diff --git a/CHANGELOG.md b/CHANGELOG.md
index 3830eb4..d03b81b 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -4,6 +4,7 @@
 
 ### JSON-RPC
 - fix: let non-interactive RPC startup proceed without a Contacts prompt while rejecting ambiguous name targets when Contacts is unavailable (#186, #187, thanks @SebTardif).
+- fix: fail vanished bridge queue requests immediately without treating an unobserved claim as safe to retry, avoiding long stalls and duplicate sends (#199, thanks @omarshahine).
 
 ### Reliability
 - fix: bound osascript send, reaction, and helper-process waits with process-tree cleanup so stalled subprocesses cannot hang CLI or RPC work (#197, thanks @SebTardif).
diff --git a/Sources/IMsgCore/IMsgBridgeClient.swift b/Sources/IMsgCore/IMsgBridgeClient.swift
index 10dc261..d5c8337 100644
--- a/Sources/IMsgCore/IMsgBridgeClient.swift
+++ b/Sources/IMsgCore/IMsgBridgeClient.swift
@@ -97,30 +97,97 @@ public final class IMsgBridgeClient: @unchecked Sendable {
     let deadline = Date().addingTimeInterval(timeout)
     while Date() < deadline {
       try await Task.sleep(nanoseconds: UInt64(pollInterval * 1_000_000_000))
-      guard
-        let data = try? Data(contentsOf: URL(fileURLWithPath: outPath)),
-        data.count > 1
-      else { continue }
-      // Best-effort cleanup; ignore failures (dylib may also unlink).
-      try? FileManager.default.removeItem(atPath: outPath)
-
-      guard
-        let raw = try? JSONSerialization.jsonObject(with: data, options: [])
-          as? [String: Any]
-      else {
-        throw IMsgBridgeError.malformedResponse("non-object body")
+      if let response = try readV2Response(outPath: outPath) {
+        return try unwrapV2Response(response)
       }
-      let response = try BridgeResponse.parse(raw)
-      if response.success {
-        return response.data
+      // No response yet. If the request itself is gone from the inbox, the
+      // queue was cleared out from under us — `MessagesLauncher` wipes both
+      // queue directories when it relaunches Messages.app with the dylib, so a
+      // request that disappears without a reply can never be answered. Polling
+      // on to the deadline just burns the caller's full send timeout (2.5
+      // minutes for sends) waiting for a reply that no longer has a writer.
+      //
+      // A request in normal flight is still on disk: unclaimed as
+      // `<id>.json`, or claimed by the dylib as `<id>.processing.<pid>`.
+      switch requestQueueState(inboxDir: inboxDir, id: id) {
+      case .unclaimed:
+        continue
+      case .claimed:
+        continue
+      case .absent:
+        // Re-check the outbox once: the reply is renamed into place before the
+        // claim is dropped, so a reply may have landed between our two checks.
+        if let response = try readV2Response(outPath: outPath) {
+          return try unwrapV2Response(response)
+        }
+        // A claim can be created, acted on, and removed between two polls. An
+        // absent request therefore never proves that the action did not run,
+        // even when this client did not observe the claimed state. Use the
+        // existing timeout case so callers cannot mistake this for a
+        // retry-safe bridge-not-ready failure.
+        throw IMsgBridgeError.timeout(action: action.rawValue)
       }
-      throw IMsgBridgeError.dylibReturnedError(response.error ?? "unknown")
     }
 
     try? FileManager.default.removeItem(atPath: final)
     throw IMsgBridgeError.timeout(action: action.rawValue)
   }
 
+  /// Read and consume a v2 reply if one is present.
+  private func readV2Response(outPath: String) throws -> BridgeResponse? {
+    guard
+      let data = try? Data(contentsOf: URL(fileURLWithPath: outPath)),
+      data.count > 1
+    else { return nil }
+    // Best-effort cleanup; ignore failures (dylib may also unlink).
+    try? FileManager.default.removeItem(atPath: outPath)
+
+    guard
+      let raw = try? JSONSerialization.jsonObject(with: data, options: [])
+        as? [String: Any]
+    else {
+      throw IMsgBridgeError.malformedResponse("non-object body")
+    }
+    return try BridgeResponse.parse(raw)
+  }
+
+  private func unwrapV2Response(_ response: BridgeResponse) throws -> [String: Any] {
+    if response.success {
+      return response.data
+    }
+    throw IMsgBridgeError.dylibReturnedError(response.error ?? "unknown")
+  }
+
+  /// On-disk state of a request still awaiting a reply.
+  enum RequestQueueState: Equatable {
+    /// `<id>.json` is present; nothing has read it yet.
+    case unclaimed
+    /// `<id>.processing.<pid>` is present; the dylib is handling it.
+    case claimed
+    /// Neither is present, so it was removed by something other than a
+    /// completed reply.
+    case absent
+  }
+
+  /// Classify the request's on-disk state.
+  ///
+  /// The dylib claims a request by renaming `<id>.json` to
+  /// `<id>.processing.<pid>` (see `processV2InboxFile`). The distinction
+  /// matters because only a never-claimed request is guaranteed not to have
+  /// run.
+  func requestQueueState(inboxDir: String, id: String) -> RequestQueueState {
+    let fm = FileManager.default
+    if fm.fileExists(atPath: (inboxDir as NSString).appendingPathComponent("\(id).json")) {
+      return .unclaimed
+    }
+    guard let entries = try? fm.contentsOfDirectory(atPath: inboxDir) else {
+      // Cannot enumerate: treat as still queued rather than ending a live
+      // request on a transient read error.
+      return .unclaimed
+    }
+    return entries.contains { $0.hasPrefix("\(id).processing.") } ? .claimed : .absent
+  }
+
   // MARK: - Legacy path
 
   private func invokeLegacy(
diff --git a/Tests/IMsgCoreTests/IMsgBridgeClientQueueTests.swift b/Tests/IMsgCoreTests/IMsgBridgeClientQueueTests.swift
new file mode 100644
index 0000000..4250b87
--- /dev/null
+++ b/Tests/IMsgCoreTests/IMsgBridgeClientQueueTests.swift
@@ -0,0 +1,105 @@
+import Foundation
+import Testing
+
+@testable import IMsgCore
+
+/// A v2 request that vanishes from the inbox without a reply can never be
+/// answered: `MessagesLauncher` wipes both queue directories when it relaunches
+/// Messages.app with the dylib. These cover the on-disk shapes the poll loop
+/// distinguishes, so a live request is never mistaken for a discarded one.
+@Suite("IMsgBridgeClient queue detection")
+struct IMsgBridgeClientQueueTests {
+  private func makeInbox() throws -> String {
+    let dir = (NSTemporaryDirectory() as NSString)
+      .appendingPathComponent("imsg-queue-tests-\(UUID().uuidString)")
+    try FileManager.default.createDirectory(
+      atPath: dir, withIntermediateDirectories: true
+    )
+    return dir
+  }
+
+  private func write(_ dir: String, _ name: String) {
+    FileManager.default.createFile(
+      atPath: (dir as NSString).appendingPathComponent(name),
+      contents: Data("{}".utf8)
+    )
+  }
+
+  private var client: IMsgBridgeClient {
+    IMsgBridgeClient(launcher: MessagesLauncher.shared)
+  }
+
+  @Test
+  func unclaimedRequestIsPending() throws {
+    let inbox = try makeInbox()
+    defer { try? FileManager.default.removeItem(atPath: inbox) }
+    let id = UUID().uuidString
+    write(inbox, "\(id).json")
+
+    #expect(client.requestQueueState(inboxDir: inbox, id: id) == .unclaimed)
+  }
+
+  @Test
+  func claimedRequestIsClaimed() throws {
+    let inbox = try makeInbox()
+    defer { try? FileManager.default.removeItem(atPath: inbox) }
+    let id = UUID().uuidString
+    // The dylib claims a request by renaming it to `<id>.processing.<pid>`
+    // (see processV2InboxFile); that is still in flight, not discarded.
+    write(inbox, "\(id).processing.4242")
+
+    #expect(client.requestQueueState(inboxDir: inbox, id: id) == .claimed)
+  }
+
+  @Test
+  func missingRequestIsAbsent() throws {
+    let inbox = try makeInbox()
+    defer { try? FileManager.default.removeItem(atPath: inbox) }
+    // An unrelated request must not keep ours alive.
+    write(inbox, "\(UUID().uuidString).json")
+
+    #expect(client.requestQueueState(inboxDir: inbox, id: UUID().uuidString) == .absent)
+  }
+
+  @Test
+  func unreadableInboxFailsSafeAsPending() {
+    // Cannot enumerate: keep waiting rather than ending a live request.
+    #expect(
+      client.requestQueueState(
+        inboxDir: "/nonexistent/imsg-queue-tests", id: UUID().uuidString
+      ) == .unclaimed
+    )
+  }
+
+  /// Both observable paths can end absent. The client must not infer delivery
+  /// safety from whether it happened to observe the short-lived claim state.
+  @Test
+  func absentStateDoesNotEncodeClaimHistory() throws {
+    let inbox = try makeInbox()
+    defer { try? FileManager.default.removeItem(atPath: inbox) }
+
+    let neverClaimed = UUID().uuidString
+    write(inbox, "\(neverClaimed).json")
+    #expect(client.requestQueueState(inboxDir: inbox, id: neverClaimed) == .unclaimed)
+    try FileManager.default.removeItem(
+      atPath: (inbox as NSString).appendingPathComponent("\(neverClaimed).json")
+    )
+    #expect(client.requestQueueState(inboxDir: inbox, id: neverClaimed) == .absent)
+
+    let claimed = UUID().uuidString
+    write(inbox, "\(claimed).json")
+    #expect(client.requestQueueState(inboxDir: inbox, id: claimed) == .unclaimed)
+    // Dylib claims it.
+    try FileManager.default.moveItem(
+      atPath: (inbox as NSString).appendingPathComponent("\(claimed).json"),
+      toPath: (inbox as NSString).appendingPathComponent("\(claimed).processing.99")
+    )
+    #expect(client.requestQueueState(inboxDir: inbox, id: claimed) == .claimed)
+    // Dylib dies; a later scan or relaunch clears the orphaned claim.
+    try FileManager.default.removeItem(
+      atPath: (inbox as NSString).appendingPathComponent("\(claimed).processing.99")
+    )
+    #expect(client.requestQueueState(inboxDir: inbox, id: claimed) == .absent)
+  }
+
+}