It might be difficult on a different level.

Dr.Hipp mentioned GMail bouncing email sent to him - but hosting email yourself, will just move you to a different side of the bounce - now GMail will be bouncing emails sent by you! See, for example, first comments on the recent HN thread here: https://news.ycombinator.com/item?id=27707857 (ctrl+f for "pain in the" if it's not the first one).

So it looks like convincing GMail to respect your small server is a non-technical problem, which might be an issue for a person with "only engineering" mindset. On the other side, Dr.Hipp looks like a right person to try to convince GMail to respect smaller mailservers!

My own personal experience (with a server that has SPF/DKIM/DMARC all set up, and not listed on public RBLs) has been that GMail, Hotmail, Comcast, and Charter have not been problems.

On the other hand, AT&T is most definitely a problem. They run their own internal RBL, and the best I can guess is that they're blocking Linode. Any mail I send to an AT&T customer gets bounced, and forwarding that bounce to the address they indicate it should be sent to to get delisted accomplishes nothing.

I have found that many RBL's block whole IP blocks owned by various vendors. I believe this is why Linode and others like Digital Ocean now block port 25 on VPSs and make you beg for them to open it. Too many spammers.

This is also a good reason to keep a VPS even if you aren't using it at the moment: it keeps the IP "clean" so that when you put it back into use, it is useful, as opposed to (possibly) some random IP that up until a month ago was spammer central.

> This is also a good reason to keep a VPS even if you aren't using it at the moment: it keeps the IP "clean" so that when you put it back into use, it is useful, as opposed to (possibly) some random IP that up until a month ago was spammer central.

That won't protect you from the block getting on a blacklist though.

No, it won't. But it's better than trying to send mail from an IP that a month ago was hosting phishing sites.

I once wrote some production email handling code. It is amazing email works at all given how poorly so many servers and clients stick to the spec. It was really eye opening. Email is more duct tape and bailing wire than I’ve ever seen anywhere else.