Outlook email - attachment suggestions

Question

When i want to attach a file to an email, i get a long list of suggestions (below "on this mac" etc.) but they're all very old files. The list does not correspond in any way to my recent activity. How do i reset it (or just get rid of the list completely)? Thanks

Answer 1

Dear @Pete Russo,

Welcome to Microsoft Q&A Forum!

Based on your descriptions, I’ve tested this behavior on my own Mac and wanted to share my insights of what’s happening, along with the available workarounds for you to consider using them.

In the New Outlook for Mac, the Recent files list that appears when you click the paperclip does not use macOS’s Recent Files history. Instead, it relies on Outlook’s own internal cache and cloud‑related metadata (for example, older attachments or OneDrive files). Because of this design, the list can appear outdated and does not refresh when you open or save local files on your Mac.

To confirm this, I also ran a test:

• When choosing Attach > Browse this Mac, Outlook hands off to Finder
• Finder’s Recents view correctly shows the files I recently opened or modified

This proves:

• MacOS Recent Files is working correctly
• File permissions and indexing are fine
• The issue is specific to how New Outlook for Mac builds its suggested file list

Therefore, I have these recommended workarounds:

1.Use “Browse this Mac” (recommended):

When attaching files, select Browse this Mac, then use Finder’s Recents section. This reliably shows your most recently opened or edited files and avoids the outdated suggestion list.

2.Switch temporarily to Legacy (Classic) Outlook for Mac to see if the Recent files can be solved in this version. Legacy Outlook uses a traditional recent‑files model and may behave as expected for local files.

Please note: Microsoft has announced that Legacy Outlook for Mac will reach end of support in October 2026, so this should be considered a temporary workaround only. See this article: End of support for legacy Outlook for Mac

3.However, this behavior has been reported by many users and may be considered as by design of the product. Also, as a forum moderator, my testing environment is very limited, and this error is completely out of my control in this role. I understand that it is not comfortable and you may not be satisfied with this feature on macOS. Therefore, the best course of action at this time is to send feedback directly to Microsoft.

You can do this by going to the Microsoft Feedback Portal. Sharing your experience helps Microsoft prioritize feature improvements in this scenario. Once you submit your feedback there, other users and I can locate your post and vote for it, which increases your visibility and priority to the product team. And I appreciate you raising this issue. Your action can help others in our community who face the same concern.

Once again, I really understand the discomfort this behavior causes and thank you for your patience and understanding. I hope this information can give you some insights to do in this case and we are looking forward to the future updates.

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Answer 2

To reset or clear the attachment suggestions in Outlook on Mac, you may need to clear the AutoComplete list or reset the recent files list. Unfortunately, the specific steps for managing attachment suggestions in the Mac version of Outlook are not detailed in the provided context. However, you can try the following general steps:

1. Clear Recent Files: If Outlook has a recent files list, you can often find an option to clear it in the application settings or preferences.
2. Reset AutoComplete List: While the context does not provide specific instructions for Mac, in other versions of Outlook, you can clear the AutoComplete list through the options menu. Look for settings related to email or AutoComplete.
3. Check for Updates: Ensure your Outlook application is up to date, as updates may improve functionality or fix bugs related to attachment suggestions.

If these steps do not resolve the issue, consider reaching out to Microsoft support for more specific guidance related to your version of Outlook on Mac.

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References:

• The Outlook AutoComplete list