Hi @Tate Crawford,
Welcome to Microsoft Q&A forum.
Thank you for reaching out about the draft-saving issue in Classic Outlook. Given that this is often related to subtle configuration or profile corruption within the Classic Windows application, please follow the steps below sequentially, starting with the recommended workaround. Kindly inform us of the outcome after completing each step.
Step 1/ Compose an email in a dedicated window
- When creating a new email, reply, or forward, immediately double-click the message to pop it out into a separate, full window before you start typing any content. Compose a test message and close the separate window. Check the Drafts folder to see if it saved.
Step 2/ Verify auto-save timing settings
We need to confirm that the automatic save function is active and set to a frequent interval.
- Go to File > Options > Mail.
- Scroll down to the Save messages section.
- Ensure that "Automatically save items that have not been sent after this many minutes" is checked and set to a low number (e.g., 1 or 2 minutes).
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Step 3/ Test cached exchange mode
Since this is a business environment, disabling the local cache temporarily can rule out local synchronization file corruption.
- Go to File > Account Settings > Account Settings.
- Select your primary account and click Change.
- Uncheck the box next to "Use Cached Exchange Mode to download email to an Outlook data file."
- Click Change and Finish, then restart Outlook.
- After that, create a new draft in this online mode. Does it save successfully now? (If it does, the issue is with your local cache file).
Step 4/ Create a new outlook profile
If the above steps fail, the most common root cause is a corrupted local profile or associated data file.
- Close Outlook completely.
- Open the Windows Control Panel and search for Mail (Microsoft Outlook).
- Click Show Profiles... > Add. Name the new profile (e.g., "NewTest").
- Set up your company email account under this new profile.
- Set Outlook to "Prompt for a profile to be used" when starting and then launch Outlook using the NewTest profile.
- Then create a draft in this completely fresh profile.
Step 5/ Contact Microsoft support
Should the problem persist after you have completed all four phases, please contact your internal IT administrator and request that they open a support ticket with Microsoft in the admin center. Leveraging a Microsoft support agent provides access to specialized diagnostic tools and the ability to apply official, high-level fixes directly from the product developer.
For detailed instructions on how to get support, please refer to Get support - Microsoft 365 admin.
I hope the information provided proves useful. Please proceed with the outlined steps and let me know whether they resolve the issue. If not, I’ll be glad to continue working with you to find a solution.
Thank you for your patience and understanding throughout this process. Should you have any questions or need further assistance, feel free to reach out at any time. I look forward to hearing from you.
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