Sending, receiving, and organizing email in Outlook.com
Check the non-delivery report from the postmaster and look for the "Diagnostic information for administrators" section. That section usually states why delivery failed.
For a message sent to 12 people, the most likely fixes supported here are:
- Verify each recipient address
- Open the message again.
- In the To box, delete each recipient address that may be wrong.
- Start typing the address and, if it appears in Auto-Complete, remove the old suggestion.
- Re-enter the full address carefully and send again.
- This helps if one or more saved addresses are outdated or misspelled.
- Reduce recipients and test in smaller batches
- Try sending to 1 to 3 recipients first.
- If that works, send the remaining recipients in smaller groups.
- This can help if the send attempt triggered anti-spam protection.
- Check attachment size
- If the meeting minutes include an attachment, Outlook.com cannot send the message if an attachment is larger than 25 MB.
- Some failed delivery guidance also notes problems when the original message had an attachment larger than 10 MB.
- If the file is large, upload it to OneDrive and send a link instead.
- If the error mentions mailbox full
- The recipient’s mailbox cannot accept new mail.
- The message can still be delivered to other recipients.
- If the error mentions server timeout, connection timed out, or message expired
- Wait a short time and resend.
- These errors often resolve on their own.
- If the error mentions blocked, blacklist, spamcop, dynablock, blackhole, or spamhaus
- The recipient’s mail server blocked the message as suspected spam.
- The recipient’s email provider support team must unblock the account or domain.
- If sending from Outlook or another mail app
- Try sending the same message directly from Outlook.com.
If the addresses are correct and the message still fails, check whether the message has a signature and try removing it before resending.
- Failed delivery messages from the postmaster at outlook.com, microsoft.com, or service.microsoft.com
- Sent email in Outlook.com comes back "delivery failed"
- Can't send or receive email in Outlook.com
- How to send emails to multiple recipients i.e. 26 individuals? - Microsoft Q&A
- Mail delivery failed due to recipient's full mailbox - Microsoft Q&A