diff --git a/swift/apple/FirezoneNetworkExtension/Adapter.swift b/swift/apple/FirezoneNetworkExtension/Adapter.swift
index 45cf357ee..cc905f394 100644
--- a/swift/apple/FirezoneNetworkExtension/Adapter.swift
+++ b/swift/apple/FirezoneNetworkExtension/Adapter.swift
@@ -416,15 +416,17 @@ extension Adapter: CallbackHandlerDelegate {
   }
 
   func onDisconnect(error: DisconnectError) {
-    // Immediately invalidate our session pointer to prevent workQueue items from trying to use it.
-    // Assigning to `nil` will invoke `Drop` on the Rust side.
-    session = nil
-
     // Since connlib has already shutdown by this point, we queue this callback
     // to ensure that we can clean up even if connlib exits before we are done.
     workQueue.async { [weak self] in
       guard let self = self else { return }
 
+      // Immediately invalidate our session pointer to prevent workQueue items from trying to use it.
+      // Assigning to `nil` will invoke `Drop` on the Rust side.
+      // This must happen asynchronously and not as part of the callback to allow Rust to break
+      // cyclic dependencies between the runtime and the task that is executing the callback.
+      self.session = nil
+
       // If auth expired/is invalid, delete stored token and save the reason why so the GUI can act upon it.
       if error.isAuthenticationError() {
         do {