diff --git a/config/config.go b/config/config.go
index 0326f8e..508261c 100644
--- a/config/config.go
+++ b/config/config.go
@@ -82,7 +82,7 @@ type SystemConfiguration struct {
 		Gid int
 	}
 
-	// Determines wether or not server data should be synced when the Daemon is started.
+	// Determines whether or not server data should be synced when the Daemon is started.
 	// If set to false, data will only be synced when a server process is started, or
 	// detected as started when booting.
 	SyncServersOnBoot bool `default:"true" yaml:"sync_servers_on_boot"`
diff --git a/installer/installer.go b/installer/installer.go
index 4ee7f32..d450baf 100644
--- a/installer/installer.go
+++ b/installer/installer.go
@@ -84,7 +84,7 @@ func New(data []byte) (*Installer, error) {
 
 	// Create a new server instance using the configuration we wrote to the disk
 	// so that everything gets instantiated correctly on the struct.
-	s2, err := server.FromConfiguration(b, &config.Get().System)
+	s2, err := server.FromConfiguration(b, &config.Get().System, true)
 
 	return &Installer{
 		server: s2,
diff --git a/router/error.go b/router/error.go
index ed84fe5..aa985d2 100644
--- a/router/error.go
+++ b/router/error.go
@@ -5,6 +5,7 @@ import (
 	"github.com/gin-gonic/gin"
 	"github.com/google/uuid"
 	"github.com/pkg/errors"
+	"github.com/pterodactyl/wings/config"
 	"github.com/pterodactyl/wings/server"
 	"go.uber.org/zap"
 	"net/http"
@@ -68,6 +69,12 @@ func (e *RequestError) AbortWithStatus(status int, c *gin.Context) {
 		}
 
 		c.Error(errors.WithStack(e))
+	} else if config.Get().Debug {
+		if e.server != nil {
+			zap.S().Debugw("encountered error while handling HTTP request", zap.String("server", e.server.Uuid), zap.String("error_id", e.Uuid), zap.Error(e.Err))
+		} else {
+			zap.S().Debugw("encountered error while handling HTTP request", zap.String("error_id", e.Uuid), zap.Error(e.Err))
+		}
 	}
 
 	msg := "An unexpected error was encountered while processing this request."
diff --git a/server/server.go b/server/server.go
index 05eb264..b095b84 100644
--- a/server/server.go
+++ b/server/server.go
@@ -179,7 +179,7 @@ func LoadDirectory(dir string, cfg *config.SystemConfiguration) error {
 				return
 			}
 
-			s, err := FromConfiguration(b, cfg)
+			s, err := FromConfiguration(b, cfg, false)
 			if err != nil {
 				if IsServerDoesNotExistError(err) {
 					zap.S().Infow("server does not exist on remote system", zap.String("server", file.Name()))
@@ -209,7 +209,7 @@ func (s *Server) Init() {
 // Initializes a server using a data byte array. This will be marshaled into the
 // given struct using a YAML marshaler. This will also configure the given environment
 // for a server.
-func FromConfiguration(data []byte, cfg *config.SystemConfiguration) (*Server, error) {
+func FromConfiguration(data []byte, cfg *config.SystemConfiguration, forceSync bool) (*Server, error) {
 	s := new(Server)
 
 	if err := defaults.Set(s); err != nil {
@@ -244,7 +244,7 @@ func FromConfiguration(data []byte, cfg *config.SystemConfiguration) (*Server, e
 	// This is also done when the server is booted, however we need to account for instances
 	// where the server is already running and the Daemon reboots. In those cases this will
 	// allow us to you know, stop servers.
-	if cfg.SyncServersOnBoot {
+	if forceSync || cfg.SyncServersOnBoot {
 		if err := s.Sync(); err != nil {
 			return nil, err
 		}
@@ -414,4 +414,4 @@ func (s *Server) HandlePowerAction(action PowerAction) error {
 	default:
 		return errors.New("an invalid power action was provided")
 	}
-}
\ No newline at end of file
+}