windows 10 (October 2018 update) (version 1809) deleted all my files

I have been going through my small business updating test PC's using the ISO, making sure to click the "keep all my files" setting.  On the 5th PC, the contents of the Documents folder were deleted, while the rest of the user profile (Desktop, AppData), etc remained.

The descriptions of the problem reported are accurate.  The customer dissatisfaction is definitely justified here.  It's by far the worst Windows update bug I've ever encountered, and I'm a long time user from the MS-DOS days.  The local Documents folder should not be corrupted by the upgrade process.

I'm running backups on every Win10 machine now, since I am fearful of this 1809 update.

have any of you actually compared before and after hdd space used? if it is still the same size the files are there. nobody claiming lost files has answered that...

I did, and I can confirm that there is a difference. In my case more the 100GB.

Hmmmm. All of the documents in the doc folder on the c drive has vanished. All good everywhere else. Not a clean install. Update to 1809 killed the files, can't even find then with recovery software.

That's what I wanted to say. Unfortunately, Robert is missing 220 GB - & OneDrive only holds 5 GB unless more was purchased. (Can it be MSFT gave him the extra real estate & plans to send him a bill?) But maybe the upgrade did the following automatically.

Before my upgrade to 1809 (still in 1803) - I had set Desktop, Pictures, & Documents to go to OneDrive. That's at "OneDrive Settings, Auto Save tab, Update folders button".  That moved the contents of those folders from C:\Users<Username> to corresponding folders in C:\Users<Username>\OneDrive. The C:\Users<Username> folders remain, but are empty. Any content previously in any of the OneDrive folders also remained, was not wiped out.

This is an interesting point, I use Onedrive. In my case there are some files from the  c:\users%username\documents in the C:\Users%username%\OneDrive\documents folder (and synced online). I don't know how much of the original folder it is and if it was there from before before 1809 or not. However, I do know that the VM file actually really miss of over 100GB isn't among them.

I have experienced the same problem.

previous feature updates have applied without issue.

no files were found in my documents folder after the upgrade.

they could not be found in the windows.old folder

rolling back did not restore them

they cannot be found in one drive.

I am lucky that I store my documents on backed folder on the LAN, but kept a local copy of a number of files for when I am offlline.

I have lost some work from this and lost a few hours today trying to figure out what happened.