Thank you everyone for your input.
After reading the various comments, I decided to try creating a connector in 365, specifically for emails going to the Gmail domain.
Funnily enough, the emails are now delivered to Google's servers, albeit the messages end up in users spam folders, as opposed to their inboxes.
Would this be an SPF issue or something else?
This afternoon I opened another case with Microsoft and explained what has taken place and about the connector.
They have admitted that they are having issues with messages not being delivered to Google, after spending the past week saying the opposite!
Thanks,
Simon
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-----Original Message-----
From: Al Iverson <aiver...@wombatmail.com>
Sent: Wednesday, April 24, 2024 4:05 PM
To: Mailop Mailing List <mailop@mailop.org>
Subject: Re: [mailop] Cannot send messages to Google Mail users
Is disabling IPv6 an option here? A prior poster suggested as such, but I don't know if that was just a general suggestion or if that's actually possible in O365 settings.
But if you can .... yes, try sending outbound mail only via IPv4. A "well known secret" is that Gmail filters mail from IPv6 connections more harshly than IPv4. Maybe less than they once did, and certainly you could question if it's fair or not, but I saw clear evidence of it in the past. I personally have IPv6 disabled on my MTA because of it.
Also make sure your DKIM is set up as YOU and not just as the default *.onmicrosoft.com that Microsoft sticks on there for those who aren't fully configured.
If you want folks to look at headers and offer up additional suggestions, run a test using https://aboutmy.email and share the results link here. I'll take a look and advise, and I imagine others will, too.
Cheers,
Al Iverson
--
Al Iverson // 312-725-0130 // Chicago
http://www.spamresource.com // Deliverability http://www.aliverson.com // All about me https://xnnd.com/calendar // Book my calendar
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