diff --git a/ccw/src/templates/dashboard-css/06-cards.css b/ccw/src/templates/dashboard-css/06-cards.css
index 84fc7079..0df38ce8 100644
--- a/ccw/src/templates/dashboard-css/06-cards.css
+++ b/ccw/src/templates/dashboard-css/06-cards.css
@@ -1500,16 +1500,17 @@ code.ctx-meta-chip-value {
 /* Toast Notifications */
 .status-toast {
   position: fixed;
-  bottom: 2rem;
+  bottom: 1.5rem;
   left: 50%;
   transform: translateX(-50%);
-  padding: 0.75rem 1.5rem;
-  border-radius: 0.5rem;
-  font-size: 0.85rem;
+  padding: 0.5rem 1rem;
+  border-radius: 0.375rem;
+  font-size: 0.8125rem;
   font-weight: 500;
   z-index: 10000;
   animation: toastSlideUp 0.3s ease;
   box-shadow: 0 4px 12px hsl(0 0% 0% / 0.15);
+  max-width: 280px;
 }
 
 .status-toast.success {
diff --git a/ccw/src/templates/dashboard-css/09-explorer.css b/ccw/src/templates/dashboard-css/09-explorer.css
index 0ed00693..66bfbaee 100644
--- a/ccw/src/templates/dashboard-css/09-explorer.css
+++ b/ccw/src/templates/dashboard-css/09-explorer.css
@@ -1346,23 +1346,24 @@
   color: hsl(var(--muted-foreground));
 }
 
-/* Toast Notification */
+/* Toast Notification - Compact */
 .notif-toast {
   position: fixed;
   top: 70px;
-  right: 20px;
+  right: 16px;
   display: flex;
   align-items: center;
-  gap: 8px;
-  padding: 12px 16px;
+  gap: 6px;
+  padding: 8px 12px;
   background: hsl(var(--card));
   border: 1px solid hsl(var(--border));
-  border-radius: 8px;
-  box-shadow: 0 4px 16px hsl(var(--foreground) / 0.15);
+  border-radius: 6px;
+  box-shadow: 0 4px 12px hsl(var(--foreground) / 0.12);
   z-index: 1000;
   opacity: 0;
   transform: translateX(100%);
   transition: all 0.3s ease;
+  max-width: 260px;
 }
 
 .notif-toast.show {
@@ -1379,12 +1380,13 @@
 }
 
 .notif-toast .toast-icon {
-  font-size: 16px;
+  font-size: 14px;
 }
 
 .notif-toast .toast-message {
-  font-size: 13px;
+  font-size: 0.8125rem;
   color: hsl(var(--foreground));
+  line-height: 1.3;
 }
 
 /* Mobile responsive for global notifications */
diff --git a/ccw/src/templates/dashboard-css/10-cli.css b/ccw/src/templates/dashboard-css/10-cli.css
index 3370b18e..54a1a065 100644
--- a/ccw/src/templates/dashboard-css/10-cli.css
+++ b/ccw/src/templates/dashboard-css/10-cli.css
@@ -31,6 +31,27 @@
   overflow: hidden;
 }
 
+/* CLI Section - No card wrapper */
+.cli-section {
+  /* No background, border, or card styling */
+}
+
+.cli-section .section-header {
+  padding: 0 0 0.75rem 0;
+  border-bottom: none;
+  background: transparent;
+}
+
+.cli-section .section-header h3 {
+  font-size: 0.9375rem;
+}
+
+.cli-section .tools-list,
+.cli-section .ccw-list,
+.cli-section .endpoint-tools-grid {
+  padding: 0;
+}
+
 /* Section Header */
 .section-header {
   display: flex;
@@ -84,6 +105,8 @@
   padding: 0.75rem;
   border-radius: 0.5rem;
   margin-bottom: 0.375rem;
+  background: hsl(var(--card));
+  border: 1px solid hsl(var(--border));
   transition: all 0.15s ease;
 }
 
@@ -93,19 +116,19 @@
 
 .tool-item:hover {
   background: hsl(var(--hover));
+  border-color: hsl(var(--primary) / 0.3);
 }
 
 .tool-item.available {
-  border-left: 3px solid hsl(var(--success));
+  /* No left border - use status dot instead */
 }
 
 .tool-item.unavailable {
-  border-left: 3px solid hsl(var(--muted-foreground) / 0.3);
   opacity: 0.7;
 }
 
 .tool-item.endpoint {
-  border-left: 3px solid hsl(var(--indigo));
+  /* No left border */
 }
 
 .tool-item-left {
@@ -209,6 +232,7 @@
   padding: 0.75rem;
   border-radius: 0.5rem;
   margin-bottom: 0.375rem;
+  background: hsl(var(--card));
   border: 1px solid hsl(var(--border));
   transition: all 0.15s ease;
 }
@@ -1642,12 +1666,14 @@
   justify-content: flex-end;
 }
 
-/* Danger Button */
+/* Danger Button (icon style - subtle) */
 .btn-icon.btn-danger {
-  color: hsl(var(--destructive));
+  color: hsl(var(--muted-foreground));
+  background: transparent;
 }
 
 .btn-icon.btn-danger:hover {
+  color: hsl(var(--destructive));
   background: hsl(var(--destructive) / 0.1);
 }
 
@@ -1754,7 +1780,7 @@
   display: flex;
   flex-direction: column;
   padding: 0.875rem;
-  background: hsl(var(--background));
+  background: hsl(var(--card));
   border: 1px solid hsl(var(--border));
   border-radius: 0.5rem;
   cursor: pointer;
@@ -2232,6 +2258,23 @@
   cursor: not-allowed;
 }
 
+/* Override for icon-style danger buttons (subtle, not solid red) */
+.btn-icon.btn-danger,
+.history-item-actions .btn-danger,
+.cli-history-actions .btn-danger {
+  background: transparent;
+  color: hsl(var(--muted-foreground));
+  border: none;
+}
+
+.btn-icon.btn-danger:hover,
+.history-item-actions .btn-danger:hover,
+.cli-history-actions .btn-danger:hover {
+  background: hsl(var(--destructive) / 0.1);
+  color: hsl(var(--destructive));
+  opacity: 1;
+}
+
 /* Multi-Select Checkbox */
 .history-checkbox-wrapper {
   display: flex;
@@ -2557,59 +2600,74 @@
  * ======================================== */
 
 .cli-settings-section {
-  margin-top: 1.5rem;
-  padding-top: 1.25rem;
-  border-top: 1px solid hsl(var(--border));
+  /* No card wrapper - just title and cards */
 }
 
-.cli-settings-header {
-  margin-bottom: 1rem;
+.cli-settings-section .section-header {
+  padding: 0 0 0.75rem 0;
+  border-bottom: none;
+  background: transparent;
 }
 
-.cli-settings-header h4 {
-  display: flex;
-  align-items: center;
-  gap: 0.5rem;
-  font-size: 0.875rem;
-  font-weight: 600;
-  color: hsl(var(--foreground));
+.cli-settings-section .section-header h3 {
+  font-size: 0.9375rem;
 }
 
 .cli-settings-grid {
   display: grid;
-  grid-template-columns: repeat(auto-fit, minmax(220px, 1fr));
-  gap: 1rem;
+  grid-template-columns: repeat(4, 1fr);
+  gap: 0.75rem;
+}
+
+@media (max-width: 1200px) {
+  .cli-settings-grid {
+    grid-template-columns: repeat(2, 1fr);
+  }
+}
+
+@media (max-width: 640px) {
+  .cli-settings-grid {
+    grid-template-columns: 1fr;
+  }
 }
 
 .cli-setting-item {
-  padding: 0.875rem;
-  background: hsl(var(--muted) / 0.3);
+  padding: 0.75rem;
+  background: hsl(var(--card));
   border: 1px solid hsl(var(--border));
   border-radius: 0.5rem;
+  display: flex;
+  flex-direction: column;
+  min-height: 90px;
 }
 
 .cli-setting-label {
   display: flex;
   align-items: center;
   gap: 0.375rem;
-  font-size: 0.75rem;
+  font-size: 0.6875rem;
   font-weight: 600;
-  color: hsl(var(--foreground));
+  color: hsl(var(--muted-foreground));
+  text-transform: uppercase;
+  letter-spacing: 0.025em;
   margin-bottom: 0.5rem;
 }
 
 .cli-setting-label i {
   color: hsl(var(--primary));
+  width: 12px;
+  height: 12px;
 }
 
 .cli-setting-control {
-  margin-bottom: 0.375rem;
+  margin-bottom: 0.5rem;
+  flex-shrink: 0;
 }
 
 .cli-setting-select {
   width: 100%;
-  padding: 0.5rem 0.625rem;
-  font-size: 0.75rem;
+  padding: 0.4375rem 0.5rem;
+  font-size: 0.8125rem;
   background: hsl(var(--background));
   border: 1px solid hsl(var(--border));
   border-radius: 0.375rem;
@@ -2631,5 +2689,68 @@
 .cli-setting-desc {
   font-size: 0.6875rem;
   color: hsl(var(--muted-foreground));
-  line-height: 1.4;
+  line-height: 1.3;
+  margin-top: auto;
+}
+
+.cli-setting-value {
+  font-size: 0.875rem;
+  color: hsl(var(--foreground));
+  font-weight: 500;
+}
+
+/* Toggle Switch */
+.cli-toggle {
+  position: relative;
+  display: inline-block;
+  width: 36px;
+  height: 20px;
+}
+
+.cli-toggle input {
+  opacity: 0;
+  width: 0;
+  height: 0;
+}
+
+.cli-toggle-slider {
+  position: absolute;
+  cursor: pointer;
+  top: 0;
+  left: 0;
+  right: 0;
+  bottom: 0;
+  background-color: hsl(var(--muted));
+  transition: 0.3s;
+  border-radius: 20px;
+}
+
+.cli-toggle-slider:before {
+  position: absolute;
+  content: "";
+  height: 14px;
+  width: 14px;
+  left: 3px;
+  bottom: 3px;
+  background-color: white;
+  transition: 0.3s;
+  border-radius: 50%;
+}
+
+.cli-toggle input:checked + .cli-toggle-slider {
+  background-color: hsl(var(--primary));
+}
+
+.cli-toggle input:checked + .cli-toggle-slider:before {
+  transform: translateX(16px);
+}
+
+.cli-toggle input:focus + .cli-toggle-slider {
+  box-shadow: 0 0 0 2px hsl(var(--primary) / 0.2);
+}
+
+/* Disabled state for settings */
+.cli-setting-item.disabled {
+  opacity: 0.5;
+  pointer-events: none;
 }
diff --git a/ccw/src/templates/dashboard-js/components/cli-status.js b/ccw/src/templates/dashboard-js/components/cli-status.js
index 604f8234..28462637 100644
--- a/ccw/src/templates/dashboard-js/components/cli-status.js
+++ b/ccw/src/templates/dashboard-js/components/cli-status.js
@@ -8,6 +8,10 @@ let semanticStatus = { available: false };
 let defaultCliTool = 'gemini';
 let promptConcatFormat = localStorage.getItem('ccw-prompt-format') || 'plain'; // plain, yaml, json
 
+// Smart Context settings
+let smartContextEnabled = localStorage.getItem('ccw-smart-context') === 'true';
+let smartContextMaxFiles = parseInt(localStorage.getItem('ccw-smart-context-max-files') || '10', 10);
+
 // ========== Initialization ==========
 function initCliStatus() {
   // Load CLI status on init
@@ -235,12 +239,36 @@ function renderCliStatus() {
             Storage Backend
           </label>
           <div class="cli-setting-control">
-            <select class="cli-setting-select" onchange="setStorageBackend(this.value)">
-              <option value="sqlite" ${storageBackend === 'sqlite' ? 'selected' : ''}>SQLite (Recommended)</option>
-              <option value="json" ${storageBackend === 'json' ? 'selected' : ''}>JSON Files</option>
+            <span class="cli-setting-value">SQLite</span>
+          </div>
+          <p class="cli-setting-desc">CLI history stored in SQLite with FTS search</p>
+        </div>
+        <div class="cli-setting-item">
+          <label class="cli-setting-label">
+            <i data-lucide="sparkles" class="w-3 h-3"></i>
+            Smart Context
+          </label>
+          <div class="cli-setting-control">
+            <label class="cli-toggle">
+              <input type="checkbox" ${smartContextEnabled ? 'checked' : ''} onchange="setSmartContextEnabled(this.checked)">
+              <span class="cli-toggle-slider"></span>
+            </label>
+          </div>
+          <p class="cli-setting-desc">Auto-analyze prompt and add relevant file paths</p>
+        </div>
+        <div class="cli-setting-item ${!smartContextEnabled ? 'disabled' : ''}">
+          <label class="cli-setting-label">
+            <i data-lucide="files" class="w-3 h-3"></i>
+            Max Context Files
+          </label>
+          <div class="cli-setting-control">
+            <select class="cli-setting-select" onchange="setSmartContextMaxFiles(this.value)" ${!smartContextEnabled ? 'disabled' : ''}>
+              <option value="5" ${smartContextMaxFiles === 5 ? 'selected' : ''}>5 files</option>
+              <option value="10" ${smartContextMaxFiles === 10 ? 'selected' : ''}>10 files</option>
+              <option value="20" ${smartContextMaxFiles === 20 ? 'selected' : ''}>20 files</option>
             </select>
           </div>
-          <p class="cli-setting-desc">History storage: SQLite for search, JSON for portability</p>
+          <p class="cli-setting-desc">Maximum files to include in smart context</p>
         </div>
       </div>
     </div>
@@ -280,20 +308,23 @@ function setPromptFormat(format) {
   showRefreshToast(`Prompt format set to ${format.toUpperCase()}`, 'success');
 }
 
-function setStorageBackendSetting(backend) {
-  storageBackend = backend;
-  localStorage.setItem('ccw-storage-backend', backend);
-  // Notify server about backend change
-  fetch('/api/cli/settings', {
-    method: 'POST',
-    headers: { 'Content-Type': 'application/json' },
-    body: JSON.stringify({ storageBackend: backend })
-  }).catch(err => console.error('Failed to update backend setting:', err));
-  showRefreshToast(`Storage backend set to ${backend === 'sqlite' ? 'SQLite' : 'JSON'}`, 'success');
+function setSmartContextEnabled(enabled) {
+  smartContextEnabled = enabled;
+  localStorage.setItem('ccw-smart-context', enabled.toString());
+  // Re-render the appropriate settings panel
+  if (typeof renderCliSettingsSection === 'function') {
+    renderCliSettingsSection();
+  } else {
+    renderCliStatus();
+  }
+  showRefreshToast(`Smart Context ${enabled ? 'enabled' : 'disabled'}`, 'success');
 }
 
-// Expose to window for select onchange
-window.setStorageBackend = setStorageBackendSetting;
+function setSmartContextMaxFiles(max) {
+  smartContextMaxFiles = parseInt(max, 10);
+  localStorage.setItem('ccw-smart-context-max-files', max);
+  showRefreshToast(`Smart Context max files set to ${max}`, 'success');
+}
 
 async function refreshAllCliStatus() {
   await Promise.all([loadCliToolStatus(), loadCodexLensStatus()]);
diff --git a/ccw/src/templates/dashboard-js/i18n.js b/ccw/src/templates/dashboard-js/i18n.js
index 76c24e43..439c8dce 100644
--- a/ccw/src/templates/dashboard-js/i18n.js
+++ b/ccw/src/templates/dashboard-js/i18n.js
@@ -200,6 +200,15 @@ const i18n = {
     'cli.codexLensDescFull': 'Full-text code search engine',
     'cli.semanticDesc': 'AI-powered code understanding',
     'cli.semanticDescFull': 'Natural language code search',
+    'cli.settings': 'CLI Execution Settings',
+    'cli.promptFormat': 'Prompt Format',
+    'cli.promptFormatDesc': 'Format for multi-turn conversation concatenation',
+    'cli.storageBackend': 'Storage Backend',
+    'cli.storageBackendDesc': 'CLI history stored in SQLite with FTS search',
+    'cli.smartContext': 'Smart Context',
+    'cli.smartContextDesc': 'Auto-analyze prompt and add relevant file paths',
+    'cli.maxContextFiles': 'Max Context Files',
+    'cli.maxContextFilesDesc': 'Maximum files to include in smart context',
     
     // CCW Install
     'ccw.install': 'CCW Install',
@@ -711,6 +720,15 @@ const i18n = {
     'cli.codexLensDescFull': '全文代码搜索引擎',
     'cli.semanticDesc': 'AI 驱动的代码理解',
     'cli.semanticDescFull': '自然语言代码搜索',
+    'cli.settings': 'CLI 调用设置',
+    'cli.promptFormat': '提示词格式',
+    'cli.promptFormatDesc': '多轮对话拼接格式',
+    'cli.storageBackend': '存储后端',
+    'cli.storageBackendDesc': 'CLI 历史使用 SQLite 存储，支持全文搜索',
+    'cli.smartContext': '智能上下文',
+    'cli.smartContextDesc': '自动分析提示词并添加相关文件路径',
+    'cli.maxContextFiles': '最大上下文文件数',
+    'cli.maxContextFilesDesc': '智能上下文包含的最大文件数',
     
     // CCW Install
     'ccw.install': 'CCW 安装',
diff --git a/ccw/src/tools/smart-context.ts b/ccw/src/tools/smart-context.ts
new file mode 100644
index 00000000..ad6b20bb
--- /dev/null
+++ b/ccw/src/tools/smart-context.ts
@@ -0,0 +1,228 @@
+/**
+ * Smart Context Generator
+ * Extracts keywords from prompts and finds relevant files via CodexLens
+ * Auto-generates contextual file references for CLI execution
+ */
+
+import { executeCodexLens, ensureReady as ensureCodexLensReady } from './codex-lens.js';
+
+// Options for smart context generation
+export interface SmartContextOptions {
+  enabled: boolean;
+  maxFiles: number; // Default: 10
+  searchMode: 'semantic' | 'text'; // Default: 'text'
+}
+
+// Result of smart context generation
+export interface SmartContextResult {
+  files: string[];
+  keywords: string[];
+  searchQuery: string;
+  searchMode: string;
+}
+
+// Common stopwords to filter out
+const STOPWORDS = new Set([
+  'the', 'a', 'an', 'is', 'are', 'was', 'were', 'be', 'been', 'being',
+  'have', 'has', 'had', 'do', 'does', 'did', 'will', 'would', 'could',
+  'should', 'may', 'might', 'must', 'shall', 'can', 'need', 'to', 'of',
+  'in', 'for', 'on', 'with', 'at', 'by', 'from', 'as', 'into', 'through',
+  'during', 'before', 'after', 'above', 'below', 'between', 'under',
+  'again', 'further', 'then', 'once', 'here', 'there', 'when', 'where',
+  'why', 'how', 'all', 'each', 'few', 'more', 'most', 'other', 'some',
+  'such', 'no', 'nor', 'not', 'only', 'own', 'same', 'so', 'than', 'too',
+  'very', 'just', 'and', 'but', 'or', 'if', 'because', 'until', 'while',
+  'this', 'that', 'these', 'those', 'what', 'which', 'who', 'whom',
+  'i', 'you', 'he', 'she', 'it', 'we', 'they', 'my', 'your', 'his', 'her',
+  'its', 'our', 'their', 'me', 'him', 'us', 'them',
+  'please', 'help', 'want', 'like', 'make', 'use', 'file', 'code', 'add',
+  'create', 'update', 'delete', 'remove', 'change', 'modify', 'fix', 'find',
+  'get', 'set', 'show', 'display', 'list', 'new', 'now', 'also', 'any',
+]);
+
+/**
+ * Extract meaningful keywords from prompt
+ * Uses simple NLP: remove stopwords, extract technical terms
+ */
+export function extractKeywords(prompt: string): string[] {
+  // Split into words, convert to lowercase, filter stopwords
+  const words = prompt
+    .toLowerCase()
+    .replace(/[^\w\s\-_./]/g, ' ')
+    .split(/\s+/)
+    .filter((w) => w.length > 2 && !STOPWORDS.has(w));
+
+  // Extract potential technical terms (camelCase, snake_case, paths)
+  const camelCaseMatches = prompt.match(/[a-z][a-z0-9]*[A-Z][a-zA-Z0-9]*/g) || [];
+  const snakeCaseMatches = prompt.match(/[a-z]+_[a-z_]+/g) || [];
+  const pathMatches = prompt.match(/[\w\-./]+\.(ts|js|tsx|jsx|py|go|rs|java|cpp|c|h)/g) || [];
+  const quotedMatches = prompt.match(/"([^"]+)"|'([^']+)'/g) || [];
+
+  const technicalTerms = [
+    ...camelCaseMatches.map((t) => t.toLowerCase()),
+    ...snakeCaseMatches,
+    ...pathMatches,
+    ...quotedMatches.map((t) => t.replace(/['"]/g, '')),
+  ];
+
+  // Combine and deduplicate, prioritize longer terms
+  const allKeywords = [...new Set([...technicalTerms, ...words])];
+
+  // Sort by length (longer terms are more specific) and take top 5
+  return allKeywords
+    .sort((a, b) => b.length - a.length)
+    .slice(0, 5);
+}
+
+/**
+ * Build search query from keywords
+ */
+function buildSearchQuery(keywords: string[]): string {
+  return keywords.join(' ');
+}
+
+/**
+ * Extract file paths from various CodexLens result formats
+ * Handles nested structures like {files: {result: {files: [...]}}}
+ */
+function extractFilesFromResult(parsed: unknown): string[] {
+  if (!parsed || typeof parsed !== 'object') {
+    return [];
+  }
+
+  const obj = parsed as Record<string, unknown>;
+
+  // Direct array of strings
+  if (Array.isArray(parsed)) {
+    return parsed
+      .map((item) => (typeof item === 'string' ? item : (item as Record<string, string>)?.file || (item as Record<string, string>)?.path || ''))
+      .filter((f) => f && f.length > 0);
+  }
+
+  // {files: [...]} format
+  if (Array.isArray(obj.files)) {
+    return extractFilesFromResult(obj.files);
+  }
+
+  // {files: {result: {files: [...]}}} nested format
+  if (obj.files && typeof obj.files === 'object') {
+    const filesObj = obj.files as Record<string, unknown>;
+    if (filesObj.result && typeof filesObj.result === 'object') {
+      const resultObj = filesObj.result as Record<string, unknown>;
+      if (Array.isArray(resultObj.files)) {
+        return resultObj.files.filter((f): f is string => typeof f === 'string' && f.length > 0);
+      }
+    }
+    // {files: {files: [...]}}
+    if (Array.isArray(filesObj.files)) {
+      return extractFilesFromResult(filesObj.files);
+    }
+  }
+
+  // {results: [...]} format
+  if (Array.isArray(obj.results)) {
+    return obj.results
+      .map((r: Record<string, string>) => r?.file || r?.path || '')
+      .filter((f) => f && f.length > 0);
+  }
+
+  // {result: {files: [...]}} format
+  if (obj.result && typeof obj.result === 'object') {
+    return extractFilesFromResult(obj.result);
+  }
+
+  return [];
+}
+
+/**
+ * Generate smart context using CodexLens
+ * Uses multi-keyword search strategy: search each keyword and merge results
+ */
+export async function generateSmartContext(
+  prompt: string,
+  options: SmartContextOptions,
+  cwd: string
+): Promise<SmartContextResult> {
+  // Return empty result if disabled
+  if (!options.enabled) {
+    return { files: [], keywords: [], searchQuery: '', searchMode: '' };
+  }
+
+  // Extract keywords from prompt
+  const keywords = extractKeywords(prompt);
+  if (keywords.length === 0) {
+    return { files: [], keywords: [], searchQuery: '', searchMode: '' };
+  }
+
+  const searchMode = options.searchMode || 'text';
+  const searchQuery = buildSearchQuery(keywords);
+
+  try {
+    // Ensure CodexLens is ready
+    await ensureCodexLensReady();
+
+    // Search each keyword individually and collect unique files
+    const allFiles = new Set<string>();
+    const filesPerKeyword = Math.ceil(options.maxFiles / keywords.length);
+
+    for (const keyword of keywords.slice(0, 3)) { // Limit to top 3 keywords
+      const args = [
+        'search',
+        keyword,
+        '--files-only',
+        '--limit',
+        filesPerKeyword.toString(),
+        '--json',
+      ];
+
+      const result = await executeCodexLens(args, { cwd });
+
+      if (result.success && result.output) {
+        try {
+          const parsed = JSON.parse(result.output);
+          const files = extractFilesFromResult(parsed);
+          files.forEach((f) => allFiles.add(f));
+        } catch {
+          // Skip if parse fails
+        }
+      }
+    }
+
+    // Convert to array and limit to maxFiles
+    const files = Array.from(allFiles).slice(0, options.maxFiles);
+
+    return { files, keywords, searchQuery, searchMode };
+  } catch (err) {
+    console.error('[Smart Context] Error:', err);
+    return { files: [], keywords, searchQuery, searchMode };
+  }
+}
+
+/**
+ * Format smart context as prompt appendage
+ */
+export function formatSmartContext(result: SmartContextResult): string {
+  if (result.files.length === 0) {
+    return '';
+  }
+
+  const lines = [
+    '',
+    '--- SMART CONTEXT ---',
+    `Relevant files (searched: "${result.searchQuery}"):`,
+    ...result.files.map((f) => `- ${f}`),
+    '--- END SMART CONTEXT ---',
+    '',
+  ];
+
+  return lines.join('\n');
+}
+
+/**
+ * Default options for smart context
+ */
+export const defaultSmartContextOptions: SmartContextOptions = {
+  enabled: false,
+  maxFiles: 10,
+  searchMode: 'text',
+};
diff --git a/ccw/src/tools/smart-search.ts b/ccw/src/tools/smart-search.ts
index da9c4d39..d0724ec6 100644
--- a/ccw/src/tools/smart-search.ts
+++ b/ccw/src/tools/smart-search.ts
@@ -21,6 +21,7 @@ import {
 const ParamsSchema = z.object({
   query: z.string().min(1, 'Query is required'),
   mode: z.enum(['auto', 'exact', 'fuzzy', 'semantic', 'graph']).default('auto'),
+  output_mode: z.enum(['full', 'files_only', 'count']).default('full'),
   paths: z.array(z.string()).default([]),
   contextLines: z.number().default(0),
   maxResults: z.number().default(100),
@@ -616,6 +617,12 @@ Modes: auto (default), exact, fuzzy, semantic, graph`,
         description: 'Search mode (default: auto)',
         default: 'auto',
       },
+      output_mode: {
+        type: 'string',
+        enum: ['full', 'files_only', 'count'],
+        description: 'Output mode: full (default), files_only (paths only), count (per-file counts)',
+        default: 'full',
+      },
       paths: {
         type: 'array',
         description: 'Paths to search within (default: current directory)',
@@ -644,6 +651,36 @@ Modes: auto (default), exact, fuzzy, semantic, graph`,
   },
 };
 
+/**
+ * Transform results based on output_mode
+ */
+function transformOutput(
+  results: ExactMatch[] | SemanticMatch[] | GraphMatch[],
+  outputMode: 'full' | 'files_only' | 'count'
+): unknown {
+  switch (outputMode) {
+    case 'files_only': {
+      // Extract unique file paths
+      const files = [...new Set(results.map((r) => r.file))];
+      return { files, count: files.length };
+    }
+    case 'count': {
+      // Count matches per file
+      const counts: Record<string, number> = {};
+      for (const r of results) {
+        counts[r.file] = (counts[r.file] || 0) + 1;
+      }
+      return {
+        files: Object.entries(counts).map(([file, count]) => ({ file, count })),
+        total: results.length,
+      };
+    }
+    case 'full':
+    default:
+      return results;
+  }
+}
+
 // Handler function
 export async function handler(params: Record<string, unknown>): Promise<ToolResult<SearchResult>> {
   const parsed = ParamsSchema.safeParse(params);
@@ -651,7 +688,7 @@ export async function handler(params: Record<string, unknown>): Promise<ToolResu
     return { success: false, error: `Invalid params: ${parsed.error.message}` };
   }
 
-  const { mode } = parsed.data;
+  const { mode, output_mode } = parsed.data;
 
   try {
     let result: SearchResult;
@@ -676,6 +713,11 @@ export async function handler(params: Record<string, unknown>): Promise<ToolResu
         throw new Error(`Unsupported mode: ${mode}`);
     }
 
+    // Transform output based on output_mode
+    if (result.success && result.results && output_mode !== 'full') {
+      result.results = transformOutput(result.results, output_mode) as typeof result.results;
+    }
+
     return result.success ? { success: true, result } : { success: false, error: result.error };
   } catch (error) {
     return { success: false, error: (error as Error).message };