Windows 10 October 2018 Update is Deleting User Data For Many (windowscentral.com)
New submitter CaptainPhoton writes: I updated my test PC using the Windows 10 October Update (1809). That seemed safe enough, so I proceeded to upgrade my production PC. I just encountered an issue where everything in the Documents folder was deleted, even though I had clicked the option to keep my files. Everything else in my user profile remains intact. I am curious, how widespread is this issue? Has anyone else here encountered this issue? Some articles are starting to crop up acknowledging this failure. Citing complaints from several users, Windows Central reports: Sometimes, when you perform an upgrade to a new version of Windows 10, the setup may move the user files to the previous installation backup located inside the "Windows.old" folder. However, according to those users experiencing sudden data loss, they looked everywhere, and their personal files are nowhere to be found.
[...] "even though I had clicked the option to keep my files. [...]
As far as I remember, this option is available only when you start system installation from scratch...
Why would you overwrite running production system with "fresh" install?
We did 25 Pros update so far and no sign of trouble. Using Windows Update of course. Systems are being updated like that since 1607 and it never failed.
Enterprise version will likely get update over the weekend as it is, as usual, delayed a few days.
All of the content in the documents folder were deleted. In addition, the recycle bin was empty! Luckily I had a backup from the previous week.