The main thing I’m hoping to recover is the webmail (I think) service most of my family used. That went down in September, and we’ve lost access to a number of other accounts because of that.

At first, I self-hosted email on home server. Paid extra for a dedicated IPv4 address in the cable broadband bill at a residence.

I then started dealing with critical business emails, and a single server at the house is not reliable for that so I migrated to semi-self-hosted by paying for business-class email package. I still use my custom domain and point the DNS MX records the the hosting company’s server. That was 15 years ago and had a few family & friends also use that for email.

But I’m now in the process of getting everyone off my email server except for me and migrating them to GMail and Microsoft 365 Outlook. They need simple reliable email and my 1-man-army of IT staff (me & myself & I) cannot support them if I’m in the hospital for a month.

My custom email setup has “too many moving parts”. There’s a login in at the registrar to constantly renew the domain. And there’s another login at the hosting company and pay that yearly bill with a credit card. There are multiple points of failure. I’m the proverbial “if he gets hit by a bus” problem:

No, I can’t write up some documentation with screenshots so they know how to navigate the process at the registrar and hosting company. E.g. if they try to login from their “unrecognized” computer to takeover email administrator tasks, a 2FA email confirmation with random 6-digit code would be sent to guess where? To my email, not theirs. The interconnected dependencies are complicated and invisible because the recovery procedures are not stress-tested. Besides, the web UI changes constantly at those companies so the “oh shit what do I do” documentation would quickly get out of date anyway.

The redditor’s story just reinforces my decision to not let people depend on my email server anymore.

If you’re hosting email for family & friends, carefully think through all possible failure modes so they’re not in trouble if you’re not around.

Forwarded from Y18, right remains to the original author