diff --git a/Sources/OmniFocusAutomation/BridgeClient.swift b/Sources/OmniFocusAutomation/BridgeClient.swift
index 3e3721a..1cb89e2 100644
--- a/Sources/OmniFocusAutomation/BridgeClient.swift
+++ b/Sources/OmniFocusAutomation/BridgeClient.swift
@@ -500,8 +500,13 @@ final class BridgeClient: @unchecked Sendable {
 
         let timeoutSeconds = String(format: "%.1f", timeout)
         let lastReadDetail = lastReadError.map { String(describing: $0) } ?? "none"
+        let pickupState = bridgePickupState(
+            requestExists: requestExists,
+            responseExists: responseExists,
+            lockExists: lockExists
+        )
         throw AutomationError.executionFailed(
-            "Bridge response timed out after \(timeoutSeconds)s (requestId=\(requestId), requestExists=\(requestExists), responseExists=\(responseExists), lockExists=\(lockExists), lastReadError=\(lastReadDetail))"
+            "Bridge response timed out after \(timeoutSeconds)s (requestId=\(requestId), pickupState=\(pickupState), requestExists=\(requestExists), responseExists=\(responseExists), lockExists=\(lockExists), strandedRedispatched=\(hasRedispatchedStrandedRequest), lastReadError=\(lastReadDetail))"
         )
     }
 
@@ -611,6 +616,13 @@ func strandedRedispatchDelay(timeout: TimeInterval) -> TimeInterval {
     min(2.0, max(0.5, timeout * 0.1))
 }
 
+func bridgePickupState(requestExists: Bool, responseExists: Bool, lockExists: Bool) -> String {
+    if responseExists { return "response_written" }
+    if lockExists { return "bridge_processing" }
+    if requestExists { return "stranded_not_picked_up" }
+    return "request_missing"
+}
+
 func lateStrandedRecoveryGrace(timeout: TimeInterval) -> TimeInterval {
     min(10.0, max(3.0, timeout * 0.2))
 }
diff --git a/Tests/OmniFocusIntegrationTests/BridgeClientTests.swift b/Tests/OmniFocusIntegrationTests/BridgeClientTests.swift
index a28c314..e142043 100644
--- a/Tests/OmniFocusIntegrationTests/BridgeClientTests.swift
+++ b/Tests/OmniFocusIntegrationTests/BridgeClientTests.swift
@@ -106,3 +106,30 @@ func lateStrandedRecoveryOnlyAppliesToURLTransportWithoutLock() {
         lockExists: false
     ))
 }
+
+@Test
+func bridgePickupStateNamesTimeoutCause() {
+    #expect(bridgePickupState(
+        requestExists: true,
+        responseExists: false,
+        lockExists: false
+    ) == "stranded_not_picked_up")
+
+    #expect(bridgePickupState(
+        requestExists: true,
+        responseExists: false,
+        lockExists: true
+    ) == "bridge_processing")
+
+    #expect(bridgePickupState(
+        requestExists: true,
+        responseExists: true,
+        lockExists: false
+    ) == "response_written")
+
+    #expect(bridgePickupState(
+        requestExists: false,
+        responseExists: false,
+        lockExists: false
+    ) == "request_missing")
+}