Looks like I can send and receive emails from my own server without hiccups. Setup SPF for my domain with my webhost, which seems to be working

Down side is that all my emails to Gmail accounts end up in spam

I don't know if that's a permanent issue or whether I'll need to do something about it. I've decided that I'm really not gonna bother too much. Placating Google's high standards isn't worth my energy right now when I've got a laser cutter to build in the mean time
This is the command I'm using to send email:

# fold myemail.txt |\
mailx -r "me@domain" \
-s"Subject" "recipient@domain"

I just prefer to write out my emails as text files first. I'm terrible at spelling and grammar and need a few reads first
Daniel Moch mastodon (AP)
Well, not I feel like I don't understand the difference between fold and fmt (other than the former appears to be part of POSIX).
I'm on OpenBSD and I just got used to fold. It's really just because of habit more than features
Daniel Moch mastodon (AP)
I actually only discovered fmt like a month ago, but I'm happy to know there's something like it that's part of POSIX. Another trick to keep in the back sleeve.

Before that I thought Vim was pretty much the only way to do this.
Nano does this too, both soft and hard wrapping. But I think it only wraps to screen width because I couldn’t figure out how to set a custom column size
Daniel Moch mastodon (AP)
I'm increasingly of the opinion that a simple utility like fold is the right answer anyway. Text editors are complicated enough just carrying out their core function.
What excuse is Google giving? They’re usually at least decent about explaining their reasoning.
I think they're picky about DKIM (which wasn't hard, but I just didn't have the time to fiddle with it)

I say this because an email that I had previously contacted had no trouble getting my email again after I setup SPF. But a different Gmail got my email in the spam when I sent it for the first time

After I labeled it not spam, it got the rest of the emails in the inbox. So I think I'll be OK as long as I don't need to make first contact by email
Oof, yeah, they can be twitchy about that. I’m grateful that OpenDKIM is so well documented.
I'm probably going to get around to it eventually. I already sent my host the public key so it's really just down to my end
My experience is that if you set SPF and DMARC records right (as well as PTR reverse DNS of course) then Gmail is fine with it.
My host handled PTR already so I’m OK there, I think. I setup SPF yesterday and just added DMARC. Should take 24 hours maybe
Nice.My experience is that the "big" DNS providers (say Google, OpenDNS, Cloudflare) usually pick up DNS changes within 5 to 10 minutes. That is what I see when doing Let's Encrypt cert requests via DNS, and doing other DNS changes. That means you can do DMARC tests pretty soon with e.g. a site like mxtoolbox.com and similar sites - Good luck with the better email delivery.
Thanks! I hope I find enough people to email :P
a friend of mine runs his own mail server, and as I recall he mentioned that you need to set up signing for Gmail to accept the emails. So it's definitely possible, but a bit more hassle.
I just didn’t have time to setup DKIM before I moved on to other stuff, so I setup SPF (yesterday) and DMARC (today) and let it sit. I might finish DKIM later because my host already has the public key, but I don’t have a signing utility installed yet

Either way, I seem to be able to get to the inbox if I first got an email from that Gmail address. It’s only when I send a fresh email that I land in spam
VVelox Friendica
Make sure you have reverse DNS properly set too. The name record the server identifies it's self ass should be what the A record is.

RDNS and SPF are the two big ons.
Luckily, my host set up RDNS for me when I added the domain. SPF seems to be working fine now. I added DMARC today, but it will probably take until tomorrow to take effect
VVelox Friendica
That said, congrats on moving forward and hosting your own email. Dovecot+Postfix+Roundcube+SA make email a truly lovely experience. More people should really do it.

That said if using SA, use a DB backend. Filebackend is a bit twitchy.
Thanks! I'm going super limited in that I'm mostly using stock tools that came OpenBSD. I'm trying to see how little I can use for hosting everything

For web, I think the biggest package I've added so far is PHP
penguin42 mastodon (AP)
there's a mail tester domain where you can send mails and it'll tell you it you've done it all OK.
Oh, I think that’s part of a firewall blocklist because those tools were being used to find misconfigured servers to send spam
penguin42 mastodon (AP)
try mail-tester.com - it can't send spam, you go to it's website and it gives you a unique email address. You send it a mail and then check back at the website and it tells you if anything was wrong.
The entire domain is blocked at the firewall, it seems
VVelox Friendica
Also if you are looking for a handy tool for email testing, I highly suggest swaks.