server/filesystem.go
index c996938..c7aa643 100644
--- a/server/filesystem.go
+++ b/server/filesystem.go
@@ -1,7 +1,7 @@
 package server
 
 import (
-	"github.com/pkg/errors"
+	"emperror.dev/errors"
 	"github.com/pterodactyl/wings/server/filesystem"
 	"os"
 )
@@ -13,12 +13,12 @@ func (s *Server) Filesystem() *filesystem.Filesystem {
 // Ensures that the data directory for the server instance exists.
 func (s *Server) EnsureDataDirectoryExists() error {
 	if _, err := os.Stat(s.fs.Path()); err != nil && !os.IsNotExist(err) {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	} else if err != nil {
 		// Create the server data directory because it does not currently exist
 		// on the system.
 		if err := os.MkdirAll(s.fs.Path(), 0700); err != nil {
-			return errors.WithStack(err)
+			return errors.WithStackIf(err)
 		}
 
 		if err := s.fs.Chown("/"); err != nil {
diff --git a/server/filesystem/compress.go b/server/filesystem/compress.go
index fc2a4e2..c83e4d3 100644
--- a/server/filesystem/compress.go
+++ b/server/filesystem/compress.go
@@ -2,9 +2,9 @@ package filesystem
 
 import (
 	"context"
+	"emperror.dev/errors"
 	"fmt"
 	"github.com/karrick/godirwalk"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/server/backup"
 	ignore "github.com/sabhiram/go-gitignore"
 	"os"
@@ -41,7 +41,7 @@ func (fs *Filesystem) GetIncludedFiles(dir string, ignored []string) (*backup.In
 			if e.IsSymlink() {
 				sp, err = fs.SafePath(p)
 				if err != nil {
-					if errors.Is(err, ErrBadPathResolution) {
+					if IsBadPathResolutionError(err) {
 						return godirwalk.SkipThis
 					}
 
@@ -65,7 +65,7 @@ func (fs *Filesystem) GetIncludedFiles(dir string, ignored []string) (*backup.In
 		},
 	})
 
-	return inc, errors.WithStack(err)
+	return inc, errors.WithStackIf(err)
 }
 
 // Compresses all of the files matching the given paths in the specified directory. This function
@@ -115,7 +115,7 @@ func (fs *Filesystem) CompressFiles(dir string, paths []string) (os.FileInfo, er
 						// use the resolved location for the rest of this function.
 						sp, err = fs.SafePath(p)
 						if err != nil {
-							if errors.Is(err, ErrBadPathResolution) {
+							if IsBadPathResolutionError(err) {
 								return godirwalk.SkipThis
 							}
 
@@ -141,7 +141,7 @@ func (fs *Filesystem) CompressFiles(dir string, paths []string) (os.FileInfo, er
 	d := path.Join(cleanedRootDir, fmt.Sprintf("archive-%s.tar.gz", strings.ReplaceAll(time.Now().Format(time.RFC3339), ":", "")))
 
 	if err := a.Create(d, context.Background()); err != nil {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	}
 
 	f, err := os.Stat(d)
diff --git a/server/filesystem/decompress.go b/server/filesystem/decompress.go
index 1c5cb3a..213282b 100644
--- a/server/filesystem/decompress.go
+++ b/server/filesystem/decompress.go
@@ -4,9 +4,9 @@ import (
 	"archive/tar"
 	"archive/zip"
 	"compress/gzip"
+	"emperror.dev/errors"
 	"fmt"
 	"github.com/mholt/archiver/v3"
-	"github.com/pkg/errors"
 	"os"
 	"path/filepath"
 	"reflect"
@@ -47,10 +47,10 @@ func (fs *Filesystem) SpaceAvailableForDecompression(dir string, file string) (b
 			return false, ErrUnknownArchiveFormat
 		}
 
-		return false, errors.WithStack(err)
+		return false, errors.WithStackIf(err)
 	}
 
-	return true, errors.WithStack(err)
+	return true, errors.WithStackIf(err)
 }
 
 // Decompress a file in a given directory by using the archiver tool to infer the file
@@ -60,12 +60,12 @@ func (fs *Filesystem) SpaceAvailableForDecompression(dir string, file string) (b
 func (fs *Filesystem) DecompressFile(dir string, file string) error {
 	source, err := fs.SafePath(filepath.Join(dir, file))
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	// Make sure the file exists basically.
 	if _, err := os.Stat(source); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	// Walk over all of the files spinning up an additional go-routine for each file we've encountered
@@ -93,17 +93,17 @@ func (fs *Filesystem) DecompressFile(dir string, file string) error {
 
 		p, err := fs.SafePath(filepath.Join(dir, name))
 		if err != nil {
-			return errors.Wrap(err, "failed to generate a safe path to server file")
+			return errors.WrapIf(err, "failed to generate a safe path to server file")
 		}
 
-		return errors.Wrap(fs.Writefile(p, f), "could not extract file from archive")
+		return errors.WrapIf(fs.Writefile(p, f), "could not extract file from archive")
 	})
 	if err != nil {
 		if strings.HasPrefix(err.Error(), "format ") {
-			return errors.WithStack(ErrUnknownArchiveFormat)
+			return errors.WithStackIf(ErrUnknownArchiveFormat)
 		}
 
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	return nil
diff --git a/server/filesystem/disk_space.go b/server/filesystem/disk_space.go
index 9efd2cc..8c0a7ff 100644
--- a/server/filesystem/disk_space.go
+++ b/server/filesystem/disk_space.go
@@ -1,9 +1,9 @@
 package filesystem
 
 import (
+	"emperror.dev/errors"
 	"github.com/apex/log"
 	"github.com/karrick/godirwalk"
-	"github.com/pkg/errors"
 	"sync"
 	"sync/atomic"
 	"syscall"
@@ -153,7 +153,7 @@ func (fs *Filesystem) updateCachedDiskUsage() (int64, error) {
 func (fs *Filesystem) DirectorySize(dir string) (int64, error) {
 	d, err := fs.SafePath(dir)
 	if err != nil {
-		return 0, errors.WithStack(err)
+		return 0, errors.WithStackIf(err)
 	}
 
 	var size int64
@@ -167,7 +167,7 @@ func (fs *Filesystem) DirectorySize(dir string) (int64, error) {
 			// it. Otherwise, allow it to continue.
 			if e.IsSymlink() {
 				if _, err := fs.SafePath(p); err != nil {
-					if errors.Is(err, ErrBadPathResolution) {
+					if IsBadPathResolutionError(err) {
 						return godirwalk.SkipThis
 					}
 
@@ -184,7 +184,7 @@ func (fs *Filesystem) DirectorySize(dir string) (int64, error) {
 		},
 	})
 
-	return size, errors.WithStack(err)
+	return size, errors.WithStackIf(err)
 }
 
 // Helper function to determine if a server has space available for a file of a given size.
diff --git a/server/filesystem/errors.go b/server/filesystem/errors.go
index d2cb01e..e44ad53 100644
--- a/server/filesystem/errors.go
+++ b/server/filesystem/errors.go
@@ -1,16 +1,43 @@
 package filesystem
 
 import (
+	"emperror.dev/errors"
+	"fmt"
 	"github.com/apex/log"
-	"github.com/pkg/errors"
 	"os"
 	"path/filepath"
 )
 
-var ErrIsDirectory = errors.New("filesystem: is a directory")
-var ErrNotEnoughDiskSpace = errors.New("filesystem: not enough disk space")
-var ErrBadPathResolution = errors.New("filesystem: invalid path resolution")
-var ErrUnknownArchiveFormat = errors.New("filesystem: unknown archive format")
+var ErrIsDirectory = errors.Sentinel("filesystem: is a directory")
+var ErrNotEnoughDiskSpace = errors.Sentinel("filesystem: not enough disk space")
+var ErrUnknownArchiveFormat = errors.Sentinel("filesystem: unknown archive format")
+
+type BadPathResolutionError struct {
+	path     string
+	resolved string
+}
+
+// Returns the specific error for a bad path resolution.
+func (b *BadPathResolutionError) Error() string {
+	r := b.resolved
+	if r == "" {
+		r = "<empty>"
+	}
+	return fmt.Sprintf("filesystem: server path [%s] resolves to a location outside the server root: %s", b.path, r)
+}
+
+// Returns a new BadPathResolution error.
+func NewBadPathResolution(path string, resolved string) *BadPathResolutionError {
+	return &BadPathResolutionError{path, resolved}
+}
+
+// Determines if the given error is a bad path resolution error.
+func IsBadPathResolutionError(err error) bool {
+	if _, ok := err.(*BadPathResolutionError); ok {
+		return true
+	}
+	return false
+}
 
 // Generates an error logger instance with some basic information.
 func (fs *Filesystem) error(err error) *log.Entry {
@@ -23,8 +50,8 @@ func (fs *Filesystem) error(err error) *log.Entry {
 // directory, otherwise return nil. Returning this error for a file will stop the walking
 // for the remainder of the directory. This is assuming an os.FileInfo struct was even returned.
 func (fs *Filesystem) handleWalkerError(err error, f os.FileInfo) error {
-	if !errors.Is(err, ErrBadPathResolution) {
-		return err
+	if !IsBadPathResolutionError(err) {
+		return errors.WithStackIf(err)
 	}
 
 	if f != nil && f.IsDir() {
@@ -32,4 +59,4 @@ func (fs *Filesystem) handleWalkerError(err error, f os.FileInfo) error {
 	}
 
 	return nil
-}
\ No newline at end of file
+}
diff --git a/server/filesystem/filesystem.go b/server/filesystem/filesystem.go
index a6b89a5..be1cdc0 100644
--- a/server/filesystem/filesystem.go
+++ b/server/filesystem/filesystem.go
@@ -2,9 +2,9 @@ package filesystem
 
 import (
 	"bufio"
+	"emperror.dev/errors"
 	"github.com/gabriel-vasile/mimetype"
 	"github.com/karrick/godirwalk"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/config"
 	"github.com/pterodactyl/wings/system"
 	"io"
@@ -80,7 +80,7 @@ func (fs *Filesystem) Readfile(p string, w io.Writer) error {
 func (fs *Filesystem) Writefile(p string, r io.Reader) error {
 	cleaned, err := fs.SafePath(p)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	var currentSize int64
@@ -88,15 +88,15 @@ func (fs *Filesystem) Writefile(p string, r io.Reader) error {
 	// to it and an empty file. We'll then write to it later on after this completes.
 	if stat, err := os.Stat(cleaned); err != nil {
 		if !os.IsNotExist(err) {
-			return errors.WithStack(err)
+			return errors.WithStackIf(err)
 		}
 
 		if err := os.MkdirAll(filepath.Dir(cleaned), 0755); err != nil {
-			return errors.WithStack(err)
+			return errors.WithStackIf(err)
 		}
 
 		if err := fs.Chown(filepath.Dir(cleaned)); err != nil {
-			return errors.WithStack(err)
+			return errors.WithStackIf(err)
 		}
 	} else {
 		if stat.IsDir() {
@@ -119,7 +119,7 @@ func (fs *Filesystem) Writefile(p string, r io.Reader) error {
 	// truncate the existing file.
 	file, err := o.open(cleaned, os.O_RDWR|os.O_CREATE|os.O_TRUNC, 0644)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 	defer file.Close()
 
@@ -138,7 +138,7 @@ func (fs *Filesystem) Writefile(p string, r io.Reader) error {
 func (fs *Filesystem) CreateDirectory(name string, p string) error {
 	cleaned, err := fs.SafePath(path.Join(p, name))
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	return os.MkdirAll(cleaned, 0755)
@@ -148,12 +148,12 @@ func (fs *Filesystem) CreateDirectory(name string, p string) error {
 func (fs *Filesystem) Rename(from string, to string) error {
 	cleanedFrom, err := fs.SafePath(from)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	cleanedTo, err := fs.SafePath(to)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	// If the target file or directory already exists the rename function will fail, so just
@@ -171,7 +171,7 @@ func (fs *Filesystem) Rename(from string, to string) error {
 	// we're not at the root directory level.
 	if d != fs.Path() {
 		if mkerr := os.MkdirAll(d, 0755); mkerr != nil {
-			return errors.Wrap(mkerr, "failed to create directory structure for file rename")
+			return errors.WrapIf(mkerr, "failed to create directory structure for file rename")
 		}
 	}
 
@@ -185,7 +185,7 @@ func (fs *Filesystem) Rename(from string, to string) error {
 func (fs *Filesystem) Chown(path string) error {
 	cleaned, err := fs.SafePath(path)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	if fs.isTest {
@@ -197,7 +197,7 @@ func (fs *Filesystem) Chown(path string) error {
 
 	// Start by just chowning the initial path that we received.
 	if err := os.Chown(cleaned, uid, gid); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	// If this is not a directory we can now return from the function, there is nothing
@@ -268,12 +268,12 @@ func (fs *Filesystem) findCopySuffix(dir string, name string, extension string)
 func (fs *Filesystem) Copy(p string) error {
 	cleaned, err := fs.SafePath(p)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	s, err := os.Stat(cleaned)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	} else if s.IsDir() || !s.Mode().IsRegular() {
 		// If this is a directory or not a regular file, just throw a not-exist error
 		// since anything calling this function should understand what that means.
@@ -300,7 +300,7 @@ func (fs *Filesystem) Copy(p string) error {
 
 	source, err := os.Open(cleaned)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 	defer source.Close()
 
@@ -324,7 +324,7 @@ func (fs *Filesystem) Delete(p string) error {
 	// exists within the data directory.
 	resolved := fs.unsafeFilePath(p)
 	if !fs.unsafeIsInDataDirectory(resolved) {
-		return ErrBadPathResolution
+		return NewBadPathResolution(p, resolved)
 	}
 
 	// Block any whoopsies.
diff --git a/server/filesystem/filesystem_test.go b/server/filesystem/filesystem_test.go
index a1a418b..49ab4f5 100644
--- a/server/filesystem/filesystem_test.go
+++ b/server/filesystem/filesystem_test.go
@@ -134,22 +134,22 @@ func TestFilesystem_SafePath(t *testing.T) {
 		g.It("blocks access to files outside the root directory", func() {
 			p, err := fs.SafePath("../test.txt")
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 			g.Assert(p).Equal("")
 
 			p, err = fs.SafePath("/../test.txt")
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 			g.Assert(p).Equal("")
 
 			p, err = fs.SafePath("./foo/../../test.txt")
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 			g.Assert(p).Equal("")
 
 			p, err = fs.SafePath("..")
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 			g.Assert(p).Equal("")
 		})
 	})
@@ -185,7 +185,7 @@ func TestFilesystem_Blocks_Symlinks(t *testing.T) {
 
 			err := fs.Readfile("symlinked.txt", &b)
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 		})
 	})
 
@@ -195,7 +195,7 @@ func TestFilesystem_Blocks_Symlinks(t *testing.T) {
 
 			err := fs.Writefile("symlinked.txt", r)
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 		})
 
 		g.It("cannot write a file to a directory symlinked outside the root", func() {
@@ -203,7 +203,7 @@ func TestFilesystem_Blocks_Symlinks(t *testing.T) {
 
 			err := fs.Writefile("external_dir/foo.txt", r)
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 		})
 	})
 
@@ -211,19 +211,19 @@ func TestFilesystem_Blocks_Symlinks(t *testing.T) {
 		g.It("cannot create a directory outside the root", func() {
 			err := fs.CreateDirectory("my_dir", "external_dir")
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 		})
 
 		g.It("cannot create a nested directory outside the root", func() {
 			err := fs.CreateDirectory("my/nested/dir", "external_dir/foo/bar")
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 		})
 
 		g.It("cannot create a nested directory outside the root", func() {
 			err := fs.CreateDirectory("my/nested/dir", "external_dir/server")
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 		})
 	})
 
@@ -231,13 +231,13 @@ func TestFilesystem_Blocks_Symlinks(t *testing.T) {
 		g.It("cannot rename a file symlinked outside the directory root", func() {
 			err := fs.Rename("symlinked.txt", "foo.txt")
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 		})
 
 		g.It("cannot rename a symlinked directory outside the root", func() {
 			err := fs.Rename("external_dir", "foo")
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 		})
 
 		g.It("cannot rename a file to a location outside the directory root", func() {
@@ -245,7 +245,7 @@ func TestFilesystem_Blocks_Symlinks(t *testing.T) {
 
 			err := fs.Rename("my_file.txt", "external_dir/my_file.txt")
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 		})
 	})
 
@@ -253,13 +253,13 @@ func TestFilesystem_Blocks_Symlinks(t *testing.T) {
 		g.It("cannot chown a file symlinked outside the directory root", func() {
 			err := fs.Chown("symlinked.txt")
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 		})
 
 		g.It("cannot chown a directory symlinked outside the directory root", func() {
 			err := fs.Chown("external_dir")
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 		})
 	})
 
@@ -267,7 +267,7 @@ func TestFilesystem_Blocks_Symlinks(t *testing.T) {
 		g.It("cannot copy a file symlinked outside the directory root", func() {
 			err := fs.Copy("symlinked.txt")
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 		})
 	})
 
@@ -325,7 +325,7 @@ func TestFilesystem_Readfile(t *testing.T) {
 
 			err = fs.Readfile("/../test.txt", buf)
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 		})
 
 		g.AfterEach(func() {
@@ -386,7 +386,7 @@ func TestFilesystem_Writefile(t *testing.T) {
 
 			err := fs.Writefile("/some/../foo/../../test.txt", r)
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 		})
 
 		g.It("cannot write a file that exceeds the disk limits", func() {
@@ -477,7 +477,7 @@ func TestFilesystem_CreateDirectory(t *testing.T) {
 		g.It("should not allow the creation of directories outside the root", func() {
 			err := fs.CreateDirectory("test", "e/../../something")
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 		})
 
 		g.It("should not increment the disk usage", func() {
@@ -527,7 +527,7 @@ func TestFilesystem_Rename(t *testing.T) {
 		g.It("does not allow renaming to a location outside the root", func() {
 			err := fs.Rename("source.txt", "../target.txt")
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 		})
 
 		g.It("does not allow renaming from a location outside the root", func() {
@@ -535,7 +535,7 @@ func TestFilesystem_Rename(t *testing.T) {
 
 			err = fs.Rename("/../ext-source.txt", "target.txt")
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 		})
 
 		g.It("allows a file to be renamed", func() {
@@ -613,7 +613,7 @@ func TestFilesystem_Copy(t *testing.T) {
 
 			err = fs.Copy("../ext-source.txt")
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 		})
 
 		g.It("should return an error if the source directory is outside the root", func() {
@@ -625,11 +625,11 @@ func TestFilesystem_Copy(t *testing.T) {
 
 			err = fs.Copy("../nested/in/dir/ext-source.txt")
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 
 			err = fs.Copy("nested/in/../../../nested/in/dir/ext-source.txt")
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 		})
 
 		g.It("should return an error if the source is a directory", func() {
@@ -721,7 +721,7 @@ func TestFilesystem_Delete(t *testing.T) {
 
 			err = fs.Delete("../ext-source.txt")
 			g.Assert(err).IsNotNil()
-			g.Assert(errors.Is(err, ErrBadPathResolution)).IsTrue()
+			g.Assert(IsBadPathResolutionError(err)).IsTrue()
 		})
 
 		g.It("does not allow the deletion of the root directory", func() {
diff --git a/server/filesystem/path.go b/server/filesystem/path.go
index 6476a9d..8b3cd44 100644
--- a/server/filesystem/path.go
+++ b/server/filesystem/path.go
@@ -2,6 +2,7 @@ package filesystem
 
 import (
 	"context"
+	"emperror.dev/errors"
 	"golang.org/x/sync/errgroup"
 	"os"
 	"path/filepath"
@@ -23,9 +24,9 @@ func (fs *Filesystem) SafePath(p string) (string, error) {
 
 	// At the same time, evaluate the symlink status and determine where this file or folder
 	// is truly pointing to.
-	p, err := filepath.EvalSymlinks(r)
+	ep, err := filepath.EvalSymlinks(r)
 	if err != nil && !os.IsNotExist(err) {
-		return "", err
+		return "", errors.WithStackIf(err)
 	} else if os.IsNotExist(err) {
 		// The requested directory doesn't exist, so at this point we need to iterate up the
 		// path chain until we hit a directory that _does_ exist and can be validated.
@@ -53,7 +54,7 @@ func (fs *Filesystem) SafePath(p string) (string, error) {
 	// attempt going on, and we should NOT resolve this path for them.
 	if nonExistentPathResolution != "" {
 		if !fs.unsafeIsInDataDirectory(nonExistentPathResolution) {
-			return "", ErrBadPathResolution
+			return "", NewBadPathResolution(p, nonExistentPathResolution)
 		}
 
 		// If the nonExistentPathResolution variable is not empty then the initial path requested
@@ -66,11 +67,11 @@ func (fs *Filesystem) SafePath(p string) (string, error) {
 	// If the requested directory from EvalSymlinks begins with the server root directory go
 	// ahead and return it. If not we'll return an error which will block any further action
 	// on the file.
-	if fs.unsafeIsInDataDirectory(p) {
-		return p, nil
+	if fs.unsafeIsInDataDirectory(ep) {
+		return ep, nil
 	}
 
-	return "", ErrBadPathResolution
+	return "", NewBadPathResolution(p, r)
 }
 
 // Generate a path to the file by cleaning it up and appending the root server path to it. This
diff --git a/server/filesystem/stat.go b/server/filesystem/stat.go
index 7896f9f..a9fdca4 100644
--- a/server/filesystem/stat.go
+++ b/server/filesystem/stat.go
@@ -1,6 +1,7 @@
 package filesystem
 
 import (
+	"emperror.dev/errors"
 	"encoding/json"
 	"github.com/gabriel-vasile/mimetype"
 	"os"
@@ -50,14 +51,14 @@ func (fs *Filesystem) Stat(p string) (*Stat, error) {
 func (fs *Filesystem) unsafeStat(p string) (*Stat, error) {
 	s, err := os.Stat(p)
 	if err != nil {
-		return nil, err
+		return nil, errors.WithStackIf(err)
 	}
 
 	var m *mimetype.MIME
 	if !s.IsDir() {
 		m, err = mimetype.DetectFile(p)
 		if err != nil {
-			return nil, err
+			return nil, errors.WithStackIf(err)
 		}
 	}
 
diff --git a/server/install.go b/server/install.go
index 0186591..0126b6b 100644
--- a/server/install.go
+++ b/server/install.go
@@ -4,12 +4,12 @@ import (
 	"bufio"
 	"bytes"
 	"context"
+	"emperror.dev/errors"
 	"github.com/apex/log"
 	"github.com/docker/docker/api/types"
 	"github.com/docker/docker/api/types/container"
 	"github.com/docker/docker/api/types/mount"
 	"github.com/docker/docker/client"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/api"
 	"github.com/pterodactyl/wings/config"
 	"github.com/pterodactyl/wings/environment"
@@ -90,7 +90,7 @@ func (s *Server) internalInstall() error {
 	script, err := api.New().GetInstallationScript(s.Id())
 	if err != nil {
 		if !api.IsRequestError(err) {
-			return errors.WithStack(err)
+			return errors.WithStackIf(err)
 		}
 
 		return errors.New(err.Error())
@@ -98,7 +98,7 @@ func (s *Server) internalInstall() error {
 
 	p, err := NewInstallationProcess(s, &script)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	s.Log().Info("beginning installation process for server")
@@ -130,7 +130,7 @@ func NewInstallationProcess(s *Server, script *api.InstallationScript) (*Install
 	s.installer.cancel = &cancel
 
 	if c, err := environment.DockerClient(); err != nil {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	} else {
 		proc.client = c
 		proc.context = ctx
@@ -193,7 +193,7 @@ func (ip *InstallationProcess) RemoveContainer() {
 	})
 
 	if err != nil && !client.IsErrNotFound(err) {
-		ip.Server.Log().WithField("error", errors.WithStack(err)).Warn("failed to delete server install container")
+		ip.Server.Log().WithField("error", errors.WithStackIf(err)).Warn("failed to delete server install container")
 	}
 }
 
@@ -218,14 +218,14 @@ func (ip *InstallationProcess) Run() error {
 	}()
 
 	if err := ip.BeforeExecute(); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	cid, err := ip.Execute()
 	if err != nil {
 		ip.RemoveContainer()
 
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	// If this step fails, log a warning but don't exit out of the process. This is completely
@@ -248,12 +248,12 @@ func (ip *InstallationProcess) writeScriptToDisk() error {
 	// Make sure the temp directory root exists before trying to make a directory within it. The
 	// ioutil.TempDir call expects this base to exist, it won't create it for you.
 	if err := os.MkdirAll(ip.tempDir(), 0700); err != nil {
-		return errors.Wrap(err, "could not create temporary directory for install process")
+		return errors.WrapIf(err, "could not create temporary directory for install process")
 	}
 
 	f, err := os.OpenFile(filepath.Join(ip.tempDir(), "install.sh"), os.O_RDWR|os.O_CREATE|os.O_TRUNC, 0644)
 	if err != nil {
-		return errors.Wrap(err, "failed to write server installation script to disk before mount")
+		return errors.WrapIf(err, "failed to write server installation script to disk before mount")
 	}
 	defer f.Close()
 
@@ -265,7 +265,7 @@ func (ip *InstallationProcess) writeScriptToDisk() error {
 	}
 
 	if err := scanner.Err(); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	w.Flush()
@@ -277,7 +277,7 @@ func (ip *InstallationProcess) writeScriptToDisk() error {
 func (ip *InstallationProcess) pullInstallationImage() error {
 	r, err := ip.client.ImagePull(ip.context, ip.Script.ContainerImage, types.ImagePullOptions{})
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	// Block continuation until the image has been pulled successfully.
@@ -287,7 +287,7 @@ func (ip *InstallationProcess) pullInstallationImage() error {
 	}
 
 	if err := scanner.Err(); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	return nil
@@ -298,11 +298,11 @@ func (ip *InstallationProcess) pullInstallationImage() error {
 // manner, if either one fails the error is returned.
 func (ip *InstallationProcess) BeforeExecute() error {
 	if err := ip.writeScriptToDisk(); err != nil {
-		return errors.Wrap(err, "failed to write installation script to disk")
+		return errors.WrapIf(err, "failed to write installation script to disk")
 	}
 
 	if err := ip.pullInstallationImage(); err != nil {
-		return errors.Wrap(err, "failed to pull updated installation container image for server")
+		return errors.WrapIf(err, "failed to pull updated installation container image for server")
 	}
 
 	opts := types.ContainerRemoveOptions{
@@ -312,7 +312,7 @@ func (ip *InstallationProcess) BeforeExecute() error {
 
 	if err := ip.client.ContainerRemove(ip.context, ip.Server.Id()+"_installer", opts); err != nil {
 		if !client.IsErrNotFound(err) {
-			return errors.Wrap(err, "failed to remove existing install container for server")
+			return errors.WrapIf(err, "failed to remove existing install container for server")
 		}
 	}
 
@@ -338,12 +338,12 @@ func (ip *InstallationProcess) AfterExecute(containerId string) error {
 	})
 
 	if err != nil && !client.IsErrNotFound(err) {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	f, err := os.OpenFile(ip.GetLogPath(), os.O_WRONLY|os.O_CREATE|os.O_TRUNC, 0600)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 	defer f.Close()
 
@@ -372,15 +372,15 @@ func (ip *InstallationProcess) AfterExecute(containerId string) error {
 | ------------------------------
 `)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	if err := tmpl.Execute(f, ip); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	if _, err := io.Copy(f, reader); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	return nil
@@ -448,7 +448,7 @@ func (ip *InstallationProcess) Execute() (string, error) {
 
 	r, err := ip.client.ContainerCreate(ip.context, conf, hostConf, nil, ip.Server.Id()+"_installer")
 	if err != nil {
-		return "", errors.WithStack(err)
+		return "", errors.WithStackIf(err)
 	}
 
 	ip.Server.Log().WithField("container_id", r.ID).Info("running installation script for server in container")
@@ -468,7 +468,7 @@ func (ip *InstallationProcess) Execute() (string, error) {
 	select {
 	case err := <-eChan:
 		if err != nil {
-			return "", errors.WithStack(err)
+			return "", errors.WithStackIf(err)
 		}
 	case <-sChan:
 	}
@@ -487,7 +487,7 @@ func (ip *InstallationProcess) StreamOutput(id string) error {
 	})
 
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	defer reader.Close()
@@ -500,7 +500,7 @@ func (ip *InstallationProcess) StreamOutput(id string) error {
 	if err := s.Err(); err != nil {
 		ip.Server.Log().WithFields(log.Fields{
 			"container_id": id,
-			"error":        errors.WithStack(err),
+			"error":        errors.WithStackIf(err),
 		}).Warn("error processing scanner line in installation output for server")
 	}
 
@@ -515,7 +515,7 @@ func (s *Server) SyncInstallState(successful bool) error {
 	err := api.New().SendInstallationStatus(s.Id(), successful)
 	if err != nil {
 		if !api.IsRequestError(err) {
-			return errors.WithStack(err)
+			return errors.WithStackIf(err)
 		}
 
 		return errors.New(err.Error())
diff --git a/server/listeners.go b/server/listeners.go
index 6284ae1..f9a3648 100644
--- a/server/listeners.go
+++ b/server/listeners.go
@@ -1,9 +1,9 @@
 package server
 
 import (
+	"emperror.dev/errors"
 	"encoding/json"
 	"github.com/apex/log"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/api"
 	"github.com/pterodactyl/wings/config"
 	"github.com/pterodactyl/wings/environment"
@@ -77,7 +77,7 @@ func (s *Server) StartEventListeners() {
 							s.Environment.SetState(environment.ProcessRunningState)
 						}
 
-						s.Log().WithField("error", errors.WithStack(err)).Error("failed to terminate environment after triggering throttle")
+						s.Log().WithField("error", errors.WithStackIf(err)).Error("failed to terminate environment after triggering throttle")
 					}
 				}()
 			}
@@ -106,7 +106,7 @@ func (s *Server) StartEventListeners() {
 	stats := func(e events.Event) {
 		st := new(environment.Stats)
 		if err := json.Unmarshal([]byte(e.Data), st); err != nil {
-			s.Log().WithField("error", errors.WithStack(err)).Warn("failed to unmarshal server environment stats")
+			s.Log().WithField("error", errors.WithStackIf(err)).Warn("failed to unmarshal server environment stats")
 			return
 		}
 
diff --git a/server/loader.go b/server/loader.go
index 6a8d1af..fd27938 100644
--- a/server/loader.go
+++ b/server/loader.go
@@ -1,12 +1,12 @@
 package server
 
 import (
+	"emperror.dev/errors"
 	"encoding/json"
 	"fmt"
 	"github.com/apex/log"
 	"github.com/creasty/defaults"
 	"github.com/gammazero/workerpool"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/api"
 	"github.com/pterodactyl/wings/config"
 	"github.com/pterodactyl/wings/environment"
@@ -35,7 +35,7 @@ func LoadDirectory() error {
 	configs, err := api.New().GetServers()
 	if err != nil {
 		if !api.IsRequestError(err) {
-			return errors.WithStack(err)
+			return errors.WithStackIf(err)
 		}
 
 		return errors.New(err.Error())
@@ -89,12 +89,12 @@ func LoadDirectory() error {
 func FromConfiguration(data api.ServerConfigurationResponse) (*Server, error) {
 	cfg := Configuration{}
 	if err := defaults.Set(&cfg); err != nil {
-		return nil, errors.Wrap(err, "failed to set struct defaults for server configuration")
+		return nil, errors.WrapIf(err, "failed to set struct defaults for server configuration")
 	}
 
 	s := new(Server)
 	if err := defaults.Set(s); err != nil {
-		return nil, errors.Wrap(err, "failed to set struct defaults for server")
+		return nil, errors.WrapIf(err, "failed to set struct defaults for server")
 	}
 
 	s.cfg = cfg
diff --git a/server/power.go b/server/power.go
index f9af920..49ff416 100644
--- a/server/power.go
+++ b/server/power.go
@@ -2,7 +2,7 @@ package server
 
 import (
 	"context"
-	"github.com/pkg/errors"
+	"emperror.dev/errors"
 	"github.com/pterodactyl/wings/config"
 	"github.com/pterodactyl/wings/environment"
 	"github.com/pterodactyl/wings/server/filesystem"
@@ -80,13 +80,13 @@ func (s *Server) HandlePowerAction(action PowerAction, waitSeconds ...int) error
 			// time than that passes an error will be propagated back up the chain and this
 			// request will be aborted.
 			if err := s.powerLock.Acquire(ctx, 1); err != nil {
-				return errors.Wrap(err, "could not acquire lock on power state")
+				return errors.WrapIf(err, "could not acquire lock on power state")
 			}
 		} else {
 			// If no wait duration was provided we will attempt to immediately acquire the lock
 			// and bail out with a context deadline error if it is not acquired immediately.
 			if ok := s.powerLock.TryAcquire(1); !ok {
-				return errors.Wrap(context.DeadlineExceeded, "could not acquire lock on power state")
+				return errors.WrapIf(context.DeadlineExceeded, "could not acquire lock on power state")
 			}
 		}
 
@@ -149,7 +149,7 @@ func (s *Server) HandlePowerAction(action PowerAction, waitSeconds ...int) error
 func (s *Server) onBeforeStart() error {
 	s.Log().Info("syncing server configuration with panel")
 	if err := s.Sync(); err != nil {
-		return errors.Wrap(err, "unable to sync server data from Panel instance")
+		return errors.WrapIf(err, "unable to sync server data from Panel instance")
 	}
 
 	// Disallow start & restart if the server is suspended. Do this check after performing a sync
@@ -185,7 +185,7 @@ func (s *Server) onBeforeStart() error {
 		s.PublishConsoleOutputFromDaemon("Ensuring file permissions are set correctly, this could take a few seconds...")
 		// Ensure all of the server file permissions are set correctly before booting the process.
 		if err := s.Filesystem().Chown("/"); err != nil {
-			return errors.Wrap(err, "failed to chown root server directory during pre-boot process")
+			return errors.WrapIf(err, "failed to chown root server directory during pre-boot process")
 		}
 	}
 
diff --git a/server/server.go b/server/server.go
index 68f8b59..8eff4f2 100644
--- a/server/server.go
+++ b/server/server.go
@@ -2,9 +2,9 @@ package server
 
 import (
 	"context"
+	"emperror.dev/errors"
 	"fmt"
 	"github.com/apex/log"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/api"
 	"github.com/pterodactyl/wings/config"
 	"github.com/pterodactyl/wings/environment"
@@ -115,7 +115,7 @@ func (s *Server) Sync() error {
 	cfg, err := api.New().GetServerConfiguration(s.Id())
 	if err != nil {
 		if !api.IsRequestError(err) {
-			return errors.WithStack(err)
+			return errors.WithStackIf(err)
 		}
 
 		if err.(*api.RequestError).Status == "404" {
@@ -131,7 +131,7 @@ func (s *Server) Sync() error {
 func (s *Server) SyncWithConfiguration(cfg api.ServerConfigurationResponse) error {
 	// Update the data structure and persist it to the disk.
 	if err := s.UpdateDataStructure(cfg.Settings); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	s.Lock()
@@ -171,7 +171,7 @@ func (s *Server) IsBootable() bool {
 func (s *Server) CreateEnvironment() error {
 	// Ensure the data directory exists before getting too far through this process.
 	if err := s.EnsureDataDirectoryExists(); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	return s.Environment.Create()
diff --git a/server/state.go b/server/state.go
index 3d6ae19..bc1e942 100644
--- a/server/state.go
+++ b/server/state.go
@@ -1,8 +1,8 @@
 package server
 
 import (
+	"emperror.dev/errors"
 	"encoding/json"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/config"
 	"github.com/pterodactyl/wings/environment"
 	"io"
@@ -22,14 +22,14 @@ func CachedServerStates() (map[string]string, error) {
 	// Open the states file.
 	f, err := os.OpenFile(config.Get().System.GetStatesPath(), os.O_RDONLY|os.O_CREATE, 0644)
 	if err != nil {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	}
 	defer f.Close()
 
 	// Convert the json object to a map.
 	states := map[string]string{}
 	if err := json.NewDecoder(f).Decode(&states); err != nil && err != io.EOF {
-		return nil, errors.WithStack(err)
+		return nil, errors.WithStackIf(err)
 	}
 
 	return states, nil
@@ -46,7 +46,7 @@ func saveServerStates() error {
 	// Convert the map to a json object.
 	data, err := json.Marshal(states)
 	if err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	stateMutex.Lock()
@@ -54,7 +54,7 @@ func saveServerStates() error {
 
 	// Write the data to the file
 	if err := ioutil.WriteFile(config.Get().System.GetStatesPath(), data, 0644); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	return nil
diff --git a/server/update.go b/server/update.go
index f6261e6..41258ad 100644
--- a/server/update.go
+++ b/server/update.go
@@ -1,10 +1,10 @@
 package server
 
 import (
+	"emperror.dev/errors"
 	"encoding/json"
 	"github.com/buger/jsonparser"
 	"github.com/imdario/mergo"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/environment"
 )
 
@@ -18,7 +18,7 @@ import (
 func (s *Server) UpdateDataStructure(data []byte) error {
 	src := new(Configuration)
 	if err := json.Unmarshal(data, src); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	// Don't allow obviously corrupted data to pass through into this function. If the UUID
@@ -47,7 +47,7 @@ func (s *Server) UpdateDataStructure(data []byte) error {
 	// Merge the new data object that we have received with the existing server data object
 	// and then save it to the disk so it is persistent.
 	if err := mergo.Merge(&c, src, mergo.WithOverride); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	// Don't explode if we're setting CPU limits to 0. Mergo sees that as an empty value
@@ -65,7 +65,7 @@ func (s *Server) UpdateDataStructure(data []byte) error {
 	// request is going to be boolean. Allegedly.
 	if v, err := jsonparser.GetBoolean(data, "container", "oom_disabled"); err != nil {
 		if err != jsonparser.KeyPathNotFoundError {
-			return errors.WithStack(err)
+			return errors.WithStackIf(err)
 		}
 	} else {
 		c.Build.OOMDisabled = v
@@ -74,7 +74,7 @@ func (s *Server) UpdateDataStructure(data []byte) error {
 	// Mergo also cannot handle this boolean value.
 	if v, err := jsonparser.GetBoolean(data, "suspended"); err != nil {
 		if err != jsonparser.KeyPathNotFoundError {
-			return errors.WithStack(err)
+			return errors.WithStackIf(err)
 		}
 	} else {
 		c.Suspended = v
@@ -82,7 +82,7 @@ func (s *Server) UpdateDataStructure(data []byte) error {
 
 	if v, err := jsonparser.GetBoolean(data, "skip_egg_scripts"); err != nil {
 		if err != jsonparser.KeyPathNotFoundError {
-			return errors.WithStack(err)
+			return errors.WithStackIf(err)
 		}
 	} else {
 		c.SkipEggScripts = v
diff --git a/server/websockets.go b/server/websockets.go
index ff7f441..bfa87fa 100644
--- a/server/websockets.go
+++ b/server/websockets.go
@@ -7,7 +7,7 @@ import (
 )
 
 type WebsocketBag struct {
-	mu sync.Mutex
+	mu    sync.Mutex
 	conns map[uuid.UUID]*context.CancelFunc
 }
 
@@ -58,4 +58,4 @@ func (w *WebsocketBag) CancelAll() {
 
 	// Reset the connections.
 	w.conns = make(map[uuid.UUID]*context.CancelFunc)
-}
\ No newline at end of file
+}
diff --git a/sftp/handler.go b/sftp/handler.go
index 04e46c4..e0e37f3 100644
--- a/sftp/handler.go
+++ b/sftp/handler.go
@@ -1,9 +1,9 @@
 package sftp
 
 import (
+	"emperror.dev/errors"
 	"github.com/apex/log"
 	"github.com/patrickmn/go-cache"
-	"github.com/pkg/errors"
 	"github.com/pkg/sftp"
 	"io"
 	"io/ioutil"
@@ -58,14 +58,14 @@ func (fs FileSystem) Fileread(request *sftp.Request) (io.ReaderAt, error) {
 	if _, err := os.Stat(p); os.IsNotExist(err) {
 		return nil, sftp.ErrSshFxNoSuchFile
 	} else if err != nil {
-		fs.logger.WithField("error", errors.WithStack(err)).Error("error while processing file stat")
+		fs.logger.WithField("error", errors.WithStackIf(err)).Error("error while processing file stat")
 
 		return nil, sftp.ErrSshFxFailure
 	}
 
 	file, err := os.Open(p)
 	if err != nil {
-		fs.logger.WithField("source", p).WithField("error", errors.WithStack(err)).Error("could not open file for reading")
+		fs.logger.WithField("source", p).WithField("error", errors.WithStackIf(err)).Error("could not open file for reading")
 		return nil, sftp.ErrSshFxFailure
 	}
 
@@ -108,7 +108,7 @@ func (fs FileSystem) Filewrite(request *sftp.Request) (io.WriterAt, error) {
 		if err := os.MkdirAll(filepath.Dir(p), 0755); err != nil {
 			l.WithFields(log.Fields{
 				"path":  filepath.Dir(p),
-				"error": errors.WithStack(err),
+				"error": errors.WithStackIf(err),
 			}).Error("error making path for file")
 
 			return nil, sftp.ErrSshFxFailure
@@ -116,7 +116,7 @@ func (fs FileSystem) Filewrite(request *sftp.Request) (io.WriterAt, error) {
 
 		file, err := os.Create(p)
 		if err != nil {
-			l.WithField("error", errors.WithStack(err)).Error("failed to create file")
+			l.WithField("error", errors.WithStackIf(err)).Error("failed to create file")
 
 			return nil, sftp.ErrSshFxFailure
 		}
@@ -124,7 +124,7 @@ func (fs FileSystem) Filewrite(request *sftp.Request) (io.WriterAt, error) {
 		// Not failing here is intentional. We still made the file, it is just owned incorrectly
 		// and will likely cause some issues.
 		if err := os.Chown(p, fs.User.Uid, fs.User.Gid); err != nil {
-			l.WithField("error", errors.WithStack(err)).Warn("failed to set permissions on file")
+			l.WithField("error", errors.WithStackIf(err)).Warn("failed to set permissions on file")
 		}
 
 		return file, nil
@@ -133,7 +133,7 @@ func (fs FileSystem) Filewrite(request *sftp.Request) (io.WriterAt, error) {
 	// If the stat error isn't about the file not existing, there is some other issue
 	// at play and we need to go ahead and bail out of the process.
 	if statErr != nil {
-		l.WithField("error", errors.WithStack(statErr)).Error("encountered error performing file stat")
+		l.WithField("error", errors.WithStackIf(statErr)).Error("encountered error performing file stat")
 
 		return nil, sftp.ErrSshFxFailure
 	}
@@ -159,14 +159,14 @@ func (fs FileSystem) Filewrite(request *sftp.Request) (io.WriterAt, error) {
 			return nil, sftp.ErrSSHFxNoSuchFile
 		}
 
-		l.WithField("flags", request.Flags).WithField("error", errors.WithStack(err)).Error("failed to open existing file on system")
+		l.WithField("flags", request.Flags).WithField("error", errors.WithStackIf(err)).Error("failed to open existing file on system")
 		return nil, sftp.ErrSshFxFailure
 	}
 
 	// Not failing here is intentional. We still made the file, it is just owned incorrectly
 	// and will likely cause some issues.
 	if err := os.Chown(p, fs.User.Uid, fs.User.Gid); err != nil {
-		l.WithField("error", errors.WithStack(err)).Warn("error chowning file")
+		l.WithField("error", errors.WithStackIf(err)).Warn("error chowning file")
 	}
 
 	return file, nil
@@ -220,7 +220,7 @@ func (fs FileSystem) Filecmd(request *sftp.Request) error {
 				return sftp.ErrSSHFxNoSuchFile
 			}
 
-			l.WithField("error", errors.WithStack(err)).Error("failed to perform setstat on item")
+			l.WithField("error", errors.WithStackIf(err)).Error("failed to perform setstat on item")
 			return sftp.ErrSSHFxFailure
 		}
 		return nil
@@ -234,7 +234,7 @@ func (fs FileSystem) Filecmd(request *sftp.Request) error {
 				return sftp.ErrSSHFxNoSuchFile
 			}
 
-			l.WithField("target", target).WithField("error", errors.WithStack(err)).Error("failed to rename file")
+			l.WithField("target", target).WithField("error", errors.WithStackIf(err)).Error("failed to rename file")
 
 			return sftp.ErrSshFxFailure
 		}
@@ -246,7 +246,7 @@ func (fs FileSystem) Filecmd(request *sftp.Request) error {
 		}
 
 		if err := os.RemoveAll(p); err != nil {
-			l.WithField("error", errors.WithStack(err)).Error("failed to remove directory")
+			l.WithField("error", errors.WithStackIf(err)).Error("failed to remove directory")
 
 			return sftp.ErrSshFxFailure
 		}
@@ -258,7 +258,7 @@ func (fs FileSystem) Filecmd(request *sftp.Request) error {
 		}
 
 		if err := os.MkdirAll(p, 0755); err != nil {
-			l.WithField("error", errors.WithStack(err)).Error("failed to create directory")
+			l.WithField("error", errors.WithStackIf(err)).Error("failed to create directory")
 
 			return sftp.ErrSshFxFailure
 		}
@@ -270,7 +270,7 @@ func (fs FileSystem) Filecmd(request *sftp.Request) error {
 		}
 
 		if err := os.Symlink(p, target); err != nil {
-			l.WithField("target", target).WithField("error", errors.WithStack(err)).Error("failed to create symlink")
+			l.WithField("target", target).WithField("error", errors.WithStackIf(err)).Error("failed to create symlink")
 
 			return sftp.ErrSshFxFailure
 		}
@@ -286,7 +286,7 @@ func (fs FileSystem) Filecmd(request *sftp.Request) error {
 				return sftp.ErrSSHFxNoSuchFile
 			}
 
-			l.WithField("error", errors.WithStack(err)).Error("failed to remove a file")
+			l.WithField("error", errors.WithStackIf(err)).Error("failed to remove a file")
 
 			return sftp.ErrSshFxFailure
 		}
@@ -305,7 +305,7 @@ func (fs FileSystem) Filecmd(request *sftp.Request) error {
 	// and will likely cause some issues. There is no logical check for if the file was removed
 	// because both of those cases (Rmdir, Remove) have an explicit return rather than break.
 	if err := os.Chown(fileLocation, fs.User.Uid, fs.User.Gid); err != nil {
-		l.WithField("error", errors.WithStack(err)).Warn("error chowning file")
+		l.WithField("error", errors.WithStackIf(err)).Warn("error chowning file")
 	}
 
 	return sftp.ErrSshFxOk
@@ -327,7 +327,7 @@ func (fs FileSystem) Filelist(request *sftp.Request) (sftp.ListerAt, error) {
 
 		files, err := ioutil.ReadDir(p)
 		if err != nil {
-			fs.logger.WithField("error", errors.WithStack(err)).Error("error while listing directory")
+			fs.logger.WithField("error", errors.WithStackIf(err)).Error("error while listing directory")
 
 			return nil, sftp.ErrSshFxFailure
 		}
@@ -342,7 +342,7 @@ func (fs FileSystem) Filelist(request *sftp.Request) (sftp.ListerAt, error) {
 		if os.IsNotExist(err) {
 			return nil, sftp.ErrSshFxNoSuchFile
 		} else if err != nil {
-			fs.logger.WithField("source", p).WithField("error", errors.WithStack(err)).Error("error performing stat on file")
+			fs.logger.WithField("source", p).WithField("error", errors.WithStackIf(err)).Error("error performing stat on file")
 
 			return nil, sftp.ErrSshFxFailure
 		}
diff --git a/sftp/sftp.go b/sftp/sftp.go
index dcd870f..3c73f0b 100644
--- a/sftp/sftp.go
+++ b/sftp/sftp.go
@@ -1,8 +1,8 @@
 package sftp
 
 import (
+	"emperror.dev/errors"
 	"github.com/apex/log"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/api"
 	"github.com/pterodactyl/wings/config"
 	"github.com/pterodactyl/wings/server"
@@ -28,14 +28,14 @@ func Initialize(config config.SystemConfiguration) error {
 	}
 
 	if err := New(s); err != nil {
-		return errors.WithStack(err)
+		return errors.WithStackIf(err)
 	}
 
 	// Initialize the SFTP server in a background thread since this is
 	// a long running operation.
 	go func(s *Server) {
 		if err := s.Initialize(); err != nil {
-			log.WithField("subsystem", "sftp").WithField("error", errors.WithStack(err)).Error("failed to initialize SFTP subsystem")
+			log.WithField("subsystem", "sftp").WithField("error", errors.WithStackIf(err)).Error("failed to initialize SFTP subsystem")
 		}
 	}(s)