[Discuss] Running a mail server, or not

[jabr at blu.org (John Abreau)]

Last time I was in a similar situation, I started with a dry run by setting
up the new system with a different domain for testing.

Once everything was working correctly with the test domain, I switched the
new system to the original domain but didn't update the MX records, and did
further testing. That way, real incoming mail continued to be routed to the
old system, while I used hand-crafted SMTP protocol and telnet connections
to port 25 of the new system for incoming test messages.

Once I had tested thoroughly and confirmed that the new system was
functioning correctly, I then switched over the MX records.



On Wed, Jun 20, 2018 at 4:26 AM, David Kramer <david at thekramers.net> wrote:

> 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.
>
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>



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John Abreau / Executive Director, Boston Linux & Unix
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