diff --git a/apps/frontend/src/main/agent/agent-queue.ts b/apps/frontend/src/main/agent/agent-queue.ts
index 93f716aa..1d18be76 100644
--- a/apps/frontend/src/main/agent/agent-queue.ts
+++ b/apps/frontend/src/main/agent/agent-queue.ts
@@ -38,6 +38,40 @@ export class AgentQueueManager {
     this.emitter = emitter;
   }
 
+  /**
+   * Ensure Python environment is ready before spawning processes.
+   * Prevents the race condition where generation starts before dependencies are installed,
+   * which would cause it to fall back to system Python and fail with ModuleNotFoundError.
+   *
+   * @param projectId - The project ID for error event emission
+   * @param eventType - The error event type to emit on failure
+   * @returns true if environment is ready, false if initialization failed (error already emitted)
+   */
+  private async ensurePythonEnvReady(
+    projectId: string,
+    eventType: 'ideation-error' | 'roadmap-error'
+  ): Promise<boolean> {
+    const autoBuildSource = this.processManager.getAutoBuildSourcePath();
+
+    if (!pythonEnvManager.isEnvReady()) {
+      debugLog('[Agent Queue] Python environment not ready, waiting for initialization...');
+      if (autoBuildSource) {
+        const status = await pythonEnvManager.initialize(autoBuildSource);
+        if (!status.ready) {
+          debugError('[Agent Queue] Python environment initialization failed:', status.error);
+          this.emitter.emit(eventType, projectId, `Python environment not ready: ${status.error || 'initialization failed'}`);
+          return false;
+        }
+        debugLog('[Agent Queue] Python environment now ready');
+      } else {
+        debugError('[Agent Queue] Cannot initialize Python - auto-build source not found');
+        this.emitter.emit(eventType, projectId, 'Python environment not ready: auto-build source not found');
+        return false;
+      }
+    }
+    return true;
+  }
+
   /**
    * Start roadmap generation process
    *
@@ -195,6 +229,15 @@ export class AgentQueueManager {
   ): Promise<void> {
     debugLog('[Agent Queue] Spawning ideation process:', { projectId, projectPath });
 
+    // Run from auto-claude source directory so imports work correctly
+    const autoBuildSource = this.processManager.getAutoBuildSourcePath();
+    const cwd = autoBuildSource || process.cwd();
+
+    // Ensure Python environment is ready before spawning
+    if (!await this.ensurePythonEnvReady(projectId, 'ideation-error')) {
+      return;
+    }
+
     // Kill existing process for this project if any
     const wasKilled = this.processManager.killProcess(projectId);
     if (wasKilled) {
@@ -205,9 +248,6 @@ export class AgentQueueManager {
     const spawnId = this.state.generateSpawnId();
     debugLog('[Agent Queue] Generated spawn ID:', spawnId);
 
-    // Run from auto-claude source directory so imports work correctly
-    const autoBuildSource = this.processManager.getAutoBuildSourcePath();
-    const cwd = autoBuildSource || process.cwd();
 
     // Get combined environment variables
     const combinedEnv = this.processManager.getCombinedEnv(projectPath);
@@ -516,6 +556,15 @@ export class AgentQueueManager {
   ): Promise<void> {
     debugLog('[Agent Queue] Spawning roadmap process:', { projectId, projectPath });
 
+    // Run from auto-claude source directory so imports work correctly
+    const autoBuildSource = this.processManager.getAutoBuildSourcePath();
+    const cwd = autoBuildSource || process.cwd();
+
+    // Ensure Python environment is ready before spawning
+    if (!await this.ensurePythonEnvReady(projectId, 'roadmap-error')) {
+      return;
+    }
+
     // Kill existing process for this project if any
     const wasKilled = this.processManager.killProcess(projectId);
     if (wasKilled) {
@@ -526,9 +575,6 @@ export class AgentQueueManager {
     const spawnId = this.state.generateSpawnId();
     debugLog('[Agent Queue] Generated roadmap spawn ID:', spawnId);
 
-    // Run from auto-claude source directory so imports work correctly
-    const autoBuildSource = this.processManager.getAutoBuildSourcePath();
-    const cwd = autoBuildSource || process.cwd();
 
     // Get combined environment variables
     const combinedEnv = this.processManager.getCombinedEnv(projectPath);
diff --git a/apps/frontend/src/main/ipc-handlers/roadmap/transformers.ts b/apps/frontend/src/main/ipc-handlers/roadmap/transformers.ts
index 0eb8b3aa..62f9faee 100644
--- a/apps/frontend/src/main/ipc-handlers/roadmap/transformers.ts
+++ b/apps/frontend/src/main/ipc-handlers/roadmap/transformers.ts
@@ -96,6 +96,57 @@ function transformPhase(raw: RawRoadmapPhase): RoadmapPhase {
   };
 }
 
+/**
+ * Maps all known backend status values to canonical Kanban column statuses.
+ * Includes valid statuses as identity mappings for consistent lookup.
+ * Module-level constant for efficiency (not recreated on each call).
+ */
+const STATUS_MAP: Record<string, RoadmapFeature['status']> = {
+  // Canonical Kanban statuses (identity mappings)
+  'under_review': 'under_review',
+  'planned': 'planned',
+  'in_progress': 'in_progress',
+  'done': 'done',
+  // Early-stage / ideation statuses → under_review
+  'idea': 'under_review',
+  'backlog': 'under_review',
+  'proposed': 'under_review',
+  'pending': 'under_review',
+  // Approved / scheduled statuses → planned
+  'approved': 'planned',
+  'scheduled': 'planned',
+  // Active development statuses → in_progress
+  'active': 'in_progress',
+  'building': 'in_progress',
+  // Completed statuses → done
+  'complete': 'done',
+  'completed': 'done',
+  'shipped': 'done'
+};
+
+/**
+ * Normalizes a feature status string to a valid Kanban column status.
+ * Handles case-insensitive matching and maps backend values to canonical statuses.
+ *
+ * @param status - The raw status string from the backend
+ * @returns A valid RoadmapFeature status for Kanban display
+ */
+function normalizeFeatureStatus(status: string | undefined): RoadmapFeature['status'] {
+  if (!status) return 'under_review';
+
+  const normalized = STATUS_MAP[status.toLowerCase()];
+
+  if (!normalized) {
+    // Debug log for unmapped statuses to aid future mapping additions
+    if (process.env.NODE_ENV === 'development') {
+      console.debug(`[Roadmap] normalizeFeatureStatus: unmapped status "${status}", defaulting to "under_review"`);
+    }
+    return 'under_review';
+  }
+
+  return normalized;
+}
+
 function transformFeature(raw: RawRoadmapFeature): RoadmapFeature {
   return {
     id: raw.id,
@@ -107,7 +158,7 @@ function transformFeature(raw: RawRoadmapFeature): RoadmapFeature {
     impact: (raw.impact as RoadmapFeature['impact']) || 'medium',
     phaseId: raw.phase_id || raw.phaseId || '',
     dependencies: raw.dependencies || [],
-    status: (raw.status as RoadmapFeature['status']) || 'under_review',
+    status: normalizeFeatureStatus(raw.status),
     acceptanceCriteria: raw.acceptance_criteria || raw.acceptanceCriteria || [],
     userStories: raw.user_stories || raw.userStories || [],
     linkedSpecId: raw.linked_spec_id || raw.linkedSpecId,
@@ -115,6 +166,7 @@ function transformFeature(raw: RawRoadmapFeature): RoadmapFeature {
   };
 }
 
+
 export function transformRoadmapFromSnakeCase(
   raw: RawRoadmap,
   projectId: string,
diff --git a/apps/frontend/src/renderer/components/roadmap/RoadmapTabs.tsx b/apps/frontend/src/renderer/components/roadmap/RoadmapTabs.tsx
index 689fd28c..ca5de7d9 100644
--- a/apps/frontend/src/renderer/components/roadmap/RoadmapTabs.tsx
+++ b/apps/frontend/src/renderer/components/roadmap/RoadmapTabs.tsx
@@ -37,6 +37,7 @@ export function RoadmapTabs({
       {/* Kanban View */}
       <TabsContent value="kanban" className="flex-1 overflow-hidden">
         <RoadmapKanbanView
+          key={roadmap.updatedAt?.toString()}
           roadmap={roadmap}
           onFeatureClick={onFeatureSelect}
           onConvertToSpec={onConvertToSpec}