diff --git a/artifacts/api-server/src/routes/sessions.ts b/artifacts/api-server/src/routes/sessions.ts
index 036d79e..7cb4a5c 100644
--- a/artifacts/api-server/src/routes/sessions.ts
+++ b/artifacts/api-server/src/routes/sessions.ts
@@ -228,6 +228,7 @@ router.get("/sessions/:id", async (req: Request, res: Response) => {
         .update(sessions)
         .set({ state: "expired", updatedAt: new Date() })
         .where(eq(sessions.id, id));
+      await db.delete(sessionMessages).where(eq(sessionMessages.sessionId, id));
       session = (await getSessionById(id))!;
     }
 
@@ -314,6 +315,11 @@ router.post("/sessions/:id/request", async (req: Request, res: Response) => {
 
     // Load conversation history for context injection
     const history = await getSessionHistory(id, 8, 4000);
+    // Defensive check: log a warning if history still exceeds budget
+    const currentTokenCount = history.reduce((sum, msg) => sum + Math.ceil(msg.content.length / 4), 0);
+    if (currentTokenCount > 4000) {
+      console.warn(`Session ${id}: History exceeds 4000 token budget after retrieval. Actual: ${currentTokenCount}`);
+    }
 
     // Eval phase
     const evalResult = await agentService.evaluateRequest(requestText);