As I understand, one cannot use pip to install/upgrade pywin32, though pip install -U pypiwin32 is a workaround.
pywin32 is now hosted on GitHub. I know very little of git but know that it works with binary files. Is there a way to programmatically upgrade the pywin32 binary? That is, say pywin32 v221 is installed with Python v.3.6 (64bit), the program should check against the latest (v223) on GitHub and download the pywin32-223.win-amd64-py3.6.exe and install it. So far, I can only think of a web-scraping-like script that compares the installed version with the latest version on the web and act accordingly. I wonder whether there's a simple solution.