π’π‘π΅π’π«π΅πͺπ¨πͺπ©
Wladimir PalantSPF: β
β
DKIM: β
β
DMARC: β
β
TLS: β
β
GMail: 554 5.7.1 Spam message rejected
πβ
Jerry π¦ππ¦@WPalant reverse DNS set?
@WPalant reverse dns kept tripping me up. I think the only other thing it could be is a block list or the content of the mail itself. also, are dkim/spf set to deny?
kravietz π¦@jerry
DKIM and MTA-STS reports occasionally contain useful hints why the receiving end thinks thereβs something wrong with the email. Also, having your MX addresses whitelisted is important β before it was Dnswl, now I think Abusix.
DKIM and MTA-STS reports occasionally contain useful hints why the receiving end thinks thereβs something wrong with the email. Also, having your MX addresses whitelisted is important β before it was Dnswl, now I think Abusix.
@jerry I went through the Gmail rulebook years ago, multiple times. Yes, everything is set up correctly. Iβve also configured DMARC to reject invalid mails a long time ago because mine never are. Content is also unsuspicious unless you count the word βmaliciousβ (itβs actually the notification about this comment reply: https://palant.info/2023/06/08/another-cluster-of-potentially-malicious-chrome-extensions/#c000006r000001)
But Gmail just does these things randomly. Iβm pretty sure that sending the exact same email again will succeed. I just donβt care enough to try.
@WPalant there used to be a gmail security person here - I don't recall who it was nor if they're still here but I'll boost in case
@jerry Thank you, even though I donβt think this will help. Gmail is losing their fight against the spam, so they are increasingly rejecting valid mail from any servers but a few big names.
@WPalant π
β I guess I should check whether my mail server still has deliverability
@jerry I regularly send important emails to my own Gmail account first β they frequently land in the spam folder, something that you cannot even see from the outside. If I mark it as βnot spam,β this improves the chances of the actual recipient getting this mail.
Life hacks. πβ
@WPalant I used mailgun for a while (for infosec.exchange) and ended up ditching it because the volume of emails was starting to cost a lot AND I was getting a lot of rejections, so started self hosting. Perhaps I'm just lucky or got a good IP address, but it's been working well.
@jerry Volume makes a huge difference. My server has very little volume, itβs never more than 1-2 mails per day going towards Gmail (or Microsoft which hasnβt been any less problematic). Iβve been fighting random rejections and my mails being sorted into spam for years, until I eventually gave up and started using my hosting providerβs email server as a relay. Now itβs actually way better.
Michael Potts (HMHackMaster)@WPalant I am gonna note this for the future when I get asked why I have so many monitoring alert emails being generated (that I don't get around to immediately resolving or silencing): keeping the mail volume from my own mail server to my Gmail/Gapps account high is keeping me on the good side of Gmail's spam filters! π€£
Colin the MathmoThis is a really useful thread that I'll want to come back to, so I'll document it for my own use.
Thank you everyone.
Calling @Chartodon Spine ...
mangymagi:~#
@jerry
I'm a big self-hoster, and looking to migrate my email to self-hosted as well. What are you using as your server and what relay do you recommend?
I'm a big self-hoster, and looking to migrate my email to self-hosted as well. What are you using as your server and what relay do you recommend?
@mangymagi I have a server running webmin/virtualmin - itβs fully self hosted - no other relay. Mailgun worked well for low volumes if youβre ok with occasionally having mail rejected.
AlisonW βΏπ³οΈβπβΎοΈ@jerry @mangymagi
I've run my own mailserver from home (fixed ip) for over 20 years using a number of different OS and package options. My own thought on seeing the OP was dns but if that's set correctly then I've no idea. Just sent a message from me to Gmail and it arrived in seconds no issues.
Are the failed messages bouncing back with anything interesting in the headers?
I've run my own mailserver from home (fixed ip) for over 20 years using a number of different OS and package options. My own thought on seeing the OP was dns but if that's set correctly then I've no idea. Just sent a message from me to Gmail and it arrived in seconds no issues.
Are the failed messages bouncing back with anything interesting in the headers?
BjΓΆrn Heiker
Guillaume Rossolini@WPalant @molly0xfff has a great write-up about this recently
Thereβs also domain warmup, possibly ip warmup or decay, etc
0bondo7@WPalant tell me about it
XenoPhage 
@WPalant Yes, gmail is, in fact, the worst. I've been fighting this for years. Best I can tell, there's nothing you can actually do. It magically clears itself up every so often, despite not making any changes.
β§-440729 [sophie raven]@XenoPhage @WPalant Honestly I feel like microsoft has become a lot worse than gmail. They just silently sort mails into spam, sometimes even apparently discarding them entirely.
amiloradovsky@WPalant I've set all that except DMARC, and for TLS they've lowered the rating because "forward secrecy" (they didn't like the algorithms Let's Encrypt used for the cert)
actually I wouldn't even bother with SPF or DKIM, it's not for countering spam, but I still did for fuck's sake even though I have no reasons to send e-mail to gmail (if it's their only address, I don't want to contact them)
actually I wouldn't even bother with SPF or DKIM, it's not for countering spam, but I still did for fuck's sake even though I have no reasons to send e-mail to gmail (if it's their only address, I don't want to contact them)
~n@WPalant @number137 At the same time: Inbox full of spam from gmail π
Rose@WPalant better than outlook, who accepts and silently drops your message, even with all of the green checkmarks π
snaeqe@WPalant
You not being Google is a Yellow Flag to Google when delivering mail to Google.
You not being Google is a Yellow Flag to Google when delivering mail to Google.
Jim Fenton πΊπΈπ¨π¦@WPalant what is the reputation of your IP addresses (both v4 and v6) with Spamhaus?
http @WPalant Some random thoughts:
Reverse DNS ok?
In a static IP range?
SRS?
Sending reputation history of many years?
Big volume each day?
Not on any blocklist?
Content bad wordlist check?
Secret rejection reason?
Reverse DNS ok?
In a static IP range?
SRS?
Sending reputation history of many years?
Big volume each day?
Not on any blocklist?
Content bad wordlist check?
Secret rejection reason?