diff --git a/src/websocket/listen-client.ts b/src/websocket/listen-client.ts
index 831c082..0a60e05 100644
--- a/src/websocket/listen-client.ts
+++ b/src/websocket/listen-client.ts
@@ -136,6 +136,12 @@ interface GetStatusMessage {
   type: "get_status";
 }
 
+interface RecoverPendingApprovalsMessage {
+  type: "recover_pending_approvals";
+  agentId?: string;
+  conversationId?: string;
+}
+
 interface StatusResponseMessage {
   type: "status_response";
   currentMode: "default" | "acceptEdits" | "plan" | "bypassPermissions";
@@ -149,6 +155,7 @@ type ServerMessage =
   | IncomingMessage
   | ModeChangeMessage
   | GetStatusMessage
+  | RecoverPendingApprovalsMessage
   | WsControlResponse;
 type ClientMessage =
   | PingMessage
@@ -185,6 +192,8 @@ type ListenerRuntime = {
   pendingTurns: number;
   /** Optional debug hook for WS event logging. */
   onWsEvent?: StartListenerOptions["onWsEvent"];
+  /** Prevent duplicate concurrent pending-approval recovery passes. */
+  isRecoveringApprovals: boolean;
 };
 
 type ApprovalSlot =
@@ -249,6 +258,7 @@ function createRuntime(): ListenerRuntime {
     sessionId: `listen-${crypto.randomUUID()}`,
     lastStopReason: null,
     isProcessing: false,
+    isRecoveringApprovals: false,
     pendingTurns: 0,
     // queueRuntime assigned below — needs runtime ref in callbacks
     queueRuntime: null as unknown as QueueRuntime,
@@ -375,7 +385,8 @@ export function parseServerMessage(
       parsed.type === "status" ||
       parsed.type === "message" ||
       parsed.type === "mode_change" ||
-      parsed.type === "get_status"
+      parsed.type === "get_status" ||
+      parsed.type === "recover_pending_approvals"
     ) {
       return parsed as ServerMessage;
     }
@@ -673,6 +684,213 @@ function buildApprovalExecutionPlan(
   return { slots, decisions };
 }
 
+async function recoverPendingApprovals(
+  runtime: ListenerRuntime,
+  socket: WebSocket,
+  msg: RecoverPendingApprovalsMessage,
+): Promise<void> {
+  if (runtime.isProcessing || runtime.isRecoveringApprovals) {
+    return;
+  }
+
+  runtime.isRecoveringApprovals = true;
+  try {
+    const agentId = msg.agentId;
+    if (!agentId) {
+      return;
+    }
+
+    const requestedConversationId = msg.conversationId || undefined;
+    const conversationId = requestedConversationId ?? "default";
+
+    const client = await getClient();
+    const agent = await client.agents.retrieve(agentId);
+
+    let resumeData: Awaited<ReturnType<typeof getResumeData>>;
+    try {
+      resumeData = await getResumeData(client, agent, requestedConversationId, {
+        includeMessageHistory: false,
+      });
+    } catch (error) {
+      if (
+        error instanceof APIError &&
+        (error.status === 404 || error.status === 422)
+      ) {
+        return;
+      }
+      throw error;
+    }
+
+    const pendingApprovals = resumeData.pendingApprovals || [];
+    if (pendingApprovals.length === 0) {
+      return;
+    }
+
+    type Decision =
+      | {
+          type: "approve";
+          approval: {
+            toolCallId: string;
+            toolName: string;
+            toolArgs: string;
+          };
+        }
+      | {
+          type: "deny";
+          approval: {
+            toolCallId: string;
+            toolName: string;
+            toolArgs: string;
+          };
+          reason: string;
+        };
+
+    const { autoAllowed, autoDenied, needsUserInput } = await classifyApprovals(
+      pendingApprovals,
+      {
+        alwaysRequiresUserInput: isInteractiveApprovalTool,
+        treatAskAsDeny: false,
+        requireArgsForAutoApprove: true,
+      },
+    );
+
+    for (const ac of autoAllowed) {
+      emitToWS(socket, {
+        type: "auto_approval",
+        tool_call: {
+          name: ac.approval.toolName,
+          tool_call_id: ac.approval.toolCallId,
+          arguments: ac.approval.toolArgs,
+        },
+        reason: ac.permission.reason || "auto-approved",
+        matched_rule:
+          "matchedRule" in ac.permission && ac.permission.matchedRule
+            ? ac.permission.matchedRule
+            : "auto-approved",
+        session_id: runtime.sessionId,
+        uuid: `auto-approval-${ac.approval.toolCallId}`,
+      } as AutoApprovalMessage);
+    }
+
+    const decisions: Decision[] = [
+      ...autoAllowed.map((ac) => ({
+        type: "approve" as const,
+        approval: ac.approval,
+      })),
+      ...autoDenied.map((ac) => ({
+        type: "deny" as const,
+        approval: ac.approval,
+        reason: ac.denyReason || ac.permission.reason || "Permission denied",
+      })),
+    ];
+
+    if (needsUserInput.length > 0) {
+      if (!runtime.controlResponseCapable) {
+        runtime.lastStopReason = "requires_approval";
+        return;
+      }
+
+      for (const ac of needsUserInput) {
+        const requestId = `perm-${ac.approval.toolCallId}`;
+        const diffs = await computeDiffPreviews(
+          ac.approval.toolName,
+          ac.parsedArgs,
+        );
+
+        const controlRequest: ControlRequest = {
+          type: "control_request",
+          request_id: requestId,
+          request: {
+            subtype: "can_use_tool",
+            tool_name: ac.approval.toolName,
+            input: ac.parsedArgs,
+            tool_call_id: ac.approval.toolCallId,
+            permission_suggestions: [],
+            blocked_path: null,
+            ...(diffs.length > 0 ? { diffs } : {}),
+          },
+        };
+
+        const responseBody = await requestApprovalOverWS(
+          runtime,
+          socket,
+          requestId,
+          controlRequest,
+        );
+
+        if (responseBody.subtype === "success") {
+          const response = responseBody.response as
+            | CanUseToolResponse
+            | undefined;
+          if (response?.behavior === "allow") {
+            const finalApproval = response.updatedInput
+              ? {
+                  ...ac.approval,
+                  toolArgs: JSON.stringify(response.updatedInput),
+                }
+              : ac.approval;
+            decisions.push({ type: "approve", approval: finalApproval });
+
+            emitToWS(socket, {
+              type: "auto_approval",
+              tool_call: {
+                name: finalApproval.toolName,
+                tool_call_id: finalApproval.toolCallId,
+                arguments: finalApproval.toolArgs,
+              },
+              reason: "Approved via WebSocket",
+              matched_rule: "canUseTool callback",
+              session_id: runtime.sessionId,
+              uuid: `auto-approval-${ac.approval.toolCallId}`,
+            } as AutoApprovalMessage);
+          } else {
+            decisions.push({
+              type: "deny",
+              approval: ac.approval,
+              reason: response?.message || "Denied via WebSocket",
+            });
+          }
+        } else {
+          decisions.push({
+            type: "deny",
+            approval: ac.approval,
+            reason:
+              responseBody.subtype === "error"
+                ? responseBody.error
+                : "Unknown error",
+          });
+        }
+      }
+    }
+
+    if (decisions.length === 0) {
+      runtime.lastStopReason = "requires_approval";
+      return;
+    }
+
+    const executionResults = await executeApprovalBatch(decisions);
+
+    await handleIncomingMessage(
+      {
+        type: "message",
+        agentId,
+        conversationId,
+        messages: [
+          {
+            type: "approval",
+            approvals: executionResults,
+          },
+        ],
+        supportsControlResponse: runtime.controlResponseCapable,
+      },
+      socket,
+      runtime,
+    );
+  } finally {
+    runtime.isRecoveringApprovals = false;
+  }
+}
+
 /**
  * Start the listener WebSocket client with automatic retry.
  */
@@ -843,6 +1061,53 @@ async function connectWithRetry(
       return;
     }
 
+    if (parsed.type === "recover_pending_approvals") {
+      if (runtime !== activeRuntime || runtime.intentionallyClosed) {
+        return;
+      }
+
+      // Recovery requests are only sent by the modern cloud listener protocol.
+      runtime.controlResponseCapable = true;
+
+      // Serialize recovery with normal message handling to avoid concurrent
+      // handleIncomingMessage execution when user messages arrive concurrently.
+      runtime.pendingTurns++;
+      runtime.messageQueue = runtime.messageQueue
+        .then(async () => {
+          try {
+            if (runtime !== activeRuntime || runtime.intentionallyClosed) {
+              return;
+            }
+
+            await recoverPendingApprovals(runtime, socket, parsed);
+          } catch (error) {
+            const errorMessage =
+              error instanceof Error ? error.message : String(error);
+            emitToWS(socket, {
+              type: "error",
+              message: `Pending approval recovery failed: ${errorMessage}`,
+              stop_reason: "error",
+              session_id: runtime.sessionId,
+              uuid: `error-${crypto.randomUUID()}`,
+            });
+          } finally {
+            runtime.pendingTurns--;
+            if (runtime.pendingTurns === 0) {
+              runtime.queueRuntime.resetBlockedState();
+            }
+          }
+        })
+        .catch((error: unknown) => {
+          if (process.env.DEBUG) {
+            console.error(
+              "[Listen] Error handling queued pending approval recovery:",
+              error,
+            );
+          }
+        });
+      return;
+    }
+
     // Handle incoming messages (queued for sequential processing)
     if (parsed.type === "message") {
       // Queue lifecycle tracking: only enqueue if first payload is a