Hi Eric Karpus,
Welcome to Microsoft Q&A.
Based on your symptoms (Contact List shows 0 members in the message, but the Edit/pencil view shows the correct members, and sending results in "Failed to send"), this behavior may occur when the new Outlook for Windows doesn't properly resolve the Contact List into individual recipients at send-time. This can be more noticeable with Gmail accounts.
Steps that typically fix it:
- Start a new email and add the Contact List in the
Tofield. - In the recipient line, click the "+" next to the Contact List name to expand it into individual addresses.
- Send the message again.
Once expanded, Outlook can properly resolve recipients and the message should send.
If you don't see the "+", try recreating the list in People (new Outlook) and test again:
- People > create a new Contact List > add members > email it (and expand with "+" if offered)
Alternative: If your "lists" are actually Google Contacts labels or Google Groups, consider using Google Groups (a single group email address) for the most reliable list sending across clients.
Note: New Outlook's support for Gmail accounts is still evolving, and some features (including Contact Lists) may not work as reliably as with Microsoft 365 accounts. If you're using a managed Google Workspace environment, your admin may also want to confirm OAuth/app access settings, though the expand-with-"+" behavior typically points to a client-side recipient resolution issue in new Outlook.
Please let me know if this proves useful to you, or if you would like further assistance.
I'm looking forward to your reply.
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