diff --git a/cmd/root.go b/cmd/root.go
index efc5b6a..a90eab2 100644
--- a/cmd/root.go
+++ b/cmd/root.go
@@ -164,6 +164,12 @@ func rootCmdRun(cmd *cobra.Command, _ []string) {
 	for _, serv := range server.GetServers().All() {
 		s := serv
 
+		// For each server we encounter make sure the root data directory exists.
+		if err := s.EnsureDataDirectoryExists(); err != nil {
+			s.Log().Error("could not create root data directory for server: not loading server...")
+			continue
+		}
+
 		pool.Submit(func() {
 			s.Log().Info("configuring server environment and restoring to previous state")
 
diff --git a/server/filesystem.go b/server/filesystem.go
deleted file mode 100644
index d86b526..0000000
--- a/server/filesystem.go
+++ /dev/null
@@ -1,30 +0,0 @@
-package server
-
-import (
-	"os"
-
-	"github.com/pterodactyl/wings/server/filesystem"
-)
-
-func (s *Server) Filesystem() *filesystem.Filesystem {
-	return s.fs
-}
-
-// 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 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 err
-		}
-
-		if err := s.fs.Chown("/"); err != nil {
-			s.Log().WithField("error", err).Warn("failed to chown server data directory")
-		}
-	}
-
-	return nil
-}
diff --git a/server/server.go b/server/server.go
index f7acc9a..0e1fb05 100644
--- a/server/server.go
+++ b/server/server.go
@@ -3,6 +3,7 @@ package server
 import (
 	"context"
 	"fmt"
+	"os"
 	"strings"
 	"sync"
 
@@ -221,3 +222,27 @@ func (s *Server) ProcessConfiguration() *api.ProcessConfiguration {
 
 	return s.procConfig
 }
+
+// Filesystem returns an instance of the filesystem for this server.
+func (s *Server) Filesystem() *filesystem.Filesystem {
+	return s.fs
+}
+
+// EnsureDataDirectoryExists ensures that the data directory for the server
+// instance exists.
+func (s *Server) EnsureDataDirectoryExists() error {
+	if _, err := os.Lstat(s.fs.Path()); err != nil {
+		if os.IsNotExist(err) {
+			s.Log().Debug("server: creating root directory and setting permissions")
+			if err := os.MkdirAll(s.fs.Path(), 0700); err != nil {
+				return errors.WithStack(err)
+			}
+			if err := s.fs.Chown("/"); err != nil {
+				s.Log().WithField("error", err).Warn("server: failed to chown server data directory")
+			}
+		} else {
+			return errors.WrapIf(err, "server: failed to stat server root directory")
+		}
+	}
+	return nil
+}
\ No newline at end of file