unable to send emails

Hi Andy Colgan

From your description, I understand how confusing this can be, especially when Outlook shows “Connected to: Microsoft Exchange” and there’s nothing stuck in the Outbox.

In addition to Q&A Assist reply, please try the following:

1, Temporarily disable Outlook add‑ins

• In Outlook, go to “File” > “Options” > “Add‑ins”
• At the bottom, next to “Manage: COM Add‑ins”, click “Go…”
• Uncheck all add‑ins, click OK
• Restart Outlook and try sending a test email

2, Send using Outlook on the web

• Go to https://outlook.live.com
• Sign in with the same account
• Send a test email

3, Create a new Outlook profile

If Outlook is connected but fails silently when sending, the local profile may be corrupted.

• Close Outlook
• Open “Control Panel” > “Mail” > “Show Profiles”
• Click “Add…” and create a new profile
• Set it as “Always use this profile”
• Open Outlook and test sending again

Please feel free to let me know how it goes. I truly appreciate your time and understanding.

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1. I am seeing Connected to: Microsoft Exchange
2. I have internet connectivity
3. There is nothing in my Outbox

Use the following checks and steps in classic Outlook for Windows:

1. Check Outlook’s connection status
   • Look at the status bar at the bottom of the Outlook window.
   • If it shows Disconnected, Working Offline, or Trying to connect…, Outlook cannot reach the mail server.
   • Go to the Send/Receive tab on the ribbon.
   • In the Preferences group, select Work Offline once to toggle back online.
   • Then choose Send/Receive or open the stuck message and select Send again.
2. Confirm internet connectivity
   • Open a browser (for example, Microsoft Edge or Google Chrome).
   • Browse to http://www.microsoft.com or http://www.bing.com.
   • If these sites do not load, resolve the network issue first (for example, by following Fix network connection issues in Windows). Outlook cannot send mail without internet access.
3. Check for large attachments in the Outbox
   • Go to the Outbox folder.
   • Open the oldest message that is not sending.
   • If it has large attachments (for many providers, anything over about 20 MB can cause problems), remove the attachment, attach a smaller file, or replace it with a cloud link.
   • Save and send again.
   • Repeat for any other stuck messages.

If messages still only send when using Send Again, repeat the connection and Outbox checks above and then contact support from Outlook if needed.

References:

• I can't send or receive messages in Outlook