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Hi there, my name is*****'s something to try.
Place the contact group as the recipient of your message. Next to the contact group, there is a + sign. Click the + sign and Outlook will expand the contact group so it becomes a message to multiple people instead of a message to the contact group. You should be able to send it that way.
If that doesn't work, try recreating the message and sending it according to the instructions above.
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