[fiddly_bits]

A recent problem I ran into was sending Xmas cards to friends and family. We had over a hundred addresses to send to and I didn't want to send them all by hand. So, I wrote a script. Of course, most of the emails went straight into the spam folders because, I guess, doing this just made them look like spam to most filters.

Granted, the emails were all sent from a shared hosting account, the mail server of which I had no control over as far as certificates and reputation were concerned. But my feeling is that anything I could have done to improve my Xmas greetings' success rate would have been exactly what spammers also try to do.

Aggressive filters assume everyone is a bad actor until proven otherwise, and I think that's a problem. Our quality of life is degraded whenever we make this calculation.

[lobotryas]

What about using BCC? The email will reach multiple recipients, but none will know about the others.

[fiddly_bits]

My script wrote an individual email to every recipient in my list; so none of them knew about the others anyway. I speculate that the email servers that received them, particularly the larger service providers, might have seen multiple copies going to different addresses, noticed that the emails were identical, and assumed they were spam. Usually, a pretty good rule for a filter. But in my case, not so much.