Yeah I really will give people a pass here. The state of email is one of the worst collective mistakes I think we've made.
You can literally be an expert in everything relevant - and your mail will still not get delivered just because you're not google/mailgun/etc.
I was trying to do a very simple email-to-self use-case. I was sending mail from my VPS (residential IP not even allowed at all) which was an IPv4 i'd had for literally 2+ years to exactly only myself - my personal gmail. I had it all set up - SPF, DKIM, TLS, etc etc. And I was STILL randomly getting emails sent directly to spam / showing up with the annoying ! icon (grates on my sensibilities). I ended up determining - after tremendous, tremendous pain in researching / debugging - that my DKIM sigs and SPF were all indeed perfect (I had been doubting myself until I realized I could just check what gmail thought about SPF/DKIM/etc. It all passed). And my only sin was just not being in the in-crowd.
Incredibly frustrating. The only winning move is not to play. I ended up just switching from emails-to-self to using a discord webhook to @ myself in my private discord server, so I get a push notification.
And this was just me, sending to myself! Low volume (0-2 emails per WEEK). Literally not even trying to actually send emails to other people.
1) use a specialized distribution (I use yunohost but there are others). This makes configuring SPF, DKIM, TLS and more a breeze
2) use a reputable relay to send your emails (I use OVH but again there are plenty of other choices)
Of course it means you are not "pure" because emails you send will go trough a 3rd party (the relay) but it solved the delivery issue entirely for me, so that I can continue to benefit from all the other benefits of self-hosting.
I'm self-hosting my mail server without a relay. It is still possible, you just need to be persistent. In the beginning Microsoft might just let your mails vanish and while they won't confirm this when you contact them doing so eventually resolved my delivery issues with their mail servers. With Google I didn't have any issues.
Yeah I really will give people a pass here. The state of email is one of the worst collective mistakes I think we've made.
You can literally be an expert in everything relevant - and your mail will still not get delivered just because you're not google/mailgun/etc.
I was trying to do a very simple email-to-self use-case. I was sending mail from my VPS (residential IP not even allowed at all) which was an IPv4 i'd had for literally 2+ years to exactly only myself - my personal gmail. I had it all set up - SPF, DKIM, TLS, etc etc. And I was STILL randomly getting emails sent directly to spam / showing up with the annoying ! icon (grates on my sensibilities). I ended up determining - after tremendous, tremendous pain in researching / debugging - that my DKIM sigs and SPF were all indeed perfect (I had been doubting myself until I realized I could just check what gmail thought about SPF/DKIM/etc. It all passed). And my only sin was just not being in the in-crowd.
Incredibly frustrating. The only winning move is not to play. I ended up just switching from emails-to-self to using a discord webhook to @ myself in my private discord server, so I get a push notification.
And this was just me, sending to myself! Low volume (0-2 emails per WEEK). Literally not even trying to actually send emails to other people.
I'm self-hosting for 17 years and counting.
In my opinion, the pragmatic solution I use is:
1) use a specialized distribution (I use yunohost but there are others). This makes configuring SPF, DKIM, TLS and more a breeze
2) use a reputable relay to send your emails (I use OVH but again there are plenty of other choices)
Of course it means you are not "pure" because emails you send will go trough a 3rd party (the relay) but it solved the delivery issue entirely for me, so that I can continue to benefit from all the other benefits of self-hosting.
I'm self-hosting my mail server without a relay. It is still possible, you just need to be persistent. In the beginning Microsoft might just let your mails vanish and while they won't confirm this when you contact them doing so eventually resolved my delivery issues with their mail servers. With Google I didn't have any issues.