I was again “Successfully removed from all lists” at SPAM Eating Monkey, but, when I follow their confirmation link, I’m still on the SEM-URIRED list, which was (and still is) the only one I was on before and afterwards – and it’s also the one from where I clicked on the “Request Removal” link. I guess “SPAM Eating Monkey” and I speak different languages where “removed from all blacklists” means something different to them than it does to me. It’s like pulling hen’s teeth. I’m guessing there is no other way to contact this outfit, except via their links. On MXTools they show this is the only blacklist I’m on, but apparently that’s enough. (Just venting, sorry.)
This might give you some hope. When I set up on DO, gmail worked, and keeps working. Well, I had to fix some issues with the various configuration as it was being set to junk. But since then it works fine.
I had an issue with outlook blocking emails completely. I signed up to MS snds service and registered my IP. https://postmaster.live.com/snds/ Took a while, and then some days later I could send email to outlook again. Unfortunately it goes to junk now. But apparently, it takes time to build up a better reputation with them.
I did check the ip address on the spam lists first however. The first one DO gave me was on a list, and also the host was buggy. So I ditched that ‘droplet’, and got a new IP.
Also, I reported the issue to DO through support and got a cookie-cutter response saying it was too hard for them to deal with spam, but they try. Also, they recommended to use a third party service to send mail, and also to try snapshot-moving a droplet to get a new IP address.
My domain is old, so that probably helps. I’ve also seen advice to get a dedicated server from a company that is a bit more reputable, and verifies its customers more. But I’d prefer to wait for the moment, and see how it goes. Dedicated servers have taken too much administration time for me before. And I like the double backup that DO+mailinabox do by default.
I feel this is unfortunately just the administration cost of looking after a mail system. Not sure of a way to reduce that cost for good actors. Mailinabox definitely makes it a LOT less work than completely running a mail server yourself.
When I first fired up DigitalOcean instance of MIAB, I was also having problem with Gmail recipients filing to spam. Not sure if this is coincidental with my sending a request to Gmail to whitelist my ip, but I also had the recipient move the message out of the junk folder (or maybe there’s a button to indicate “not spam” - can’t remember). I did this for my test messages to my own gmail account also. Shortly afterwards the problems went away, not just for these recipients but others too.
Again, may be coincidental but worth a try.