Using Classic Outlook on Windows for personal email, calendar, and contact management
For an Outlook.com account that can receive mail but cannot send or reply, and the message is being flagged as spam, use these checks:
- Send a simple test message from Outlook on the web.
- Remove attachments, links, repeated text, and anything that could look spam-like.
- Send plain text only.
- If that works, add content back gradually to identify what triggers the block.
- Check the sending address in Outlook on the web.
- Go to Settings > Mail > Sync email.
- Verify the From address is correct.
- Then go to Settings > Mail > Compose and reply and reset the default From address.
- Remove the email signature and try again.
- Signatures can sometimes prevent sending.
- Confirm the message size is not too large.
- Outlook.com cannot send a message with an attachment larger than 25 MB.
- Review account security.
- If unusual sign-in activity was detected, the account might be temporarily blocked.
- Check recent sign-in activity and, if needed, change the password.
- If the password was changed recently, update it in Outlook.
- If the message is still blocked, use the non-delivery report details with Microsoft support through Sender Support in Outlook.com.
Since incoming and outgoing settings are already correct, the most relevant next step is to test with a plain-text message in Outlook on the web and verify the From address configuration there.
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