I used to work IT helpdesk and once spent weeks trying to find out why my company’s emails were getting bounced all of the sudden. We had just switched to Microsoft’s hosted exchange (office 365) so we figured that must be it. I escalated the issue until I got some very technical folks on the phone, but all they could say was that everything looked 100% fine and that something we were sending was tripping the spam filters. I thought about it and realized we recently changed our email signatures to include a bit.ly shortened link. I guess spammers also use that to obfuscate their links so we were indeed sending out sketchy email
I mean that one was pretty obvious. Why on earth send a bit.ly link in every email? You have a-hrefs in email, so the link doesn’t even need to be shortened.
> I got some very technical folks on the phone, but all they could say was that everything looked 100% fine and that something we were sending was tripping the spam filters
This “we won’t tell you what triggered it because it helps the spammers” is… questionable, and it feels like security by obscurity. Yes, it may help the spammers a little but not possibly enough to warrant the black hole of debugging legit issues.
The right way to fight spammers isn’t about arms racing with hyper-advanced content filtering. Instead, we need to make it uneconomical.
The bit.ly link was to track how many people clicked on it, for marketing purposes I guess.
As for the support team on our email provider’s side, they didn’t know what was tripping it. We simply got to a point where we ruled everything else out. The only thing left was the content of the email being legitimately spammy, somehow.
Our email provider wasn’t the one that was filtering our emails, at any rate, rather it was the recipient email systems.
