diff --git a/docs/changelog.rst b/docs/changelog.rst
index b42a55432..69638b953 100644
--- a/docs/changelog.rst
+++ b/docs/changelog.rst
@@ -154,6 +154,10 @@ Detailed list of changes
 
 - Automatic color scheme switching: Fix title bar and scroll bar colors not being updated (:iss:`9167`)
 
+- macOS: Fix cycle through OS windows only swapping between the two most recent
+  OS Windows. Also add a cycle through OS Windows backwards action.
+  (:iss:`9215`)
+
 
 0.44.0 [2025-11-03]
 ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
diff --git a/kitty/boss.py b/kitty/boss.py
index 3611fe9eb..b275946d6 100644
--- a/kitty/boss.py
+++ b/kitty/boss.py
@@ -1318,7 +1318,11 @@ class Boss:
 
     @ac('misc', 'Cycle through OS windows on macOS')
     def macos_cycle_through_os_windows(self) -> None:
-        macos_cycle_through_os_windows()
+        macos_cycle_through_os_windows(False)
+
+    @ac('misc', 'Cycle through OS windows backwards on macOS')
+    def macos_cycle_through_os_windows_backwards(self) -> None:
+        macos_cycle_through_os_windows(True)
 
     @ac('misc', 'Hide macOS kitty application')
     def hide_macos_app(self) -> None:
diff --git a/kitty/child-monitor.c b/kitty/child-monitor.c
index a13511914..4ed473a19 100644
--- a/kitty/child-monitor.c
+++ b/kitty/child-monitor.c
@@ -1241,6 +1241,7 @@ process_cocoa_pending_actions(void) {
     if (cocoa_pending_actions[RELOAD_CONFIG]) { call_boss(load_config_file, NULL); }
     if (cocoa_pending_actions[TOGGLE_MACOS_SECURE_KEYBOARD_ENTRY]) { call_boss(toggle_macos_secure_keyboard_entry, NULL); }
     if (cocoa_pending_actions[MACOS_CYCLE_THROUGH_OS_WINDOWS]) { call_boss(macos_cycle_through_os_windows, NULL); }
+    if (cocoa_pending_actions[MACOS_CYCLE_THROUGH_OS_WINDOWS_BACKWARDS]) { call_boss(macos_cycle_through_os_windows_backwards, NULL); }
     if (cocoa_pending_actions[TOGGLE_FULLSCREEN]) { call_boss(toggle_fullscreen, NULL); }
     if (cocoa_pending_actions[OPEN_KITTY_WEBSITE]) { call_boss(open_kitty_website, NULL); }
     if (cocoa_pending_actions[HIDE]) { call_boss(hide_macos_app, NULL); }
diff --git a/kitty/cocoa_window.h b/kitty/cocoa_window.h
index a723c5a53..b9d916380 100644
--- a/kitty/cocoa_window.h
+++ b/kitty/cocoa_window.h
@@ -31,6 +31,7 @@ typedef enum {
     RELOAD_CONFIG,
     TOGGLE_MACOS_SECURE_KEYBOARD_ENTRY,
     MACOS_CYCLE_THROUGH_OS_WINDOWS,
+    MACOS_CYCLE_THROUGH_OS_WINDOWS_BACKWARDS,
     TOGGLE_FULLSCREEN,
     OPEN_KITTY_WEBSITE,
     HIDE,
@@ -51,7 +52,7 @@ void cocoa_system_beep(const char*);
 void cocoa_set_activation_policy(bool);
 bool cocoa_alt_option_key_pressed(unsigned long);
 void cocoa_toggle_secure_keyboard_entry(void);
-void cocoa_cycle_through_os_windows(void);
+void cocoa_cycle_through_os_windows(bool);
 void cocoa_hide(void);
 void cocoa_clear_global_shortcuts(void);
 void cocoa_hide_others(void);
diff --git a/kitty/cocoa_window.m b/kitty/cocoa_window.m
index 9d20468bc..7f3d947c0 100644
--- a/kitty/cocoa_window.m
+++ b/kitty/cocoa_window.m
@@ -259,6 +259,7 @@ PENDING(clear_last_command, CLEAR_LAST_COMMAND)
 PENDING(reload_config, RELOAD_CONFIG)
 PENDING(toggle_macos_secure_keyboard_entry, TOGGLE_MACOS_SECURE_KEYBOARD_ENTRY)
 PENDING(macos_cycle_through_os_windows, MACOS_CYCLE_THROUGH_OS_WINDOWS)
+PENDING(macos_cycle_through_os_windows_backwards, MACOS_CYCLE_THROUGH_OS_WINDOWS_BACKWARDS)
 PENDING(toggle_fullscreen, TOGGLE_FULLSCREEN)
 PENDING(open_kitty_website, OPEN_KITTY_WEBSITE)
 PENDING(hide_macos_app, HIDE)
@@ -320,7 +321,7 @@ typedef struct {
     GlobalShortcut clear_terminal_and_scrollback, clear_screen, clear_scrollback, clear_last_command;
     GlobalShortcut toggle_macos_secure_keyboard_entry, toggle_fullscreen, open_kitty_website;
     GlobalShortcut hide_macos_app, hide_macos_other_apps, minimize_macos_window, quit;
-    GlobalShortcut macos_cycle_through_os_windows;
+    GlobalShortcut macos_cycle_through_os_windows, macos_cycle_through_os_windows_backwards;
 } GlobalShortcuts;
 static GlobalShortcuts global_shortcuts;
 
@@ -338,7 +339,8 @@ cocoa_set_global_shortcut(PyObject *self UNUSED, PyObject *args) {
     else Q(clear_terminal_and_scrollback); else Q(clear_scrollback); else Q(clear_screen); else Q(clear_last_command);
     else Q(reload_config); else Q(toggle_macos_secure_keyboard_entry); else Q(toggle_fullscreen);
     else Q(open_kitty_website); else Q(hide_macos_app); else Q(hide_macos_other_apps);
-    else Q(minimize_macos_window); else Q(quit); else Q(macos_cycle_through_os_windows);
+    else Q(minimize_macos_window); else Q(quit);
+    else Q(macos_cycle_through_os_windows); else Q(macos_cycle_through_os_windows_backwards);
 #undef Q
     if (gs == NULL) { PyErr_SetString(PyExc_KeyError, "Unknown shortcut name"); return NULL; }
     int cocoa_mods;
@@ -808,6 +810,7 @@ cocoa_create_global_menu(void) {
                    keyEquivalent:@""];
     [windowMenu addItem:[NSMenuItem separatorItem]];
     MENU_ITEM(windowMenu, @"Cycle Through OS Windows", macos_cycle_through_os_windows);
+    MENU_ITEM(windowMenu, @"Cycle Through OS Windows backwards", macos_cycle_through_os_windows_backwards);
     [windowMenu addItem:[NSMenuItem separatorItem]];
     [windowMenu addItemWithTitle:@"Bring All to Front"
                           action:@selector(arrangeInFront:)
@@ -925,20 +928,24 @@ cocoa_toggle_secure_keyboard_entry(void) {
 }
 
 void
-cocoa_cycle_through_os_windows(void) {
-    NSArray *allWindows = [NSApp orderedWindows];
+cocoa_cycle_through_os_windows(bool backwards) {
+    NSArray *allWindows = [NSApp windows];
     if (allWindows.count < 2) return;
     NSMutableArray<NSWindow *> *filteredWindows = [NSMutableArray array];
-        for (NSWindow *window in allWindows) {
+    for (NSWindow *window in allWindows) {
         NSRect windowFrame = [window frame];
         // Exclude zero size windows which are likely zombie windows from the Tahoe bug
-        if (windowFrame.size.width > 0 && windowFrame.size.height > 0) [filteredWindows addObject:window];
+        if (windowFrame.size.width > 0 && windowFrame.size.height > 0 && !window.isMiniaturized && window.isVisible) [filteredWindows addObject:window];
     }
     if (filteredWindows.count < 2) return;
     NSWindow *keyWindow = [NSApp keyWindow];
     NSUInteger index = [filteredWindows indexOfObject:keyWindow];
-    if (index < 0) return;
-    NSUInteger nextIndex = (index + 1) % filteredWindows.count;
+    NSUInteger nextIndex = 0;
+    if (index != NSNotFound) {
+        if (backwards) {
+            nextIndex = (index == 0) ? [filteredWindows count] - 1 : index - 1;
+        } else nextIndex = (index + 1) % filteredWindows.count;
+    }
     NSWindow *nextWindow = filteredWindows[nextIndex];
     [nextWindow makeKeyAndOrderFront:nil];
 }
diff --git a/kitty/fast_data_types.pyi b/kitty/fast_data_types.pyi
index f2f5fa7c4..54064b70e 100644
--- a/kitty/fast_data_types.pyi
+++ b/kitty/fast_data_types.pyi
@@ -948,7 +948,7 @@ def toggle_secure_input() -> None:
     pass
 
 
-def macos_cycle_through_os_windows() -> None:
+def macos_cycle_through_os_windows(backwards: bool) -> None:
     pass
 
 
diff --git a/kitty/glfw.c b/kitty/glfw.c
index b62d4ae47..b641633d9 100644
--- a/kitty/glfw.c
+++ b/kitty/glfw.c
@@ -1922,9 +1922,11 @@ toggle_secure_input(PYNOARG) {
 }
 
 static PyObject*
-macos_cycle_through_os_windows(PYNOARG) {
+macos_cycle_through_os_windows(PyObject *self UNUSED, PyObject *backwards) {
 #ifdef __APPLE__
-    cocoa_cycle_through_os_windows();
+    cocoa_cycle_through_os_windows(PyObject_IsTrue(backwards));
+#else
+    (void)backwards;
 #endif
     Py_RETURN_NONE;
 }
@@ -2616,7 +2618,7 @@ static PyMethodDef module_methods[] = {
     METHODB(set_clipboard_data_types, METH_VARARGS),
     METHODB(get_clipboard_mime, METH_VARARGS),
     METHODB(toggle_secure_input, METH_NOARGS),
-    METHODB(macos_cycle_through_os_windows, METH_NOARGS),
+    METHODB(macos_cycle_through_os_windows, METH_O),
     METHODB(get_content_scale_for_window, METH_NOARGS),
     METHODB(ring_bell, METH_VARARGS),
     METHODB(toggle_fullscreen, METH_VARARGS),
diff --git a/kitty/main.py b/kitty/main.py
index f862659d2..15564a099 100644
--- a/kitty/main.py
+++ b/kitty/main.py
@@ -193,7 +193,7 @@ def set_cocoa_global_shortcuts(opts: Options) -> dict[str, SingleKey]:
 
         for ac in ('new_os_window', 'close_os_window', 'close_tab', 'edit_config_file', 'previous_tab',
                    'next_tab', 'new_tab', 'new_window', 'close_window', 'toggle_macos_secure_keyboard_entry',
-                   'toggle_fullscreen', 'macos_cycle_through_os_windows',
+                   'toggle_fullscreen', 'macos_cycle_through_os_windows', 'macos_cycle_through_os_windows_backwards',
                    'hide_macos_app', 'hide_macos_other_apps', 'minimize_macos_window', 'quit'):
             val = get_macos_shortcut_for(func_map, ac)
             if val is not None:
diff --git a/kitty/options/definition.py b/kitty/options/definition.py
index 0544a413b..ef7e17af2 100644
--- a/kitty/options/definition.py
+++ b/kitty/options/definition.py
@@ -4429,6 +4429,7 @@ map('Toggle macOS secure keyboard entry',
     )
 
 map('macOS Cycle through OS Windows', 'macos_cycle_through_os_windows cmd+` macos_cycle_through_os_windows', only='macos')
+map('macOS Cycle through OS Windows backwards', 'macos_cycle_through_os_windows_backwards cmd+shift+` macos_cycle_through_os_windows_backwards', only='macos')
 
 map('Unicode input',
     'input_unicode_character kitty_mod+u kitten unicode_input',
diff --git a/kitty/options/types.py b/kitty/options/types.py
index cd9d8b8b6..c15a34e08 100644
--- a/kitty/options/types.py
+++ b/kitty/options/types.py
@@ -1006,6 +1006,7 @@ if is_macos:
     defaults.map.append(KeyDefinition(trigger=SingleKey(mods=12, key=102), definition='toggle_fullscreen'))
     defaults.map.append(KeyDefinition(trigger=SingleKey(mods=10, key=115), definition='toggle_macos_secure_keyboard_entry'))
     defaults.map.append(KeyDefinition(trigger=SingleKey(mods=8, key=96), definition='macos_cycle_through_os_windows'))
+    defaults.map.append(KeyDefinition(trigger=SingleKey(mods=9, key=96), definition='macos_cycle_through_os_windows_backwards'))
     defaults.map.append(KeyDefinition(trigger=SingleKey(mods=12, key=32), definition='kitten unicode_input'))
     defaults.map.append(KeyDefinition(trigger=SingleKey(mods=8, key=44), definition='edit_config_file'))
     defaults.map.append(KeyDefinition(trigger=SingleKey(mods=10, key=114), definition='clear_terminal reset active'))