diff --git a/CHANGELOG.md b/CHANGELOG.md
index abfa42b4..e548a28d 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -9,6 +9,7 @@ This project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0.htm
 - Improved SIP detection logic [#716](https://github.com/koekeishiya/yabai/issues/716)
 - Windows that do not report a title at all should be treated as having the empty string as its title [#707](https://github.com/koekeishiya/yabai/issues/707)
 - Allow *SPACE_SEL* to be used instead of *mission-control index* when specifying config options for a specific space [#705](https://github.com/koekeishiya/yabai/issues/705)
+- Native fullscreen transitions would freeze on macOS Mojave due to internal API differences between macOS version [#690](https://github.com/koekeishiya/yabai/issues/690)
 
 ## [3.3.4] - 2020-11-14
 ### Changed
diff --git a/src/event.c b/src/event.c
index 7a1498e2..4f8f0e50 100644
--- a/src/event.c
+++ b/src/event.c
@@ -423,18 +423,7 @@ static EVENT_CALLBACK(EVENT_HANDLER_WINDOW_RESIZED)
             window_manager_purify_window(&g_window_manager, window);
         }
     } else if (was_fullscreen && !is_fullscreen) {
-        uint32_t did = window_display_id(window);
-
-        do {
-
-            //
-            // NOTE(koekeishiya): Window has exited native-fullscreen mode.
-            // We need to spin lock until the display is finished animating
-            // because we are not actually able to interact with the window.
-            //
-
-            usleep(100000);
-        } while (display_manager_display_is_animating(did));
+        window_manager_wait_for_native_fullscreen_transition(window);
 
         if (window_manager_should_manage_window(window) && !window_manager_find_managed_window(&g_window_manager, window)) {
             struct view *view = space_manager_tile_window_on_space(&g_space_manager, window, window_space(window));
diff --git a/src/window_manager.c b/src/window_manager.c
index dcb38794..bc98a154 100644
--- a/src/window_manager.c
+++ b/src/window_manager.c
@@ -1357,6 +1357,40 @@ void window_manager_toggle_window_shadow(struct space_manager *sm, struct window
     if (scripting_addition_set_shadow(window->id, shadow)) window->has_shadow = shadow;
 }
 
+void window_manager_wait_for_native_fullscreen_transition(struct window *window)
+{
+    if (workspace_is_macos_mojave()) {
+        while (!space_is_user(space_manager_active_space())) {
+
+            //
+            // NOTE(koekeishiya): Window has exited native-fullscreen mode.
+            // We need to spin lock until the display is finished animating
+            // because we are not actually able to interact with the window.
+            //
+            // macOS Mojave freezes fullscreen applications when using the
+            // display_manager API to check for animation status:
+            //
+            //  - https://github.com/koekeishiya/yabai/issues/690
+            //
+
+            usleep(100000);
+        }
+    } else {
+        uint32_t did = window_display_id(window);
+
+        do {
+
+            //
+            // NOTE(koekeishiya): Window has exited native-fullscreen mode.
+            // We need to spin lock until the display is finished animating
+            // because we are not actually able to interact with the window.
+            //
+
+            usleep(100000);
+        } while (display_manager_display_is_animating(did));
+    }
+}
+
 void window_manager_toggle_window_native_fullscreen(struct space_manager *sm, struct window_manager *wm, struct window *window)
 {
     uint32_t sid = window_space(window);
diff --git a/src/window_manager.h b/src/window_manager.h
index e3051c02..c098dfde 100644
--- a/src/window_manager.h
+++ b/src/window_manager.h
@@ -181,6 +181,7 @@ void window_manager_toggle_window_native_fullscreen(struct space_manager *sm, st
 void window_manager_toggle_window_expose(struct window_manager *wm, struct window *window);
 void window_manager_toggle_window_pip(struct space_manager *sm, struct window_manager *wm, struct window *window);
 void window_manager_toggle_window_border(struct window_manager *wm, struct window *window);
+void window_manager_wait_for_native_fullscreen_transition(struct window *window);
 void window_manager_validate_and_check_for_windows_on_space(struct space_manager *sm, struct window_manager *wm, uint64_t sid);
 void window_manager_handle_display_add_and_remove(struct space_manager *sm, struct window_manager *wm, uint32_t did);
 void window_manager_begin(struct space_manager *sm, struct window_manager *window_manager);
diff --git a/src/workspace.h b/src/workspace.h
index 408e7a27..784483ef 100644
--- a/src/workspace.h
+++ b/src/workspace.h
@@ -19,6 +19,7 @@ void workspace_application_observe_finished_launching(void *context, struct proc
 void workspace_application_observe_activation_policy(void *context, struct process *process);
 bool workspace_is_macos_bigsur(void);
 bool workspace_is_macos_catalina(void);
+bool workspace_is_macos_mojave(void);
 bool workspace_is_macos_highsierra(void);
 
 #endif
diff --git a/src/workspace.m b/src/workspace.m
index cc2fb5b6..c32bb99a 100644
--- a/src/workspace.m
+++ b/src/workspace.m
@@ -113,6 +113,12 @@ bool workspace_is_macos_catalina(void)
     return version.majorVersion == 10 && version.minorVersion == 15;
 }
 
+bool workspace_is_macos_mojave(void)
+{
+    NSOperatingSystemVersion version = [[NSProcessInfo processInfo] operatingSystemVersion];
+    return version.majorVersion == 10 && version.minorVersion == 14;
+}
+
 bool workspace_is_macos_highsierra(void)
 {
     NSOperatingSystemVersion version = [[NSProcessInfo processInfo] operatingSystemVersion];