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Unable to email Contact Groups in Outlook 2011

We have a user who has sent a monthly email to 3 contact groups for the last year.  Beginning this month, the emails fail with error "Email address or itemid must be included in the request."  If you expand the Contact Group, the email will send.  

I have tried creating a new contact group with new members and receive the same message.

Any assistance is greatly appreciated.
OutlookApple OS

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8/22/2022 - Mon
Manpreet SIngh Khatra

What if the user tries to send an email using OWA\Webmail ?
What if you create a new Outlook profile as it could be possible Outlook profile corruption issue

- Rancy

He is able to send to contact groups using webmail.  It is a remote user so will contact him and try to set up a new profile.

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