diff --git a/.astra/tests/stress/.astra/cache/259a37934ead3910a8722b82054d46d2ca2057b05c488be1dcf439166ac5a9a1.json b/.astra/tests/stress/.astra/cache/259a37934ead3910a8722b82054d46d2ca2057b05c488be1dcf439166ac5a9a1.json
index f3a270f..0b8439c 100644
--- a/.astra/tests/stress/.astra/cache/259a37934ead3910a8722b82054d46d2ca2057b05c488be1dcf439166ac5a9a1.json
+++ b/.astra/tests/stress/.astra/cache/259a37934ead3910a8722b82054d46d2ca2057b05c488be1dcf439166ac5a9a1.json
@@ -1,5 +1,5 @@
 {
   "result": "Final report with inconsistencies. This should be long enough to pass validation.",
-  "createdAt": 1778684049645,
+  "createdAt": 1778685193682,
   "modelVersion": "unknown"
 }
\ No newline at end of file
diff --git a/.astra/tests/stress/.astra/cache/65775be352df43297b63c7af59c9f4f39d2bc368f77456c37b5eef9a94a66b5c.json b/.astra/tests/stress/.astra/cache/65775be352df43297b63c7af59c9f4f39d2bc368f77456c37b5eef9a94a66b5c.json
index 8f780e6..1f3597d 100644
--- a/.astra/tests/stress/.astra/cache/65775be352df43297b63c7af59c9f4f39d2bc368f77456c37b5eef9a94a66b5c.json
+++ b/.astra/tests/stress/.astra/cache/65775be352df43297b63c7af59c9f4f39d2bc368f77456c37b5eef9a94a66b5c.json
@@ -1,5 +1,5 @@
 {
   "result": "[CONFLICT WARNING] 성능이 200% 증가했습니다. vs 그러나 동시에 50% 감소했습니다. 최적화와 성능 저하가 동시에 발견됨.",
-  "createdAt": 1778684049641,
+  "createdAt": 1778685193681,
   "modelVersion": "unknown"
 }
\ No newline at end of file
diff --git a/.astra/tests/stress/.astra/cache/6894d26c5b0a55d25d756a473225c7a44d7661af673b24e3f49551a7a2e50280.json b/.astra/tests/stress/.astra/cache/6894d26c5b0a55d25d756a473225c7a44d7661af673b24e3f49551a7a2e50280.json
index 2a4c637..7e0f67b 100644
--- a/.astra/tests/stress/.astra/cache/6894d26c5b0a55d25d756a473225c7a44d7661af673b24e3f49551a7a2e50280.json
+++ b/.astra/tests/stress/.astra/cache/6894d26c5b0a55d25d756a473225c7a44d7661af673b24e3f49551a7a2e50280.json
@@ -1,5 +1,5 @@
 {
   "result": "Detailed Execution Plan: 1. Research 2. Analyze 3. Write report with high quality.",
-  "createdAt": 1778684049636,
+  "createdAt": 1778685193680,
   "modelVersion": "unknown"
 }
\ No newline at end of file
diff --git a/.astra/tests/stress/.astra/cache/88cb61499f88ed38165b64bd3e8adc543795e4b427b64540a49c9ab27c7fe213.json b/.astra/tests/stress/.astra/cache/88cb61499f88ed38165b64bd3e8adc543795e4b427b64540a49c9ab27c7fe213.json
index ed5eb8c..eded489 100644
--- a/.astra/tests/stress/.astra/cache/88cb61499f88ed38165b64bd3e8adc543795e4b427b64540a49c9ab27c7fe213.json
+++ b/.astra/tests/stress/.astra/cache/88cb61499f88ed38165b64bd3e8adc543795e4b427b64540a49c9ab27c7fe213.json
@@ -1,5 +1,5 @@
 {
-  "result": "---\nid: stress_conflict_1778684049621\ndate: 2026-05-13T14:54:09.649Z\ntype: knowledge_artifact\nstandard: P-Reinforce v3.0\ntags: [automated, connect_ai, brain_sync]\n---\n\n## 📌 Brief Summary\nFinal report with inconsistencies. This should be long enough to pass validation.\n\nFinal report with inconsistencies. This should be long enough to pass validation.\n\n---\n## 💡 Astra의 선제적 제안 (Proactive Next Actions)\nFinal report with inconsistencies. This should be long enough to pass validation.\n---\n## 🛡️ Reliability & Audit Summary\n> [!NOTE]\n> 이 문서는 ConnectAI의 **Intelligent Resilience** 엔진에 의해 검증 및 정제되었습니다.\n\n| Metric | Value | Status |\n| :--- | :--- | :--- |\n| **Conflict Risk** | `60/100` | ⚠️ Medium |\n| **Fallbacks Used** | `0` | ✅ None |\n| **Auto Retries** | `0` | ✅ Stable |\n| **Deduplication** | `0` | Standard |\n| **Processing Time** | `0.0s` | ✅ Fast |\n\n### 🔍 Decision Audit Trail\n- **[PLANNER]** 전략 수립 중... (11ms)\n- **[RESEARCHER]** 핵심 정보 수집 및 분석 중... (5ms)\n- **[WRITER]** 최종 리포트 작성 및 편집 중... (8ms)\n",
-  "createdAt": 1778684049649,
+  "result": "---\nid: stress_conflict_1778685193665\ndate: 2026-05-13T15:13:13.682Z\ntype: knowledge_artifact\nstandard: P-Reinforce v3.0\ntags: [automated, connect_ai, brain_sync]\n---\n\n## 📌 Brief Summary\nFinal report with inconsistencies. This should be long enough to pass validation.\n\nFinal report with inconsistencies. This should be long enough to pass validation.\n\n---\n## 💡 Astra의 선제적 제안 (Proactive Next Actions)\nFinal report with inconsistencies. This should be long enough to pass validation.\n---\n## 🛡️ Reliability & Audit Summary\n> [!NOTE]\n> 이 문서는 ConnectAI의 **Intelligent Resilience** 엔진에 의해 검증 및 정제되었습니다.\n\n| Metric | Value | Status |\n| :--- | :--- | :--- |\n| **Conflict Risk** | `60/100` | ⚠️ Medium |\n| **Fallbacks Used** | `0` | ✅ None |\n| **Auto Retries** | `0` | ✅ Stable |\n| **Deduplication** | `0` | Standard |\n| **Processing Time** | `0.0s` | ✅ Fast |\n\n### 🔍 Decision Audit Trail\n- **[PLANNER]** 전략 수립 중... (10ms)\n- **[RESEARCHER]** 핵심 정보 수집 및 분석 중... (5ms)\n- **[WRITER]** 최종 리포트 작성 및 편집 중... (0ms)\n",
+  "createdAt": 1778685193682,
   "modelVersion": "unknown"
 }
\ No newline at end of file
diff --git a/.astra/tests/stress/.astra/missions/stress_conflict_1778684049621.json b/.astra/tests/stress/.astra/missions/stress_conflict_1778685193665.json
similarity index 80%
rename from .astra/tests/stress/.astra/missions/stress_conflict_1778684049621.json
rename to .astra/tests/stress/.astra/missions/stress_conflict_1778685193665.json
index bdcea08..fcf87f5 100644
--- a/.astra/tests/stress/.astra/missions/stress_conflict_1778684049621.json
+++ b/.astra/tests/stress/.astra/missions/stress_conflict_1778685193665.json
@@ -1,8 +1,8 @@
 {
-  "missionId": "stress_conflict_1778684049621",
+  "missionId": "stress_conflict_1778685193665",
   "status": "completed",
-  "startTime": "2026-05-13T14:54:09.621Z",
-  "totalElapsedMs": 29,
+  "startTime": "2026-05-13T15:13:13.666Z",
+  "totalElapsedMs": 16,
   "results": {
     "planner": "Detailed Execution Plan: 1. Research 2. Analyze 3. Write report with high quality.",
     "researcher": "[CONFLICT WARNING] 성능이 200% 증가했습니다. vs 그러나 동시에 50% 감소했습니다. 최적화와 성능 저하가 동시에 발견됨.",
@@ -16,30 +16,30 @@
     {
       "from": "idle",
       "to": "planner",
-      "durationMs": 11,
+      "durationMs": 10,
       "message": "전략 수립 중...",
-      "ts": "2026-05-13T14:54:09.632Z"
+      "ts": "2026-05-13T15:13:13.676Z"
     },
     {
       "from": "planner",
       "to": "researcher",
       "durationMs": 5,
       "message": "핵심 정보 수집 및 분석 중...",
-      "ts": "2026-05-13T14:54:09.637Z"
+      "ts": "2026-05-13T15:13:13.681Z"
     },
     {
       "from": "researcher",
       "to": "writer",
-      "durationMs": 8,
+      "durationMs": 0,
       "message": "최종 리포트 작성 및 편집 중...",
-      "ts": "2026-05-13T14:54:09.645Z"
+      "ts": "2026-05-13T15:13:13.681Z"
     },
     {
       "from": "writer",
       "to": "completed",
-      "durationMs": 5,
+      "durationMs": 1,
       "message": "미션 완료",
-      "ts": "2026-05-13T14:54:09.650Z"
+      "ts": "2026-05-13T15:13:13.682Z"
     }
   ],
   "resilienceMetrics": {
diff --git a/PATCHNOTES.md b/PATCHNOTES.md
index 1e4d1c9..a371da7 100644
--- a/PATCHNOTES.md
+++ b/PATCHNOTES.md
@@ -1,5 +1,15 @@
 # Astra Patch Notes
 
+## v2.0.6 (2026-05-14)
+### 🚀 Intelligence & UX Optimization
+- **UI & UX 정교화:** 사이드바(`sidebar.js`, `sidebar.css`)의 인터랙션과 스타일을 개선하여 더욱 매끄러운 사용자 경험을 제공합니다.
+- **텔레그램 대화 기록 관리:** `conversationHistory.ts`를 도입하여 텔레그램 연동 시의 대화 맥락 유지 기능을 강화했습니다.
+- **비즈니스 엔진 고도화:** `dispatcher.ts` 및 `promptBuilder.ts` 최적화를 통해 CEO 에이전트의 의사결정 및 작업 할당 정밀도를 높였습니다.
+- **아키텍처 분석 강화:** 프로젝트 구조 스캔 및 컨텍스트 주입 로직을 보완하여 더 깊은 코드 이해가 가능하도록 개선했습니다.
+- **신규 패키징:** `astra-2.0.6.vsix` 패키지를 통해 통합된 성능 및 인터페이스 개선 사항을 배포합니다.
+
+---
+
 ## v2.0.5 (2026-05-13)
 ### 📢 Telegram Business Reporting & Core Resilience
 - **텔레그램 비즈니스 리포팅 도입:** 비즈니스 에이전트의 성과를 실시간으로 보고하는 `telegramReport.ts`를 추가하여 원격 모니터링 기능을 강화했습니다.
diff --git a/media/sidebar.css b/media/sidebar.css
index 2620a85..4853eb3 100644
--- a/media/sidebar.css
+++ b/media/sidebar.css
@@ -469,7 +469,7 @@
         .company-phase-card .cph-meta { color: var(--text-dim); font-size: 10px; }
         .company-phase-card.report .cph-head { color: var(--accent); }
 
-        /* Project Architecture chip — sits just above the input when project mode is on. */
+        /* Project Architecture chip — three-state surface above the input. */
         .arch-chip {
             display: none;
             align-items: center;
@@ -481,7 +481,20 @@
             border-radius: 8px;
             font-size: 11px;
         }
-        .arch-chip[data-active="true"] { display: flex; }
+        .arch-chip[data-state="active"],
+        .arch-chip[data-state="inactive"] { display: flex; }
+        /* Inactive state has a muted look so it doesn't compete with active chips. */
+        .arch-chip[data-state="inactive"] {
+            background: var(--bg-secondary);
+            border-style: dashed;
+        }
+        .arch-chip[data-state="inactive"] .arch-chip-title { color: var(--text-dim); }
+        /* Per-state button visibility — JS only flips the chip's data-state. */
+        .arch-chip[data-state="active"] .arch-chip-inactive-only { display: none; }
+        .arch-chip[data-state="inactive"] .arch-chip-active-only { display: none; }
+        .arch-chip[data-state="inactive"] #archAttachBtn {
+            color: var(--accent); border-color: var(--accent);
+        }
         .arch-chip-icon { font-size: 14px; flex-shrink: 0; }
         .arch-chip-info { flex: 1; min-width: 0; line-height: 1.3; }
         .arch-chip-title {
@@ -505,6 +518,22 @@
             border-color: var(--border-bright);
         }
 
+        /* Inline refresh-result card so the user sees what the refresh did. */
+        .arch-refresh-card {
+            border: 1px solid var(--border);
+            background: var(--surface);
+            border-radius: 8px;
+            padding: 6px 10px;
+            margin: 4px 0;
+            font-size: 10.5px;
+            color: var(--text-primary);
+        }
+        .arch-refresh-card .arc-head {
+            color: var(--text-bright); font-weight: 600; margin-bottom: 2px;
+        }
+        .arch-refresh-card .arc-meta { color: var(--text-dim); font-size: 9.5px; }
+        .arch-refresh-card.no-changes { border-style: dashed; }
+
         /* Inline model picker that lives in the input footer, next to the attach
            button. Replaces the (now-removed) bottom model row + the separate
            "Model: ..." status text — one surface, click to change. */
diff --git a/media/sidebar.html b/media/sidebar.html
index f9a12ac..d9bc85c 100644
--- a/media/sidebar.html
+++ b/media/sidebar.html
@@ -292,16 +292,28 @@
             message with active=true. Click "Open" / "Refresh" / "Detach" to
             route back to the chatHandlers cases.
         -->
-        <div id="archChip" class="arch-chip" data-active="false">
+        <!--
+            Three-state chip:
+              data-state="hidden"   → completely collapsed
+              data-state="active"   → full info + Open / Refresh / Detach
+              data-state="inactive" → project name + Attach (or Re-attach) only
+            JS switches the state attribute on every `architectureStatus`
+            event so the user always has a one-click path back into project
+            mode after a Detach.
+        -->
+        <div id="archChip" class="arch-chip" data-state="hidden">
             <span class="arch-chip-icon">📋</span>
             <div class="arch-chip-info">
                 <div class="arch-chip-title" id="archChipTitle">—</div>
-                <div class="arch-chip-meta" id="archChipMeta">Auto-load Off</div>
+                <div class="arch-chip-meta" id="archChipMeta">—</div>
             </div>
-            <div class="arch-chip-actions">
-                <button class="arch-chip-btn" id="archOpenBtn" title="Architecture 문서 열기">Open</button>
-                <button class="arch-chip-btn" id="archRefreshBtn" title="지금 다시 스캔">Refresh</button>
-                <button class="arch-chip-btn" id="archDetachBtn" title="자동 첨부 끄기">Detach</button>
+            <div class="arch-chip-actions" id="archChipActions">
+                <!-- active state buttons -->
+                <button class="arch-chip-btn arch-chip-active-only" id="archOpenBtn" title="Architecture 문서 열기">Open</button>
+                <button class="arch-chip-btn arch-chip-active-only" id="archRefreshBtn" title="지금 다시 스캔">Refresh</button>
+                <button class="arch-chip-btn arch-chip-active-only" id="archDetachBtn" title="자동 첨부 끄기">Detach</button>
+                <!-- inactive state button -->
+                <button class="arch-chip-btn arch-chip-inactive-only" id="archAttachBtn" title="이 프로젝트에 architecture 자동 첨부 켜기">Attach</button>
             </div>
         </div>
         <div id="agentConfigPanel" class="panel">
diff --git a/media/sidebar.js b/media/sidebar.js
index d9b3bf6..2be9fda 100644
--- a/media/sidebar.js
+++ b/media/sidebar.js
@@ -804,21 +804,28 @@
                     break;
                 }
                 case 'architectureStatus': {
-                    // Show / hide the chip + reflect current state.
+                    // Three-state chip:
+                    //   active   — full info + Open/Refresh/Detach
+                    //   inactive — name + [Attach] button (user previously detached, OR doc not yet generated)
+                    //   hidden   — no project + no workspace
                     const chip = document.getElementById('archChip');
                     const title = document.getElementById('archChipTitle');
                     const meta = document.getElementById('archChipMeta');
                     if (!chip || !title || !meta) break;
                     const v = msg.value || {};
-                    if (!v.active) {
-                        chip.setAttribute('data-active', 'false');
-                        break;
+                    if (v.active) {
+                        chip.setAttribute('data-state', 'active');
+                        title.textContent = `${v.projectName || 'Project'} architecture`;
+                        const updatedLabel = v.lastUpdated ? `updated ${formatRelativeTime(v.lastUpdated)}` : 'just attached';
+                        const autoLabel = v.autoUpdate === false ? 'Auto-update Off' : 'Auto-update On';
+                        meta.textContent = `${updatedLabel} · ${autoLabel}`;
+                    } else if (v.canAttach && v.projectName) {
+                        chip.setAttribute('data-state', 'inactive');
+                        title.textContent = `${v.projectName} architecture`;
+                        meta.textContent = v.detached ? 'detached — click Attach to re-enable' : 'not yet activated';
+                    } else {
+                        chip.setAttribute('data-state', 'hidden');
                     }
-                    chip.setAttribute('data-active', 'true');
-                    title.textContent = `${v.projectName || 'Project'} architecture`;
-                    const updatedLabel = v.lastUpdated ? `updated ${formatRelativeTime(v.lastUpdated)}` : 'just attached';
-                    const autoLabel = v.autoUpdate === false ? 'Auto-update Off' : 'Auto-update On';
-                    meta.textContent = `${updatedLabel} · ${autoLabel}`;
                     break;
                 }
                 case 'architectureRefreshFailed': {
@@ -830,6 +837,34 @@
                     }
                     break;
                 }
+                case 'architectureRefreshResult': {
+                    // Trust-building stats card: shows exactly what the
+                    // refresh did so users don't have to guess whether the
+                    // 0.1s click actually accomplished anything.
+                    const v = msg.value || {};
+                    const card = document.createElement('div');
+                    card.className = 'arch-refresh-card';
+                    const noChanges = (v.newlyAnalyzed | 0) === 0 && (v.deleted | 0) === 0;
+                    if (noChanges) card.classList.add('no-changes');
+                    const head = noChanges
+                        ? `📋 ${escAttr(v.projectName || 'Project')} architecture — 변경 사항 없음`
+                        : `📋 ${escAttr(v.projectName || 'Project')} architecture refreshed`;
+                    const parts = [
+                        `${v.newlyAnalyzed | 0} newly analysed`,
+                        `${v.cached | 0} cached`,
+                    ];
+                    if ((v.deleted | 0) > 0) parts.push(`${v.deleted | 0} deleted`);
+                    parts.push(`${v.durationMs | 0}ms`);
+                    card.innerHTML =
+                        `<div class="arc-head">${head}</div>` +
+                        `<div class="arc-meta">${parts.join(' · ')}</div>`;
+                    const chatEl = document.getElementById('chat');
+                    if (chatEl) {
+                        chatEl.appendChild(card);
+                        chatEl.scrollTop = chatEl.scrollHeight;
+                    }
+                    break;
+                }
                 case 'knowledgeMix': {
                     // Initial sync: reflect whatever weight is currently in settings.
                     if (msg.value && typeof msg.value.weight === 'number') {
@@ -1386,6 +1421,10 @@
         if (_archOpenBtn) _archOpenBtn.onclick = () => vscode.postMessage({ type: 'openArchitectureDoc' });
         if (_archRefreshBtn) _archRefreshBtn.onclick = () => vscode.postMessage({ type: 'refreshArchitecture' });
         if (_archDetachBtn) _archDetachBtn.onclick = () => vscode.postMessage({ type: 'detachArchitecture' });
+        // [Attach] is visible only in the inactive chip state; clicking it
+        // re-enables architecture mode for the current workspace's project.
+        const _archAttachBtn = document.getElementById('archAttachBtn');
+        if (_archAttachBtn) _archAttachBtn.onclick = () => vscode.postMessage({ type: 'attachArchitecture' });
 
         // ── 1인 기업 (Company) Mode chip + manage overlay ─────────────────────
         // The chip itself toggles enabled/disabled. The ▾ button opens the
diff --git a/package.json b/package.json
index 453889f..50a3f5d 100644
--- a/package.json
+++ b/package.json
@@ -2,7 +2,7 @@
   "name": "astra",
   "displayName": "Astra",
   "description": "The personal intelligence layer for Antigravity and VS Code. A private cognitive partner for deep project context, memory, and proactive strategic decision-making.",
-  "version": "2.0.5",
+  "version": "2.0.6",
   "publisher": "g1nation",
   "license": "MIT",
   "icon": "assets/icon.png",
@@ -111,6 +111,10 @@
         "command": "g1nation.architecture.detach",
         "title": "Astra: Detach Project Architecture Context"
       },
+      {
+        "command": "g1nation.architecture.attach",
+        "title": "Astra: Attach Project Architecture Context"
+      },
       {
         "command": "g1nation.architecture.open",
         "title": "Astra: Open Project Architecture Doc"
diff --git a/src/extension.ts b/src/extension.ts
index e8b1c41..3213cd2 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -306,9 +306,24 @@ export async function activate(context: vscode.ExtensionContext) {
             }
 
             const systemPrompt = buildTelegramSystemPrompt(!!contextBlock);
-            const userMessage = contextBlock
-                ? `[SECOND BRAIN CONTEXT]\n${contextBlock}\n\n[USER MESSAGE]\n${text}`
-                : text;
+            // Per-chat conversation history — without this every inbound
+            // is a fresh turn, so the user "tells the bot something" and
+            // it gets immediately forgotten. We inline the recent N
+            // exchanges into the user message because the AI service's
+            // {system, user} surface doesn't carry a messages array.
+            const { appendTelegramMessage, getRecentMessages, formatHistoryForPrompt } =
+                await import('./integrations/telegram/conversationHistory');
+            const history = getRecentMessages(chatId, 10);
+            const historyBlock = formatHistoryForPrompt(history);
+            const pieces: string[] = [];
+            if (contextBlock) pieces.push(`[SECOND BRAIN CONTEXT]\n${contextBlock}`);
+            if (historyBlock) pieces.push(historyBlock);
+            pieces.push(`[USER MESSAGE]\n${text}`);
+            const userMessage = pieces.join('\n\n');
+
+            // Persist the user's message *before* the AI call so failures
+            // still leave a trail (next inbound will see what they said).
+            appendTelegramMessage({ chatId, role: 'user', text, kind: 'user' });
 
             try {
                 const result = await telegramAi.chat({ system: systemPrompt, user: userMessage });
@@ -330,6 +345,10 @@ export async function activate(context: vscode.ExtensionContext) {
                     ].join('\n');
                 }
 
+                // Persist the assistant's reply so the *next* inbound sees
+                // what we just said. Without this, the bot would forget its
+                // own answer the moment the user follows up.
+                appendTelegramMessage({ chatId, role: 'assistant', text: result.content, kind: 'reply' });
                 // Telegram has a hard 4096 char/message limit. Long replies are
                 // chunked and joined with a "(이어서)" hint so the user knows
                 // multiple messages belong together.
@@ -446,6 +465,11 @@ export async function activate(context: vscode.ExtensionContext) {
             await provider._detachArchitecture();
             vscode.window.showInformationMessage('Astra: Project architecture auto-attach turned off.');
         }),
+        vscode.commands.registerCommand('g1nation.architecture.attach', async () => {
+            if (!provider) return;
+            await provider._attachArchitecture();
+            vscode.window.showInformationMessage('Astra: Project architecture auto-attach turned on.');
+        }),
         vscode.commands.registerCommand('g1nation.architecture.open', async () => {
             if (!provider) return;
             await provider._openArchitectureDoc();
diff --git a/src/features/company/dispatcher.ts b/src/features/company/dispatcher.ts
index 2b0e6db..c71fa66 100644
--- a/src/features/company/dispatcher.ts
+++ b/src/features/company/dispatcher.ts
@@ -284,7 +284,8 @@ async function _dispatchOne(
         // hit disk / shell. The report (e.g. "✅ Created: foo.py") is
         // appended to the response so the user sees what really happened.
         let finalResponse = rawResponse || '_(empty response)_';
-        if (rawResponse && deps.executeActionTags && _hasActionTag(rawResponse)) {
+        const hasTag = !!rawResponse && _hasActionTag(rawResponse);
+        if (rawResponse && deps.executeActionTags && hasTag) {
             try {
                 const report = await deps.executeActionTags(rawResponse);
                 if (report.length > 0) {
@@ -297,12 +298,30 @@ async function _dispatchOne(
                 logError('company.dispatcher: action-tag execution failed.', { agentId, err });
                 finalResponse = `${rawResponse}\n\n---\n⚠️ Action 실행 실패: ${err}`;
             }
+        } else if (rawResponse && !hasTag && _claimsFileCreation(rawResponse)) {
+            // Hallucination guard: small models love to *narrate* file
+            // creation ("foo.py를 생성했습니다 …") without emitting the
+            // <create_file> tag — so the user sees ✅ in chat but nothing
+            // on disk. Catch the mismatch here and flag it loudly so the
+            // CEO synthesis (which reads this response) and the user both
+            // know nothing was actually written.
+            const warning = '⚠️ **실제 파일이 생성되지 않았습니다.** Agent가 파일 생성을 텍스트로 설명했지만 ConnectAI 액션 태그(`<create_file>` 등)를 사용하지 않아 디스크에 아무것도 만들어지지 않았어요. 같은 요청을 다시 시도하거나, 사용자가 직접 만드세요.';
+            finalResponse = `${rawResponse}\n\n---\n${warning}`;
+            logInfo('company.dispatcher: agent claimed creation without action tag.', { agentId });
         }
+        // `error: 'no-action-tag-but-claimed'` is *advisory* — we still let
+        // the turn complete because some agents (Writer, Researcher) are
+        // legitimately answer-only. But by flagging the agent output we
+        // mark it as not-fully-successful so the CEO synthesis can read
+        // the warning verbatim.
+        const claimedButDidnt = rawResponse && !hasTag && _claimsFileCreation(rawResponse);
         return {
             agentId, task,
             response: finalResponse,
             durationMs: Date.now() - startedAt,
-            error: rawResponse ? undefined : 'empty-response',
+            error: rawResponse
+                ? (claimedButDidnt ? 'claimed-creation-no-tag' : undefined)
+                : 'empty-response',
         };
     } catch (e: any) {
         const err = e?.message ?? String(e);
@@ -325,3 +344,27 @@ async function _dispatchOne(
 function _hasActionTag(text: string): boolean {
     return /<\s*(?:create_file|edit_file|delete_file|read_file|list_files|list_brain|run_command|read_brain|reveal_in_explorer|open_file|glob|grep)\b/i.test(text);
 }
+
+/**
+ * Heuristic: does the response *narrate* having created files/folders?
+ *
+ * We look for the combination of (a) a Korean / English creation verb and
+ * (b) a filename-like or "folder" mention. The intent is to catch the
+ * hallucination pattern where an agent writes "foo.py 파일을 생성했습니다"
+ * or "Created `bar/` directory" without emitting the corresponding
+ * `<create_file>` tag, so the dispatcher can flag it back to the CEO and
+ * the user instead of silently reporting success.
+ *
+ * Kept narrow on purpose — a *plan* like "다음에는 X를 만들어야 합니다"
+ * shouldn't trigger this. We require past-tense / completion phrasing.
+ */
+function _claimsFileCreation(text: string): boolean {
+    // Past-tense creation verbs (Korean + English).
+    const claimRe = /(?:생성했|만들었|작성했|저장했|구현했|created|wrote|saved|built|generated)/i;
+    if (!claimRe.test(text)) return false;
+    // Combined with either an explicit filename (something.ext) or the word
+    // "폴더" / "directory" / "folder" near the verb.
+    const fileLike = /\b[\w\-./]+\.(?:py|js|ts|tsx|jsx|md|json|html|css|sh|yaml|yml|sql|java|go|rs|c|cpp|rb|php)\b/i.test(text);
+    const folderLike = /(?:폴더|디렉토리|directory|folder)/i.test(text);
+    return fileLike || folderLike;
+}
diff --git a/src/features/company/promptBuilder.ts b/src/features/company/promptBuilder.ts
index af9ba8f..f29441f 100644
--- a/src/features/company/promptBuilder.ts
+++ b/src/features/company/promptBuilder.ts
@@ -77,15 +77,39 @@ export function buildSpecialistPrompt(inputs: SpecialistPromptInputs): string {
     parts.push('- 추측·일반론·placeholder 금지. 가진 정보만 인용.');
 
     // ── Tool contract ──
-    // ConnectAI's existing AgentExecutor parses these tags automatically
-    // after the streaming response completes. Keeping the syntax identical
-    // means specialists can write files / run commands the same way the
-    // base chat already does — no new plumbing on the agent side.
+    // Hard rule about action tags. Earlier wording ("태그 없이 평문으로만
+    // 답해도 됩니다") let small models (gemma 4 e2b etc.) emit ```python
+    // code blocks and then *claim* to have created files — the user got
+    // ✅ in chat but nothing on disk. This block is now phrased so the
+    // model cannot rationalise its way out of the tag contract.
     parts.push('');
-    parts.push('## 도구 사용 규칙 (필요할 때만)');
-    parts.push('실제 파일 생성·명령 실행이 필요하면 ConnectAI의 액션 태그를 사용하세요.');
-    parts.push('예) `<create_file path="...">내용</create_file>`, `<run_command>npm test</run_command>` 등.');
-    parts.push('태그 없이 평문으로만 답해도 됩니다 — 기획·분석·아이디어 작업은 보통 태그가 필요 없습니다.');
+    parts.push('## ⚠️ 실제 파일·명령 실행 (이 섹션 매우 중요)');
+    parts.push('당신은 사용자의 **실제** 파일 시스템과 터미널에 직접 연결되어 있습니다.');
+    parts.push('**텍스트로 "만들었다 / 작성했다 / 생성했다 / 저장했다" 라고 말해도 사용자 디스크엔 아무 일도 안 일어납니다.**');
+    parts.push('파일을 만들거나 명령을 실행하려면 **반드시** 아래 액션 태그로 감싸세요. 시스템이 자동으로 디스크에 적용합니다:');
+    parts.push('');
+    parts.push('  • `<create_file path="...">내용</create_file>` — 새 파일 생성·덮어쓰기');
+    parts.push('  • `<edit_file path="..."><find>옛 내용</find><replace>새 내용</replace></edit_file>` — 부분 편집');
+    parts.push('  • `<read_file path="..."/>` — 32KB까지 읽기 (편집 전엔 반드시 먼저 read)');
+    parts.push('  • `<delete_file path="..."/>` — 파일·디렉토리 삭제');
+    parts.push('  • `<list_files path="..."/>` — 디렉토리 목록 보기');
+    parts.push('  • `<run_command>명령</run_command>` — 셸 실행 (디렉토리 생성 등)');
+    parts.push('');
+    parts.push('🛑 **경로 규칙 (위반 시 권한 거부됨)**:');
+    parts.push('- 경로는 **워크스페이스 루트 상대 경로**로 쓰세요. 예: `timertest/timer.py`, `src/utils.py`');
+    parts.push('- 절대 경로 가능하지만 **반드시 워크스페이스 내부**여야 함. `/antigravity/...` `/tmp/...` 같은 시스템 루트 경로는 거부됨.');
+    parts.push('- 디렉토리는 `<create_file>`이 자동으로 만들어줍니다 (mkdir -p). 별도 명령 불필요.');
+    parts.push('');
+    parts.push('❌ **하지 말아야 할 패턴**:');
+    parts.push('  - ```python\\nprint("...")\\n``` 코드 블록만 답하고 "생성 완료"라고 말하기 → 디스크엔 만들어지지 않음');
+    parts.push('  - `<create_file path="/antigravity/foo.py">` 같은 시스템 루트 경로 → 거부됨');
+    parts.push('  - 사용자가 "X 만들어줘"라고 했는데 코드만 보여주고 끝내기 → 사용자는 결과물을 받지 못함');
+    parts.push('');
+    parts.push('✅ **올바른 패턴**:');
+    parts.push('  사용자: "타이머 파이썬 스크립트 만들어줘"');
+    parts.push('  당신: 짧은 설명 한두 줄 + `<create_file path="timer.py">import time\\n...</create_file>` + 자가평가');
+    parts.push('');
+    parts.push('기획·분석·아이디어처럼 *결과물이 파일 아닌 경우*에는 액션 태그 없이 마크다운으로만 답해도 됩니다.');
 
     // ── Peer context (this turn) ──
     const peers = inputs.peerOutputs ?? [];
diff --git a/src/features/company/telegramReport.ts b/src/features/company/telegramReport.ts
index 47bf4da..e6a2fdd 100644
--- a/src/features/company/telegramReport.ts
+++ b/src/features/company/telegramReport.ts
@@ -25,6 +25,7 @@
 import * as vscode from 'vscode';
 import { logError, logInfo } from '../../utils';
 import { TelegramHttpClient } from '../../integrations/telegram/telegramClient';
+import { appendTelegramMessage } from '../../integrations/telegram/conversationHistory';
 import { COMPANY_AGENTS } from './agents';
 import { AgentTurnOutput, CompanyState, CompanyTaskPlan } from './types';
 
@@ -72,6 +73,13 @@ export async function buildTelegramReporter(
 
     return async (text: string): Promise<boolean> => {
         if (!text || !text.trim()) return false;
+        // Append to the per-chat history *before* the send. The bot's
+        // next inbound turn reads this history, so even if delivery
+        // fails the user's follow-up question still has context for
+        // "what did you just say to me?". Persisting on attempt also
+        // means timing matches the user's perception ("the bot reported
+        // X, then I replied").
+        appendTelegramMessage({ chatId, role: 'assistant', text, kind: 'company-mirror' });
         try {
             await client.sendMessage({ chatId, text, parseMode: 'Markdown' });
             return true;
diff --git a/src/features/projectArchitecture/index.ts b/src/features/projectArchitecture/index.ts
index 423b56a..cc17644 100644
--- a/src/features/projectArchitecture/index.ts
+++ b/src/features/projectArchitecture/index.ts
@@ -115,6 +115,14 @@ export interface BuildResult {
     created: boolean;
     /** Result of the scan that fed this build. */
     scan: ArchitectureScanResult;
+    /**
+     * What the underlying deep-scan actually did this run — how many files
+     * were freshly analysed vs. served from the on-disk cache, and whether
+     * any tracked files have disappeared. The sidebar surfaces these counts
+     * after every Refresh so users can trust the operation actually ran
+     * (instead of the previous mysterious "updated just now in 0.1s").
+     */
+    refreshStats: RefreshStats;
 }
 
 /** Resolve the architecture doc path for a given project root. */
@@ -181,7 +189,7 @@ export function buildOrRefreshArchitectureDoc(
             newlyAnalyzed: deep.refreshStats.newlyAnalyzed,
             cached: deep.refreshStats.cached,
         });
-        return { docPath, created: true, scan };
+        return { docPath, created: true, scan, refreshStats: deep.refreshStats };
     }
 
     // In-place refresh: rewrite the auto-managed block, keep user-owned sections.
@@ -196,7 +204,7 @@ export function buildOrRefreshArchitectureDoc(
             deleted: deep.refreshStats.deleted.length,
         });
     }
-    return { docPath, created: false, scan };
+    return { docPath, created: false, scan, refreshStats: deep.refreshStats };
 }
 
 /**
diff --git a/src/integrations/telegram/conversationHistory.ts b/src/integrations/telegram/conversationHistory.ts
new file mode 100644
index 0000000..5a8d53f
--- /dev/null
+++ b/src/integrations/telegram/conversationHistory.ts
@@ -0,0 +1,154 @@
+/**
+ * Per-chat conversation history for the Telegram bot.
+ *
+ * Why this exists: the previous bot was *stateless* — every inbound
+ * message hit `AIService.chat({system, user})` in isolation, with no
+ * memory of what the user said two minutes ago or what the secretary
+ * just reported. Users hit this immediately: "I just told you about
+ * project X, why don't you remember?"
+ *
+ * This module solves it with a thin append-only log:
+ *
+ *   - Each `(chatId, role, text)` triple is appended to a JSONL file at
+ *     `<workspace>/.astra/company/_agents/secretary/telegram_history.jsonl`.
+ *     One file per workspace, scoped by `chatId` at read time, so
+ *     multi-chat setups don't bleed into each other.
+ *   - A small in-memory cache (last 200 entries) sits in front so the
+ *     hot path is `O(1)` lookup, not "scan the whole file".
+ *   - `getRecentMessages` returns the most recent N entries for a chat,
+ *     including the secretary's company-turn mirror entries that the
+ *     dispatcher appends — so when the user asks a follow-up question
+ *     ("저 폴더가 없다고"), the AI sees its own report from 30 seconds ago.
+ *
+ * The file is human-readable on purpose — users can grep it / delete it
+ * to clear history without any CLI.
+ */
+import * as fs from 'fs';
+import * as path from 'path';
+import * as vscode from 'vscode';
+import { logError } from '../../utils';
+
+export interface TelegramHistoryEntry {
+    chatId: number;
+    role: 'user' | 'assistant';
+    text: string;
+    /** ISO timestamp at append time. */
+    ts: string;
+    /** Optional tag: `'company-mirror'` for secretary's auto-reports, `'reply'` for normal replies. */
+    kind?: 'company-mirror' | 'reply' | 'user';
+}
+
+/** Max entries kept across all chats in the in-memory cache. */
+const MEMORY_CAP = 200;
+/** Max entries returned by `getRecentMessages`. */
+const DEFAULT_RECENT = 12;
+
+let _cache: TelegramHistoryEntry[] = [];
+let _hydratedForWorkspace: string | null = null;
+
+function _historyPath(): string {
+    const ws = vscode.workspace.workspaceFolders?.[0]?.uri.fsPath;
+    if (!ws) return '';
+    return path.join(ws, '.astra', 'company', '_agents', 'secretary', 'telegram_history.jsonl');
+}
+
+/**
+ * Lazy-load the on-disk JSONL into the cache the first time we need it
+ * for the current workspace. Switching workspaces re-hydrates from the
+ * new file — that way each project keeps its own chat memory.
+ */
+function _hydrateIfNeeded(): void {
+    const ws = vscode.workspace.workspaceFolders?.[0]?.uri.fsPath ?? '';
+    if (_hydratedForWorkspace === ws) return;
+    _hydratedForWorkspace = ws;
+    _cache = [];
+    const p = _historyPath();
+    if (!p || !fs.existsSync(p)) return;
+    try {
+        const lines = fs.readFileSync(p, 'utf8').split('\n').filter((l) => l.trim());
+        // Trim to the cap from the *end* so we keep the freshest entries.
+        const tail = lines.length > MEMORY_CAP ? lines.slice(-MEMORY_CAP) : lines;
+        for (const line of tail) {
+            try {
+                const entry = JSON.parse(line) as Partial<TelegramHistoryEntry>;
+                if (typeof entry.chatId === 'number'
+                    && (entry.role === 'user' || entry.role === 'assistant')
+                    && typeof entry.text === 'string'
+                    && typeof entry.ts === 'string') {
+                    _cache.push(entry as TelegramHistoryEntry);
+                }
+            } catch {
+                // Skip malformed line — keep going so a single bad write doesn't poison everything.
+            }
+        }
+    } catch (e: any) {
+        logError('telegram.history: read failed.', { error: e?.message ?? String(e) });
+    }
+}
+
+/**
+ * Append one entry. Best-effort: cache always updates so the *current*
+ * session sees its own writes immediately even if the disk write fails.
+ */
+export function appendTelegramMessage(entry: Omit<TelegramHistoryEntry, 'ts'> & { ts?: string }): void {
+    _hydrateIfNeeded();
+    const fullEntry: TelegramHistoryEntry = {
+        chatId: entry.chatId,
+        role: entry.role,
+        text: entry.text,
+        kind: entry.kind,
+        ts: entry.ts ?? new Date().toISOString(),
+    };
+    _cache.push(fullEntry);
+    if (_cache.length > MEMORY_CAP) _cache.splice(0, _cache.length - MEMORY_CAP);
+    const p = _historyPath();
+    if (!p) return;
+    try {
+        fs.mkdirSync(path.dirname(p), { recursive: true });
+        fs.appendFileSync(p, JSON.stringify(fullEntry) + '\n', 'utf8');
+    } catch (e: any) {
+        logError('telegram.history: append failed.', { chatId: entry.chatId, error: e?.message ?? String(e) });
+    }
+}
+
+/**
+ * Return the most recent N messages for one chat, oldest-first so the
+ * caller can feed them to an LLM in turn order. `maxEntries` defaults to
+ * 12 — enough for a couple of follow-up turns without exploding the
+ * context window of a small local model.
+ */
+export function getRecentMessages(
+    chatId: number,
+    maxEntries: number = DEFAULT_RECENT,
+): TelegramHistoryEntry[] {
+    _hydrateIfNeeded();
+    const forChat = _cache.filter((e) => e.chatId === chatId);
+    return forChat.slice(-Math.max(1, maxEntries));
+}
+
+/**
+ * Format recent history as a readable block we can inline into the user
+ * message. We don't use the AI service's multi-message API because
+ * `IAIService.chat({system, user})` only takes one user turn — embedding
+ * the back-and-forth in the user message keeps the API surface unchanged
+ * while still giving the model the context it needs.
+ */
+export function formatHistoryForPrompt(history: TelegramHistoryEntry[]): string {
+    if (!history.length) return '';
+    const lines: string[] = ['[Previous conversation in this Telegram chat]'];
+    for (const e of history) {
+        const speaker = e.role === 'user' ? 'User' : 'Bot';
+        // Keep each message bounded so a single huge company-mirror report
+        // doesn't dominate the prompt budget.
+        const trimmed = e.text.length > 800 ? e.text.slice(0, 800) + '…' : e.text;
+        lines.push(`${speaker}: ${trimmed}`);
+    }
+    lines.push('[End of previous conversation]');
+    return lines.join('\n');
+}
+
+/** For tests + the "clear history" command. */
+export function _resetCacheForTests(): void {
+    _cache = [];
+    _hydratedForWorkspace = null;
+}
diff --git a/src/sidebar/chatHandlers.ts b/src/sidebar/chatHandlers.ts
index fda1fe4..62310e4 100644
--- a/src/sidebar/chatHandlers.ts
+++ b/src/sidebar/chatHandlers.ts
@@ -151,6 +151,11 @@ export async function handleChatMessage(provider: SidebarChatProvider, data: any
         case 'detachArchitecture':
             await provider._detachArchitecture();
             return true;
+        case 'attachArchitecture':
+            // Re-enable architecture context for the current workspace —
+            // user clicked the inactive chip's [Attach] button.
+            await provider._attachArchitecture();
+            return true;
         case 'activateArchitectureFromText': {
             // Optional explicit-toggle path: webview can pass arbitrary text
             // (e.g. the current input draft) for one-shot intent detection.
diff --git a/src/sidebarProvider.ts b/src/sidebarProvider.ts
index e2ace34..4f7e30b 100644
--- a/src/sidebarProvider.ts
+++ b/src/sidebarProvider.ts
@@ -1121,8 +1121,16 @@ export class SidebarChatProvider implements vscode.WebviewViewProvider, BridgeIn
         logInfo('architecture: detached.', { projectId: profile.projectId });
     }
 
-    /** Force a refresh of the architecture doc for the active project. */
+    /**
+     * Force a refresh of the architecture doc for the active project.
+     *
+     * Always rewrites the auto-managed block (so the "Last Refresh" stamp +
+     * stats reflect the click). Emits an `architectureRefreshResult` event
+     * with the per-file work breakdown — that's what makes the operation
+     * visibly trustworthy in the UI (no more "0.1s, nothing visible").
+     */
     async _refreshArchitecture(): Promise<void> {
+        const startedAt = Date.now();
         const profile = this._getActiveChronicleProject();
         if (!profile || !profile.projectRoot) {
             this._view?.webview.postMessage({
@@ -1145,6 +1153,111 @@ export class SidebarChatProvider implements vscode.WebviewViewProvider, BridgeIn
             : p);
         await this._putChronicleProjects(next);
         await this._sendArchitectureStatus();
+        // Tell the webview exactly what the scan did so the user can
+        // trust the "Refresh" button actually ran. The three numbers
+        // (newly / cached / deleted) together explain whether the doc
+        // changed or just had its timestamp bumped.
+        this._view?.webview.postMessage({
+            type: 'architectureRefreshResult',
+            value: {
+                projectName: profile.projectName,
+                docPath: result.docPath,
+                newlyAnalyzed: result.refreshStats.newlyAnalyzed,
+                cached: result.refreshStats.cached,
+                deleted: result.refreshStats.deleted.length,
+                durationMs: Date.now() - startedAt,
+            },
+        });
+    }
+
+    /**
+     * Re-attach the architecture context for the active project after a
+     * prior Detach. Rebuilds the doc (so the user gets a fresh scan),
+     * flips `architectureAutoAttach=true`, re-registers the watcher, and
+     * broadcasts the chip back to its active state. The complement of
+     * `_detachArchitecture`.
+     */
+    async _attachArchitecture(): Promise<void> {
+        // `_ensureActiveProjectForWorkspace` guarantees the active project
+        // matches the current VS Code workspace — without that, hitting
+        // Attach right after opening a different folder would silently
+        // attach to whatever was last active in the *previous* workspace.
+        const profile = await this._ensureActiveProjectForWorkspace();
+        if (!profile || !profile.projectRoot) {
+            this._view?.webview.postMessage({
+                type: 'architectureRefreshFailed',
+                value: { reason: 'no-active-project' },
+            });
+            return;
+        }
+        await this._activateArchitectureForProject(profile.projectId, {
+            fallbackName: profile.projectName,
+            fallbackRoot: profile.projectRoot,
+        });
+    }
+
+    /**
+     * Make sure the active chronicle project actually corresponds to the
+     * folder the user has open in VS Code. Three cases:
+     *
+     *   1. Active project already matches workspace → return it as-is.
+     *   2. A *different* chronicle project matches the workspace → flip
+     *      the active id to that one (the user switched folders since
+     *      last session).
+     *   3. No chronicle project matches → synthesise a new one from the
+     *      workspace folder name + register it.
+     *
+     * Returns the (possibly newly created) active project, or `null` when
+     * no workspace is open. Idempotent — calling repeatedly with no change
+     * is free.
+     */
+    async _ensureActiveProjectForWorkspace(): Promise<ProjectProfile | null> {
+        const workspaceRoot = vscode.workspace.workspaceFolders?.[0]?.uri.fsPath;
+        if (!workspaceRoot) return null;
+        const projects = this._getChronicleProjects();
+        const active = this._getActiveChronicleProject();
+        const norm = (p: string | undefined) => (p || '').replace(/[\\/]+$/, '').toLowerCase();
+        if (active && active.projectRoot && norm(active.projectRoot) === norm(workspaceRoot)) {
+            return active;
+        }
+        // Case 2: another chronicle project matches → switch active to it
+        const matching = projects.find((p) => norm(p.projectRoot) === norm(workspaceRoot));
+        if (matching) {
+            await this._context.globalState.update(
+                SidebarChatProvider.activeChronicleProjectStateKey,
+                matching.projectId,
+            );
+            logInfo('architecture: switched active project to match workspace.', {
+                from: active?.projectId,
+                to: matching.projectId,
+            });
+            return matching;
+        }
+        // Case 3: synthesise a fresh entry for this workspace
+        const projectName = path.basename(workspaceRoot) || 'Current Project';
+        const projectId = this._slugify(projectName);
+        const now = new Date().toISOString();
+        const profile: ProjectProfile = {
+            projectId,
+            projectName,
+            projectRoot: workspaceRoot,
+            recordRoot: path.join(workspaceRoot, 'docs', 'records', projectName),
+            description: 'Auto-detected from workspace folder.',
+            corePurpose: '',
+            detailLevel: 'standard',
+            createdAt: now,
+            updatedAt: now,
+        };
+        const nextProjects = projects.filter((p) => p.projectId !== projectId).concat(profile);
+        await this._putChronicleProjects(nextProjects);
+        await this._context.globalState.update(
+            SidebarChatProvider.activeChronicleProjectStateKey,
+            projectId,
+        );
+        logInfo('architecture: registered new project from workspace.', {
+            projectId, projectRoot: workspaceRoot,
+        });
+        return profile;
     }
 
     /**
@@ -1166,24 +1279,84 @@ export class SidebarChatProvider implements vscode.WebviewViewProvider, BridgeIn
         });
     }
 
-    /** Webview chip data — shown above the input box when active. */
+    /**
+     * Webview chip data. Three states:
+     *
+     *   1. **active**     — project mode is on; doc is being auto-attached.
+     *   2. **inactive**   — there's a project + workspace, but architecture
+     *                       is either never-activated or user-detached.
+     *                       The chip shows an `[Attach]` button instead of
+     *                       hiding entirely, so users always have a one-
+     *                       click path back into project mode.
+     *   3. **hidden**     — no workspace open and no project at all.
+     *
+     * Also does an auto-activation pass for the *fresh-workspace* case:
+     * when the active project has no `architectureDocPath` yet AND the
+     * user hasn't explicitly detached, we generate the doc + flip
+     * `autoAttach=true` so the user opens a new folder and immediately
+     * sees the architecture context working. Existing detach choices are
+     * always respected.
+     */
     async _sendArchitectureStatus(): Promise<void> {
         if (!this._view) return;
-        const p = this._getActiveChronicleProject();
-        const active = !!(p && p.architectureDocPath && p.architectureAutoAttach !== false);
-        this._view.webview.postMessage({
-            type: 'architectureStatus',
-            value: active && p
-                ? {
+        // Always sync the active project to the current VS Code workspace
+        // before reporting — otherwise switching workspaces leaves the
+        // chip pointing at the *previous* project's doc.
+        const p = await this._ensureActiveProjectForWorkspace();
+        if (!p) {
+            this._view.webview.postMessage({ type: 'architectureStatus', value: { active: false } });
+            return;
+        }
+        const wasDetached = p.architectureAutoAttach === false;
+        const hasDoc = !!(p.architectureDocPath && fs.existsSync(p.architectureDocPath));
+
+        // Auto-activation for fresh workspaces: never been activated AND
+        // never been detached → kick off a build and re-broadcast. Single
+        // recursion is safe because the post-activate state will hit the
+        // `active` branch below.
+        if (!hasDoc && !wasDetached && p.projectRoot) {
+            try {
+                await this._activateArchitectureForProject(p.projectId, {
+                    fallbackName: p.projectName,
+                    fallbackRoot: p.projectRoot,
+                });
+                return; // _activateArchitectureForProject sends its own status
+            } catch (e: any) {
+                logError('architecture: auto-activate failed.', { error: e?.message ?? String(e) });
+                // Fall through to the inactive state so the user still sees an Attach button.
+            }
+        }
+
+        const fullyActive = hasDoc && !wasDetached;
+        if (fullyActive) {
+            this._view.webview.postMessage({
+                type: 'architectureStatus',
+                value: {
                     active: true,
                     projectId: p.projectId,
                     projectName: p.projectName,
                     docPath: p.architectureDocPath,
                     lastUpdated: p.architectureLastUpdated || '',
                     autoUpdate: p.architectureAutoUpdate !== false,
-                }
-                : { active: false },
-        });
+                },
+            });
+            // Re-register the watcher in case it was disposed (e.g. workspace switch).
+            this._registerArchitectureWatcher(p);
+        } else {
+            // Inactive but attachable: surface the project name + an Attach hook.
+            this._view.webview.postMessage({
+                type: 'architectureStatus',
+                value: {
+                    active: false,
+                    canAttach: !!p.projectRoot,
+                    projectId: p.projectId,
+                    projectName: p.projectName,
+                    // Distinguishes "never activated" from "detached" so the
+                    // chip can choose the right label ("Activate" vs "Re-attach").
+                    detached: wasDetached,
+                },
+            });
+        }
     }
 
     // ─── 1인 기업 (Company) Mode ────────────────────────────────────────────