diff --git a/apps/macos/Sources/Clawdbot/ExecApprovals.swift b/apps/macos/Sources/Clawdbot/ExecApprovals.swift
index 53e0b10a8..537ceeaad 100644
--- a/apps/macos/Sources/Clawdbot/ExecApprovals.swift
+++ b/apps/macos/Sources/Clawdbot/ExecApprovals.swift
@@ -475,8 +475,8 @@ enum ExecApprovalsStore {
 
     private static func mergeAgents(
         current: ExecApprovalsAgent,
-        legacy: ExecApprovalsAgent
-    ) -> ExecApprovalsAgent {
+        legacy: ExecApprovalsAgent) -> ExecApprovalsAgent
+    {
         var seen = Set<String>()
         var allowlist: [ExecAllowlistEntry] = []
         func append(_ entry: ExecAllowlistEntry) {
@@ -486,8 +486,12 @@ enum ExecApprovalsStore {
             seen.insert(key)
             allowlist.append(entry)
         }
-        for entry in current.allowlist ?? [] { append(entry) }
-        for entry in legacy.allowlist ?? [] { append(entry) }
+        for entry in current.allowlist ?? [] {
+            append(entry)
+        }
+        for entry in legacy.allowlist ?? [] {
+            append(entry)
+        }
 
         return ExecApprovalsAgent(
             security: current.security ?? legacy.security,
diff --git a/apps/macos/Sources/Clawdbot/ExecApprovalsGatewayPrompter.swift b/apps/macos/Sources/Clawdbot/ExecApprovalsGatewayPrompter.swift
index 4b8389625..dbe80ecfe 100644
--- a/apps/macos/Sources/Clawdbot/ExecApprovalsGatewayPrompter.swift
+++ b/apps/macos/Sources/Clawdbot/ExecApprovalsGatewayPrompter.swift
@@ -63,26 +63,38 @@ final class ExecApprovalsGatewayPrompter {
         let mode = AppStateStore.shared.connectionMode
         let activeSession = WebChatManager.shared.activeSessionKey?.trimmingCharacters(in: .whitespacesAndNewlines)
         let requestSession = request.request.sessionKey?.trimmingCharacters(in: .whitespacesAndNewlines)
-        let recentlyActive = self.isRecentlyActive(mode: mode, thresholdSeconds: 120)
+        return Self.shouldPresent(
+            mode: mode,
+            activeSession: activeSession,
+            requestSession: requestSession,
+            lastInputSeconds: Self.lastInputSeconds(),
+            thresholdSeconds: 120)
+    }
 
-        if let session = requestSession, !session.isEmpty {
-            if let active = activeSession, !active.isEmpty {
+    private static func shouldPresent(
+        mode: AppState.ConnectionMode,
+        activeSession: String?,
+        requestSession: String?,
+        lastInputSeconds: Int?,
+        thresholdSeconds: Int) -> Bool
+    {
+        let active = activeSession?.trimmingCharacters(in: .whitespacesAndNewlines)
+        let requested = requestSession?.trimmingCharacters(in: .whitespacesAndNewlines)
+        let recentlyActive = lastInputSeconds.map { $0 <= thresholdSeconds } ?? (mode == .local)
+
+        if let session = requested, !session.isEmpty {
+            if let active, !active.isEmpty {
                 return active == session
             }
             return recentlyActive
         }
 
-        if let active = activeSession, !active.isEmpty {
+        if let active, !active.isEmpty {
             return true
         }
         return mode == .local
     }
 
-    private func isRecentlyActive(mode: AppState.ConnectionMode, thresholdSeconds: Int) -> Bool {
-        guard let seconds = Self.lastInputSeconds() else { return mode == .local }
-        return seconds <= thresholdSeconds
-    }
-
     private static func lastInputSeconds() -> Int? {
         let anyEvent = CGEventType(rawValue: UInt32.max) ?? .null
         let seconds = CGEventSource.secondsSinceLastEventType(.combinedSessionState, eventType: anyEvent)
@@ -90,3 +102,22 @@ final class ExecApprovalsGatewayPrompter {
         return Int(seconds.rounded())
     }
 }
+
+#if DEBUG
+extension ExecApprovalsGatewayPrompter {
+    static func _testShouldPresent(
+        mode: AppState.ConnectionMode,
+        activeSession: String?,
+        requestSession: String?,
+        lastInputSeconds: Int?,
+        thresholdSeconds: Int = 120) -> Bool
+    {
+        self.shouldPresent(
+            mode: mode,
+            activeSession: activeSession,
+            requestSession: requestSession,
+            lastInputSeconds: lastInputSeconds,
+            thresholdSeconds: thresholdSeconds)
+    }
+}
+#endif
diff --git a/apps/macos/Sources/Clawdbot/GatewayEndpointStore.swift b/apps/macos/Sources/Clawdbot/GatewayEndpointStore.swift
index 418d0b810..633b7d872 100644
--- a/apps/macos/Sources/Clawdbot/GatewayEndpointStore.swift
+++ b/apps/macos/Sources/Clawdbot/GatewayEndpointStore.swift
@@ -560,13 +560,13 @@ actor GatewayEndpointStore {
     {
         switch bindMode {
         case "tailnet":
-            return tailscaleIP ?? "127.0.0.1"
+            tailscaleIP ?? "127.0.0.1"
         case "auto":
-            return "127.0.0.1"
+            "127.0.0.1"
         case "custom":
-            return customBindHost ?? "127.0.0.1"
+            customBindHost ?? "127.0.0.1"
         default:
-            return "127.0.0.1"
+            "127.0.0.1"
         }
     }
 }
diff --git a/apps/macos/Sources/Clawdbot/MenuSessionsInjector.swift b/apps/macos/Sources/Clawdbot/MenuSessionsInjector.swift
index 6aab7910e..b39138277 100644
--- a/apps/macos/Sources/Clawdbot/MenuSessionsInjector.swift
+++ b/apps/macos/Sources/Clawdbot/MenuSessionsInjector.swift
@@ -192,7 +192,8 @@ extension MenuSessionsInjector {
             let headerItem = NSMenuItem()
             headerItem.tag = self.tag
             headerItem.isEnabled = false
-            let statusText = self.cachedErrorText ?? (isConnected ? nil : self.controlChannelStatusText(for: channelState))
+            let statusText = self
+                .cachedErrorText ?? (isConnected ? nil : self.controlChannelStatusText(for: channelState))
             let hosted = self.makeHostedView(
                 rootView: AnyView(MenuSessionsHeaderView(
                     count: rows.count,
diff --git a/apps/macos/Tests/ClawdbotIPCTests/ExecApprovalsGatewayPrompterTests.swift b/apps/macos/Tests/ClawdbotIPCTests/ExecApprovalsGatewayPrompterTests.swift
new file mode 100644
index 000000000..88fb02f2b
--- /dev/null
+++ b/apps/macos/Tests/ClawdbotIPCTests/ExecApprovalsGatewayPrompterTests.swift
@@ -0,0 +1,56 @@
+import Testing
+@testable import Clawdbot
+
+@Suite
+@MainActor
+struct ExecApprovalsGatewayPrompterTests {
+    @Test func sessionMatchPrefersActiveSession() {
+        let matches = ExecApprovalsGatewayPrompter._testShouldPresent(
+            mode: .remote,
+            activeSession: " main ",
+            requestSession: "main",
+            lastInputSeconds: nil)
+        #expect(matches)
+
+        let mismatched = ExecApprovalsGatewayPrompter._testShouldPresent(
+            mode: .remote,
+            activeSession: "other",
+            requestSession: "main",
+            lastInputSeconds: 0)
+        #expect(!mismatched)
+    }
+
+    @Test func sessionFallbackUsesRecentActivity() {
+        let recent = ExecApprovalsGatewayPrompter._testShouldPresent(
+            mode: .remote,
+            activeSession: nil,
+            requestSession: "main",
+            lastInputSeconds: 10,
+            thresholdSeconds: 120)
+        #expect(recent)
+
+        let stale = ExecApprovalsGatewayPrompter._testShouldPresent(
+            mode: .remote,
+            activeSession: nil,
+            requestSession: "main",
+            lastInputSeconds: 200,
+            thresholdSeconds: 120)
+        #expect(!stale)
+    }
+
+    @Test func defaultBehaviorMatchesMode() {
+        let local = ExecApprovalsGatewayPrompter._testShouldPresent(
+            mode: .local,
+            activeSession: nil,
+            requestSession: nil,
+            lastInputSeconds: 400)
+        #expect(local)
+
+        let remote = ExecApprovalsGatewayPrompter._testShouldPresent(
+            mode: .remote,
+            activeSession: nil,
+            requestSession: nil,
+            lastInputSeconds: 400)
+        #expect(!remote)
+    }
+}
diff --git a/apps/macos/Tests/ClawdbotIPCTests/GatewayProcessManagerTests.swift b/apps/macos/Tests/ClawdbotIPCTests/GatewayProcessManagerTests.swift
index 18e529389..05c96f8be 100644
--- a/apps/macos/Tests/ClawdbotIPCTests/GatewayProcessManagerTests.swift
+++ b/apps/macos/Tests/ClawdbotIPCTests/GatewayProcessManagerTests.swift
@@ -1,3 +1,4 @@
+import ClawdbotKit
 import Foundation
 import os
 import Testing