diff --git a/docs/changelog.rst b/docs/changelog.rst
index 643102ce4..dfece10f6 100644
--- a/docs/changelog.rst
+++ b/docs/changelog.rst
@@ -41,6 +41,8 @@ Detailed list of changes
 
 - Sessions: Fix :code:`os_window_size` and :code:`os_window_class` not applying to the first OS Window (:iss:`4957`)
 
+- Allow using the cwd of the oldest as well as the newest foreground process for :option:`launch --cwd` (:disc:`4869`)
+
 
 0.25.0 [2022-04-11]
 ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
diff --git a/kitty/child.py b/kitty/child.py
index e676c2c23..e64cf4eeb 100644
--- a/kitty/child.py
+++ b/kitty/child.py
@@ -352,8 +352,7 @@ class Child:
             return cwd_of_process(self.pid)
         return None
 
-    @property
-    def pid_for_cwd(self) -> Optional[int]:
+    def get_pid_for_cwd(self, oldest: bool = False) -> Optional[int]:
         with suppress(Exception):
             assert self.child_fd is not None
             pgrp = os.tcgetpgrp(self.child_fd)
@@ -369,25 +368,32 @@ class Child:
                 # vim
                 # With this script , the foreground process group will contain
                 # both the bash instance running the script and vim.
-                return max(foreground_processes)
+                return min(foreground_processes) if oldest else max(foreground_processes)
         return self.pid
 
     @property
-    def foreground_cwd(self) -> Optional[str]:
+    def pid_for_cwd(self) -> Optional[int]:
+        return self.get_pid_for_cwd()
+
+    def get_foreground_cwd(self, oldest: bool = False) -> Optional[str]:
         with suppress(Exception):
-            assert self.pid_for_cwd is not None
-            return cwd_of_process(self.pid_for_cwd) or None
+            pid = self.get_pid_for_cwd(oldest)
+            if pid is not None:
+                return cwd_of_process(pid) or None
         return None
 
+    @property
+    def foreground_cwd(self) -> Optional[str]:
+        return self.get_foreground_cwd()
+
     @property
     def foreground_environ(self) -> Dict[str, str]:
-        try:
-            assert self.pid_for_cwd is not None
-            return environ_of_process(self.pid_for_cwd)
-        except Exception:
-            try:
-                assert self.pid is not None
-                return environ_of_process(self.pid)
-            except Exception:
-                pass
+        pid = self.pid_for_cwd
+        if pid is not None:
+            with suppress(Exception):
+                return environ_of_process(pid)
+        pid = self.pid
+        if pid is not None:
+            with suppress(Exception):
+                return environ_of_process(pid)
         return {}
diff --git a/kitty/launch.py b/kitty/launch.py
index 3e48ba980..9276d6e6f 100644
--- a/kitty/launch.py
+++ b/kitty/launch.py
@@ -67,7 +67,10 @@ to the newly opened window.
 The working directory for the newly launched child. Use the special value
 :code:`current` to use the working directory of the currently active window.
 The special value :code:`last_reported` uses the last working directory
-reported by the shell (needs :ref:`shell_integration` to work).
+reported by the shell (needs :ref:`shell_integration` to work). The special
+value :code:`oldest` works like :code:`current` but uses the working directory
+of the oldest foreground process associated with the currently active window
+rather than the newest foreground process.
 
 
 --env
@@ -382,6 +385,8 @@ def launch(
         elif opts.cwd == 'last_reported':
             if active:
                 kw['cwd_from'] = CwdRequest(active, CwdRequestType.last_reported)
+        elif opts.cwd == 'oldest':
+                kw['cwd_from'] = CwdRequest(active, CwdRequestType.last_reported)
         else:
             kw['cwd'] = opts.cwd
     if opts.location != 'default':
diff --git a/kitty/window.py b/kitty/window.py
index 09276dc29..54077d3cf 100644
--- a/kitty/window.py
+++ b/kitty/window.py
@@ -61,6 +61,7 @@ if TYPE_CHECKING:
 class CwdRequestType(Enum):
     current: int = auto()
     last_reported: int = auto()
+    oldest: int = auto()
 
 
 class CwdRequest:
@@ -84,7 +85,7 @@ class CwdRequest:
         reported_cwd = path_from_osc7_url(window.screen.last_reported_cwd) if window.screen.last_reported_cwd else ''
         if reported_cwd and not window.child_is_remote and (self.request_type is CwdRequestType.last_reported or window.at_prompt):
             return reported_cwd
-        return window.cwd_of_child or ''
+        return window.get_cwd_of_child(oldest=self.request_type is CwdRequestType.oldest) or ''
 
     def modify_argv_for_launch_with_cwd(self, argv: List[str]) -> str:
         window = self.window
@@ -1272,9 +1273,12 @@ class Window:
     def cmd_output(self, which: CommandOutput = CommandOutput.last_run, as_ansi: bool = False, add_wrap_markers: bool = False) -> str:
         return cmd_output(self.screen, which, as_ansi, add_wrap_markers)
 
+    def get_cwd_of_child(self, oldest: bool = False) -> Optional[str]:
+        return self.child.get_foreground_cwd(oldest) or self.child.current_cwd
+
     @property
     def cwd_of_child(self) -> Optional[str]:
-        return self.child.foreground_cwd or self.child.current_cwd
+        return self.get_cwd_of_child()
 
     @property
     def child_is_remote(self) -> bool: