The old, old story of the Gordian knot traces back over 2 millennia. It’s meant to illustrate that difficult problems may be overcome by a variety of means. Usually, as with the original story itself, some of them are drastic. When unable to untie the knot, Alexander the Great drew his sword and cut it through instead. He lost the rope, but solved the problem. And so it is with some Windows problems, where a clean install still cuts gordian knot issues that other repairs cannot address.

If Clean Install Still Cuts Gordian Knot, What Made it Necessary This Time?

I’ve been helping a friend over the past two weekends try to solve an iCloud to Outlook synchronization problem. To his credit, he put in two lengthy calls with MS Support, and performed an in-place upgrade repair install. His primary symptoms were:

1. Unable to download iCloud from the MS Store
2. If installed manually, unable to get iCloud and Outlook to synchronize. Interesting but weird error messages about “no default Outlook profile” suggested possible fixes, but none of those worked.

After attempting numerous manual repairs and tricks last weekend without success, I showed up this weekend planning to perform a clean install on his wife’s laptop, a Dell Latitude 7155 (i5, 4th gen Intel CPU). It took me somewhat longer to get the disk cleaned up and a pristine image laid down on her NVMe SSD than I had thought it would.

But once a clean Windows 10 image was installed and updates applied, I was able to download iCloud from the Store. Next, I revisited office.microsoft.com and re-installed Office 365. The acid test followed immediately thereafter: I attempted to synch with iCloud for messages, contacts, and other Outlook items.

To nobody’s particular surprise, it worked. But gosh, it sure took a while to get everything ready (Macrium Reflect came in hand indeed). And it took longer to install and update the OS image than I was expecting. But in the end, the outcome was as desired. So far, we’ve put about 7 hours into this repair effort. Alas, it’s still not quite done just yet.

One More Thing…

I mounted the Macrium backup to make it available for copying older files to the rebuilt desktop. But because of permissions problems I wasn’t able to access some key stuff. So, I’m going back in one more time to fix those and grab the additional stuff my friend needs. Hopefully, that will be as routine as I anticipate. In the meantime, I’m boning up on the ICACLS command so I can reset permissions wholesale, and make everything one might need from the backup available in one go.

At the end of the day, it’s nice to know the tried-and-true methods work like they’re supposed to. I can only guess that some vital plumbing between the Outlook and iCloud APIs got munged in the old runtime environment. By creating a new, pristine one, we have apparently fixed what was broken. Old school still rules. Good-oh!