diff --git a/ASYNC_MESSAGE_FUTURE.md b/ASYNC_MESSAGE_FUTURE.md
new file mode 100644
index 0000000..2aed782
--- /dev/null
+++ b/ASYNC_MESSAGE_FUTURE.md
@@ -0,0 +1,124 @@
+# Future: Async Message Visibility in Debug-Agent
+
+## Current Limitation
+
+The debug-agent (and any pi session) operates in a **synchronous turn-based model**:
+- When processing a user prompt, the LLM generates a response
+- During this generation, incoming `send_to_session` messages are queued
+- These queued messages are **invisible** until the current turn completes
+- Only then does pi process the queue and present them as new user prompts
+
+This creates confusion in debug/observability scenarios where admins expect real-time interaction.
+
+## Short-term Mitigation (this PR)
+
+- Document the limitation clearly
+- Add `/ready` command to signal completion
+- Advise keeping responses short
+- Provide socket checking workarounds
+
+## Long-term Solutions
+
+### Option 1: Pi Core Enhancement - Message Queue API
+
+Extend pi's `ExtensionAPI` to expose pending message count:
+
+```typescript
+interface ExtensionAPI {
+  // ... existing methods
+  
+  /**
+   * Get count of pending send_to_session messages in queue
+   * Returns 0 if no messages pending, N if messages queued
+   */
+  getPendingMessageCount(): number;
+  
+  /**
+   * Get preview of pending messages (if available)
+   * Useful for dashboard indicators
+   */
+  getPendingMessagePreviews(): Array<{
+    from: string; // sender session ID or name
+    preview: string; // first 50 chars
+    timestamp: Date;
+  }>;
+}
+```
+
+Then the dashboard could show:
+```
+┌─────────────────────────────────────────────────────┐
+│ 📬 3 messages queued (complete turn to process)     │
+│   • control-agent: "can you check..."              │
+│   • user: "status update?"                          │
+└─────────────────────────────────────────────────────┘
+```
+
+**Implementation**: Requires changes to pi's session control layer (WebSocket/message routing)
+
+### Option 2: Streaming Response with Message Interruption
+
+More ambitious - allow interrupting mid-generation:
+
+```typescript
+pi.on("message_received_during_turn", async (event, ctx) => {
+  // Opportunity to abort current generation
+  // Present queued message immediately
+  // Or queue for "after this sentence"
+});
+```
+
+**Challenges**:
+- Requires streaming/incremental generation support
+- Complex state management (partial responses)
+- May confuse conversation context
+
+### Option 3: Parallel Session Mode
+
+Create a "monitor" mode for debug-agent that spawns a parallel session:
+
+```typescript
+// Main session: normal turn-based interaction
+// Monitor session: async-only, polls for messages every 2s
+
+pi.registerExtension("async-monitor", {
+  async init(ctx) {
+    if (ctx.sessionRole === "debug-observer") {
+      setInterval(() => {
+        // Poll session control for pending messages
+        // Display in dashboard without blocking main turn
+      }, 2000);
+    }
+  }
+});
+```
+
+**Pros**: No pi core changes needed
+**Cons**: Complex dual-session architecture, more resources
+
+### Option 4: Event-Driven Dashboard Widget
+
+The dashboard widget already runs outside the LLM turn. Enhance it to:
+1. Listen on the session socket directly (bypassing pi's queue)
+2. Display pending messages in the widget itself (not as user prompts)
+3. Use `/accept-message <id>` command to pull from queue into conversation
+
+**Pros**: Clean separation of monitoring vs. conversation
+**Cons**: Two different interaction modes (in-chat vs. dashboard commands)
+
+## Recommendation
+
+**Phase 1** (this PR): Documentation + workarounds
+**Phase 2**: Implement Option 1 (message queue API in pi core)
+**Phase 3**: Consider Option 4 if Option 1 proves insufficient
+
+Option 1 is the cleanest long-term solution as it:
+- Preserves pi's turn-based model
+- Adds visibility without changing core behavior
+- Minimal API surface area
+- Useful for all session types, not just debug-agent
+
+## Related Pi Issues
+
+- (TODO: check if @mariozechner/pi-coding-agent has issue tracker)
+- Consider proposing this enhancement upstream
diff --git a/pi/skills/debug-agent/SKILL.md b/pi/skills/debug-agent/SKILL.md
index c62fc25..24cbc8b 100644
--- a/pi/skills/debug-agent/SKILL.md
+++ b/pi/skills/debug-agent/SKILL.md
@@ -32,6 +32,16 @@ The activity feed tails the control-agent's session JSONL file — it updates au
 - **Run diagnostics**: check bridge health, socket state, process trees
 - **Make code changes**: edit extensions, skills, configs — same tools as any agent
 
+## Known limitations
+
+**Async message visibility**: Messages sent to this session via `send_to_session` are queued by pi but won't be visible until you complete your current response. This is a fundamental limitation of pi's turn-based conversation model.
+
+**Workaround**: If you suspect messages are queued:
+1. Keep responses short to release the turn quickly
+2. Say "Ready for next message" or use `/ready` to signal completion
+3. The queued messages will then appear as new user prompts
+4. Check your session socket in `/session-control/` to see if connections are pending
+
 ## What you should NOT do
 
 - Don't send disruptive messages to the control-agent while it's mid-task (check activity feed first)
@@ -53,3 +63,4 @@ The activity feed tails the control-agent's session JSONL file — it updates au
 ## Commands
 
 - `/dashboard` — force-refresh the health metrics
+- `/ready` — signal completion and allow queued messages to be processed
diff --git a/pi/skills/debug-agent/debug-dashboard.ts b/pi/skills/debug-agent/debug-dashboard.ts
index 19242cb..d76c862 100644
--- a/pi/skills/debug-agent/debug-dashboard.ts
+++ b/pi/skills/debug-agent/debug-dashboard.ts
@@ -807,6 +807,14 @@ export default function dashboardExtension(pi: ExtensionAPI): void {
     },
   });
 
+  // /ready command — signal completion for queued messages
+  pi.registerCommand("ready", {
+    description: "Signal completion to allow queued send_to_session messages to be processed",
+    handler: async (_args, ctx) => {
+      ctx.ui.notify("Ready for next message. Complete your response to process queue.", "info");
+    },
+  });
+
   pi.on("session_start", async (_event, ctx) => {
     savedCtx = ctx;
     await refresh();