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Re:Mox: Modern full-featured mail server for low-maintenance... by 1vuio0pswjnm7 on Thursday February 23, 2023 @06:14AM (#34909099)
This sums up the problem quite nicely.

IMO, what needs to happen is for people to see the 1 in 1000 as a problem with Gmail et al. rather than a problem with someone hosting their own STMP server.

Generally speaking, people I know who self-host their email do not have problems. However, inevitably there is the 1 in 1000. IMO, unreached recipients using Gmail et al. are likely to see the problem as with the self-hosted sender, not their own third party email provider.

One idea is to have a backup for emergencies. That is, a Gmail user could have an alternative, self-hosted means of receiving email on port 587 or 2525. By default, this mail drop accepts mail from no one. When there's a 1 in 1000 problem, the recipient could add the sender to a list of acceptable senders, either temporaily or permanently. The sender can then use the alternative instead of Gmail.

Re:Mox: Modern full-featured mail server for low-maintenance... by creshal on Thursday February 23, 2023 @06:50AM (#34909312)
To be honest, in the last 20 years or so of self-hosting emails, the most common failure points were

• Gmail marked an email as spam, but still delivered it. Easily cleared up, no hard feelings on either side.

• Someone else self-hosts some abysmally maintained Exchange 2003 setup that just about barely works with GMail and Office365, after the MSP irresponsible for it gets enough verbal beatings. Impossible to get to work.