This is the scenario:
- Delegate of Gmail account sends an email to customer from within delegated Gmail account
- Customer receives the email "From: Delegated Account email@example.com" and forwards the email with MS Outlook to colleague
- Colleague receives the email "From: firstname.lastname@example.org On Behalf of Delegate Account" - the email@example.com email address is stripped from this email's "From" information.
- Colleague replies to the email and the reply is sent to the account of firstname.lastname@example.org instead of to email@example.com
After several discussions with G Suite Support the conclusion is that on the G Suite/Gmail side everything is working correctly. For some reason MS Outlook is not respecting the originating email address in the "From" fields of the emails it is forwarding.
We have tested this with Thunderbird and with Gmail itself, and could not reproduce the problem. At this point we have to assume that the problem is with MS Outlook.
Has anyone else had this problem, and if so was there any solution/workaround?