diff --git a/src/poetry/utils/shell.py b/src/poetry/utils/shell.py
index f8c413afd81..6e7301fc5e0 100644
--- a/src/poetry/utils/shell.py
+++ b/src/poetry/utils/shell.py
@@ -70,7 +70,13 @@ def get(cls) -> Shell:
 
     def activate(self, env: VirtualEnv) -> int | None:
         activate_script = self._get_activate_script()
-        bin_dir = "Scripts" if WINDOWS else "bin"
+        if WINDOWS:
+            bin_path = env.path / "Scripts"
+            # Python innstalled via msys2 on Windows might produce a POSIX-like venv
+            # See https://github.com/python-poetry/poetry/issues/8638
+            bin_dir = "Scripts" if bin_path.exists() else "bin"
+        else:
+            bin_dir = "bin"
         activate_path = env.path / bin_dir / activate_script
 
         # mypy requires using sys.platform instead of WINDOWS constant