diff --git a/CHANGES.txt b/CHANGES.txt
index 7fe29bddd..7f4e5c28b 100644
--- a/CHANGES.txt
+++ b/CHANGES.txt
@@ -14,6 +14,7 @@ https://mhammond.github.io/pywin32_installers.html.
 Coming in build 309, as yet unreleased
 --------------------------------------
 
+* Added support for relative path for `pywin32_postinstall`'s `-destination` argument (#2447, @Avasam)
 * Restored axdebug builds on Python 3.10 (#2416, @Avasam)
 * Pythonwin: Bumped Scintilla from 1.77 to 4.4.6. The full changelog can be found here: https://www.scintilla.org/ScintillaHistory.html
 * Fixed `ddeclient` and `ddeserver` demos import error (#2290, @Avasam)
diff --git a/pywin32_postinstall.py b/pywin32_postinstall.py
index e90e354d9..6974c8eb5 100644
--- a/pywin32_postinstall.py
+++ b/pywin32_postinstall.py
@@ -642,9 +642,12 @@ def uninstall(lib_dir):
 # Out of principle, we're still not using system exits.
 
 
-def verify_destination(location):
+def verify_destination(location: str) -> str:
+    location = os.path.abspath(location)
     if not os.path.isdir(location):
-        raise argparse.ArgumentTypeError(f'Path "{location}" does not exist!')
+        raise argparse.ArgumentTypeError(
+            f'Path "{location}" is not an existing directory!'
+        )
     return location
 
 
diff --git a/setup.py b/setup.py
index b9a664f44..01aa47d62 100644
--- a/setup.py
+++ b/setup.py
@@ -856,16 +856,6 @@ def run(self):
         This is only run for local installs. Wheel-based installs won't run this code.
         """
         install.run(self)
-        # If self.root has a value, it means we are being "installed" into some other
-        # directory than Python itself - in which case we must *not* run our installer.
-        # bdist_wininst used to trigger this by using a temp directory.
-        # Is this still a concern ?
-        if self.root:
-            print(
-                "Not executing post install script when "
-                + f"not installing in Python itself (self.root={self.root})"
-            )
-            return
         self.execute(self._postinstall, (), msg="Executing post install script...")
 
     def _postinstall(self):
@@ -874,17 +864,16 @@ def _postinstall(self):
             raise RuntimeError(f"Can't find '{filename}'")
         # As of setuptools>=74.0.0, we no longer need to
         # be concerned about distutils calling win32api
-        subprocess.Popen(
-            [
+        subprocess.check_call(
+            (
                 sys.executable,
                 filename,
                 "-install",
                 "-destination",
                 self.install_lib,
-                "-quiet",
                 "-wait",
                 str(os.getpid()),
-            ]
+            )
         )