diff --git a/kitty/boss.py b/kitty/boss.py
index 9ce4e3641..4bd92a05d 100644
--- a/kitty/boss.py
+++ b/kitty/boss.py
@@ -62,7 +62,7 @@ from .utils import (
     safe_print, set_primary_selection, single_instance,
     startup_notification_handler, which
 )
-from .window import CommandOutput, MatchPatternType, Window
+from .window import CommandOutput, CwdRequest, MatchPatternType, Window
 
 
 class OSWindowDict(TypedDict):
@@ -439,7 +439,7 @@ class Boss:
                         return os_window_id
         return None
 
-    def _new_os_window(self, args: Union[SpecialWindowInstance, Iterable[str]], cwd_from: Optional[Window] = None) -> int:
+    def _new_os_window(self, args: Union[SpecialWindowInstance, Iterable[str]], cwd_from: Optional[CwdRequest] = None) -> int:
         if isinstance(args, SpecialWindowInstance):
             sw: Optional[SpecialWindowInstance] = args
         else:
@@ -461,7 +461,7 @@ class Boss:
     @ac('win', 'New OS Window with the same working directory as the currently active window')
     def new_os_window_with_cwd(self, *args: str) -> None:
         w = self.active_window_for_cwd
-        self._new_os_window(args, w)
+        self._new_os_window(args, CwdRequest(w))
 
     def new_os_window_with_wd(self, wd: str) -> None:
         special_window = SpecialWindow(None, cwd=wd)
@@ -1717,7 +1717,7 @@ class Boss:
         self, cmd: List[str],
         window: Optional[Window] = None,
         stdin: Optional[str] = None,
-        cwd_from: Optional[Window] = None,
+        cwd_from: Optional[CwdRequest] = None,
         as_overlay: bool = False
     ) -> SpecialWindowInstance:
         w = window or self.active_window
@@ -1739,7 +1739,7 @@ class Boss:
         cwd: Optional[str] = None,
         env: Optional[Dict[str, str]] = None,
         stdin: Optional[bytes] = None,
-        cwd_from: Optional[Window] = None
+        cwd_from: Optional[CwdRequest] = None
     ) -> None:
         import subprocess
         env = env or None
@@ -1766,7 +1766,8 @@ class Boss:
 
     def pipe(self, source: str, dest: str, exe: str, *args: str) -> Optional[Window]:
         cmd = [exe] + list(args)
-        window = cwd_from = self.active_window
+        window = self.active_window
+        cwd_from = CwdRequest(window) if window else None
 
         def create_window() -> SpecialWindowInstance:
             return self.special_window_for_cmd(
@@ -1794,7 +1795,7 @@ class Boss:
             self.run_background_process(cmd, cwd_from=cwd_from, stdin=stdin, env=env)
         return None
 
-    def args_to_special_window(self, args: Iterable[str], cwd_from: Optional[Window] = None) -> SpecialWindowInstance:
+    def args_to_special_window(self, args: Iterable[str], cwd_from: Optional[CwdRequest] = None) -> SpecialWindowInstance:
         args = list(args)
         stdin = None
         w = self.active_window
@@ -1815,7 +1816,7 @@ class Boss:
             cmd.append(arg)
         return SpecialWindow(cmd, stdin, cwd_from=cwd_from)
 
-    def _new_tab(self, args: Union[SpecialWindowInstance, Iterable[str]], cwd_from: Optional[Window] = None, as_neighbor: bool = False) -> Optional[Tab]:
+    def _new_tab(self, args: Union[SpecialWindowInstance, Iterable[str]], cwd_from: Optional[CwdRequest] = None, as_neighbor: bool = False) -> Optional[Tab]:
         special_window = None
         if args:
             if isinstance(args, SpecialWindowInstance):
@@ -1827,7 +1828,7 @@ class Boss:
             return tm.new_tab(special_window=special_window, cwd_from=cwd_from, as_neighbor=as_neighbor)
         return None
 
-    def _create_tab(self, args: List[str], cwd_from: Optional[Window] = None) -> None:
+    def _create_tab(self, args: List[str], cwd_from: Optional[CwdRequest] = None) -> None:
         as_neighbor = False
         if args and args[0].startswith('!'):
             as_neighbor = 'neighbor' in args[0][1:].split(',')
@@ -1840,7 +1841,7 @@ class Boss:
 
     @ac('tab', 'Create a new tab with working directory for the window in it set to the same as the active window')
     def new_tab_with_cwd(self, *args: str) -> None:
-        self._create_tab(list(args), cwd_from=self.active_window_for_cwd)
+        self._create_tab(list(args), cwd_from=CwdRequest(self.active_window_for_cwd))
 
     def new_tab_with_wd(self, wd: str) -> None:
         if not self.os_window_map:
@@ -1848,7 +1849,7 @@ class Boss:
         special_window = SpecialWindow(None, cwd=wd)
         self._new_tab(special_window)
 
-    def _new_window(self, args: List[str], cwd_from: Optional[Window] = None) -> Optional[Window]:
+    def _new_window(self, args: List[str], cwd_from: Optional[CwdRequest] = None) -> Optional[Window]:
         tab = self.active_tab
         if tab is None:
             return None
@@ -1876,7 +1877,7 @@ class Boss:
         w = self.active_window_for_cwd
         if w is None:
             return self.new_window(*args)
-        self._new_window(list(args), cwd_from=w)
+        self._new_window(list(args), cwd_from=CwdRequest(w))
 
     @ac('misc', '''
         Launch the specified program in a new window/tab/etc.
diff --git a/kitty/child.py b/kitty/child.py
index a210630b5..f08b57932 100644
--- a/kitty/child.py
+++ b/kitty/child.py
@@ -21,7 +21,7 @@ try:
 except ImportError:
     TypedDict = dict
 if TYPE_CHECKING:
-    from .window import Window
+    from .window import CwdRequest
 
 
 if is_macos:
@@ -194,12 +194,12 @@ class Child:
         cwd: str,
         stdin: Optional[bytes] = None,
         env: Optional[Dict[str, str]] = None,
-        cwd_from: Optional['Window'] = None,
+        cwd_from: Optional['CwdRequest'] = None,
         allow_remote_control: bool = False
     ):
         self.allow_remote_control = allow_remote_control
         self.argv = list(argv)
-        if cwd_from is not None:
+        if cwd_from:
             try:
                 cwd = cwd_from.modify_argv_for_launch_with_cwd(self.argv) or cwd
             except Exception as err:
diff --git a/kitty/launch.py b/kitty/launch.py
index 9c9cf4432..c5762ac77 100644
--- a/kitty/launch.py
+++ b/kitty/launch.py
@@ -14,7 +14,7 @@ from .options.utils import env as parse_env
 from .tabs import Tab, TabManager
 from .types import run_once
 from .utils import log_error, resolve_custom_file, set_primary_selection, which
-from .window import Watchers, Window
+from .window import CwdRequest, Watchers, Window
 
 try:
     from typing import TypedDict
@@ -290,7 +290,7 @@ def load_watch_modules(watchers: Iterable[str]) -> Optional[Watchers]:
 class LaunchKwds(TypedDict):
 
     allow_remote_control: bool
-    cwd_from: Optional[Window]
+    cwd_from: Optional[CwdRequest]
     cwd: Optional[str]
     location: Optional[str]
     override_title: Optional[str]
@@ -358,7 +358,7 @@ def launch(
     if opts.cwd:
         if opts.cwd == 'current':
             if active:
-                kw['cwd_from'] = active
+                kw['cwd_from'] = CwdRequest(active)
         else:
             kw['cwd'] = opts.cwd
     if opts.location != 'default':
diff --git a/kitty/session.py b/kitty/session.py
index 105d20f79..c46b9c59a 100644
--- a/kitty/session.py
+++ b/kitty/session.py
@@ -16,7 +16,7 @@ from .utils import log_error, resolved_shell
 
 
 if TYPE_CHECKING:
-    from .window import Window
+    from .window import CwdRequest
 
 
 def get_os_window_sizing_data(opts: Options, session: Optional['Session'] = None) -> WindowSizeData:
@@ -150,7 +150,7 @@ def create_sessions(
     opts: Options,
     args: Optional[CLIOptions] = None,
     special_window: Optional['SpecialWindowInstance'] = None,
-    cwd_from: Optional['Window'] = None,
+    cwd_from: Optional['CwdRequest'] = None,
     respect_cwd: bool = False,
     default_session: Optional[str] = None
 ) -> Generator[Session, None, None]:
diff --git a/kitty/tabs.py b/kitty/tabs.py
index 2d60ef3c0..a906e71aa 100644
--- a/kitty/tabs.py
+++ b/kitty/tabs.py
@@ -30,7 +30,7 @@ from .tab_bar import TabBar, TabBarData
 from .types import ac
 from .typing import EdgeLiteral, SessionTab, SessionType, TypedDict
 from .utils import log_error, platform_window_id, resolved_shell
-from .window import Watchers, Window, WindowDict
+from .window import CwdRequest, Watchers, Window, WindowDict
 from .window_list import WindowList
 
 
@@ -58,7 +58,7 @@ class SpecialWindowInstance(NamedTuple):
     cmd: Optional[List[str]]
     stdin: Optional[bytes]
     override_title: Optional[str]
-    cwd_from: Optional[Window]
+    cwd_from: Optional[CwdRequest]
     cwd: Optional[str]
     overlay_for: Optional[int]
     env: Optional[Dict[str, str]]
@@ -69,7 +69,7 @@ def SpecialWindow(
     cmd: Optional[List[str]],
     stdin: Optional[bytes] = None,
     override_title: Optional[str] = None,
-    cwd_from: Optional[Window] = None,
+    cwd_from: Optional[CwdRequest] = None,
     cwd: Optional[str] = None,
     overlay_for: Optional[int] = None,
     env: Optional[Dict[str, str]] = None,
@@ -98,7 +98,7 @@ class Tab:  # {{{
         tab_manager: 'TabManager',
         session_tab: Optional['SessionTab'] = None,
         special_window: Optional[SpecialWindowInstance] = None,
-        cwd_from: Optional[Window] = None,
+        cwd_from: Optional[CwdRequest] = None,
         no_initial_window: bool = False
     ):
         self.tab_manager_ref = weakref.ref(tab_manager)
@@ -347,7 +347,7 @@ class Tab:  # {{{
         use_shell: bool = False,
         cmd: Optional[List[str]] = None,
         stdin: Optional[bytes] = None,
-        cwd_from: Optional[Window] = None,
+        cwd_from: Optional[CwdRequest] = None,
         cwd: Optional[str] = None,
         env: Optional[Dict[str, str]] = None,
         allow_remote_control: bool = False
@@ -414,7 +414,7 @@ class Tab:  # {{{
         cmd: Optional[List[str]] = None,
         stdin: Optional[bytes] = None,
         override_title: Optional[str] = None,
-        cwd_from: Optional[Window] = None,
+        cwd_from: Optional[CwdRequest] = None,
         cwd: Optional[str] = None,
         overlay_for: Optional[int] = None,
         env: Optional[Dict[str, str]] = None,
@@ -942,7 +942,7 @@ class TabManager:  # {{{
     def new_tab(
         self,
         special_window: Optional[SpecialWindowInstance] = None,
-        cwd_from: Optional[Window] = None,
+        cwd_from: Optional[CwdRequest] = None,
         as_neighbor: bool = False,
         empty_tab: bool = False,
         location: str = 'last'
diff --git a/kitty/window.py b/kitty/window.py
index bdfb7158e..57c4fd6b5 100644
--- a/kitty/window.py
+++ b/kitty/window.py
@@ -7,7 +7,7 @@ import re
 import sys
 import weakref
 from collections import deque
-from enum import IntEnum
+from enum import Enum, IntEnum, auto
 from functools import partial
 from gettext import gettext as _
 from itertools import chain
@@ -57,6 +57,30 @@ if TYPE_CHECKING:
     from .file_transmission import FileTransmission
 
 
+class CwdRequestType(Enum):
+    current: int = auto()
+    last_reported: int = auto()
+
+
+class CwdRequest:
+
+    def __init__(self, window: Optional['Window'] = None, request_type: CwdRequestType = CwdRequestType.current) -> None:
+        self.window_id = -1 if window is None else window.id
+        self.request_type = request_type
+
+    def __bool__(self) -> bool:
+        return self.window_id > -1
+
+    def modify_argv_for_launch_with_cwd(self, argv: List[str]) -> str:
+        window = get_boss().window_id_map.get(self.window_id)
+        return window.modify_argv_for_launch_with_cwd(argv) if window else ''
+
+    @property
+    def cwd_of_child(self) -> Optional[str]:
+        window = get_boss().window_id_map.get(self.window_id)
+        return window.cwd_of_child if window else None
+
+
 def process_title_from_child(title: str, is_base64: bool) -> str:
     if is_base64:
         from base64 import standard_b64decode