Outlook Attachments drop-down does not reflect Mac-based usage

Question

I've been hammering MS Tech Support for months about the way that the "Attach File" drop-down in Outlook presents an inaccurate list of Recent Files:

• my Recent Files only showed 1-2 recent and 8 much older Powerpoint files
• first they told me that Outlook draws the list from the Mac's Recent Files list. But then I showed them the Finder "Recent Files" list, which had none of the same files
• we went back and forth 5-6 times, with them insisting that it draws from the Mac, and me demonstrating with screenshots, videos and finally a live session that this was wrong
• each time they insisted that this was by design, which was nonsense
• finally I noticed that the Outlook Recent Files list was identical to my Office.com/m365 Recent Files list. I only use m365 for online presentations, so all the recent files are Powerpoints
• I shared screenshots with them and they insisted that this was not the case
• Finally we did a screenshare and I showed them Outlook Recent Files and m365 Recent Files, plus the Mac's Recent files. First two identical, last one completely different.
• then they went back to insisting that Outlook is designed this way.

Here is their pitifully uninformed formal response:

"This is by design. Outlook for Mac is now integrated more tightly with Microsoft 365, so what customer is seeing in Outlook (under "Recent Attachments" or in the file picker when attaching something) often reflects the recent activity across the Microsoft 365 suite.- When you open, edit, or attach files in Word, Excel, PowerPoint, or Outlook (on any device logged in with your Microsoft 365 account), those files get logged in your Microsoft Graph activityIn Outlook for Mac - 

• When you're composing an email and click the paperclip to attach a file, the "Recent" tab now shows files you've worked on recently in OneDrive, SharePoint, or even your local device .- This matches what you see on the M365 home screen under the “Recent” files section. ALL of which I had just proven by screenshare to be untrue.  

Here was my final response: 

It's monumentally f--ked up for my Outlook Recent Files to reflect m365 unless that’s my main point of usage with Microsoft – which it clearly is not. But that IS what Microsoft wants it to be. Like those times when some Microsoft facility only displays OneDrive as a storage option, even though I don't use OneDrive. It says that because Microsoft WANTS you to use OneDrive. 

But I’m a happy Mac user, and I want my Outlook experience to be what your inept tech support originally claimed was “by Design” (before they did a 180-degree turn and back again.)  

– that it should reflect the Mac’s Recent Files list. Because that would clearly be to my greatest benefit – seeing the most recent 10 or so MS Office documents I had worked with, because there’s a very high chance that one or more of those are the ones I want to share with a friend or colleague. 

But no, Micrososft wants me to live in m365, so it perverts a well-intentioned feature of Outlook for Mac to serve its own purposes.  And in the process drives me even further away from the Microsoft ecosystem towards Google. (Which I don’t even like that much: I just don’t HATE it like Microsoft). 

So if Microsoft wants to claim that this bug is actually a feature, so be it. I’m done trying to convince them. 

PS - and typical of Microsoft, the Mac is not even listed under the "Platform" selection in the Feedback facility, even though I designated MacOS as my environment to create it. Typical, typical Microsoft.

 

Answer 1

TiNo - I appreciate the workarounds, but the simple fact of the matter is that most users - Mac or not - are using local file storage. Personally I use DropBox as an excellent blend between local and cloud storage.

So in the spirit of defaulting to the most common use case, Outlook really should reflect the Recently Used files on the Mac, not m365.com, which many people probably don't even know about...

Larry

Answer 2

Dear @lkhill`

Thank you so much for contacting Microsoft Q&A Support. 

I truly appreciate for your incredibly thorough investigation and for sharing your findings. I completely understand your frustration, especially after spending so much time trying to get clarity. 

You're absolutely right: Outlook for Mac currently pulls its "Recent Files" list from your Microsoft 365 activity (via Microsoft Graph), not from macOS Finder’s recent files. This means that if your primary usage is local (e.g., working on Word or Excel files stored on your Mac), those files may not appear in Outlook’s "Recent" list unless they’ve also been accessed via OneDrive, SharePoint, or other M365 services. 

This design choice can feel limiting, especially for Mac users who don’t rely heavily on cloud-based workflows. While Microsoft has stated this is “by design,” I agree that it doesn’t serve all users equally well. 

So, I did a few tests myself to get a better feel for how things work, and I noticed something interesting. When I’m composing an email in Outlook and click the “Attach File” button, the recent files it shows are only from OneDrive (via Microsoft Graph), not the ones I’ve recently opened in Finder. 

Here’s what I tried: 

• I create a Word file and save it in desktop (avoid tracking by Microsoft Graph):

• I create a Word file and save it in OneDrive: 

• In Outlook, the Attach File only shows the Word file that I saved in OneDrive and the Word file in Finder list does not show: 

However, you can click "Browse this Mac" (see image above) and it can allow you to choose the file from Finder's lists: 

Additionally, I find one more idea that may help you: Using the Finder to locate recent files manually and drag them into your email. 

Your insights are incredibly valuable, and I appreciate your persistence in uncovering the root of the issue. I hope this information can help you in this limitation of Outlook in Mac. 

Once again, thank you for your patience and understanding. 

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