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outlook user can't send to dynamic group, message stuck in sent item

we have everybody dynamic distribution group, and only notification account (Helpdesk Notification) have permission to send to everybody

one user i give him (Helpdesk Notification) send as permission. he can send to everybody from OWA no problem but when he use Outlook, message stuck in sent item and didn't deliver to everybody

we try to login by his account from another computer but same thing happened



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