Wladimir PalantSPF: ✅
DKIM: ✅
DMARC: ✅
TLS: ✅
GMail: 554 5.7.1 Spam message rejected
🙄
Jerry 🦙💝🦙@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?
@jerry I went through the Gmail rulebook years ago, multiple times. Yes, everything is set up correctly. I’ve also configured DMARC to reject invalid mails a long time ago because mine never are. Content is also unsuspicious unless you count the word “malicious” (it’s 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. I’m pretty sure that sending the exact same email again will succeed. I just don’t 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 don’t 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 😅 I guess I should check whether my mail server still has deliverability
@jerry I regularly send important emails to my own Gmail account first – they frequently land in the spam folder, something that you cannot even see from the outside. If I mark it as “not spam,” this improves the chances of the actual recipient getting this mail.
Life hacks. 🙄
@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, it’s never more than 1-2 mails per day going towards Gmail (or Microsoft which hasn’t been any less problematic). I’ve been fighting random rejections and my mails being sorted into spam for years, until I eventually gave up and started using my hosting provider’s email server as a relay. Now it’s 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! 🤣
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 ...