[Discuss] Running a mail server, or not

[david at thekramers.net (David Kramer)]

So.. it seems the say to filter and save mail to different folders in 
the way I was with Procmail, is a Dovecot plugin called Pigeonhole 
(https://wiki.dovecot.org/Pigeonhole/), which happens to be configurable 
in the Sieve language.? Integration was pretty trivial, as was 
translating Procmail's configuration language to Sieve.? My one 
disappointment is that procmail's configuration was procedural, like a 
script.? That allowed you to do things like, change debugging levels for 
sections of the script you are working on.? With Pigeonhole debugging 
level is global, making it hard to debug one particular part.

Spam and antivirus was a little harder.? I'm using Amavis, which is kind 
of a meta tool that passes mail through other filters, like clamav and 
spamassassin.? I'm still getting errors from that process I haven't 
looked into yet.? And I also haven't found how to train spamassassin on 
spam it missed yet in a way that doesn't require ssh access to the 
server (so my wife can do it too).

Next is installing groupware.? My current server has a VERY old version 
of Owncloud, which is now Nextcloud.? Their software doesn't seem to be 
able to do some very basic things, like schedule a calendar event based 
on the third Wednesday of each month.? My forum posts have not been 
answered.? I am strongly considering Horde, and will probably try that 
out this weekend.? I need shared calendaring, address book, webmail, 
CalDav server, and CardDav server at the very least.

I will also move over my wordpress site too, but that's all up to date 
software so it should be lift and shift.


On 06/23/2018 02:45 PM, David Kramer wrote:
> Update: Mostly successful!? I set up postfix and dovecot using MySQL 
> for the virtual users and domains, using a domain name I wasn't using 
> for anything else (bostongeeks.net), as a test.
>
> Most of the details I followed were from 
> https://www.linode.com/docs/email/postfix/email-with-postfix-dovecot-and-mysql/ 
> with higher level details coming from 
> https://www.linode.com/docs/email/running-a-mail-server/.? Also 
> followed their pages for securing the server, and [tried to] follow 
> their directions for installing the certs.? Here are some interesting 
> things I ran into:
>
> Installing mysql-server no longer prompts you for a root password on 
> install.? it does this crazy thing where if you run mysql/mysqladmin 
> as root, it lets you in without a password.? Even if you set the root 
> password, you can't get into mysql as root unless you're logged in as 
> root, and then it ignores the password.? In the mysql.user table, the 
> record for root has a plugin of auth_socket instead of 
> mysql_native_password.? I added a new record and then it worked.
>
> Another mysql problem I ran into is some of the configuration (from 
> the default files and the directions above) use localhost, and some 
> use 127.0.0.1.? It pains me that this is still a problem in 2018.? So 
> I had to add another user record so both would work.
>
> With respect to the certs, it went easier than I thought, but part of 
> the confusion is different systems call the cert and key files 
> different things with different extensions.? A lot of mail 
> documentation talks about pem files, but I had a crt file and a key 
> file.? After some searching I found a page 
> <https://stackoverflow.com/questions/991758/how-to-get-pem-file-from-key-and-crt-file> 
> that explained that pem is kind of a format, and crt files are often 
> also pem files and how to tell if yours is.? Mine was, so rock and roll.
>
> Dovecot is the strong, silent type.? It hardly ever tells you when 
> it's unhappy and why, and will die with no messages.? And worse, it 
> spits out messages like "dovecot: auth: Error: auth worker: Aborted 
> PASSV request for david at bostongeeks.net: Shutting down", when it's not 
> actually shutting down. Google says "Oh everybody gets that, ignore 
> it."? I was pretty unhappy about that.
>
> OK, here was the most fun. This one is more particular to my system 
> than helpful to others, but it could be entertaining.? When I got 
> everything together, and ran a test sending an email from my desktop 
> machine as david at thekramers.net to david at bostongeeks.net, and got 
> "RCPT TO failed: : Recipient address rejected: User unknown in virtual 
> mailbox table">? I double checked and the virtual domain and virtual 
> user were set up correctly.?? Lots of googling on this one, and I 
> finally figured out the problem wasn't the new server at all, but my 
> current mail server, which was still set up to get mail for 
> bostongeeks.net but had no users for it. This was hard to track down 
> because there were so many machines involved that are running postfix 
> and could have been the origin of that message: My desktop server, my 
> home mail server, my old Linode node mail server, and the new Linode 
> node mail server. This also took a while to diagnose because I 
> suspected that was the problem, but I grepped all of /etc on that 
> server for bostongeeks.net and found nothing, but that's because it 
> was in the database.? I deleted that virtual domain and it all worked.
>
> Thank you all for your advice.? I'm hopeful I will be able to fully 
> switch over very shortly. I still have some things to work on which I 
> will post in a separate email.
>
>
> On 06/20/2018 04:26 AM, David Kramer 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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