diff --git a/packages/app/src/utils/agent-grouping.ts b/packages/app/src/utils/agent-grouping.ts
index 8f7ebe8d9..f5dcfad26 100644
--- a/packages/app/src/utils/agent-grouping.ts
+++ b/packages/app/src/utils/agent-grouping.ts
@@ -192,6 +192,10 @@ export interface ProjectGroup {
   projectKey: string;
   projectName: string;
   agents: AggregatedAgent[];
+  /** Number of truly active agents (running or requires attention) */
+  activeCount: number;
+  /** Total agents before any limit was applied */
+  totalCount: number;
 }
 
 export interface DateGroup {
@@ -204,7 +208,7 @@ export interface GroupedAgents {
   inactiveGroups: DateGroup[];
 }
 
-const ACTIVE_GRACE_PERIOD_MS = 15 * 60 * 1000; // 15 minutes
+const ACTIVE_GRACE_PERIOD_MS = 24 * 60 * 60 * 1000; // 24 hours
 
 interface GroupAgentsOptions {
   /**
@@ -214,9 +218,15 @@ interface GroupAgentsOptions {
   getRemoteUrl?: (agent: AggregatedAgent) => string | null;
 }
 
+const MAX_INACTIVE_PER_PROJECT = 5;
+
 /**
  * Groups agents into active (by project) and inactive (by date) sections.
- * Active = running, requires attention, or had activity within the last 5 minutes.
+ * Active = running, requires attention, or had activity within the grace period (24 hours).
+ *
+ * Within each project group:
+ * - All truly active agents (running/requires attention) are always shown
+ * - Recently active (within grace period but not running) are limited to MAX_INACTIVE_PER_PROJECT
  */
 export function groupAgents(
   agents: AggregatedAgent[],
@@ -240,28 +250,61 @@ export function groupAgents(
     }
   }
 
-  // Group active agents by project
-  const projectMap = new Map<string, AggregatedAgent[]>();
+  // Group active agents by project, tracking truly active vs recently active
+  const projectMap = new Map<
+    string,
+    { trulyActive: AggregatedAgent[]; recentlyActive: AggregatedAgent[] }
+  >();
   for (const agent of activeAgents) {
     const remoteKey = deriveRemoteProjectKey(
       options?.getRemoteUrl?.(agent) ?? null
     );
     const projectKey = remoteKey ?? deriveProjectKey(agent.cwd);
-    const existing = projectMap.get(projectKey) || [];
-    existing.push(agent);
+    const existing = projectMap.get(projectKey) || {
+      trulyActive: [],
+      recentlyActive: [],
+    };
+
+    const isTrulyActive =
+      agent.status === "running" || agent.requiresAttention;
+    if (isTrulyActive) {
+      existing.trulyActive.push(agent);
+    } else {
+      existing.recentlyActive.push(agent);
+    }
+
     projectMap.set(projectKey, existing);
   }
 
-  // Sort agents within each project by lastActivityAt (newest first)
+  // Build project groups with limits applied
   const activeGroups: ProjectGroup[] = [];
-  for (const [projectKey, projectAgents] of projectMap) {
-    projectAgents.sort(
+  for (const [projectKey, { trulyActive, recentlyActive }] of projectMap) {
+    // Sort both arrays by lastActivityAt (newest first)
+    trulyActive.sort(
       (a, b) => b.lastActivityAt.getTime() - a.lastActivityAt.getTime()
     );
+    recentlyActive.sort(
+      (a, b) => b.lastActivityAt.getTime() - a.lastActivityAt.getTime()
+    );
+
+    // All truly active agents shown, limit recently active to MAX_INACTIVE_PER_PROJECT
+    const limitedRecentlyActive = recentlyActive.slice(
+      0,
+      MAX_INACTIVE_PER_PROJECT
+    );
+    const combinedAgents = [...trulyActive, ...limitedRecentlyActive];
+
+    // Re-sort combined list by lastActivityAt
+    combinedAgents.sort(
+      (a, b) => b.lastActivityAt.getTime() - a.lastActivityAt.getTime()
+    );
+
     activeGroups.push({
       projectKey,
       projectName: deriveProjectName(projectKey),
-      agents: projectAgents,
+      agents: combinedAgents,
+      activeCount: trulyActive.length,
+      totalCount: trulyActive.length + recentlyActive.length,
     });
   }
 
diff --git a/packages/server/src/client/daemon-client-v2.ts b/packages/server/src/client/daemon-client-v2.ts
index 980abc0a7..9728bd226 100644
--- a/packages/server/src/client/daemon-client-v2.ts
+++ b/packages/server/src/client/daemon-client-v2.ts
@@ -1046,6 +1046,10 @@ export class DaemonClientV2 {
     if (!requestId) {
       const existing = this.checkoutStatusInFlight.get(agentId);
       if (existing) {
+        this.logger.debug(
+          { agentId, inFlightCount: this.checkoutStatusInFlight.size },
+          "getCheckoutStatus: returning existing in-flight request"
+        );
         return existing;
       }
     }
@@ -1057,6 +1061,11 @@ export class DaemonClientV2 {
       requestId: resolvedRequestId,
     });
 
+    this.logger.debug(
+      { agentId, requestId: resolvedRequestId, waiterCount: this.waiters.size },
+      "getCheckoutStatus: creating new request"
+    );
+
     const responsePromise = (async () => {
       const response = this.waitFor(
         (msg) => {
@@ -1077,11 +1086,24 @@ export class DaemonClientV2 {
 
     if (!requestId) {
       this.checkoutStatusInFlight.set(agentId, responsePromise);
-      responsePromise.finally(() => {
-        if (this.checkoutStatusInFlight.get(agentId) === responsePromise) {
-          this.checkoutStatusInFlight.delete(agentId);
-        }
-      });
+      responsePromise
+        .then(() => {
+          this.logger.debug(
+            { agentId, requestId: resolvedRequestId },
+            "getCheckoutStatus: request completed successfully"
+          );
+        })
+        .catch((err) => {
+          this.logger.debug(
+            { agentId, requestId: resolvedRequestId, error: err?.message },
+            "getCheckoutStatus: request failed"
+          );
+        })
+        .finally(() => {
+          if (this.checkoutStatusInFlight.get(agentId) === responsePromise) {
+            this.checkoutStatusInFlight.delete(agentId);
+          }
+        });
     }
 
     return responsePromise;
@@ -2099,6 +2121,10 @@ export class DaemonClientV2 {
       this.lastErrorValue = reason.trim();
     }
 
+    // Clear all pending waiters since the connection was lost and responses
+    // from the previous connection will never arrive.
+    this.clearWaiters(new Error(reason ?? "Connection lost"));
+
     this.updateConnectionState({
       status: "disconnected",
       ...(reason ? { reason } : {}),
diff --git a/packages/server/src/server/daemon-e2e/checkout-debug.ts b/packages/server/src/server/daemon-e2e/checkout-debug.ts
new file mode 100644
index 000000000..453ae87c7
--- /dev/null
+++ b/packages/server/src/server/daemon-e2e/checkout-debug.ts
@@ -0,0 +1,168 @@
+#!/usr/bin/env npx tsx
+/**
+ * Ad-hoc script to debug checkout_status_request timeouts.
+ *
+ * Usage:
+ *   npx tsx packages/server/src/server/daemon-e2e/checkout-debug.ts [agentId1] [agentId2]
+ *
+ * To test against a different daemon:
+ *   PASEO_PORT=7777 npx tsx packages/server/src/server/daemon-e2e/checkout-debug.ts
+ */
+
+import { WebSocket } from "ws";
+import { DaemonClientV2 } from "../../client/daemon-client-v2.js";
+
+// Patch WebSocket to log all messages
+const OriginalWebSocket = WebSocket;
+class LoggingWebSocket extends OriginalWebSocket {
+  constructor(url: string, ...args: any[]) {
+    super(url, ...args);
+    console.log(`[WS] Connecting to ${url}`);
+    this.on("open", () => console.log("[WS] Connection opened"));
+    this.on("close", (code, reason) => console.log(`[WS] Connection closed: ${code} ${reason}`));
+    this.on("error", (err) => console.log(`[WS] Error: ${err}`));
+    this.on("message", (data) => {
+      const str = data.toString().slice(0, 200);
+      console.log(`[WS] Message received (${data.toString().length} bytes): ${str}...`);
+    });
+  }
+}
+
+const PASEO_HOME = process.env.PASEO_HOME ?? "/Users/moboudra/.paseo";
+const PASEO_PORT = process.env.PASEO_PORT ?? "6767";
+const DAEMON_URL = `ws://127.0.0.1:${PASEO_PORT}/ws`;
+
+async function testMultiAgentSequence() {
+  console.log("\n=== Testing multi-agent checkout sequence ===");
+  console.log(`Daemon URL: ${DAEMON_URL}`);
+
+  const client = new DaemonClientV2({
+    url: DAEMON_URL,
+    webSocketFactory: (url) => new LoggingWebSocket(url) as any,
+    reconnect: { enabled: false },
+  });
+
+  const agents: Array<{ id: string; title: string }> = [];
+
+  // Subscribe to all events for debugging
+  const unsub = client.subscribe((event) => {
+    console.log(`[Event] type=${event.type}`);
+    if (event.type === "session_state") {
+      console.log(`  ${event.agents.length} agents`);
+      agents.length = 0;
+      for (const a of event.agents) {
+        agents.push({ id: a.id, title: a.title ?? "(untitled)" });
+      }
+    }
+  });
+
+  // Also log ALL raw messages
+  client.on("session_state", (msg: any) => {
+    console.log(`[RAW session_state] agents=${msg.agents?.length}`);
+  });
+
+  // Also log raw messages for debugging
+  client.on("checkout_status_response", (msg: any) => {
+    console.log(`[RAW checkout_status_response] requestId=${msg.payload.requestId} agentId=${msg.payload.agentId}`);
+  });
+
+  // Listen to connection state changes
+  client.subscribeConnectionStatus((state) => {
+    console.log(`[Connection] status=${state.status}`);
+  });
+
+  try {
+    await client.connect();
+    console.log("Connected to daemon");
+    console.log(`Connection state: ${JSON.stringify(client.getConnectionState())}`);
+
+    // Request session state (the app does this after connecting)
+    console.log("Requesting session state...");
+    client.requestSessionState();
+
+    // Wait a bit for session state to arrive
+    console.log("Waiting 3s for session state...");
+    await new Promise((r) => setTimeout(r, 3000));
+
+    if (agents.length === 0) {
+      console.log("No agents found!");
+      return;
+    }
+
+    console.log("\nAvailable agents:");
+    for (const a of agents.slice(0, 10)) {
+      console.log(`  - ${a.id.slice(0, 8)}... ${a.title}`);
+    }
+    if (agents.length > 10) {
+      console.log(`  ... and ${agents.length - 10} more`);
+    }
+
+    // Pick first two agents (or use command line args)
+    const agent1Id = process.argv[2] ?? agents[0]?.id;
+    const agent2Id = process.argv[3] ?? agents[1]?.id ?? agents[0]?.id;
+
+    if (!agent1Id) {
+      console.log("No agents available to test");
+      return;
+    }
+
+    console.log(`\n=== Test 1: Request checkout for agent1 (${agent1Id.slice(0, 8)}...) ===`);
+    const start1 = Date.now();
+    try {
+      const status1 = await client.getCheckoutStatus(agent1Id);
+      console.log(`✓ Agent1 completed in ${Date.now() - start1}ms - branch: ${status1.currentBranch}`);
+    } catch (err) {
+      console.log(`✗ Agent1 failed after ${Date.now() - start1}ms:`, err);
+    }
+
+    console.log(`\n=== Test 2: Request checkout for agent2 (${agent2Id.slice(0, 8)}...) ===`);
+    const start2 = Date.now();
+    try {
+      const status2 = await client.getCheckoutStatus(agent2Id);
+      console.log(`✓ Agent2 completed in ${Date.now() - start2}ms - branch: ${status2.currentBranch}`);
+    } catch (err) {
+      console.log(`✗ Agent2 failed after ${Date.now() - start2}ms:`, err);
+    }
+
+    console.log(`\n=== Test 3: Request checkout for agent1 again ===`);
+    const start3 = Date.now();
+    try {
+      const status3 = await client.getCheckoutStatus(agent1Id);
+      console.log(`✓ Agent1 (retry) completed in ${Date.now() - start3}ms - branch: ${status3.currentBranch}`);
+    } catch (err) {
+      console.log(`✗ Agent1 (retry) failed after ${Date.now() - start3}ms:`, err);
+    }
+
+    console.log(`\n=== Test 4: Request both agents in parallel ===`);
+    const start4 = Date.now();
+    try {
+      const [p1, p2] = await Promise.all([
+        client.getCheckoutStatus(agent1Id),
+        client.getCheckoutStatus(agent2Id),
+      ]);
+      console.log(`✓ Parallel completed in ${Date.now() - start4}ms`);
+      console.log(`  Agent1 branch: ${p1.currentBranch}`);
+      console.log(`  Agent2 branch: ${p2.currentBranch}`);
+    } catch (err) {
+      console.log(`✗ Parallel failed after ${Date.now() - start4}ms:`, err);
+    }
+
+  } catch (error) {
+    console.error("Test failed:", error);
+  } finally {
+    unsub();
+    await client.close();
+  }
+}
+
+async function main() {
+  console.log("Checkout Debug Script - Multi-Agent Sequence Test");
+  console.log("==================================================");
+  console.log(`PASEO_HOME: ${PASEO_HOME}`);
+
+  await testMultiAgentSequence();
+
+  console.log("\n=== Done ===");
+}
+
+main().catch(console.error);