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Can't send email from Distribution Group email addresses

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I have a subscription to Office 365 Business Premium. I have created Distribution Group email addresses and I have successfully sent email out from these addresses in the Outlook web client (outlook.office365.com/owa/).

In my Outlook for Mac (15.8.1), however, I can't send email out from these addresses. I have designated my Distribution Group email addresses in the Preferences -> Accounts -> (my account) -> Advanced -> Delegates screen. These email addresses are present in the From drop down list when I compose an email. When I hit send, there is an error:

An unknown error has occurred in Outlook.

Error code: -19991

From my main default email address, I can send email out from the Outlook for Mac client. So I know email functionality is working, just not from the Distribution Group addresses. Please advise.

Thanks,
Rahim


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