Using classic Outlook for Windows in business environments
Based on my research, this issue may be related to corrupted contact entries inside the contact group.
When composing the email, please try clicking the “+” sign next to the contact group name to expand the members list and verify whether all entries appear as valid email addresses.
You may also open the Contact Group directly and review the entries in the Email column. If you notice any unusual values beginning with “/o=ExchangeLabs/...” instead of a normal email address, those contact entries may be corrupted.
In that case, please try the following steps:
-Delete the affected contact from your Outlook Contacts.
-Open the Address Book / Global Address List (GAL), search for the contact, then right-click it and select “Add to Contacts”.
-Open the contact group and add the newly saved contact back into the group.
-Remove the old broken entry from the contact group.
After that, please try sending the email again.
Reference: Contact Groups created from Outlook contacts get added with /o=ExchangeLabs - Microsoft Support
Please let me know the result after trying the steps above.
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