Using classic Outlook for Windows in business environments
I'm sorry for late response. Based on your update:
This error typically occurs when:
- You're replying to a group email using a shared mailbox.
- The email draft becomes disconnected from the server, often due to session timeout or sync issues.
- You're using a contact list in the BCC or CC field, especially in Outlook Web App (OWA).
Users have reported this issue after Windows updates, and it seems to affect Outlook Web more than the desktop version
Have you tried to Clear Cached Group Addresses?
- Start a new email.
- Type a few letters of the group name.
- When Outlook auto-suggests the address, click the (x) to remove it from cache.
- Manually retype the full group email address and try sending again
Use “Send Email As” Settings
- Go to Outlook Settings > Send Email As.
- Ensure it's set to your main account, not a shared mailbox. This resolves identity mismatch issues
Try to Switch to Outlook Desktop App
- If you're using Outlook Web, try replying from the Classic Outlook for Windows instead. This avoids web-based sync issues
Let me know if it works with all suggestions above, feel free to reach out if you have any other questions.
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