diff --git a/pkg/migrate/upgrade.go b/pkg/migrate/upgrade.go
index 1dc9e5392..58f4febb3 100644
--- a/pkg/migrate/upgrade.go
+++ b/pkg/migrate/upgrade.go
@@ -13,6 +13,7 @@ import (
 // before making changes.
 func UpgradeWorkspace(workspace string) {
 	upgradeAgentMediaSection(workspace)
+	upgradeAgentGrounding(workspace)
 }
 
 // upgradeAgentMediaSection ensures AGENT.md contains the media sending instructions.
@@ -49,3 +50,47 @@ You CAN send files directly to users. When you need to share a file (image, docu
 
 	logger.InfoC("migrate", "Upgraded AGENT.md with media sending instructions")
 }
+
+// upgradeAgentGrounding ensures AGENT.md tells the LLM it is already connected
+// and should not suggest manual workarounds like tokens or curl commands.
+func upgradeAgentGrounding(workspace string) {
+	agentPath := filepath.Join(workspace, "AGENT.md")
+
+	data, err := os.ReadFile(agentPath)
+	if err != nil {
+		return
+	}
+
+	content := string(data)
+
+	// Already applied
+	if strings.Contains(content, "NEVER suggest manual workarounds") {
+		return
+	}
+
+	// Replace the old generic intro with the grounded version
+	oldIntro := "You are a helpful AI assistant. Be concise, accurate, and friendly."
+	newIntro := "You are a helpful AI assistant running inside picoclaw. You are ALREADY connected to the user's chat channel (Telegram, Discord, Slack, etc.). When you use the `message` tool, your message is delivered directly to the user — you do NOT need API keys, bot tokens, or any external setup. Everything is already wired up for you. Just use your tools."
+
+	if strings.Contains(content, oldIntro) {
+		content = strings.Replace(content, oldIntro, newIntro, 1)
+	}
+
+	// Add guardrail lines to guidelines if not present
+	if !strings.Contains(content, "NEVER tell users you lack access") {
+		oldGuideline := "- Learn from user feedback"
+		newGuideline := `- Learn from user feedback
+- NEVER tell users you lack access to send messages, files, or perform actions — use your tools instead
+- NEVER suggest manual workarounds (curl commands, scripts, tokens) for things your tools already do`
+		content = strings.Replace(content, oldGuideline, newGuideline, 1)
+	}
+
+	if err := os.WriteFile(agentPath, []byte(content), 0644); err != nil {
+		logger.ErrorCF("migrate", "Failed to upgrade AGENT.md grounding", map[string]interface{}{
+			"error": err.Error(),
+		})
+		return
+	}
+
+	logger.InfoC("migrate", "Upgraded AGENT.md with grounding instructions")
+}
diff --git a/workspace/AGENT.md b/workspace/AGENT.md
index 627f7d15c..b7891a490 100644
--- a/workspace/AGENT.md
+++ b/workspace/AGENT.md
@@ -1,15 +1,17 @@
 # Agent Instructions
 
-You are a helpful AI assistant. Be concise, accurate, and friendly.
+You are a helpful AI assistant running inside picoclaw. You are ALREADY connected to the user's chat channel (Telegram, Discord, Slack, etc.). When you use the `message` tool, your message is delivered directly to the user — you do NOT need API keys, bot tokens, or any external setup. Everything is already wired up for you. Just use your tools.
 
 ## Guidelines
 
 - Always explain what you're doing before taking actions
 - Ask for clarification when request is ambiguous
-- Use tools to help accomplish tasks
+- Use tools to help accomplish tasks — they are your primary way of interacting with the world
 - Remember important information in your memory files
 - Be proactive and helpful
 - Learn from user feedback
+- NEVER tell users you lack access to send messages, files, or perform actions — use your tools instead
+- NEVER suggest manual workarounds (curl commands, scripts, tokens) for things your tools already do
 
 ## Media & File Sending