Using Classic Outlook on Windows for personal email, calendar, and contact management
Dear Sam CJ,
Good day!
Thank you for posting to Microsoft Community. I am glad to assist you.
As per the description you have shared, I understand that you want to clarify about sending duplicated emails when recipient is on multiple distribution list within the contact group.
For your question #1 "For recipients that belong to multiple distribution lists, would they receive multiple emails or just 1?"
I have been testing your query from my side, based on my test result, for recipients that belong to multiple distribution lists, they will receive just one email. Because Exchange expands and examines recipient addresses while emails are on transit, when a duplicate recipient address is detected, Exchange sends only one e-mail message to that recipient. You can refer to the below test and result screenshot.
Test #1 I have created two different Distribution lists with the same two members and add these DL to contact group called Test Duplicate and add one more user, then send email to this contact group.
Test Result #1 For recipients that belong to multiple distribution lists, they will receive one email.
For your question #2 "For recipients that belong to a distribution list but also have their individual email listed, would they receive multiple emails or just 1?"
As I mentioned in the description above, Exchange checks the address even if the recipient is listed twice or more times in an email or even CC'd, and if a duplicate recipient address is detected, Exchange sends a single email to that recipient. You can also refer to the test result.
I look forward to you update. I hope the above information will be helpful. Please feel free to let me know if there are any questions or if I've got you wrong. I will keep assisting you based on the information you provide. I sincerely appreciate your patience and cooperation.
Thanks for your precious time.
Have a nice day!
Sincerely,
Libeamlak | Microsoft Community Moderator