feat: add kickstart prompt and auto-compact context options

Kickstart Prompt:
- Remove Idle Timeout setting from respawn UI (uses 10s default)
- Add Kickstart Prompt field sent when /init doesn't trigger work
- New states: monitoring_init, sending_kickstart, waiting_kickstart
- Monitors 3s after /init to detect if Claude started working

Auto-Compact Context:
- Add auto-compact at 110k tokens (sends /compact with optional prompt)
- Preserves summarized context unlike /clear which wipes everything
- Optional focus prompt to guide what compact should preserve
- Blocks auto-clear while compacting to prevent conflicts

Also updates auto-clear default threshold from 100k to 140k tokens.

Co-Authored-By: Claude Opus 4.5 <noreply@anthropic.com>

src/web/public/app.js

@@ -1264,22 +1264,32 @@ class ClaudemanApp {
   // Get respawn config from modal inputs
   getModalRespawnConfig() {
     const updatePrompt = document.getElementById('modalRespawnPrompt').value;
-    const idleTimeout = parseInt(document.getElementById('modalRespawnIdleTimeout').value) || 5;
     const sendClear = document.getElementById('modalRespawnSendClear').checked;
     const sendInit = document.getElementById('modalRespawnSendInit').checked;
+    const kickstartPrompt = document.getElementById('modalRespawnKickstart').value.trim() || undefined;
     const durationStr = document.getElementById('modalRespawnDuration').value;
     const durationMinutes = durationStr ? parseInt(durationStr) : null;
+
+    // Auto-compact settings
+    const autoCompactEnabled = document.getElementById('modalAutoCompactEnabled').checked;
+    const autoCompactThreshold = parseInt(document.getElementById('modalAutoCompactThreshold').value) || 110000;
+    const autoCompactPrompt = document.getElementById('modalAutoCompactPrompt').value.trim() || undefined;
+
+    // Auto-clear settings
     const autoClearEnabled = document.getElementById('modalAutoClearEnabled').checked;
-    const autoClearThreshold = parseInt(document.getElementById('modalAutoClearThreshold').value) || 100000;
+    const autoClearThreshold = parseInt(document.getElementById('modalAutoClearThreshold').value) || 140000;
 
     return {
       respawnConfig: {
         updatePrompt,
-        idleTimeoutMs: idleTimeout * 1000,
         sendClear,
         sendInit,
+        kickstartPrompt,
       },
       durationMinutes,
+      autoCompactEnabled,
+      autoCompactThreshold,
+      autoCompactPrompt,
       autoClearEnabled,
       autoClearThreshold
     };
@@ -1291,7 +1301,15 @@ class ClaudemanApp {
       return;
     }
 
-    const { respawnConfig, durationMinutes, autoClearEnabled, autoClearThreshold } = this.getModalRespawnConfig();
+    const {
+      respawnConfig,
+      durationMinutes,
+      autoCompactEnabled,
+      autoCompactThreshold,
+      autoCompactPrompt,
+      autoClearEnabled,
+      autoClearThreshold
+    } = this.getModalRespawnConfig();
 
     try {
       // Enable respawn on the session
@@ -1303,6 +1321,15 @@ class ClaudemanApp {
       const data = await res.json();
       if (data.error) throw new Error(data.error);
 
+      // Set auto-compact if enabled
+      if (autoCompactEnabled) {
+        await fetch(`/api/sessions/${this.editingSessionId}/auto-compact`, {
+          method: 'POST',
+          headers: { 'Content-Type': 'application/json' },
+          body: JSON.stringify({ enabled: true, threshold: autoCompactThreshold, prompt: autoCompactPrompt })
+        });
+      }
+
       // Set auto-clear if enabled
       if (autoClearEnabled) {
         await fetch(`/api/sessions/${this.editingSessionId}/auto-clear`, {

src/web/public/index.html

@@ -204,14 +204,6 @@
               <input type="text" id="modalRespawnPrompt" value="update all the docs and CLAUDE.md" placeholder="Prompt to send when idle">
             </div>
 
-            <div class="form-row">
-              <label>Idle Timeout</label>
-              <div class="input-suffix">
-                <input type="number" id="modalRespawnIdleTimeout" value="5" min="1" max="60">
-                <span>sec</span>
-              </div>
-            </div>
-
             <div class="form-row">
               <label>Run Duration</label>
               <div class="input-suffix">
@@ -235,6 +227,28 @@
               </div>
             </div>
 
+            <div class="form-row">
+              <label>Kickstart Prompt</label>
+              <input type="text" id="modalRespawnKickstart" value="" placeholder="Optional: prompt if /init doesn't trigger work">
+              <span class="form-hint">Sent only when /init completes but Claude stays idle</span>
+            </div>
+
+            <div class="form-row">
+              <label>Auto-Compact Context</label>
+              <div class="auto-clear-row">
+                <label class="checkbox-inline">
+                  <input type="checkbox" id="modalAutoCompactEnabled">
+                  <span>Enable at</span>
+                </label>
+                <div class="input-suffix input-suffix-sm">
+                  <input type="number" id="modalAutoCompactThreshold" value="110000" min="10000" max="500000" step="10000">
+                  <span>tokens</span>
+                </div>
+              </div>
+              <input type="text" id="modalAutoCompactPrompt" value="" placeholder="Optional: focus prompt for compact" class="mt-sm">
+              <span class="form-hint">Summarizes context while preserving key information</span>
+            </div>
+
             <div class="form-row">
               <label>Auto-Clear Context</label>
               <div class="auto-clear-row">
@@ -243,10 +257,11 @@
                   <span>Enable at</span>
                 </label>
                 <div class="input-suffix input-suffix-sm">
-                  <input type="number" id="modalAutoClearThreshold" value="100000" min="10000" max="500000" step="10000">
+                  <input type="number" id="modalAutoClearThreshold" value="140000" min="10000" max="500000" step="10000">
                   <span>tokens</span>
                 </div>
               </div>
+              <span class="form-hint">Completely resets context (use higher threshold than compact)</span>
             </div>
 
             <div class="respawn-actions">

src/web/public/styles.css

@@ -21,6 +21,9 @@
 
 * { box-sizing: border-box; margin: 0; padding: 0; }
 
+/* Utility classes */
+.mt-sm { margin-top: 0.5rem; }
+
 body {
   font-family: -apple-system, BlinkMacSystemFont, 'Segoe UI', sans-serif;
   background: var(--bg-dark);

src/web/server.ts

@@ -515,6 +515,29 @@ export class WebServer extends EventEmitter {
       };
     });
 
+    // Set auto-compact on a session
+    this.app.post('/api/sessions/:id/auto-compact', async (req) => {
+      const { id } = req.params as { id: string };
+      const body = req.body as { enabled: boolean; threshold?: number; prompt?: string };
+      const session = this.sessions.get(id);
+
+      if (!session) {
+        return { error: 'Session not found' };
+      }
+
+      session.setAutoCompact(body.enabled, body.threshold, body.prompt);
+      this.broadcast('session:updated', session.toDetailedState());
+
+      return {
+        success: true,
+        autoCompact: {
+          enabled: session.autoCompactEnabled,
+          threshold: session.autoCompactThreshold,
+          prompt: session.autoCompactPrompt,
+        },
+      };
+    });
+
     // Quick run (create session, run prompt, return result, then cleanup)
     this.app.post('/api/run', async (req) => {
       // Prevent unbounded session creation
@@ -912,6 +935,11 @@ export class WebServer extends EventEmitter {
       this.broadcast('session:autoClear', { sessionId: session.id, ...data });
       this.broadcast('session:updated', session.toDetailedState());
     });
+
+    session.on('autoCompact', (data: { tokens: number; threshold: number; prompt?: string }) => {
+      this.broadcast('session:autoCompact', { sessionId: session.id, ...data });
+      this.broadcast('session:updated', session.toDetailedState());
+    });
   }
 
   private setupRespawnListeners(sessionId: string, controller: RespawnController): void {