Make changes so emails stop being detected as spam

[maebeale]

No description provided.

[solebared]

From slack:

grenewode Feb 23rd at 10:33 PM
It looks like the .ct.sendgrid.net/ url got on this list: https://easylist.to/easylist/easyprivacy.txt
also, my email provider (protonmail) flagged the email as Spam

mae (she/her/hers, mutual-aid-app dev)
Do you know if this is avoidable and/or reversible, @grenewode

grenewode
Well, I can just bypass the warning page
So its not really a breaking bug

mae
Well, since you know it's going to spam, but, wondering if this has a clue re how we could avoid autoemails going to spam for folks.

grenewode
Oh. Hm. I'm not sure. That might depend on what email provider you use. My guess is that bad actors are using .ct.sendgrid.net as a way to carpet spam people, so it gets on lists

grenewode
One thing I did notice is that the email got flagged as not being properly authenticated - maybe some of this stuff is messed up? https://sendgrid.com/blog/10-tips-to-keep-email-out-of-the-spam-folder/#authenticate
SendGridSendGrid
How to Stop Your Emails From Going to Spam - 10 Tips
Wondering how to keep your emails from going to spam? Here are our top tips to help keep your wanted emails out of the dreaded spam folder and in the inbox.
Jan 27th (63 kB)
https://sendgrid.com/wp-content/uploads/2014/05/iStock_000023289180Small.jpg

mae
Yup, that makes sense. I've done some research into making email be less spammy but it's soooo dense that I glaze over and have a hard time picking things to tackle.

mae
Haha. Exactly! 101 (!!!) things. Like, can someone tell me 5 that are actionable!?!! :) (Not saying you are the someone -- just that's where I'm at with this topic.)

grenewode
Yeah

grenewode
One thing is that protonmail tends to be overcautious about everything, so I'd check with different providers

grenewode
This has some more info: https://stackoverflow.com/questions/41879731/sendgrid-email-always-being-sent-to-gmail-spam
Stack OverflowStack Overflow
Sendgrid email always being sent to gmail spam
I have a clickfunnel account using sendgrid for smtp. The email being sent are all ending up in GMAILs SPAM inbox. The emails are text that contain a link to a pdf that was requested via an opt-i...

grenewode
Also, when I open the email, it looks like there's a tracking pixel being inserted by sendgrid, which might be upsetting some spam filters

grenewode
Here are the message headers:
pgp.txt

grenewode
According to senderscore.org, that ip address has a good reputation now but looks like maybe its been low over the last few days: https://www.senderscore.org/report/?lookup=167.89.12.138&authenticated=true
or months

[solebared]

NWMI is also reporting issues with DMARC authentication:

[joofsh]

Based on our research the issue comes in because we’re trying to send the emails From a gmail address, but they’re really coming from Sengrid. We’d have to make DNS changes to authenticate this mismatch in sending domains, which gmail does not support directly. So we could change the From to be the production domain, then set the relevant DNS records for that domain, and then have the reply-to value for emails be that gmail address. We believe this would fix it.

Since the mutual-add app is deployed across several instances, there is not one unified domain they come from. In which case it might be simplest to have the emails come From sendgrid directly. As next steps, I would recommend someone with access poke around within Sendgrid and see if they can change the current gmail address to be the reply-to, and to then change the From to be sendgrid's domain/email address. This might alleviate the issue without any DNS changes

CC @tylerwillingham @onebree

[maebeale]

TY for researching this and adding more documentation and a recommendation!