diff --git a/cmd/picoclaw/cmd_cron.go b/cmd/picoclaw/cmd_cron.go
index db3c4bd90..0310e2682 100644
--- a/cmd/picoclaw/cmd_cron.go
+++ b/cmd/picoclaw/cmd_cron.go
@@ -29,6 +29,7 @@ func cronCmd() {
 	cfg, err := loadConfig()
 	if err != nil {
 		fmt.Printf("Error loading config: %v\n", err)
+		fmt.Println("Run 'picoclaw doctor' to check for common problems.")
 		return
 	}
 
diff --git a/cmd/picoclaw/cmd_gateway.go b/cmd/picoclaw/cmd_gateway.go
index f42ec2b0b..3eeab0688 100644
--- a/cmd/picoclaw/cmd_gateway.go
+++ b/cmd/picoclaw/cmd_gateway.go
@@ -50,12 +50,14 @@ func gatewayCmd() {
 	cfg, err := loadConfig()
 	if err != nil {
 		fmt.Printf("Error loading config: %v\n", err)
+		fmt.Println("Run 'picoclaw doctor' to check for common problems.")
 		os.Exit(1)
 	}
 
 	provider, modelID, err := providers.CreateProvider(cfg)
 	if err != nil {
 		fmt.Printf("Error creating provider: %v\n", err)
+		fmt.Println("Run 'picoclaw doctor' to check for common problems.")
 		os.Exit(1)
 	}
 	// Use the resolved model ID from provider creation
@@ -123,6 +125,7 @@ func gatewayCmd() {
 	channelManager, err := channels.NewManager(cfg, msgBus)
 	if err != nil {
 		fmt.Printf("Error creating channel manager: %v\n", err)
+		fmt.Println("Run 'picoclaw doctor' to check for common problems.")
 		os.Exit(1)
 	}
 
diff --git a/cmd/picoclaw/cmd_onboard.go b/cmd/picoclaw/cmd_onboard.go
index 92112ab48..469b73336 100644
--- a/cmd/picoclaw/cmd_onboard.go
+++ b/cmd/picoclaw/cmd_onboard.go
@@ -64,6 +64,10 @@ func onboard() {
 	fmt.Println("     See README.md for 17+ supported providers.")
 	fmt.Println("")
 	fmt.Println("  2. Chat: picoclaw agent -m \"Hello!\"")
+	fmt.Println("")
+	fmt.Println("If something isn't working:")
+	fmt.Println("  picoclaw doctor        Check for common problems")
+	fmt.Println("  picoclaw doctor --fix  Auto-fix what it can")
 }
 
 func copyEmbeddedToTarget(targetDir string) error {
diff --git a/cmd/picoclaw/cmd_status.go b/cmd/picoclaw/cmd_status.go
index b4d36181a..f92d9040e 100644
--- a/cmd/picoclaw/cmd_status.go
+++ b/cmd/picoclaw/cmd_status.go
@@ -27,6 +27,7 @@ func statusCmd() {
 	cfg, err := loadConfig()
 	if err != nil {
 		fmt.Printf("Error loading config: %v\n", err)
+		fmt.Println("Run 'picoclaw doctor' to check for common problems.")
 		return
 	}
 
diff --git a/cmd/picoclaw/main.go b/cmd/picoclaw/main.go
index a05834dd1..566501042 100644
--- a/cmd/picoclaw/main.go
+++ b/cmd/picoclaw/main.go
@@ -133,6 +133,7 @@ func main() {
 		cfg, err := loadConfig()
 		if err != nil {
 			fmt.Printf("Error loading config: %v\n", err)
+			fmt.Println("Run 'picoclaw doctor' to check for common problems.")
 			os.Exit(1)
 		}
 
@@ -195,7 +196,7 @@ func printHelp() {
 	fmt.Println("  cron        Manage scheduled tasks")
 	fmt.Println("  migrate     Migrate from OpenClaw to PicoClaw")
 	fmt.Println("  skills      Manage skills (install, list, remove)")
-	fmt.Println("  doctor      Check for common problems (--fix to auto-repair)")
+	fmt.Println("  doctor      Diagnose and fix common problems (--fix to auto-repair)")
 	fmt.Println("  version     Show version information")
 }