diff --git a/go.mod b/go.mod
index f96f3ff..31a9967 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
diff --git a/go.sum b/go.sum
index 686af03..03b36ad 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/loggers/cli/cli.go b/loggers/cli/cli.go
index 93d3dfd..181d094 100644
--- a/loggers/cli/cli.go
+++ b/loggers/cli/cli.go
@@ -1,14 +1,13 @@
 package cli
 
 import (
+	"emperror.dev/errors"
 	"fmt"
 	"github.com/apex/log"
 	"github.com/apex/log/handlers/cli"
 	color2 "github.com/fatih/color"
 	"github.com/mattn/go-colorable"
-	"github.com/pkg/errors"
 	"io"
-	"math"
 	"os"
 	"sync"
 	"time"
@@ -42,10 +41,6 @@ func New(w io.Writer, useColors bool) *Handler {
 	return &Handler{Writer: colorable.NewNonColorable(w), Padding: 2}
 }
 
-type tracer interface {
-	StackTrace() errors.StackTrace
-}
-
 // HandleLog implements log.Handler.
 func (h *Handler) HandleLog(e *log.Entry) error {
 	color := cli.Colors[e.Level]
@@ -71,13 +66,10 @@ func (h *Handler) HandleLog(e *log.Entry) error {
 			continue
 		}
 		if err, ok := e.Fields.Get("error").(error); ok {
-			if e, ok := errors.Cause(err).(tracer); ok {
-				st := e.StackTrace()
-				l := math.Min(float64(len(st)), 10)
-				fmt.Fprintf(h.Writer, "\n%s%+v\n\n", boldred.Sprintf("Stacktrace:"), st[0:int(l)])
-			} else {
-				fmt.Fprintf(h.Writer, "\n%s\n%+v\n\n", boldred.Sprintf("Stacktrace:"), err)
-			}
+			// Attach the stacktrace if it is missing at this point, but don't point
+			// it specifically to this line since that is irrelevant.
+			err = errors.WithStackDepthIf(err, 1)
+			fmt.Fprintf(h.Writer, "\n%s\n%+v\n\n", boldred.Sprintf("Stacktrace:"), err)
 		}
 	}
 
diff --git a/router/error.go b/router/error.go
index 551d6ab..deea8f6 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"
@@ -20,6 +20,15 @@ type RequestError struct {
 	server  *server.Server
 }
 
+// Attaches an error to the gin.Context object for the request and ensures that it
+// has a proper stacktrace associated with it when doing so.
+//
+// If you just call c.Error(err) without using this function you'll likely end up
+// with an error that has no annotated stack on it.
+func WithError(c *gin.Context, err error) error {
+	return c.Error(errors.WithStackDepthIf(err, 1))
+}
+
 // Generates a new tracked error, which simply tracks the specific error that
 // is being passed in, and also assigned a UUID to the error so that it can be
 // cross referenced in the logs.
@@ -42,9 +51,9 @@ func NewServerError(err error, s *server.Server) *RequestError {
 
 func (e *RequestError) logger() *log.Entry {
 	if e.server != nil {
-		return e.server.Log().WithField("error_id", e.uuid)
+		return e.server.Log().WithField("error_id", e.uuid).WithField("error", e.err)
 	}
-	return log.WithField("error_id", e.uuid)
+	return log.WithField("error_id", e.uuid).WithField("error", e.err)
 }
 
 // Sets the output message to display to the user in the error.
@@ -67,7 +76,7 @@ func (e *RequestError) AbortWithStatus(status int, c *gin.Context) {
 	// If this error is because the resource does not exist, we likely do not need to log
 	// the error anywhere, just return a 404 and move on with our lives.
 	if errors.Is(e.err, os.ErrNotExist) {
-		e.logger().WithField("error", e.err).Debug("encountered os.IsNotExist error while handling request")
+		e.logger().Debug("encountered os.IsNotExist error while handling request")
 		c.AbortWithStatusJSON(http.StatusNotFound, gin.H{
 			"error": "The requested resource was not found on the system.",
 		})
@@ -84,9 +93,9 @@ func (e *RequestError) AbortWithStatus(status int, c *gin.Context) {
 
 	// Otherwise, log the error to zap, and then report the error back to the user.
 	if status >= 500 {
-		e.logger().WithField("error", e.err).Error("unexpected error while handling HTTP request")
+		e.logger().Error("unexpected error while handling HTTP request")
 	} else {
-		e.logger().WithField("error", e.err).Debug("non-server error encountered while handling HTTP request")
+		e.logger().Debug("non-server error encountered while handling HTTP request")
 	}
 
 	if e.message == "" {
diff --git a/router/middleware.go b/router/middleware.go
index 2fd1e70..7635f5b 100644
--- a/router/middleware.go
+++ b/router/middleware.go
@@ -1,9 +1,9 @@
 package router
 
 import (
+	"emperror.dev/errors"
 	"github.com/gin-gonic/gin"
 	"github.com/google/uuid"
-	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/config"
 	"github.com/pterodactyl/wings/server"
 	"io"
diff --git a/router/router_server_files.go b/router/router_server_files.go
index 44fcd15..0c10393 100644
--- a/router/router_server_files.go
+++ b/router/router_server_files.go
@@ -57,14 +57,11 @@ func getServerFileContents(c *gin.Context) {
 // Returns the contents of a directory for a server.
 func getServerListDirectory(c *gin.Context) {
 	s := ExtractServer(c)
-
-	stats, err := s.Filesystem().ListDirectory(c.Query("directory"))
-	if err != nil {
-		NewServerError(err, s).AbortFilesystemError(c)
-		return
+	if stats, err := s.Filesystem().ListDirectory(c.Query("directory")); err != nil {
+		WithError(c, err)
+	} else {
+		c.JSON(http.StatusOK, stats)
 	}
-
-	c.JSON(http.StatusOK, stats)
 }
 
 type renameFile struct {