diff --git a/server/environment_docker.go b/server/environment_docker.go
index dfd3f52..6c4f4b2 100644
--- a/server/environment_docker.go
+++ b/server/environment_docker.go
@@ -53,7 +53,7 @@ func NewDockerEnvironment(opts ...func(*DockerEnvironment)) (*DockerEnvironment,
 	}
 
 	env := &DockerEnvironment{
-		User: 1000,
+		User:   1000,
 		Client: cli,
 	}
 
@@ -131,6 +131,14 @@ func (d *DockerEnvironment) Start() error {
 	opts := types.ContainerStartOptions{}
 
 	d.Server.Emit(StatusEvent, ProcessStartingState)
+
+	// Reset the permissions on files for the server before actually trying
+	// to start it.
+	if err := d.Server.Filesystem.Chown("/"); err != nil {
+		d.Server.Emit(StatusEvent, ProcessOfflineState)
+		return err
+	}
+
 	if err := d.Client.ContainerStart(context.Background(), d.Server.Uuid, opts); err != nil {
 		d.Server.Emit(StatusEvent, ProcessOfflineState)
 		return err
@@ -179,7 +187,7 @@ func (d *DockerEnvironment) Attach() error {
 
 	var err error
 	d.stream, err = d.Client.ContainerAttach(ctx, d.Server.Uuid, types.ContainerAttachOptions{
-		Stdin: true,
+		Stdin:  true,
 		Stdout: true,
 		Stderr: true,
 		Stream: true,
@@ -416,7 +424,7 @@ func (d *DockerEnvironment) Readlog(len int64) ([]string, error) {
 }
 
 type dockerLogLine struct {
-	Log    string `json:"log"`
+	Log string `json:"log"`
 }
 
 // Docker stores the logs for server output in a JSON format. This function will iterate over the JSON
@@ -513,4 +521,4 @@ func (d *DockerEnvironment) exposedPorts() nat.PortSet {
 	}
 
 	return out
-}
\ No newline at end of file
+}
diff --git a/server/filesystem.go b/server/filesystem.go
index 0f8ac8b..676cf57 100644
--- a/server/filesystem.go
+++ b/server/filesystem.go
@@ -6,6 +6,7 @@ import (
 	"errors"
 	"fmt"
 	"github.com/gabriel-vasile/mimetype"
+	"github.com/pterodactyl/wings/config"
 	"go.uber.org/zap"
 	"io"
 	"io/ioutil"
@@ -23,17 +24,15 @@ import (
 var InvalidPathResolution = errors.New("invalid path resolution")
 
 type Filesystem struct {
-	// The root directory where all of the server data is contained. By default
-	// this is going to be /srv/daemon-data but can vary depending on the system.
-	Root string
-
 	// The server object associated with this Filesystem.
 	Server *Server
+
+	Configuration *config.SystemConfiguration
 }
 
 // Returns the root path that contains all of a server's data.
 func (fs *Filesystem) Path() string {
-	return filepath.Join(fs.Root, fs.Server.Uuid)
+	return filepath.Join(fs.Configuration.Data, fs.Server.Uuid)
 }
 
 // Normalizes a directory being passed in to ensure the user is not able to escape
@@ -47,7 +46,10 @@ func (fs *Filesystem) SafePath(p string) (string, error) {
 
 	// Calling filpath.Clean on the joined directory will resolve it to the absolute path,
 	// removing any ../ type of resolution arguments, and leaving us with a direct path link.
-	r := filepath.Clean(filepath.Join(fs.Path(), p))
+	//
+	// This will also trim the existing root path off the beginning of the path passed to
+	// the function since that can get a bit messy.
+	r := filepath.Clean(filepath.Join(fs.Path(), strings.TrimPrefix(p, fs.Path())))
 
 	// At the same time, evaluate the symlink status and determine where this file or folder
 	// is truly pointing to.
@@ -278,6 +280,57 @@ func (fs *Filesystem) Rename(from string, to string) error {
 	return os.Rename(cleanedFrom, cleanedTo)
 }
 
+// Recursively iterates over a directory and sets the permissions on all of the
+// underlying files.
+func (fs *Filesystem) Chown(path string) error {
+	cleaned, err := fs.SafePath(path)
+	if err != nil {
+		return err
+	}
+
+	if s, err := os.Stat(cleaned); err != nil {
+		return err
+	} else if !s.IsDir() {
+		return os.Chown(cleaned, fs.Configuration.User.Uid, fs.Configuration.User.Gid)
+	}
+
+	return fs.chownDirectory(cleaned)
+}
+
+// Iterate over all of the files and directories. If it is a file just go ahead and perform
+// the chown operation. Otherwise dig deeper into the directory until we've run out of
+// directories to dig into.
+func (fs *Filesystem) chownDirectory(path string) error {
+	var wg sync.WaitGroup
+
+	cleaned, err := fs.SafePath(path)
+	if err != nil {
+		return err
+	}
+
+	files, err := ioutil.ReadDir(cleaned)
+	if err != nil {
+		return err
+	}
+
+	for _, f := range files {
+		if f.IsDir() {
+			wg.Add(1)
+
+			go func(p string) {
+				defer wg.Done()
+				fs.chownDirectory(p)
+			}(filepath.Join(cleaned, f.Name()))
+		} else {
+			os.Chown(filepath.Join(cleaned, f.Name()), fs.Configuration.User.Uid, fs.Configuration.User.Gid)
+		}
+	}
+
+	wg.Wait()
+
+	return nil
+}
+
 // Copies a given file to the same location and appends a suffix to the file to indicate that
 // it has been copied.
 //
diff --git a/server/server.go b/server/server.go
index 888286d..d2395c5 100644
--- a/server/server.go
+++ b/server/server.go
@@ -200,7 +200,7 @@ func FromConfiguration(data []byte, cfg *config.SystemConfiguration) (*Server, e
 	s.Environment = env
 	s.Cache = cache.New(time.Minute*10, time.Minute*15)
 	s.Filesystem = &Filesystem{
-		Root:   cfg.Data,
+		Configuration: cfg,
 		Server: s,
 	}