Sending, receiving, and organizing email in Outlook.com
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I understand how frustrating this is, especially when the message is time-sensitive and you've already waited a week while trying the recommended steps.
A few questions to narrow this down:
- What exact error message do you receive when the send fails?
- Is your email address ******@outlook.com,@hotmail.com,@live.com, ******@msn.com address?
- Are all 55 recipients the same recipients that you have emailed successfully in the past, or are some of them new contacts?
In the meantime, please try the following:
1, Reduce the recipient count and test
- Instead of sending to all ~55 recipients at once, create a test email and send it to 10-15 recipients first.
Outlook.com may temporarily restrict messages that resemble bulk mail even when you are well below the documented recipient limits.
2, Review recent account activity
- Go to: Microsoft Account Activity
- Check whether there are any security alerts or unusual sign-in events.
A temporary sending restriction can be triggered by automated security checks.
3, Try sending a simplified version of the message
- Remove any attachments, hyperlinks, images, or complex formatting and send a plain-text version to a small test group.
Sometimes the content itself can trigger anti-spam protections even when the recipient count is relatively low.