[Discuss] Running a mail server, or not

[david at thekramers.net (David Kramer)]

Quick version of my situation:
- I ran my own mail server at home for a long time, and it was good.

- When I moved from Comcast Business (static IP) to FiOS years ago, 
things got complicated both because of dynamic IP address, and because 
about that time lots of sites started cracking down on SSL certs and 
reverse DNS entries and whatnot, Yahoo and others started rejecting a 
lot of mail that was accepted in the past, etc.? Lots of mail would not 
go through.

- I got a Linode server, and tried to set up a mail server for it and 
failed. I reached out for help here and it didn't work out. The 
directions for setting up postfix/dovecot/procmail/spamassassin/certs 
was incredibly long and complicated, and I'm not a SysAdmin, so I never 
got a full working solution.

- I ended up with the crazy system I have now, where incoming email goes 
to my server still running at home. Outgoing mail goes out my server at 
home and smart relayed through the linode server 
(postfix/dovecot/procmail) so it has a consistent IP address and real 
SSL certificates I bought from GoDaddy.? This... mostly works, but my 
email still can't get send mail to some people. Worse, I can't send mail 
to my family to their @thekramers.net domain name because the Linode 
server won't send them to my server at home.

- I am totally fed up with this brokenness, and from running an ancient 
server at home, and want to fix this right.? Also my certs are expiring 
and I'm getting new ones, so I need to do change things anyway.? DNS 
changes are a hassle, as are power outages.

My main motivations for running my own mail server is that I rely 
heavily on procmail rules to deliver mail to the right folders, and I am 
also not crazy about third parties scanning and storing all my mail, 
though that's negotiable.? The idea solution as I currently see it is 
all mail going through my Linode server, which would be for both 
incoming, outgoing, filtering, webmail of some sort, oh and CalDav and 
CardDav. And move my web server there too eventually. If I can move my 
super old Owncloud? to Nextcloud on the linode server too.? I will 
probably start with https://www.linode.com/docs/email/running-a-mail-server/

My main fear in all of this is that I will try to set everything up and 
it will go wrong, and my mail will bounce, possibly for days, while I am 
job hunting. So I need to go about this carefully.? I'm willing to start 
from scratch on the Linode server. incoming mail will go to my home 
server until I change MX records so at least that part has some leeway.

Questions:
- Are there any other solutions to my end goal (privacy and control over 
mail routing to mailboxes) that I'm missing, other than running my own 
mail server? Some other mail platform I can trust and also set up very 
complex routing rules with?? GMail and Office365 are right out on 
general privacy and trust principles, and client-side filtering is not 
an option because I read my email on 4+ devices.

- Are Postfix/Dovecot/procmail the best tools for me, and worth the 
insane configuration process?

- I've asked here before if anyone was willing to help me, for free or 
for money (no I can't pay $50 an hour but I can pay). Given that failure 
means my mail won't work, relying on asking questions on mailing lists 
if I run into trouble is problematic.

- Right now I have mbox, some of them pretty huge. I have to assume 
there will be a way of moving my mail over from my home server to the 
new server in maildir format, since that is newer and much better. So I 
need to get the server working then I can worry about copying over the 
old mail later.


Thanks in advance. and sorry about the long email. I like to give all 
the details to cut down on the back and forth and wrong paths so I'm not 
wasting others time as much.