diff --git a/win32/Lib/pywin32_bootstrap.py b/win32/Lib/pywin32_bootstrap.py
index 0161f27aff..0531db66ad 100644
--- a/win32/Lib/pywin32_bootstrap.py
+++ b/win32/Lib/pywin32_bootstrap.py
@@ -8,7 +8,7 @@
 
 try:
     import pywin32_system32
-except ImportError:  # Python ≥3.6: replace ImportError with ModuleNotFoundError
+except ImportError:
     pass
 else:
     import os
@@ -17,5 +17,19 @@
     # https://docs.python.org/3/reference/import.html#path-attributes-on-modules
     for path in pywin32_system32.__path__:
         if os.path.isdir(path):
-            os.add_dll_directory(path)
+            # First try the preferred method
+            if hasattr(os, "add_dll_directory"):
+                os.add_dll_directory(path)
+            # If `add_dll_directory` is missing, which can happen in Pylance early initialization,
+            # try to modify PATH if it exists (just create it if it doesn't)
+            elif "PATH" not in os.environ:
+                os.environ["PATH"] = path
+            else:
+                # This is to ensure the pywin32 path is in the beginning to find the
+                # pywin32 DLLs first and prevent other PATH entries to shadow them
+                prepend_to_path = path + os.pathsep
+                if not os.environ["PATH"].startswith(prepend_to_path):
+                    os.environ["PATH"] = prepend_to_path + os.environ["PATH"].replace(
+                        os.pathsep + path, ""
+                    )
             break