This makes me angry:

I run my own mail server in a VPS. Its IP address is NOT blacklisted, and I have both SPF and DKIM properly configured. I do NOT send bulk mail.

But still, Gmail classifies my personal emails as SPAM.

Same email with same exactly same contents, sent through PoBox SMTP server goes to INBOX. Directly from VPS, goes to SPAM. No explanations, no public blacklist. It looks like they just don't want people going "indie". Sigh.

Do you remember that "Don't be evil" motto? Because I'm pretty sure Google doesn't.

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@slp It could also be that other VPS customers are or have been sending spam, or it was your IP with a previous tenant, or you're newly sending mail from a previously unknown IP.

At the risk of giving unsolicited advice, maybe try getting your VPS provider to ask? Or checking the public blacklists for your IP? Or using an smtp health check service? Even something as a mild DNS typo could mess you up.

Good luck, mail is increasingly more of a pain for the small server with each passing year.

@slp
Do you have a ptr record set up for your instance's IP that correlates with it's publicly routable FQDN?

@benarmit @slp Yes, PTR, SPF, DKIM, DMARC, TLS... All reputation check services I've tried report maximum grade. Gmail seems to be playing their own game leaving us in the dark.

@slp have you set reverse DNS for ip4 and ip6? Don't know their current policy, but there were times when they used mark as spam without and times when they completely blocked without

@fll @slp Yes, PTR, SPF, DKIM, DMARC, TLS... All reputation check services I've tried report maximum grade. Gmail seems to be playing their own game leaving us in the dark.

@slp @slp annoying. Seems like you're right and they come up with some rules in the background

@slp I solved that problem by putting a txt record in my dns...

I think that doc should help you : support.google.com/a/answer/18

(I don't remember exactly where I saw that I need a txt record)

@HgO @slp Those instructions are for if Google is hosting your email, on your domain, I believe.

@slp Do you think it would help to send some emails to various gmail users and ask them to mark them as "not spam"?

@stricken @slp No idea. And that's the worst part, there's zero information about why's getting in Spam. The headers on the receiver side look pristine.

@slp The Pursuance Project had the same conclusion and went for MailChimp.

Google is working against the federation of email services. One can imagine what happens when Google starts using the Fediverse. Suddenly a billion GMail users get toots, but not from any instances... Yes?

When big players start confusing tiny and spammy, the edge is getting eroded...

@slp If you send email over IPv6, it may be caused by gmail requiring your IP address to have a reverse DNS.

@val
# grep inet_proto main.cf
inet_protocols = ipv4

@slp this is some bullshit
fuck gmail. cant wait to kick the habit.

@slp you might use services as mail-tester.com to check if you set *everything* up correctly. Just a simple mistake does make Google go apeshit

@Trollwut 10/10 directly from VPS (gets into Spam on Gmail). 6.4/10 relaying through Pobox (gets into INBOX). Go figure.

@slp Did you also check the orange ("not so green") checks on the site? For me I got 10/10, but google was annoyed, as I was missing a DMARC entry (which was orange there)

@Trollwut The only orange I have is for the email format, but that's because I'm sending the test message from K9 Mail.

@slp
Don't they still do this grey blocking where the mail must be resent?

@bandie @slp Greylisting is a very distinct message from spam, though. =\ Spammers generally don't resend, so anybody obeying the 451 (or whatever) are likely legit.

@slp @gargron we run our own email server on a vps for cybrespace and have never had problems with gmail, except when our dkim keys were broken. do you have a dedicated IP or do you share it with others?

@nightpool @gargron @slp same.

slp, can you pull up the email that went to spam, and look into the message details/info? sometimes there's hints there on what went wrong...

@slp @nightpool lol, i tried to reproduce with a domain that went reliably straight to Spam for _months_, ..., ...,,,.,.,. but not anymore 😂😅😂

@tethre @Gargron @nightpool Already did. Ironically, the headers indicate SPF is valid and everything looks good, on a message that got into Spam...

mail setup stuff 

@slp maybe delete the spf and go with dmarc?

mail setup stuff 

@tethre Certainly we shouldn't need to be guessing. The lack of transparency is what frustrates me the most. But I'll try it anyway, thanks.

@nightpool @Gargron IP is dedicated and static and the reputation is good. I don't think I'm blacklisted, but I'm getting "extra points" from their spam filter. Some personal emails get into Spam, others into INBOX.

@slp do you have a reverse DNS record set on the VPS IP that matches an MX record?

@slp Surprised you're having trouble with Gmail, I run my own server and have never had a problem with them even when sending from a dynamic IP in the early days. Hotmail/Outlook.com on the other hand are endless trouble. They tend to accept the email then silently drop afterwards 😫

@paul @slp at least Microsoft has an IP check and delist service, Google doesn't?

A Gmail user who moves your mails to Spam/ could affect domain score too.

@horia @slp Good point. As far as I know the way to get delisted from the Google spam list is the same way you get help with other free offerings from Google:

Know someone who works there and ask them to delist you.

@paul I've been running my own email server for years. This started happening just a few months ago. Guess they "improved" their spam filters without caring for people going "solo". Monopolists...

@slp yikes, terrible news. I was always comforted that although MS were doing it, Google had the larger share of the market and were behaving themselves.

Looks like that might be changing 😞

@slp Most likely your webhost hosts a bunch of spammers even if you don't so Gmail as their AS flagged/ blacklisted.

Also, have you checked available dnsbls?

And are you moving these spam marked messages as "not spam" when they arrive?

You could always set up a filter that files everything from your domain into your Inbox.

@gme My IP is not on any DNSBL/RBL and its reputation is reported as 'good' (I've owned it for years).

If I mark an email as 'not spam' in Gmail, the rest of emails start arriving in INBOX (at least for a while). But the point is that I can't really known if a message I'm sending to Gmail (or a GSuite hosted domain) will get noticed.

@slp Gmail is worse than that. They sometimes silently drop emails to certain individuals. Completely drop, meaning they're not in spam or anywhere, and yet a delivery confirmation is given.

@slp seriously? Your mail passes https://www.mail-tester.com with a 10/10 and you're getting marked as spam? That's insane...

@feld And if relay through Pobox (without changing SPF entries!) my score goes down to 6.4, but mails get into Gmail's INBOX. This is ridiculous.

@slp Screw Google. Along with FB et al. They're a cancer on the internet.

@slp I feel your pain. Such a vile vile monstrous system they set up. Truly fucking awful.

@slp I'm willing to bet that it's because you're using Digital Ocean.

@slp
I gave up running my own direct SMTP servers a while ago, for just that reason. I now send via Mailgun. It works, but it shouldn’t be necessary.

@slp Also when your address is stored in the addressbook in the account of the adressee? @nerdhochburg

@slp That's one of the reasons why I think the age of e-mail has to come to an end.

@slp Honestly, it's not possible to run your own email server anymore... Unless you operate at large scale, you just can't have the leverage to get your mails delivered anymore.

@slp I'm sure that most of the companies are trying to create a corporatized ecosystem for even their e-mail services. They don't like the idea that you can build your own non-proprietary service to compete with their ad-laden garbage.

I'm considering taking back control of my e-mail. I have the equipment, but I just haven't spent the time learning how to setup a server that's able to be accessed anywhere for e-mail syncing. Any tips or suggestions on how to start?

@SeanFromPVD @slp I'm new to self-hosting my email address, and enjoying full control over my Inbox 📫 with this configuration: github.com/vedetta-com/caesoni

@slp Same problem, it's normal Google behavior.

@slp

Might be related to the IP itself. I manage a bunch of self hosted mailservers, Gmail never was a problem. MS Outlook.com/Live/Hotmail on the other end. Ough.

@slp Do you use a fixed ip address for your mail server?

@seanl Yup, and Gmail acknowledges it:

security: Standard encryption (TLS)

@slp Your IP may be on a unqualified network.

@slp Gmail only considers it's best interest. I wrote an article about it in French carlchenet.com/gmail-linsideus

@slp check the reputation of your provider. I regularly see spam come from swaths of ips from the same network

@slp Google was blacklisted by SORBS just a few days ago. Gmail is not a "legitimate" E-mail service. Stay private and encourage everyone else to go private until Gmail is killed.

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