My Office 365 subscription is up for renewal so it’s time to decide if I want to keep doing this (ehhhhh) or go back to hosting my own mail (ehhh) or look at another provider (ehhhhh)

@fincham It would be nice if email were a solved concept

@fincham @Firesphere when I can find time, I'm moving back to self-hosted, from Namecheap forwarding and ProtonMail. Kinda tired of them almost working.

@car @fincham @Firesphere Been doing it for a few years. Working great. Gag at the thought of letting MSFT anywhere near my data.

@lightweight @car @Firesphere you may be aware I ran my own mail (and for others) for nearly 20 years 😂

@fincham @car @Firesphere yes. All the more reason that I'm flabbergasted you'd let MSFT anywhere near it.

@fincham @car @Firesphere and yes, as you might recall, I'm reasonably well aware of your sysadminning history, having been fairly well adjacent to it. ;)

@lightweight I run most of my stuff, yeah, but despite not minding it, it's not a simple task to maintain :/

@Firesphere I suppose it's not simple, but it's not rocket science either. Been running my own services for a bit more than 20 years. (I used Google for a few years before it became apparent that 'do no evil' was a farce, and still have a Google Apps domain, but it's mostly gathering dust these days).

@lightweight @Firesphere The biggest mistake I made was going "Oh, I probably won't ever have to touch this once it's up and running!"

What in my history with computers made me think that would be true?!

@sj_zero @Firesphere Heh - yes, the programmer's/sysadmin's crone: "I did it, not because it was easy, but because I thought it would be easy". That said I don't spend much time on my email stack - I've been helluva impressed with Mailcow (I run it dockerised) - I run several instances (and a half a dozen NextClouds with OnlyOffice, for various folks)...

@lightweight @car @fincham Your main website seems to be running an outdated version of Silverstripe... And what search does it use?

@Firesphere @car @fincham heh - well spotted. It's an heirloom. I'd say it's running the default. I inherited it - some custom dependencies mean an upgrade is painful, and I've currently got bigger fish to fry. Are you a SS dev?

@lightweight @car @fincham Used to...
I kinda build the Solr8 supporting search module, because I was fed up with running on Solr4 :P

@Firesphere I worked with Solr quite a bit over the years (ran a Drupal dev shop) and am still maintaining a few instances, but I don't go out of my way to use it.

@lightweight It's that Solr4 is large EOL, so... stubborn me made a more useable Solr8 module for it :D

@lightweight @fincham @Firesphere I'd been doing so for a long time when I quit IT three years ago, and decided I could neither afford two EC2 instances any longer, nor be arsed. But ProtonMail's client has always been strangely unloved, and lately I've had the odd email got missing somewhere between Namecheap and ProtonMail. I've got backups containing perfectly serviceable Postfix and Dovecot config. I'll stand up a single Lightsail secondary, primary at home, that'll do.

@car @fincham @Firesphere biggest problem I've found is getting external smtps (esp. Google's and and MS') to see my servers as credible. You need SPF, DKIM, and DMARC records, and managing that can be painful. My Mailcow instances facilitate that stuff for me very effectively.

@lightweight @car @fincham And even with them all correct, Google still regularly rejects emails, without telling you why...

@Firesphere @lightweight @fincham yeah, I remember there being a teething period where stuff was being filed as spam, but that was years ago. I guess I'll have to start over again. Once that passed they continued to occasionally reject stuff as spam, but not consistently for long enough that deliveries failed. I found it grimly amusing, they passed me more spam than I ever handed them.

@car @lightweight @fincham Same problem. Also, depends on the recipient it seems. A newer GMail account rejects more easily than one that exists longer, it seems...

@fincham I can highly recommend Fastmail. I'm an ex employee, but I didn't start using it for my personal mail until I left the company, and I really love it. Their website goes into detail of their privacy and security conditions.

@mattcen hey that’s actually a really nice recommendation, thank you. I conveniently use Fastmail already for my “backup” e-mail account…

@mattcen I really really value having some way to personally evaluate the quality of stuff

@fincham I hear that! And I personally never would've chosen Fastmail for myself if I hadn't worked there, just because I (a) probably wouldn't have been bothered to investigate it and (b) it was great to see behind the scenes how it so works. That said, there's mostly enough info on their website to detail their infrastructure etc.
I'd host my own mail, but I just *really* can't be bothered; it's too hard to get right and too important to not have good uptime.

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