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ScottPeterJohnson / purelymail-issues

Issues repository for the Purelymail email service.
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Outbound to Gmail does not work #94

Closed ScottPeterJohnson closed 2 years ago

ScottPeterJohnson commented 2 years ago

(This issue was imported from Gitea) jylertones on February 15, 2022: My outbound emails to Gmail are not working.

I have tried:

  1. A personal gmail account
  2. A workspace gmail account
  3. Simple messages
  4. Replies to threads

These were all working until this evening. My first failed message was around 9pm ET.

This is the response I get:

We could not deliver the attached mail for the following recipients.

@gmail.com at remote mailserver gmail-smtp-in.l.google.com. (209.85.232.27): SMTPSendFailedException: 550-5.7.1 [34.202.193.197 12] Our system has detected that this message is 550-5.7.1 likely unsolicited mail. To reduce the amount of spam sent to Gmail, 550-5.7.1 this message has been blocked. Please visit 550-5.7.1 https://support.google.com/mail/?p=UnsolicitedMessageError 550 5.7.1 for more information. h20si8431108qth.591 - gsmtp (5.0.0) Reporting-MTA: dns;purelymail.com Arrival-Date: Wed, 16 Feb 2022 02:35:56 +0000 Final-Recipient: @gmail.com Action: failed Status: 5.0.0 Diagnostic-Code: error; SMTPSendFailedException: 550-5.7.1 [34.202.193.197 12] Our system has detected that this message is 550-5.7.1 likely unsolicited mail. To reduce the amount of spam sent to Gmail, 550-5.7.1 this message has been blocked. Please visit 550-5.7.1 https://support.google.com/mail/?p=UnsolicitedMessageError 550 5.7.1 for more information. h20si8431108qth.591 - gsmtp Remote-MTA: dns; gmail-smtp-in.l.google.com. (209.85.232.27) Last-Attempt-Date: Wed, 16 Feb 2022 02:35:56 +0000
ScottPeterJohnson commented 2 years ago

Comment by jylertones on February 15, 2022: Okay, resolved. Appears there may have been old TXT SPF records on the domain. It's strange that this just today caused problems. But it appears to be resolved.

ScottPeterJohnson commented 2 years ago

Comment by Scott on February 15, 2022: I did notice the extra SPF record and would've told you about it (had you not deleted it by the time I double-checked). I don't know why Gmail would take exceptional issue to that though! Messages are all DKIM signed and should be authenticated that way. Maybe they just now added a hard rule that sites with multiple SPF records are spammers or something?

ScottPeterJohnson commented 2 years ago

Comment by jylertones on February 16, 2022: That's my best guess.

As part of my troubleshooting process, I ran into Google's recommendation to sign up for postmaster tools. Do you generally recommend that? Is that helpful at all?

ScottPeterJohnson commented 2 years ago

Comment by Scott on February 17, 2022: Signing up for Postmaster may give some deliverability bonus for a domain. But the actual site won't be very helpful.