diff --git a/CHANGELOG.md b/CHANGELOG.md
index 2eed6335aec..a3964f87577 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -6,7 +6,7 @@
 
 ### Fixed
 * <How do the end-user experience this issue? what was the impact?> ([#????](https://github.com/realm/realm-core/issues/????), since v?.?.?)
-* None.
+* Fix a race condition which could result in "operation cancelled" errors being delivered to async open callbacks rather than the actual sync error which caused things to fail ([PR #5968](https://github.com/realm/realm-core/pull/5968), since the introduction of async open).
  
 ### Breaking changes
 * None.
diff --git a/src/realm/object-store/audit.mm b/src/realm/object-store/audit.mm
index 4386504e7a5..b41af72c237 100644
--- a/src/realm/object-store/audit.mm
+++ b/src/realm/object-store/audit.mm
@@ -807,6 +807,7 @@ bool write_event(Timestamp timestamp, StringData activity, StringData event_type
         // there's any old ones sitting on disk waiting to be uploaded.
         scan_for_realms_to_upload();
     });
+    session->revive_if_needed();
 }
 
 std::string AuditRealmPool::prefixed_partition(std::string const& partition)
diff --git a/src/realm/object-store/impl/realm_coordinator.cpp b/src/realm/object-store/impl/realm_coordinator.cpp
index 97dca55def7..436380d092d 100644
--- a/src/realm/object-store/impl/realm_coordinator.cpp
+++ b/src/realm/object-store/impl/realm_coordinator.cpp
@@ -287,16 +287,20 @@ void RealmCoordinator::do_get_realm(Realm::Config config, std::shared_ptr<Realm>
     realm = Realm::make_shared_realm(std::move(config), version, shared_from_this());
     m_weak_realm_notifiers.emplace_back(realm, config.cache);
 
-    if (realm->config().audit_config) {
 #ifdef REALM_ENABLE_SYNC
+    if (m_sync_session && m_sync_session->user()->is_logged_in())
+        m_sync_session->revive_if_needed();
+
+    if (realm->config().audit_config) {
         if (m_audit_context)
             m_audit_context->update_metadata(realm->config().audit_config->metadata);
         else
             m_audit_context = make_audit_context(m_db, realm->config());
+    }
 #else
+    if (realm->config().audit_config)
         REALM_TERMINATE("Cannot use Audit interface if Realm Core is built without Sync");
 #endif
-    }
 
     realm_lock.unlock_unchecked();
     if (schema) {
@@ -408,7 +412,6 @@ void RealmCoordinator::open_db()
         m_sync_session = m_config.sync_config->user->sync_manager()->get_existing_session(m_config.path);
         if (m_sync_session) {
             m_db = SyncSession::Internal::get_db(*m_sync_session);
-            m_sync_session->revive_if_needed();
             init_external_helpers();
             return;
         }
diff --git a/src/realm/object-store/sync/async_open_task.cpp b/src/realm/object-store/sync/async_open_task.cpp
index a7e645f76f4..b08fdbef8d5 100644
--- a/src/realm/object-store/sync/async_open_task.cpp
+++ b/src/realm/object-store/sync/async_open_task.cpp
@@ -34,14 +34,14 @@ AsyncOpenTask::AsyncOpenTask(std::shared_ptr<_impl::RealmCoordinator> coordinato
 
 void AsyncOpenTask::start(util::UniqueFunction<void(ThreadSafeReference, std::exception_ptr)> callback)
 {
-    util::CheckedLockGuard lock(m_mutex);
+    util::CheckedUniqueLock lock(m_mutex);
     if (!m_session)
         return;
-
-    m_session->revive_if_needed();
+    auto session = m_session;
+    lock.unlock();
 
     std::shared_ptr<AsyncOpenTask> self(shared_from_this());
-    m_session->wait_for_download_completion([callback = std::move(callback), self, this](std::error_code ec) {
+    session->wait_for_download_completion([callback = std::move(callback), self, this](std::error_code ec) {
         std::shared_ptr<_impl::RealmCoordinator> coordinator;
         {
             util::CheckedLockGuard lock(m_mutex);
@@ -68,6 +68,8 @@ void AsyncOpenTask::start(util::UniqueFunction<void(ThreadSafeReference, std::ex
         }
         callback(std::move(realm), nullptr);
     });
+
+    session->revive_if_needed();
 }
 
 void AsyncOpenTask::cancel()
diff --git a/src/realm/object-store/sync/sync_manager.cpp b/src/realm/object-store/sync/sync_manager.cpp
index 6420f1ef095..0c69c34dd65 100644
--- a/src/realm/object-store/sync/sync_manager.cpp
+++ b/src/realm/object-store/sync/sync_manager.cpp
@@ -217,34 +217,36 @@ void SyncManager::reset_for_testing()
         m_users.clear();
         m_current_user = nullptr;
     }
-    {
-        util::CheckedLockGuard lock1(m_mutex);
 
+    {
+        util::CheckedLockGuard lock(m_mutex);
         // Stop the client. This will abort any uploads that inactive sessions are waiting for.
         if (m_sync_client)
             m_sync_client->stop();
+    }
 
-        {
-            util::CheckedLockGuard lock2(m_session_mutex);
-            // Callers of `SyncManager::reset_for_testing` should ensure there are no existing sessions
-            // prior to calling `reset_for_testing`.
-            bool no_sessions = !do_has_existing_sessions();
-            REALM_ASSERT_RELEASE(no_sessions);
-
-            // Destroy any inactive sessions.
-            // FIXME: We shouldn't have any inactive sessions at this point! Sessions are expected to
-            // remain inactive until their final upload completes, at which point they are unregistered
-            // and destroyed. Our call to `sync::Client::stop` above aborts all uploads, so all sessions
-            // should have already been destroyed.
-            m_sessions.clear();
-        }
+    {
+        util::CheckedLockGuard lock(m_session_mutex);
+        // Callers of `SyncManager::reset_for_testing` should ensure there are no existing sessions
+        // prior to calling `reset_for_testing`.
+        bool no_sessions = !do_has_existing_sessions();
+        REALM_ASSERT_RELEASE(no_sessions);
+
+        // Destroy any inactive sessions.
+        // FIXME: We shouldn't have any inactive sessions at this point! Sessions are expected to
+        // remain inactive until their final upload completes, at which point they are unregistered
+        // and destroyed. Our call to `sync::Client::stop` above aborts all uploads, so all sessions
+        // should have already been destroyed.
+        m_sessions.clear();
+    }
 
+    {
+        util::CheckedLockGuard lock(m_mutex);
         // Destroy the client now that we have no remaining sessions.
         m_sync_client = nullptr;
 
         // Reset even more state.
         m_config = {};
-
         m_sync_route = "";
     }
 
diff --git a/src/realm/object-store/sync/sync_manager.hpp b/src/realm/object-store/sync/sync_manager.hpp
index fe9fb44c300..abcf8187529 100644
--- a/src/realm/object-store/sync/sync_manager.hpp
+++ b/src/realm/object-store/sync/sync_manager.hpp
@@ -281,7 +281,7 @@ class SyncManager : public std::enable_shared_from_this<SyncManager> {
     std::vector<std::shared_ptr<SyncUser>> m_users GUARDED_BY(m_user_mutex);
     std::shared_ptr<SyncUser> m_current_user GUARDED_BY(m_user_mutex);
 
-    mutable std::unique_ptr<_impl::SyncClient> m_sync_client;
+    mutable std::unique_ptr<_impl::SyncClient> m_sync_client GUARDED_BY(m_mutex);
 
     SyncClientConfig m_config GUARDED_BY(m_mutex);
 
diff --git a/src/realm/object-store/sync/sync_user.cpp b/src/realm/object-store/sync/sync_user.cpp
index fedcfe98de7..bc570c0808c 100644
--- a/src/realm/object-store/sync/sync_user.cpp
+++ b/src/realm/object-store/sync/sync_user.cpp
@@ -186,14 +186,7 @@ void SyncUser::update_state_and_tokens(SyncUser::State state, const std::string&
                 // Call set_state() rather than update_state_and_tokens to remove a user.
                 REALM_UNREACHABLE();
             case State::LoggedIn:
-                sessions_to_revive.reserve(m_waiting_sessions.size());
-                for (auto& pair : m_waiting_sessions) {
-                    if (auto ptr = pair.second.lock()) {
-                        m_sessions[pair.first] = ptr;
-                        sessions_to_revive.emplace_back(std::move(ptr));
-                    }
-                }
-                m_waiting_sessions.clear();
+                sessions_to_revive = revive_sessions();
                 break;
             case State::LoggedOut: {
                 REALM_ASSERT(m_access_token == RealmJWT{});
@@ -217,6 +210,20 @@ void SyncUser::update_state_and_tokens(SyncUser::State state, const std::string&
     emit_change_to_subscribers(*this);
 }
 
+std::vector<std::shared_ptr<SyncSession>> SyncUser::revive_sessions()
+{
+    std::vector<std::shared_ptr<SyncSession>> sessions_to_revive;
+    sessions_to_revive.reserve(m_waiting_sessions.size());
+    for (auto& [path, weak_session] : m_waiting_sessions) {
+        if (auto ptr = weak_session.lock()) {
+            m_sessions[path] = ptr;
+            sessions_to_revive.emplace_back(std::move(ptr));
+        }
+    }
+    m_waiting_sessions.clear();
+    return sessions_to_revive;
+}
+
 void SyncUser::update_refresh_token(std::string&& token)
 {
     std::vector<std::shared_ptr<SyncSession>> sessions_to_revive;
@@ -230,16 +237,9 @@ void SyncUser::update_refresh_token(std::string&& token)
                 m_refresh_token = RealmJWT(std::move(token));
                 break;
             case State::LoggedOut: {
-                sessions_to_revive.reserve(m_waiting_sessions.size());
                 m_refresh_token = RealmJWT(std::move(token));
                 m_state = State::LoggedIn;
-                for (auto& pair : m_waiting_sessions) {
-                    if (auto ptr = pair.second.lock()) {
-                        m_sessions[pair.first] = ptr;
-                        sessions_to_revive.emplace_back(std::move(ptr));
-                    }
-                }
-                m_waiting_sessions.clear();
+                sessions_to_revive = revive_sessions();
                 break;
             }
         }
@@ -272,16 +272,9 @@ void SyncUser::update_access_token(std::string&& token)
                 m_access_token = RealmJWT(std::move(token));
                 break;
             case State::LoggedOut: {
-                sessions_to_revive.reserve(m_waiting_sessions.size());
                 m_access_token = RealmJWT(std::move(token));
                 m_state = State::LoggedIn;
-                for (auto& pair : m_waiting_sessions) {
-                    if (auto ptr = pair.second.lock()) {
-                        m_sessions[pair.first] = ptr;
-                        sessions_to_revive.emplace_back(std::move(ptr));
-                    }
-                }
-                m_waiting_sessions.clear();
+                sessions_to_revive = revive_sessions();
                 break;
             }
         }
@@ -357,10 +350,10 @@ void SyncUser::log_out()
         sync_manager_shared = m_sync_manager->shared_from_this();
         // Move all active sessions into the waiting sessions pool. If the user is
         // logged back in, they will automatically be reactivated.
-        for (auto& pair : m_sessions) {
-            if (auto ptr = pair.second.lock()) {
+        for (auto& [path, weak_session] : m_sessions) {
+            if (auto ptr = weak_session.lock()) {
                 ptr->log_out();
-                m_waiting_sessions[pair.first] = ptr;
+                m_waiting_sessions[path] = std::move(ptr);
             }
         }
         m_sessions.clear();
@@ -459,10 +452,7 @@ void SyncUser::register_session(std::shared_ptr<SyncSession> session)
     util::CheckedUniqueLock lock(m_mutex);
     switch (m_state) {
         case State::LoggedIn:
-            // Immediately ask the session to come online.
             m_sessions[path] = session;
-            lock.unlock();
-            session->revive_if_needed();
             break;
         case State::LoggedOut:
             m_waiting_sessions[path] = session;
diff --git a/src/realm/object-store/sync/sync_user.hpp b/src/realm/object-store/sync/sync_user.hpp
index dff03907e6c..3eaff9ce4f7 100644
--- a/src/realm/object-store/sync/sync_user.hpp
+++ b/src/realm/object-store/sync/sync_user.hpp
@@ -322,6 +322,8 @@ class SyncUser : public std::enable_shared_from_this<SyncUser>, public Subscriba
 
     bool do_is_logged_in() const REQUIRES(m_tokens_mutex);
 
+    std::vector<std::shared_ptr<SyncSession>> revive_sessions() REQUIRES(m_mutex);
+
     std::atomic<State> m_state GUARDED_BY(m_mutex);
 
     util::AtomicSharedPtr<SyncUserContext> m_binding_context;
diff --git a/test/object-store/realm.cpp b/test/object-store/realm.cpp
index 1b3a9ac2f28..1238f1af95b 100644
--- a/test/object-store/realm.cpp
+++ b/test/object-store/realm.cpp
@@ -847,7 +847,19 @@ TEST_CASE("Get Realm using Async Open", "[asyncOpen]") {
     }
 
     SECTION("cancels download and reports an error on auth error") {
-        SyncTestFile config(init_sync_manager.app(), "realm");
+        struct Transport : realm::app::GenericNetworkTransport {
+            void send_request_to_server(
+                const realm::app::Request&,
+                realm::util::UniqueFunction<void(const realm::app::Response&)>&& completion) override
+            {
+                completion(app::Response{403});
+            }
+        };
+        TestSyncManager::Config tsm_config;
+        tsm_config.transport = std::make_shared<Transport>();
+        TestSyncManager tsm(tsm_config);
+
+        SyncTestFile config(tsm.app(), "realm");
         config.sync_config->user->update_refresh_token(std::string(invalid_token));
         config.sync_config->user->update_access_token(std::move(invalid_token));
 
@@ -860,10 +872,10 @@ TEST_CASE("Get Realm using Async Open", "[asyncOpen]") {
         task->start([&](auto ref, auto error) {
             std::lock_guard<std::mutex> lock(mutex);
             REQUIRE(error);
+            REQUIRE_THROWS_WITH(std::rethrow_exception(error), "Client Error: 403");
             REQUIRE(!ref);
             called = true;
         });
-        init_sync_manager.network_callback(app::Response{403});
         util::EventLoop::main().run_until([&] {
             return called.load();
         });
diff --git a/test/object-store/sync/session/session.cpp b/test/object-store/sync/session/session.cpp
index 96ca3acb73c..e957f56f42a 100644
--- a/test/object-store/sync/session/session.cpp
+++ b/test/object-store/sync/session/session.cpp
@@ -108,8 +108,8 @@ TEST_CASE("SyncSession: management by SyncUser", "[sync]") {
         auto session2 = sync_session(user, "/test1c-2", [](auto, auto) {});
         // Run the runloop many iterations to see if the sessions spuriously bind.
         spin_runloop();
-        REQUIRE(sessions_are_inactive(*session1));
-        REQUIRE(sessions_are_inactive(*session2));
+        REQUIRE(session1->state() == SyncSession::State::Inactive);
+        REQUIRE(session2->state() == SyncSession::State::Inactive);
         REQUIRE(user->all_sessions().size() == 0);
         // Log the user back in via the sync manager.
         user = app->sync_manager()->get_user(user_id, ENCODE_FAKE_JWT("fake_refresh_token"),
@@ -137,8 +137,8 @@ TEST_CASE("SyncSession: management by SyncUser", "[sync]") {
         REQUIRE(user->state() == SyncUser::State::LoggedOut);
         // Run the runloop many iterations to see if the sessions spuriously rebind.
         spin_runloop();
-        REQUIRE(sessions_are_inactive(*session1));
-        REQUIRE(sessions_are_inactive(*session2));
+        REQUIRE(session1->state() == SyncSession::State::Inactive);
+        REQUIRE(session2->state() == SyncSession::State::Inactive);
         REQUIRE(user->all_sessions().size() == 0);
         // Log the user back in via the sync manager.
         user = app->sync_manager()->get_user(user_id, ENCODE_FAKE_JWT("fake_refresh_token"),
diff --git a/test/object-store/sync/session/session_util.hpp b/test/object-store/sync/session/session_util.hpp
index f055efce06c..0b910335792 100644
--- a/test/object-store/sync/session/session_util.hpp
+++ b/test/object-store/sync/session/session_util.hpp
@@ -29,6 +29,27 @@
 using namespace realm;
 using namespace realm::util;
 
+namespace Catch {
+template <>
+struct StringMaker<SyncSession::State> {
+    static std::string convert(SyncSession::State state)
+    {
+        switch (state) {
+            case SyncSession::State::Active:
+                return "Active";
+            case SyncSession::State::Dying:
+                return "Dying";
+            case SyncSession::State::Inactive:
+                return "Inactive";
+            case SyncSession::State::WaitingForAccessToken:
+                return "WaitingForAccessToken";
+            default:
+                return "Unknown";
+        }
+    }
+};
+} // namespace Catch
+
 inline bool sessions_are_active(const SyncSession& session)
 {
     return session.state() == SyncSession::State::Active;
diff --git a/test/object-store/util/test_file.cpp b/test/object-store/util/test_file.cpp
index 7a76de899c7..2f14b671110 100644
--- a/test/object-store/util/test_file.cpp
+++ b/test/object-store/util/test_file.cpp
@@ -333,11 +333,10 @@ TestAppSession::~TestAppSession()
 // MARK: - TestSyncManager
 
 TestSyncManager::TestSyncManager(const Config& config, const SyncServer::Config& sync_server_config)
-    : m_sync_server(sync_server_config)
+    : transport(config.transport ? config.transport : std::make_shared<Transport>(network_callback))
+    , m_sync_server(sync_server_config)
     , m_should_teardown_test_directory(config.should_teardown_test_directory)
 {
-    if (config.transport)
-        transport = config.transport;
     app::App::Config app_config = config.app_config;
     set_app_config_defaults(app_config, transport);
 
diff --git a/test/object-store/util/test_file.hpp b/test/object-store/util/test_file.hpp
index a6366d373dc..b6750134d74 100644
--- a/test/object-store/util/test_file.hpp
+++ b/test/object-store/util/test_file.hpp
@@ -266,7 +266,7 @@ class TestSyncManager {
 
         realm::util::UniqueFunction<void(const realm::app::Response&)>& network_callback;
     };
-    std::shared_ptr<realm::app::GenericNetworkTransport> transport = std::make_shared<Transport>(network_callback);
+    const std::shared_ptr<realm::app::GenericNetworkTransport> transport;
 
 private:
     std::shared_ptr<realm::app::App> m_app;