diff --git a/migrations/029_add_planning_mode_required.sql b/migrations/029_add_planning_mode_required.sql
new file mode 100644
index 0000000..608ad99
--- /dev/null
+++ b/migrations/029_add_planning_mode_required.sql
@@ -0,0 +1,3 @@
+-- CF-314: Add planning_mode_required flag for smart planning mode auto-detection
+-- NULL = auto-detect (scoring algorithm), true = always plan, false = never plan
+ALTER TABLE tasks ADD COLUMN IF NOT EXISTS planning_mode_required BOOLEAN DEFAULT NULL;
diff --git a/src/index.ts b/src/index.ts
index d00d929..c392119 100644
--- a/src/index.ts
+++ b/src/index.ts
@@ -120,6 +120,7 @@ server.setRequestHandler(CallToolRequestSchema, async (request) => {
           type: a.type,
           priority: a.priority,
           description: a.description,
+          planning_mode_required: a.planning_mode_required,
         });
         break;
       case 'task_list':
@@ -144,6 +145,7 @@ server.setRequestHandler(CallToolRequestSchema, async (request) => {
           priority: a.priority,
           type: a.type,
           title: a.title,
+          planning_mode_required: a.planning_mode_required,
         });
         break;
       case 'task_investigate':
diff --git a/src/tools/crud.ts b/src/tools/crud.ts
index 809892c..3198291 100644
--- a/src/tools/crud.ts
+++ b/src/tools/crud.ts
@@ -63,6 +63,7 @@ interface TaskAddArgs {
   type?: string;
   priority?: string;
   description?: string;
+  planning_mode_required?: boolean | null;
 }
 
 interface TaskListArgs {
@@ -79,13 +80,14 @@ interface TaskUpdateArgs {
   priority?: string;
   type?: string;
   title?: string;
+  planning_mode_required?: boolean | null;
 }
 
 /**
  * Create a new task
  */
 export async function taskAdd(args: TaskAddArgs): Promise<string> {
-  const { title, project = 'Unknown', type = 'task', priority = 'P2', description = '' } = args;
+  const { title, project = 'Unknown', type = 'task', priority = 'P2', description = '', planning_mode_required } = args;
 
   // Get project key
   const projectKey = await getProjectKey(project);
@@ -151,17 +153,19 @@ export async function taskAdd(args: TaskAddArgs): Promise<string> {
   const session_id = getSessionId();
 
   // Insert task with session_id
+  const planningValue = planning_mode_required !== undefined ? planning_mode_required : null;
+
   if (embeddingValue) {
     await execute(
-      `INSERT INTO tasks (id, project, title, description, type, status, priority, session_id, embedding)
-       VALUES ($1, $2, $3, $4, $5, 'open', $6, $7, $8)`,
-      [taskId, projectKey, title, description, type, priority, session_id, embeddingValue]
+      `INSERT INTO tasks (id, project, title, description, type, status, priority, session_id, embedding, planning_mode_required)
+       VALUES ($1, $2, $3, $4, $5, 'open', $6, $7, $8, $9)`,
+      [taskId, projectKey, title, description, type, priority, session_id, embeddingValue, planningValue]
     );
   } else {
     await execute(
-      `INSERT INTO tasks (id, project, title, description, type, status, priority, session_id)
-       VALUES ($1, $2, $3, $4, $5, 'open', $6, $7)`,
-      [taskId, projectKey, title, description, type, priority, session_id]
+      `INSERT INTO tasks (id, project, title, description, type, status, priority, session_id, planning_mode_required)
+       VALUES ($1, $2, $3, $4, $5, 'open', $6, $7, $8)`,
+      [taskId, projectKey, title, description, type, priority, session_id, planningValue]
     );
   }
 
@@ -326,7 +330,7 @@ export async function taskList(args: TaskListArgs): Promise<string> {
  */
 export async function taskShow(id: string): Promise<string> {
   const task = await queryOne<Task & { session_id?: string }>(
-    `SELECT id, project, title, description, type, status, priority, session_id,
+    `SELECT id, project, title, description, type, status, priority, session_id, planning_mode_required,
             to_char(created_at, 'YYYY-MM-DD HH24:MI') as created,
             to_char(updated_at, 'YYYY-MM-DD HH24:MI') as updated,
             to_char(completed_at, 'YYYY-MM-DD HH24:MI') as completed
@@ -355,6 +359,9 @@ export async function taskShow(id: string): Promise<string> {
     output += `**Created in session:** ${task.session_id}\n`;
   }
 
+  const planningLabel = task.planning_mode_required === true ? 'required' : task.planning_mode_required === false ? 'skipped' : 'auto-detect';
+  output += `**Planning:** ${planningLabel}\n`;
+
   if (task.description) {
     output += `\n**Description:**\n${task.description}\n`;
   }
@@ -476,7 +483,7 @@ export async function taskClose(id: string): Promise<string> {
  * Update a task
  */
 export async function taskUpdate(args: TaskUpdateArgs): Promise<string> {
-  const { id, status, priority, type, title } = args;
+  const { id, status, priority, type, title, planning_mode_required } = args;
 
   // Get current values for activity tracking
   const task = await queryOne<{ status: string }>(`SELECT status FROM tasks WHERE id = $1`, [id]);
@@ -507,6 +514,10 @@ export async function taskUpdate(args: TaskUpdateArgs): Promise<string> {
     updates.push(`title = $${paramIndex++}`);
     params.push(title);
   }
+  if (planning_mode_required !== undefined) {
+    updates.push(`planning_mode_required = $${paramIndex++}`);
+    params.push(planning_mode_required);
+  }
 
   if (updates.length === 0) {
     return 'No updates specified';
diff --git a/src/tools/index.ts b/src/tools/index.ts
index 7edc02d..af6369c 100644
--- a/src/tools/index.ts
+++ b/src/tools/index.ts
@@ -13,6 +13,7 @@ export const toolDefinitions = [
         type: { type: 'string', enum: ['task', 'bug', 'feature', 'debt', 'investigation'], description: 'Task type (default: task)' },
         priority: { type: 'string', enum: ['P0', 'P1', 'P2', 'P3'], description: 'Priority level (default: P2)' },
         description: { type: 'string', description: 'Optional description' },
+        planning_mode_required: { type: 'boolean', description: 'Override planning mode: true=always plan, false=never plan, omit=auto-detect' },
       },
       required: ['title'],
     },
@@ -24,7 +25,7 @@ export const toolDefinitions = [
       type: 'object',
       properties: {
         project: { type: 'string', description: 'Filter by project key' },
-        status: { type: 'string', enum: ['open', 'in_progress', 'testing', 'blocked', 'completed'], description: 'Filter by status. Omit to show all non-completed tasks.' },
+        status: { type: 'string', enum: ['open', 'in_progress', 'testing', 'blocked', 'completed'], description: 'Filter by exact status value. IMPORTANT: "open" only matches status=open, NOT in_progress/blocked/testing. Omit this parameter entirely to show ALL non-completed tasks.' },
         type: { type: 'string', enum: ['task', 'bug', 'feature', 'debt', 'investigation'], description: 'Filter by type' },
         priority: { type: 'string', enum: ['P0', 'P1', 'P2', 'P3'], description: 'Filter by priority' },
         limit: { type: 'number', description: 'Max results (default: 20)' },
@@ -64,6 +65,7 @@ export const toolDefinitions = [
         priority: { type: 'string', enum: ['P0', 'P1', 'P2', 'P3'], description: 'New priority' },
         type: { type: 'string', enum: ['task', 'bug', 'feature', 'debt', 'investigation'], description: 'New type' },
         title: { type: 'string', description: 'New title' },
+        planning_mode_required: { type: 'boolean', description: 'Override planning mode: true=always plan, false=never plan, null=auto-detect' },
       },
       required: ['id'],
     },
diff --git a/src/types.ts b/src/types.ts
index 8deb41f..3e557c0 100644
--- a/src/types.ts
+++ b/src/types.ts
@@ -10,6 +10,7 @@ export interface Task {
   priority: 'P0' | 'P1' | 'P2' | 'P3';
   version_id?: string;
   epic_id?: string;
+  planning_mode_required?: boolean | null;
   created_at: Date;
   updated_at: Date;
   completed_at?: Date;