Using Classic Outlook on Windows for personal email, calendar, and contact management
Hello Ken Hrycik
Thank you for reaching out to Microsoft Q&A Forum. I understand how frustrating it is when Outlook suddenly stops sending emails after connecting to a new Wi‑Fi.
I can see there’s a Q&A Assist reply under your post. To avoid repeating it, could you tell me if you’ve tried those steps yet, and what happens when you try?
In the meantime, please try the following steps:
1. Test on Outlook on the web
- Please sign in at Outlook on the web and try sending an email there.
- If it fails on the web, this points to an account-level restriction.
- If it works on the web but not in the app, the issue is local to the app/device.
2. Restart Outlook in safe mode
- Close Classic Outlook app completely
- Press Windows + R, type outlook.exe /safe > press Enter
- Try sending a test email in Safe Mode
3. Check Work Offline mode
- In Outlook, go to Send/Receive tab at the top > make sure Work Offline is not enabled
4. Check the Outbox folder in app
- If messages are stuck in Outbox, close Outlook, reopen it, then try sending again.
- If it still won’t send, move the message to Drafts, open it from Drafts then Send again
5. Firewall/antivirus check
Temporarily disable firewall or antivirus software to see if they are blocking outgoing mail.
For more details, please refer to this official guide: I can't send or receive messages in Outlook - Microsoft Support
Thank you for your time and understanding. Feel free to let me know how it goes.
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