New Outlook: Attach File > Suggested Files List

nuspieds · Jan 27, 2026

Hi,

In the new Outlook's Attach File menu, it lists (up to 3) files in the "Suggested files" section.

For me, these suggestions have always been from very old emails that I have sent! This feature would actually be very helpful to me, were it to use my recently-sent emails. But if that's not going to be the case, is there a way I can at least clear this useless suggestions list?

Thanks!

OAT · Jan 27, 2026

nuspieds said:
Hi,

is there a way I can at least clear this useless suggestions list?

Thanks!

The 'new' Outlook is an APP and as such is more restrictive than 'classic' Outlook as far as personal preferences are concerned.

But I must ask : You only trigger the list by clicking on Insert then Attach file, otherwise you never see that list.
You also stated you rarely used that feature. So why is that an inconvenience to you?
Please understand this is not a critique, but it is rather puzzling.
Either way, what you are requesting is not 'yet' an available option, AFAIK.

nuspieds · Jan 27, 2026

OAT said:
The 'new' Outlook is an APP and as such is more restrictive than 'classic' Outlook as far as personal preferences are concerned.

But I must ask : You only trigger the list by clicking on Insert then Attach file, otherwise you never see that list.
You also stated you rarely used that feature. So why is that an inconvenience to you?
Please understand this is not a critique, but it is rather puzzling.
Either way, what you are requesting is not 'yet' an available option, AFAIK.

No worries, I do not see it as a critique. :)

But I didn't state that I rarely used the feature; as a matter of fact, it is the opposite: I am frequently attaching files to sent emails and I want this feature to work and be useful for me. The issue/annoyance is that the "Suggested files" list is referencing attachments from old/obsolete emails.

Let me add some more details that would help further explain my issue/annoyance:

I am responding to job postings and submitting my resume;
To attach my resume, from the "Attach file" menu I have to click "Browse" and then browse for and select my resume;
The "Suggested files" list contains files that are my resume attachments from very old job submission emails I sent;
That is, I have tweaked my resume since those very old emails and, consequently, I need to attach this most recent version of my resume to the current job postings to which I am responding;
Since the "Suggested files" list references resume attachments from old/obsolete emails, I have to use the "Browse" option instead (i.e., click, click, click, ...);
On the other hand, if the "Suggested files" list was current and showed the most-recent attachments from emails sent, then I would just need to click on that file instead of manually browsing for and attaching my resume.

Believe it or not but the oldest file in my "Suggested files" list is from June 2025! Besides my resume submissions, do you know how many other files I have attached to other emails since then?! So, I have no idea how or why the "Suggested files" list is using such an old and outdated reference.

OAT · Jan 27, 2026

I see it makes more sense now. I am sorry if I misread.
Yes I get it, it would be a suggestion for the Outlook team and they've been pretty good at adding things.
Of course, you could open the folder where your latest résumé is and keep it open in the background.
Then Drag & Drop could be used.
But it wouldn't update the list.

nuspieds · Jan 27, 2026

OAT said:
I see it makes more sense now. I am sorry if I misread...

Once again, no worries!

OAT said:
Of course, you could open the folder where your latest résumé is and keep it open in the background.
Then Drag & Drop could be used.
But it wouldn't update the list.

Yes, you are correct but that could potentially lead to additional keystrokes/clicks alt-tabbing or finding that window. Again, potentially.

So, what I have done to minimize keystrokes/clicks, since the Browse window opens at the Documents folder, that's where I have my resume saved. Thus, all I ever have to do is scroll down past the folders and select my resume.

When I'm applying to one or two job postings, it's not much of an annoyance, but when there are several, it sure would be a timesaver to click on an entry in the "Suggested files" list.

Hornblower409 · Jan 30, 2026

Seeing a similar problem reported on Microsoft Q&A. Only fix suggested is to Nuke your New Outlook for Windows Profile,
New Outlook: Attach File > Suggested Files List Is Outdated - Microsoft Q&A

nuspieds · Jan 30, 2026

Yeah, that was my post.

Her suggestion to use Edge DevTools to clear cache/storage, although the option wasn't there for me, it may work but it seems like a dangerous suggestion as I'm sure such an option will do much more than just clear the "Suggested Files" list.

In addition, she missed my point that the suggestions provided to me were from email attachments and not OneDrive or SharePoint. In the screenshot below, the first line is the filename and the second line (red arrow) is the email subject.

Eventually this list will change, but I don't when, how, or why!

Edwin · Jan 30, 2026

nuspieds said:
Eventually this list will change, but I don't when, how, or why!

The list will change when you clear these lists, each in their respective apps...

nuspieds · Jan 30, 2026

Hi @Edwin,

For me, New Outlook is referencing file attachments from its Sent emails, not Word or any other app. That's why I emphasized the email subject with the red arrow in my post above: They are all real and valid emails that I sent.

I've actually used its suggested files functionality in the past when my resume hadn't changed and the attachment/email in the list was fine. The problem right now is that the attachment/emails that it suggests are old/outdated versions of my resume from old emails I sent.

Because you never know what buggy code they may have, as a test, I did clear the PowerPoint Recent Files list, cleared cache, rebooted, etc., but there was no change in New Outlook.

Edwin · Jan 30, 2026

nuspieds said:
... but there was no change in New Outlook.

Ah! The New Outlook! I just assumed it worked in the New Outlook as it does in the Classic Outlook! Sorry about that!

nuspieds · Jan 30, 2026

Edwin said:
Ah! The New Outlook! I just assumed it worked in the New Outlook as it does in the Classic Outlook! Sorry about that!

No worries!

nuspieds · Jan 30, 2026

As another test, the PowerPoint file/email in my "Suggested files" list was not an important file/email, so I permanently deleted that email (i.e., it has been completely deleted and is not in the "Deleted Items" folder). If you do a search, there are no results, so it's definitely gone, gone, gone!

Cleared cache, rebooted, and look at my "Suggested files" list now...

Well, whatever checks they are doing, they are current, but the suggestions are old!!!

Hornblower409 · Jan 30, 2026

nuspieds said:
Her suggestion to use Edge DevTools to clear cache/storage, although the option wasn't there for me, it may work but it seems like a dangerous suggestion as I'm sure such an option will do much more than just clear the "Suggested Files" list.

You can also temporarily test with a New Outlook for Windows Profile and switch back.

See the answer by Hornblower409 Dec 11, 2025, 12:11 AM in
Outlook starting error - repair/reinstall/reset doesn't fix - Microsoft Q&A

Edwin · Jan 30, 2026

nuspieds said:
... the suggestions are old

As a test, you could try exporting one of the old culprit emails as .eml or .msg, then delete the original permanently.

Edwin · Jan 30, 2026

I installed the New Outlook but can't replicate your issue.
Of course, I have nothing tied to my MS account so...

If you have Outlook, Office and perhaps OneDrive tied to your MS account, the issue may be deeply buried in the woodwork.

nuspieds · Jan 30, 2026

Hornblower409 said:
You can also temporarily test with a New Outlook for Windows Profile and switch back.

See the answer by Hornblower409 Dec 11, 2025, 12:11 AM in
Outlook starting error - repair/reinstall/reset doesn't fix - Microsoft Q&A

User Profiles are for Classic Outlook only; that functionality is not supported in the New Outlook.

But the suggestions work at least initially/early on; the problem is that they become stale and as per my post above, if I were to completely remove the Sent email for a suggested file, New Outlook replaces that file with a new suggestion from another Sent email. So, clearly, it is reading/analyzing current data, but they seem to have buggy logic that results in old/outdated suggestions.

nuspieds · Jan 30, 2026

Edwin said:
As a test, you could try exporting one of the old culprit emails as .eml or .msg, then delete the original permanently.

The PowerPoint email I permanently deleted was one of those emails.

I just didn't need to export/save it because it was not an important email.

nuspieds · Jan 30, 2026

Edwin said:
I installed the New Outlook but can't replicate your issue.
Of course, I have nothing tied to my MS account so...
If you have Outlook, Office and perhaps OneDrive tied to your MS account, the issue may be deeply buried in the woodwork.

Yeah, I wouldn't be surprised.

I have an MS Account, but it is for Windows login and administration only.

I use my M365 Account for the apps and services. So, for example, I have a OneDrive Personal account which I never use (and that's connected to the MS Account) and I also have a OneDrive Business account, which is the one I use (and it uses the M365 account).

New Outlook: Attach File > Suggested Files List

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