diff --git a/src/session.ts b/src/session.ts
index c81ae4a..a9fc39e 100644
--- a/src/session.ts
+++ b/src/session.ts
@@ -159,7 +159,8 @@ export type SessionStatus =
   | "waiting_for_user"
   | "completed"
   | "interrupted"
-  | "ask_permission";
+  | "ask_permission"
+  | "permission_denied";
 
 export type ModelUsage = {
   prompt_tokens: number;
@@ -1532,6 +1533,20 @@ ${skillMd}
     return !this.sessionControllers.has(sessionId);
   }
 
+  /**
+   * Mark a session's permission as denied by the user.
+   * Updates the session entry status and failReason so the denial is visible in the session list.
+   */
+  denySessionPermission(sessionId: string, reason?: string): void {
+    const now = new Date().toISOString();
+    this.updateSessionEntry(sessionId, (entry) => ({
+      ...entry,
+      status: "permission_denied",
+      failReason: reason ?? "Permission denied by user",
+      updateTime: now,
+    }));
+  }
+
   adjustActiveBashTimeout(deltaMs: number): BashTimeoutAdjustment | null {
     const sessionId = this.activeSessionId;
     if (!sessionId || !Number.isFinite(deltaMs)) {
@@ -2715,7 +2730,8 @@ ${skillMd}
       status === "waiting_for_user" ||
       status === "completed" ||
       status === "interrupted" ||
-      status === "ask_permission"
+      status === "ask_permission" ||
+      status === "permission_denied"
     ) {
       return status;
     }
diff --git a/src/tests/session.test.ts b/src/tests/session.test.ts
index e0a863e..95de8e3 100644
--- a/src/tests/session.test.ts
+++ b/src/tests/session.test.ts
@@ -1313,6 +1313,57 @@ test("activateSession pauses for permission when a tool call requires ask", asyn
   );
 });
 
+test("SessionManager preserves permission_denied status when sessions are reloaded", async () => {
+  const workspace = createTempDir("deepcode-permission-denied-workspace-");
+  const home = createTempDir("deepcode-permission-denied-home-");
+  setHomeDir(home);
+
+  const permissions = {
+    allow: [],
+    deny: [],
+    ask: [],
+    defaultMode: "askAll" as const,
+  };
+  const manager = createPermissionSessionManager(
+    workspace,
+    [
+      {
+        choices: [
+          {
+            message: {
+              content: "",
+              tool_calls: [
+                {
+                  id: "call-bash",
+                  type: "function",
+                  function: {
+                    name: "bash",
+                    arguments: JSON.stringify({
+                      command: "rg TODO src",
+                      description: "Search TODO markers",
+                      sideEffects: ["read-in-cwd"],
+                    }),
+                  },
+                },
+              ],
+            },
+          },
+        ],
+      },
+    ],
+    permissions
+  );
+
+  const sessionId = await manager.createSession({ text: "search todos" });
+  manager.denySessionPermission(sessionId);
+
+  const reloadedManager = createPermissionSessionManager(workspace, [], permissions);
+  const reloadedSession = reloadedManager.getSession(sessionId);
+
+  assert.equal(reloadedSession?.status, "permission_denied");
+  assert.equal(reloadedSession?.failReason, "Permission denied by user");
+});
+
 test("replySession applies permission replies, runs pending tools, and stores always allow scopes", async () => {
   const workspace = createTempDir("deepcode-permission-allow-workspace-");
   const home = createTempDir("deepcode-permission-allow-home-");
diff --git a/src/tests/sessionList.test.ts b/src/tests/sessionList.test.ts
index 3dfda33..6fe41c7 100644
--- a/src/tests/sessionList.test.ts
+++ b/src/tests/sessionList.test.ts
@@ -18,6 +18,8 @@ test("formatSessionStatus maps status values to display labels", () => {
   assert.equal(formatSessionStatus("waiting_for_user"), "waiting");
   assert.equal(formatSessionStatus("failed"), "failed");
   assert.equal(formatSessionStatus("interrupted"), "stopped");
+  assert.equal(formatSessionStatus("ask_permission"), "waiting");
+  assert.equal(formatSessionStatus("permission_denied"), "denied");
   assert.equal(formatSessionStatus("unknown_status" as any), "unknown_status");
 });
 
diff --git a/src/ui/App.tsx b/src/ui/App.tsx
index 71e9ca3..ae94fa0 100644
--- a/src/ui/App.tsx
+++ b/src/ui/App.tsx
@@ -669,6 +669,8 @@ function App({ projectRoot, initialPrompt, onRestart }: AppProps): React.ReactEl
           alwaysAllows: result.alwaysAllows,
         });
         setStatusLine("Permission denied. Add a reply, then press Enter to continue.");
+        setPromptDraft(null);
+        sessionManager.denySessionPermission(sessionId);
         return;
       }
       void handlePrompt({
@@ -686,6 +688,7 @@ function App({ projectRoot, initialPrompt, onRestart }: AppProps): React.ReactEl
     sessionManager.interruptActiveSession();
     setActiveStatus("interrupted");
     setActiveAskPermissions(undefined);
+    setPromptDraft(null);
     refreshSessionsList();
   }, [refreshSessionsList, sessionManager]);
 
diff --git a/src/ui/SessionList.tsx b/src/ui/SessionList.tsx
index 82ca797..2d83b84 100644
--- a/src/ui/SessionList.tsx
+++ b/src/ui/SessionList.tsx
@@ -332,6 +332,10 @@ export function formatSessionStatus(status: SessionStatus): string {
       return "failed";
     case "interrupted":
       return "stopped";
+    case "ask_permission":
+      return "waiting";
+    case "permission_denied":
+      return "denied";
     default:
       return status;
   }