Microsoft OneDrive Drives Me Nuts

| Editorial

Microsoft's technical support for OneDrive is like a hoary old joke I used to tell:

A pilot is lost in the skies over the Pacific. He radios for help repeatedly until he hears a faint response. "Help! We are lost. Can you tell me where we are?" The voice replies, "You're in an airplane over the Pacific ocean." The pilot then tells his copilot, "Hang a left and you should see Redmond, WA." The copilot is astonished. "How the heck did you know that?" The pilot replied, "The answer was 100% accurate as well as 100% useless, so it could only have come from Microsoft Tech Support."


I mention this not because it's a great joke, but because I'm reviewing the latest version of Office for the Mac (which is  called either Office 365 or Office for Mac 2016, depending upon how you pay for it) and have discovered that OneDrive—Microsoft's answer to iCloud—doesn't work on my Mac.

The OneDrive menu reports 3,803 problems, and has been reporting them for over a month. The problem is that when I select View Details, it crashes and leaves a broad white stripe across my display that can only be eliminated by Force Quitting OneDrive.

Microsoft OneDrive Error

I think it's fair to say OneDrive is useless to me until this bug is squashed.

So, I wrote to Microsoft technical support about the issue on February 9 providing logs, screen shots, and a complete description. It took a month but I finally got an answer. Not a solution, mind you, but at least I got an answer. The answer was 100% accurate and 100% useless to me, so I know it came from Microsoft.

Here's the sequence of events:

February 11: Received my first response:

I am sending these logs for analysis. In the meantime have a look at the Mac sync troubleshooting steps here. Thanks for reaching out if the situation changes with your sync feel free to update us.

February 29: Having heard nothing since February 11, I sent a follow-up:

You told me you were escalating this issue on February 11. It's now February 29. So far I've heard nothing from y'all, and I've tried everything in your support article (and much more), and still the problem — which renders OneDrive useless to me — persists.

Thanks in advance for any help you can provide.

March 8: No response; sent another follow-up:

I've heard nothing from y'all since February 11 - almost a month. I've tried EVERYTHING in your support article and much more, and still the problem — which pretty much renders OneDrive useless —persists.

The issue (again) is: (Mac OS X 10.11.3) -- The OneDrive menu says there are 3,803 problems with my OneDrive, but if I select View Details, the OneDrive app becomes unresponsive and paints a white stripe across one of my two displays. The only way to fix it is to Force Quit OneDrive. This happens every time and has for as long as I've been trying it (over a month now).

Thanks in advance for any help you can provide.

March 9: Received a response, but nothing even remotely useful:

Looks like your ticket was overlooked in our system. We apologize. I took a quick look at the logs you sent and do not see any issues presented there. Obviously, there is an issue and I am getting a OneDrive MAC developer to take a look. Thanks for your patience.

March 10: Received an answer. Not a solution, mind you, but not another, "we're looking into it" message, either.

Thank you for submitting your logs and for your patience while we investigated the issues. Unfortunately the sync errors reported by the OneDrive client are due to filenames which are illegal on the OneDrive sync space, such as '|', '?', ':', '"' and leading spaces.

Both the filename restrictions and the fact that the error window is not handling a big amount of errors gracefully are aspects we are working on to improve, but currently there is no workaround I can provide, and we certainly don't expect you to rename your files in order to sync them through the OneDrive client. I'm sorry for the inconvenience we might have caused you.

So, to summarize what took me a month to discover:

  • OneDrive dies when it encounters a file or folder name with a pipe (|), question mark (?), colon (:), quotation mark ("'), or leading space.
  • There is no workaround or fix at this time.
  • There is no indication of if or when it might be fixed.

Remember This

I want you to remember this story the next time Microsoft tries to say how strategically important the Mac is to them. Because Microsoft's engineers had to know that Mac file names can contain pipe, question mark, quotation mark, and leading space character (but not colons). It's been like that forever. Shipping a Mac product that chokes on any file or folder that uses any of those characters is typical of Microsoft's hubris.

Remember my joke way back at the top of this post? It turned out the joke was on me… Microsoft Tech Support was indeed 100% accurate and 100% useless.

Caveat emptor.

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The Mac can have filenames with colons, but not forward slashes. This is a long-time restriction imposed by Unix.

That said, the Mac plays some funny games with toggling “:” to “/” and back again to give the illusion of restricting colons. If you are in Terminal you can create files with : in the name. In the Finder, they appear as with /. In Terminal, you will see the file with a colon.


When I was doing IT work we used to joke that Microsoft Technical Support was an oxymoron.

We have been using OneDrive at work, a Windows shop. We find it slow and semi reliable, but the free 5GB or whatever is worth the price. We tried Office365 a while back. For our salespeople to use especially when they were on the road. We found it slow and semi reliable. Actually it was very reliable. It would work fine until they really, really needed it. Then it would start throwing network connection errors or corrupting the document you had to have right then. We abandoned it after a couple of months and the powers that be haven’t the slightest interest in ever trying it again.

Bob LeVitus

I know you can use colon’s now… but you didn’t used to be able to. I could have been clearer.

So far Office 365 underwhelms me. You’ve heard about OneDrive… Well, Word isn’t terrible, but it lost one of the features I used regularly in Word 2011 (custom toolbars). So the templates I so lovingly crafted with custom toolbars, are missing their lovingly crafted custom toolbars if I use them in Word 2016.

I am doing as much of my writing and editing as I can in Ulysses, since Microsoft apparently doesn’t give a s#*t about Mac users.


Nik Green

If it’s any consolation the PC version of OneDrive for Business is little better.

Again it is flummoxed by characters in filenames that are legal in the OS and also if file paths are too long.

We use it at work and it’s a constant source of frustration. This is just one of many articles that demonstrate how truly shocking it can be.


The timing of this article is funny, because I JUST had this same problem last week while deploying OneDrive to 3 macs.  We switched from Google Drive to OneDrive because with Office 365 it includes 1 TB of cloud storage, which we thought we would take advantage of. 

I also figured that a bit company like Microsoft could surely match or exceed the quality of Dropbox or Google Drive. 

Well…..  I was VERY wrong.  It isn’t even good enough to be beta software.  Microsoft should be ashamed!

Thank you for validating my thoughts and experiences.

Bob LeVitus

lagreca: The pleasure (of validating your thoughts and experiences) was entirely mine. And I’m sad to know that I’m not alone (when it comes to wasting time on this rubbish).

Owen McCarthy

It all comes back to me now.  I can now remember why I deleted my one-drive and now stick to drop-box and google docs. I’ve lead a blissfully uncomplicated life since then, although I have been lead a merry chase by the Microsoft help-desk circumlocutors, who appear to delight in the purity of the circle as a form for everything from speaking to troubleshooting.

Adam Tanner

When a co-worker shares a folder with me, the folder shows up in their One Drive for Business iOS app, and in their OneDrive folder on their desktop and in their OneDrive folder in their O365 web page but….

I can ONLY see this folder that’s been shared with me by
-logging into the O365 page and accessing the OneDrive site their and THEN clicking on Shared With Me
or by
-clicking on the Shared icon in the OneDrive for business mobile app.
This folder doesn’t show up AT ALL in the Desktop application (i.e. in the One Drive folder).
Every other cloud based data sharing application (Dropbox, etc) has shared folders show up in your folder for that application, not hidden away.

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