OUTLOOK NOT SENDING

Question

my outlook for Mac will receive mail but will not send. It leaves sent mail in the outgoing basket. Mail works on my iphone and the webmail works as well. I can also make it work when I set the mail up in Apple mail so all of the required information is set up.. MY PROVIDER SAYS THE PROBLEM IS WITH OUTLOOK

Answer 1

Hi Robert Breen

I understand how frustrating it is when email works everywhere else but won’t send in Outlook on your Mac.

Have you already tried the Q&A Assist suggestions?

In addition, please try the following:

1, Rebuild the Outlook database

Corruption in the local Outlook database can block sending while receiving still works.

• Quit Outlook completely
• Open Finder > Applications > Microsoft Outlook
• Hold Option and open Microsoft Database Utility
• Select your main identity > choose “Rebuild”
• Reopen Outlook and test sending

2, Create a new Outlook profile

If rebuilding doesn’t help, the Outlook profile itself may be damaged.

• Quit Outlook
• Open Finder > Applications > Utilities > Microsoft Outlook Profiles
• Select Outlook > click “+” to create a new profile
• Set the new profile as Default
• Open Outlook and add your email account again

3, Confirm you are your Outlook for Mac version

Please make sure you're using Legacy Outlook:

• In Outlook menu bar, ensure “New Outlook” is NOT enabled
• Restart Outlook after confirming

Please refer to: Outlook for Mac

Please feel free to let me know how it goes and thank you for your understanding.

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Answer 2

Try the following Outlook for Mac–specific checks and fixes, in order:

1. Confirm Outlook is online

• In Outlook for Mac, open the Outlook menu.
• Make sure Work Offline is not checked.

2. Verify Internet/network connectivity

• Use a web browser on the Mac to open any website.
• If on a corporate or school network, confirm access to other intranet sites as well.

3. Turn on SMTP authentication (common cause when receive works but send does not) Some POP/IMAP accounts require authentication on the outgoing (SMTP) server.

• In Outlook for Mac, go to Tools > Accounts.
• Select the affected account in the left pane.
• Under Outgoing server, click More Options.
• In the pop‑up menu, choose the correct authentication type (usually “Use Incoming Server Info” or “User Name and Password”).
• Enter the same user name and password used for incoming mail, if required.
• Save and try sending again.

4. Re‑check all account settings against provider’s documentation Even if Apple Mail works, Outlook may need slightly different options.

• Go to Tools > Accounts.
• Select the account and verify:
  • Email address
  • User name
  • Password
  • Incoming server type (POP or IMAP) and server name
  • Outgoing (SMTP) server name
• Ask the provider to confirm:
  • Whether SSL is required for SMTP
  • The correct SMTP port
  • Any special settings (for example, requiring a non‑default port or SSL).
• If the provider uses a different SMTP server or port than what is currently configured, update the Outgoing server field accordingly.

5. Check for firewall or network blocks on SMTP If the same account works on iPhone and webmail but not on the Mac, the Mac’s network path to the SMTP server may be blocked.

• Ask the ISP or network administrator if SMTP ports used by the provider are blocked.
• If the provider offers an alternative SMTP server or port, configure it:
  • Tools > Accounts > select account.
  • In Outgoing server, enter the alternative SMTP server name/address.

6. If the network uses a proxy Some networks require a proxy server to reach the mail server.

• Ask the network administrator if a mail proxy is required.
• Configure the proxy in macOS System Settings/Preferences as instructed by the admin, then retry sending from Outlook.

7. Confirm the email server is available Since webmail works, this is less likely, but if the issue is intermittent, confirm with the provider that the SMTP service is not experiencing outages.

If messages are still stuck in the Outbox after these steps, use the provider’s exact POP/IMAP and SMTP settings documentation and carefully compare every field in Tools > Accounts to ensure Outlook matches those requirements, including SSL and port overrides.

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References:

• I can't send or receive messages with Outlook for Mac
• I can't send or receive messages in Outlook for Mac
• My email message doesn't send
• I can't send or receive messages in Outlook