Microsoft OneDrive Word Doc Syncing Issue Causes Tech Support Nightmare

There's a weird issue affecting some Office 365 and OneDrive users, myself included, but what's even worse is the way it's being handled by Microsoft's online support system. I'll get to that in a moment, but first let's discuss the problem at hand, which is that some users recently ran into a problem getting Word 97-2007 Document files (*.doc) to upload to OneDrive.

I first encountered the issue last week, and after successfully syncing many Word 97-2007 Document files for months prior, I suddenly encountered an error message that prevented me from uploading my files to OneDrive.

OneDrive Sync Error

"SAVE AGAIN  We need to refresh your file with updates. Click Save to try again," the error message reads.

Unfortunately, clicking Save doesn't make the problem go away. Instead, it tries again to upload the file to OneDrive, and is again unsuccessful. I've probably clicked Save over 100 times at this point, along with other troubleshooting methods.

OneDrive Sync Fail

If you're also suffering this problem, you're not alone. After running through several troubleshooting steps (deleting Office cache locally, deleting local documents and downloading from OneDrive, deleting the documents from OneDrive, ensuring Office 365 and Windows 8.1 are both fully updated, running and Office 365 repair), I hit the web only to run into other users chasing their tail in a Microsoft-induced support loop.

Poor Kevin Robinson 
posted his problem on Microsoft's OneDrive support forums and was promptly advised by a forum moderator to take his question to the dedicated Office 365 forum instead. So that's what he did, and about four hours later, he was advised by a Microsoft support person to post on the OneDrive forum. Commence chasing tail.

This is a recent problem that's popped up in a few different 
support threads, none of which offer a satisfactory resolution, unless you consider saving to Word 2013 (*.docx) an acceptable answer. And indeed, I haven't run into any issues syncing Word 2013 Document files.

In any event, if you've run into this issue as well, go through and try the troubleshooting steps 
Microsoft outlines here. If that doesn't work, have some migraine medicine handy and see if you fare any better on Microsoft's support forums.