Dear Tom Blaney
Thank you for reaching out to the Microsoft Q&A forum. I understand you are having problem with a message being sent repeatedly (recipients receiving the same email 20–30 times) from Outlook on Windows (classic) after you sent it once. Please follow these steps:
- Isolate add-ins/customizations
- Start Outlook in Safe Mode (Safe Mode disables add-ins).
- Right-click Start > Run, type: Outlook.exe /safe, then OK.
- If the repeated sending stops in Safe Mode, the cause is likely something loaded in normal mode. Please continue with Step 2 and Step 3 below.
- Rebuild the Outlook profile
- Create a new Outlook profile using Create an Outlook profile - Microsoft Support:. Use the profile picker (hold Shift while starting Outlook) or Run: Outlook.exe /profiles, then create a new profile and add the account again. Then test sending a single email to yourself first (not the full distribution list) to confirm normal behavior before sending broadly.
- Repair the Office/Outlook installation
- Use Repair an Office application - Microsoft Support steps (this repairs the whole Office suite, including Outlook): Windows Settings > Apps/Apps and Features > select Microsoft 365/Office > Modify > run Quick Repair; if still failing, run Online Repair.
- When the above does not resolve it
- Visit Contact - Microsoft Support
- Type a brief description of your issue in the search box
- Scroll down to the bottom > select Sign in to contact support
- Log in to your personal Microsoft account.
- Under Products & Services, select "Other Products"; Under Categories, select a suitable Category.
- Click "Chat with a support agent in your web browser" (during business hours)
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