How do you override the warning "filename is not commonly downloaded" for a specific file?

Solution 1:

Because I couldn't find a way to resolve this properly in Chrome, I decided to resolve it outside of Chrome.

Given that I wanted to whitelist one specific file, I can also deal with this one specific download in a different manner.

@ECHO OFF
CD "C:\Users\Oliver\Documents\SU"
wget --no-check-certificate --output-document=connect.bat --user=oliver --password=secret https://vpn.secret.gov/connect.bat
connect.bat
PAUSE

Now I just pinned that to my Start menu and everything is better than it ever was.

Solution 2:

There's no client-side fix for this at the moment. There are some suggestions here for the server side: https://stackoverflow.com/questions/10606586/downloading-exe-files-from-database