I'm not sure if I'm having the same issue as you, but when I send attachments through Mail, the recipients tell me that the file name has been truncated. This is especially frustrating when the file name includes important information like date, time, etc. in the file name to help identify what version of the file it is. How do I fix this issue?
I, like you, have also made sure to check the box for "Windows friendly" attachments, but that still hasn't seemed to fix the issue. This issue also just popped up one day out of the blue. I used to be able to send attachments without the file name being truncated.
Any suggestions?