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Sergio Lopez @slp

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.

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

@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'm angry but not surprized… I want to ditch my Google account and go indie but always ending up in Spams is one of my fears.

Could you provide details about your workaround?

@Mallabori @slp Not a workaround, but the only option I've found so far is using Pobox SMTP service (20 bucks a year).

@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.

@Mallabori

Of course ! :p

I'm not saying it's a good thing or what (it's not)... But at least they are better than MicroS**t (which is easy)...

@slp

@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 πŸ˜‚πŸ˜…πŸ˜‚

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

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@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.

@nightpool

it also matters the ownership history of the address (rbl). And having PTR.

@Gargron @slp

@slp good luck. It might be difficult though, but hopefully you'll figure it out. Cheerios.

@slp like @BoF I'll check your PTR but also DNS record. check if the VPS host is allowed to send mail for your domain (MX, SPF...) and if it's named properly.

@BoF

The Port25 Solutions, Inc. team

==========================================================
Summary of Results
==========================================================
SPF check: pass
"iprev" check: pass
DKIM check: pass
SpamAssassin check: ham

@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 Oh, kafkaesque doesn’t even begin to describe the insanity of the email reputation system. This cabal of large providers run a totally unacountable system that still pretty reliably delivers a ton of spam despite INTENSE hostility to little guys.

@ewoozi @slp The Trial, except the protagonist just wants their email delivered

@ewoozi @slp "Don't be evil" would be comical if it weren't causing so much devastation.

@ewoozi @slp People using indie mail servers should put a footer in their emails that say "Did this go to your spam folder? That's because your email provider is evil!" and link to a web page about all the evil shit Google and others are doing to try to turn the Internet into CompuServ and Prodigy with a list of non-shitty providers.

@ewoozi @slp Actually instead of "evil" we should use "monopolistic" to describe Google.

@seanl @ewoozi @slp @elomatreb

Mozilla's move to eliminate text-only emails (thwarted by pushback) was a real eye-opener for me about how email "works" these days: As a sender you get blocked if not enough recipient reply or allow themselves to be tracked via HTML mail components. The big providers infer from this lack of "engagement" that the email is de facto spam.

@slp

I'm not really sure how all of this work so my question might be dumb but does checkdnsrr("yoururl","MX") returns true ? secure.php.net/manual/en/funct

@Nocta

Reverse DNS resolution is working properly. As is SPF, DMAR and DKIM.

Gmail's decision to put this emails in Spam is completely arbitrary.

@slp I had the same issue and I had to alter my DKIM TXT record. Just use k=rsa;t=s;p=yourkeygoeshere

@mindnmotion Thanks. I'll try changing my (valid) DKIM entry to see if Gmail prefers some specific format.

@mindnmotion Just played with DKIM. I always get a "DKIM: 'PASS'" on the receivers side, but still gets into SPAM. Gmail is sooo broken.

@slp what happens if you just manually tell Gmail it's not spam. Do it a couple of times and maybe Gmail will learn.