@manton It’s been a while since I’ve dealt with this issue so I’m sure you’re way more up to speed on it than I am, but do you have a dedicated IP you’re sending from? So many issues used to be caused by shared IPs at email vendors. One other thing I remember is separating transactional emails from marketing emails so one doesn’t impact the other’s reputation.

Regardless, best of luck. It’s a super frustrating issue to deal with.

@jefflopes I used to have a dedicated IP and think many of my problems stem from getting rid of it. Moving to AWS should give me some more flexibility to bring it back (at more reasonable prices).

@manton on a much, much, much tinier scale, I’ve had good success with Amazon SES (WordPress websites sending 2FA codes).

@kq Mostly to avoid bad passwords, security problems with shared passwords if my servers are hacked, and more generally I think everything is moving away from passwords.

@chailey I am using SES as well and, although I’m sure I have much smaller scale needs, I have found few problems with deliverability. There are some basic tools that help tracking bounce metrics and other things that can ding your reputation. No idea how it compares to SendGrid.

we’ve had great success at SES (we allow magic link, Microsoft, or Google auth only), but definitely found value in a few months of subscription with Demarcian to make sure things like DKIM, DMARC, SPF, and other configuration was all clean.