Outlook File Search returning different results than Explorer File Search

Customer has a Windows 7 64 bit PC running Outlook 2013 with Office 365 Exchange. When searching for a file using the Attach option it brings up nonsense results. Doing the same search using windows explorer brings up the correct results. Everything else works just fine.

Any ideas?
genusysAsked:
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JohnBusiness Consultant (Owner)Commented:
You have to go to the file extensions in index options and make sure "content" has been enabled. PDF's are not always searchable. Make Windows search work first and then the Outlook part should work
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JohnBusiness Consultant (Owner)Commented:
Are they in cached mode?  Try deleting and remaking the OST file. Then rebuild the Windows Index (overnight). Restart and test.
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genusysAuthor Commented:
Email search is fine. It is only when you try to attach a file to an email. The file results are different than the Explorer File results.
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JohnBusiness Consultant (Owner)Commented:
I think I understood that, but the file is included in the OST file.  That is why I suggested a new OST file and rebuilding the Windows Index.
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genusysAuthor Commented:
The fle is not in the .ost. The file is in the documents library. That's what makes it so confusing. For example: Start a new email, click attach file. Use the search box in that dialog and the results are different (nonsensical) than if you do the same search in the Explorer search dialog.

Does that explain it better?
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JohnBusiness Consultant (Owner)Commented:
Once attached, one would think it is part of your Exchange mail file and so OST. If not, how does Outlook enter into it and I would not be surprised the results are nonsense if not in the Email file / OST.
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JohnBusiness Consultant (Owner)Commented:
And why would your user try to search while attaching the file?  That also does not make sense.
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genusysAuthor Commented:
Because she is looking for the file she wants to attach to the email
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JohnBusiness Consultant (Owner)Commented:
Search for the file in Explorer (that is what I do), get the path and then attach after.
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genusysAuthor Commented:
Ok, but that doesn't explain the issue and doesn't help me explain what changed. I'd kinda like to know what's going on.

I'll update you if and when i figure it out.
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JohnBusiness Consultant (Owner)Commented:
Outlook Search will not find things not in Outlook. That is why it does not work.
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genusysAuthor Commented:
It's not Outlook search it is the insert file dialog box.
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JohnBusiness Consultant (Owner)Commented:
But it is part of Outlook (Attach).  I would not expect it to work. Find the file first.

Post note:  Actually I can find from Attach because that is Windows Search.

Rebuild the Windows Search (delete and re-index) . Let the index run overnight

I am using Outlook 2016 and Windows 10.
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genusysAuthor Commented:
I'm rebuilding the index now. Is there a way that you can search only content and not file name? That would explain the crazy results i'm seeing
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genusysAuthor Commented:
I'll update you in the morning. Craziest thing i've ever seen. I thought the Explorer search and Insert search were the same. Seems like they have a difference.
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JohnBusiness Consultant (Owner)Commented:
They are the same if the index is sound and not damaged
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genusysAuthor Commented:
I just found it!  I went to the little arrow below the search box and did a clear all. It must have had a filter on.  OMG
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genusysAuthor Commented:
I mean the "arrange by" Drop down.
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JohnBusiness Consultant (Owner)Commented:
I went the way you describe because I always use Search as it should be used
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JohnBusiness Consultant (Owner)Commented:
Thank you and I was very happy to assist you - natty issue. But we both learned here. Good luck.
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