diff --git a/server/app/app.go b/server/app/app.go
index 1517c9fa79..869339f3d0 100644
--- a/server/app/app.go
+++ b/server/app/app.go
@@ -139,11 +139,11 @@ func (app *App) initAnalytics(configFromDB config.Config) error {
 	return analytics.Init(configFromDB.IsAnalyticsEnabled(), app.serverID, version.Version, version.Env, app.cfg.AnalyticsServerKey(), app.cfg.AnalyticsFrontendKey())
 }
 
+// instanceID is a temporary ID for this instance of the server
+// it is regenerated on every start intentionally
 var instanceID = id.GenerateID().String()
 
 func (app *App) Start(opts ...appOption) error {
-	// instanceID is a temporary ID for this instance of the server
-	// it is regenerated on every start intentionally
 	for _, opt := range opts {
 		opt(app)
 	}
@@ -153,18 +153,18 @@ func (app *App) Start(opts ...appOption) error {
 
 	poolcfg, err := pgxpool.ParseConfig(app.cfg.PostgresConnString())
 	if err != nil {
-		return err
+		return fmt.Errorf("could not parse postgres connection string: %w", err)
 	}
 	poolcfg.MaxConns = 20
 
 	pool, err := pgxpool.NewWithConfig(context.Background(), poolcfg)
 	if err != nil {
-		return err
+		return fmt.Errorf("could not create postgres connection pool: %w", err)
 	}
 
 	db, err := testdb.Connect(app.cfg.PostgresConnString())
 	if err != nil {
-		return err
+		return fmt.Errorf("could not connect to postgres: %w", err)
 	}
 	db.SetMaxOpenConns(80)
 
@@ -173,7 +173,7 @@ func (app *App) Start(opts ...appOption) error {
 	)
 
 	if err != nil {
-		log.Fatal(err)
+		log.Fatal(fmt.Errorf("could not create testdb: %w", err))
 	}
 
 	natsConn, err := nats.Connect(app.cfg.NATSEndpoint())
@@ -189,12 +189,12 @@ func (app *App) Start(opts ...appOption) error {
 
 	tracer, err := telemetry.NewTracer(ctx, app.cfg)
 	if err != nil {
-		log.Fatal(err)
+		log.Fatal(fmt.Errorf("could not create tracer: %w", err))
 	}
 
 	meter, err := telemetry.NewMeter(ctx, app.cfg)
 	if err != nil {
-		log.Fatal(err)
+		log.Fatal(fmt.Errorf("could not create meter: %w", err))
 	}
 
 	app.registerStopFn(func() {
@@ -204,20 +204,20 @@ func (app *App) Start(opts ...appOption) error {
 
 	serverID, isNewInstall, err := testDB.ServerID()
 	if err != nil {
-		return err
+		return fmt.Errorf("could not get server ID: %w", err)
 	}
 	app.serverID = serverID
 
 	err = app.initAnalytics(configFromDB)
 	if err != nil {
-		return err
+		return fmt.Errorf("could not init analytics: %w", err)
 	}
 
 	fmt.Println("New install?", isNewInstall)
 	if isNewInstall {
 		err = analytics.SendEvent("Install", "beacon", "", nil)
 		if err != nil {
-			return err
+			return fmt.Errorf("could not send install event: %w", err)
 		}
 	}
 
@@ -304,7 +304,7 @@ func (app *App) Start(opts ...appOption) error {
 
 	err = analytics.SendEvent("Server Started", "beacon", "", nil)
 	if err != nil {
-		return err
+		return fmt.Errorf("could not send server started event: %w", err)
 	}
 
 	provisioner := provisioning.New()
diff --git a/server/cmd/root.go b/server/cmd/root.go
index a8b1de5f0f..61adeb804d 100644
--- a/server/cmd/root.go
+++ b/server/cmd/root.go
@@ -21,7 +21,7 @@ var (
 			var err error
 			appInstance, err = app.New(cfg)
 			if err != nil {
-				return err
+				return fmt.Errorf("cannot create app instance: %w", err)
 			}
 
 			return nil
@@ -44,7 +44,7 @@ func init() {
 			config.WithLogger(log.Default()),
 		)
 		if err != nil {
-			fmt.Println(err.Error())
+			fmt.Println("error loading config:", err.Error())
 			os.Exit(1)
 		}
 	})
diff --git a/server/cmd/serve.go b/server/cmd/serve.go
index 180dd5c1cb..182e0b7625 100644
--- a/server/cmd/serve.go
+++ b/server/cmd/serve.go
@@ -1,6 +1,7 @@
 package cmd
 
 import (
+	"fmt"
 	"os"
 	"os/signal"
 	"sync"
@@ -45,6 +46,7 @@ var serveCmd = &cobra.Command{
 		wg.Add(1)
 		err := appInstance.Start(app.WithProvisioningFile(provisioningFile))
 		if err != nil {
+			fmt.Println("Error starting server:", err.Error())
 			return err
 		}
 
diff --git a/server/config/appconfig.go b/server/config/appconfig.go
index 28388a7ee4..86cea6447f 100644
--- a/server/config/appconfig.go
+++ b/server/config/appconfig.go
@@ -44,7 +44,7 @@ func New(confOpts ...Option) (*AppConfig, error) {
 
 	err = cfg.vp.Unmarshal(&cfg.config)
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("cannot unmarshal config: %w", err)
 	}
 
 	if err := cfg.Validate(); err != nil {