diff --git a/src/openrouter/reviewer.test.ts b/src/openrouter/reviewer.test.ts
index febc38ebd..7f9976a88 100644
--- a/src/openrouter/reviewer.test.ts
+++ b/src/openrouter/reviewer.test.ts
@@ -194,7 +194,7 @@ describe('summarizeToolUsage', () => {
 // ─── extractUserQuestion ────────────────────────────────────────────────────
 
 describe('extractUserQuestion', () => {
-  it('extracts the first real user message', () => {
+  it('extracts the most recent user message', () => {
     const messages: ChatMessage[] = [
       { role: 'system', content: 'You are an assistant' },
       { role: 'user', content: 'What is the weather in Milan?' },
@@ -229,6 +229,26 @@ describe('extractUserQuestion', () => {
   it('returns fallback for empty messages', () => {
     expect(extractUserQuestion([])).toBe('(Unknown question)');
   });
+
+  it('picks the latest user question in multi-turn conversations', () => {
+    const messages: ChatMessage[] = [
+      { role: 'system', content: 'You are an assistant' },
+      { role: 'user', content: 'What is the capital of France?' },
+      { role: 'assistant', content: 'Paris.' },
+      { role: 'user', content: 'Now read the README.md from my repo and summarize it' },
+      { role: 'assistant', content: null, tool_calls: [{ id: 'tc1', type: 'function' as const, function: { name: 'github_read_file', arguments: '{}' } }] },
+      { role: 'tool', content: '# README content...', tool_call_id: 'tc1' },
+    ];
+    expect(extractUserQuestion(messages)).toBe('Now read the README.md from my repo and summarize it');
+  });
+
+  it('skips file injection blocks from Phase 7B.4', () => {
+    const messages: ChatMessage[] = [
+      { role: 'user', content: 'Read and summarize the project' },
+      { role: 'user', content: '[FILE: owner/repo/README.md]\n# Contents here...' },
+    ];
+    expect(extractUserQuestion(messages)).toBe('Read and summarize the project');
+  });
 });
 
 // ─── buildReviewMessages ────────────────────────────────────────────────────
diff --git a/src/openrouter/reviewer.ts b/src/openrouter/reviewer.ts
index f1792ab12..8b124638a 100644
--- a/src/openrouter/reviewer.ts
+++ b/src/openrouter/reviewer.ts
@@ -170,16 +170,19 @@ export function summarizeToolUsage(messages: readonly ChatMessage[]): string {
 }
 
 /**
- * Extract the original user question from the conversation messages.
- * Skips system messages and planning prompts.
+ * Extract the most recent user question from the conversation messages.
+ * Iterates backwards to find the latest user message, skipping injected phase prompts.
  */
 export function extractUserQuestion(messages: readonly ChatMessage[]): string {
-  for (const msg of messages) {
+  for (let i = messages.length - 1; i >= 0; i--) {
+    const msg = messages[i];
     if (msg.role !== 'user') continue;
     const text = typeof msg.content === 'string' ? msg.content : '';
     // Skip injected phase prompts
     if (text.includes('[PLANNING PHASE]') || text.includes('[REVIEW PHASE]')) continue;
     if (text.includes('STRUCTURED_PLAN_PROMPT') || text.startsWith('Before starting,')) continue;
+    // Skip file injection blocks (Phase 7B.4)
+    if (text.startsWith('[FILE:') || text.startsWith('Pre-loaded file contents')) continue;
     if (text.length > 10) return text;
   }
   return '(Unknown question)';
diff --git a/src/telegram/handler.ts b/src/telegram/handler.ts
index fe2033307..4e838eef8 100644
--- a/src/telegram/handler.ts
+++ b/src/telegram/handler.ts
@@ -2222,8 +2222,11 @@ export class TelegramHandler {
     const complexity = classifyTaskComplexity(messageText, fullHistory.length);
 
     // Route simple queries to fast models when user is on default 'auto' (Phase 7B.2)
+    // Use message-only complexity (ignoring conversation length) so that simple messages
+    // in long conversations still get routed to fast models.
     const autoRouteEnabled = await this.storage.getUserAutoRoute(userId);
-    const routing = routeByComplexity(modelAlias, complexity, autoRouteEnabled);
+    const routingComplexity = classifyTaskComplexity(messageText, 0);
+    const routing = routeByComplexity(modelAlias, routingComplexity, autoRouteEnabled);
     if (routing.wasRouted) {
       console.log(`[ModelRouter] ${routing.reason} (user=${userId})`);
       modelAlias = routing.modelAlias;