Auto Forwareded email from Outlook not arriving in users Workspace Gmail

[TwistedHelixis]

Small primary has just federated with another small primary school. I look after the Google Workspace school and someone else looks after the 365 primary school.

 

One of our office staff went over to the 365 school and was given a 356 email. She then setup forwarding to her Gmail email, so any emails the other school would send her would also forward to her main Gmail email.

 

Apparently this is not working and the 365 IT sent her the following....

Your message wasn't delivered because the recipients email provider rejected it

 

We literally never have any issues with any emails getting received, I only know of one other rejected email in the last 2 years.

 

Is there a log somewhere of rejected emails in Workspace? I have had a look but cant find anything.

 

Any other advice to help workout whats causing the issue.

[TwistedHelixis]

Just to add, I believe the user has been receiving other emails from the 365 school to her Gmail account, although I'll need to double check this with them.

If this is the case, why would emails sent directly be ok, but forwarded emails get rejected?

[DWilson1997]

I'm sure the default in 365 is block external forwarding and you add an exception in the anti spam policy

[TwistedHelixis]

Thanks, Ill get their IT to look into that.

[dapaulio]

I'm sure the default in 365 is block external forwarding and you add an exception in the anti spam policy

 

I agree if all mail were getting blocked but you mention and suggest need to find out whether the user has receive some 365 mail to her gmail. anti spam policy will be apply all if you have a redirect in place unless there is another policy more specific above it

 

Oddly though you saying this has triggered a lightbulb moment I was discussing with a colleague. So similar scenario we have they have a hybrid setup 365 and google (don’t ask why - still pains me to this day) mail was in 365 but migrate to google. All 365 accounts were then put on an auto forward rule to their respective gmail accounts.

 

Cut to the chase- recently I found a user was not receiving mail in her gmail from a forwarded 365 distribution group. However she was receiving mail in gmail forwarded that was sent direct to her 365 account. Could this match what you are experiencing. This only started happening to us about a month ago and not sure what suddenly triggered it. Suspicious as we renew licensing in the same time frame from a1 to a3 so suspicious it had something to do with that

 

I passed this on to our Helpdesk to look at and since not sure what was done about it but will try dig it out tomorrow if it any help

Edited July 10, 2024 by dapaulio

[ckedu-local]

Gmail changed policies recently and require you to setup DKIM on your domain, otherwise it just rejects it

 

Microsoft also introduced additional security policies which disables you from forwarding email externally unless you disable it or exempt the accounts in question

 

Hope this helps

[TwistedHelixis]

So, I decided to send a test email to the 365 email and got the bounce back email. The office person must have snipped just the first part of the error message that they sent me. In my test bounce back, further down it literally says, forwarding is blocked on this domain, lol.