Make Mail.app Always Send Windows Friendly Attatchments

Mail.app sends attached files in a way that is not entirely friendly to Windows users and, as a result, Windows users often see an extra file that they can do nothing with. This leads to confusion and seeding confusion via email doesn’t make you look good and doesn’t make your Mac look good. The solution? Always send Windows-friendly attachments.

Normally you have to check the Windows friendly attachment checkbox each time you attach something (an option you don’t even see if you drag and drop your attachments in like I do.) I checked Mail Preferences, but couldn’t find the option I expected to find. Over the weekend, I bumped into the solution in the drop-down menu:

Edit, Attachments, Always Send Windows Friendly Attachments

Mail.app Always Send Windows Friendly Attachments Option

Larger screenshot of the Windows friendly attachment option