diff --git a/environment/docker/container.go b/environment/docker/container.go
index 4aa87be..9318f77 100644
--- a/environment/docker/container.go
+++ b/environment/docker/container.go
@@ -149,12 +149,12 @@ func (e *Environment) Create() error {
 	if _, err := e.client.ContainerInspect(context.Background(), e.Id); err == nil {
 		return nil
 	} else if !client.IsErrNotFound(err) {
-		return err
+		return errors.Wrap(err, "environment/docker: failed to inspect container")
 	}
 
 	// Try to pull the requested image before creating the container.
 	if err := e.ensureImageExists(e.meta.Image); err != nil {
-		return err
+		return errors.WithStackIf(err)
 	}
 
 	a := e.Configuration.Allocations()
@@ -230,7 +230,7 @@ func (e *Environment) Create() error {
 	}
 
 	if _, err := e.client.ContainerCreate(context.Background(), conf, hostConf, nil, nil, e.Id); err != nil {
-		return err
+		return errors.Wrap(err, "environment/docker: failed to create container")
 	}
 
 	return nil
@@ -420,7 +420,7 @@ func (e *Environment) ensureImageExists(image string) error {
 		if ierr != nil {
 			// Well damn, something has gone really wrong here, just go ahead and abort there
 			// isn't much anything we can do to try and self-recover from this.
-			return ierr
+			return errors.Wrap(ierr, "environment/docker: failed to list images")
 		}
 
 		for _, img := range images {
@@ -441,7 +441,7 @@ func (e *Environment) ensureImageExists(image string) error {
 			}
 		}
 
-		return err
+		return errors.Wrapf(err, "environment/docker: failed to pull \"%s\" image for server", image)
 	}
 	defer out.Close()
 
diff --git a/environment/docker/power.go b/environment/docker/power.go
index 060cb72..0c01b7e 100644
--- a/environment/docker/power.go
+++ b/environment/docker/power.go
@@ -27,7 +27,7 @@ func (e *Environment) OnBeforeStart() error {
 	// Always destroy and re-create the server container to ensure that synced data from the Panel is used.
 	if err := e.client.ContainerRemove(context.Background(), e.Id, types.ContainerRemoveOptions{RemoveVolumes: true}); err != nil {
 		if !client.IsErrNotFound(err) {
-			return errors.WithMessage(err, "failed to remove server docker container during pre-boot")
+			return errors.WrapIf(err, "environment/docker: failed to remove container during pre-boot")
 		}
 	}
 
@@ -71,7 +71,7 @@ func (e *Environment) Start() error {
 		//
 		// @see https://github.com/pterodactyl/panel/issues/2000
 		if !client.IsErrNotFound(err) {
-			return err
+			return errors.WrapIf(err, "environment/docker: failed to inspect container")
 		}
 	} else {
 		// If the server is running update our internal state and continue on with the attach.
@@ -86,7 +86,7 @@ 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 err
+				return errors.Wrap(err, "environment/docker: failed to truncate instance logs")
 			}
 		}
 	}
@@ -101,14 +101,14 @@ 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 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 err
+		return errors.WrapIf(err, "environment/docker: failed to start container")
 	}
 
 	// No errors, good to continue through.