Windows 10 Windows 10 - Roaming profile operates without logging errors, but fails to synchronize files

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Preliminaries:

To get some of the preliminaries out of the way:

(a) if this isn't the correct place to post this - please advise where is - thanks.

(b) Desktop computer (hereafter referred to as 'PC') is Windows 10 build 1909 with updates through 6/26/2020 having been installed.

(c) profile directory is stored on a file server running Windows Server 2016 build 4393.3750 , hereafter referred to as "File-Server"

(d) terminal server is the same windows build as the file-server, hereafter referred to as "Terminal Server".

(e) I've been doing roaming profiles now for the better part of 2 decades at various places - while I'm not immune to making simple troubleshooting mistakes I do generally know where to look to fix problems.

Basic problem: the user reported that he cleaned up a bunch of files from his PC and logged out. Later on when he logged into the terminal server they were still there. Generally when I see this it's because the person left their roaming profile logged in to one spot or the other and logged out- golden rule, the last logout get's the changes saved even if it means putting things back. - I verified this was not happening for him so moved on an checked the second part which I find is usually when there's a problem syncing a particular file or two one one system or the other (PC or terminal server) - found an error on his PC indicating a problem syncing a particular file. Removed that file from his PC, the roaming profile directory on the file server, and the terminal server. Here's where we get to more definitive problem behavior, which later switches sides - the flag file is saved to the roaming user profile and appeared on the terminal server. I removed it there and logged out but it failed to remove the file from the server. OK - problem with the terminal server's user profile services. So at an opportune time I rebooted the terminal server and the user's PC and tried again - now the problem switches sides. I cleared the flag file from the locations and tried again - created it on the PC, verified it syncs to the file server / roaming profile folder, logged into the terminal server - it's there . Deleted the file from the terminal server and logged out - great, it's removed the file from the roaming profile folder. Logged back into the PC but it has failed to sync from the roaming profile folder and the file is still on the PC. Re verified it's missing from the roaming profile still (yes).

My co-worker suggested removing and re-setting up the folder on the server which has worked for him - OK, worth a try. I might note at this point I had checked the security on the folder. I typically set these up using batch file I created previously so that I don't miss steps including setting the user to have full control of the folder and to be the owner of the folder. I restarted the terminal server, and the PC, and removed the old profile folder and used my batch file to setup a new one. Logged into the PC, setup a flag file logged out - verified the roaming profile folder populated including the flag file. Logged into the terminal server - file is present. Deleted the file and logged back out - verified it missing from the roaming profile folder. Restarted the PC first, then logged it in - the file was still present even though it had been removed from the server. Just to remind - this behavior was reversed earlier and was operational as expected from the PC but not the terminal server.

There are no errors in the event logs on either the terminal server, file server, or PC which I usually see when there's a problem with a particular file. Please re-note I've made a unique filename for each flag file. This behaves much like a bug in the user profile service. It's misbehaved on both the terminal server side and PC side even when I've verified the file is missing. This problem doesn't show up regularly because not everybody here get's into the terminal server , and the problem generally is only noticed when a file is deleted from the desktop. Generally files are worked with from the server further reducing the frequency of time this problem is observed.

As my experiences with Microsoft of late are that I can either spend the $500 to try and prove this is a bug and maybe get my money back, and in many cases I'm told to just post to a forum where the developers are supposed to be watching - it seems I'm left with few good support choices other than to put out money I may never get back or to hope that somebody here is willing to support microsoft's products for them or a developer may see this.


If somebody has a fancy fix for this, please share and Thank You in advance.

If a Microsoft developer needs additional information to run this down please feel free to contact me and I'll see what I can do.

Is there a better way to report a possible bug and see about getting it fixed or is this whole process the best that I have available to me?

Otherwise my work around for the moment is to just have the person RDP over VPN connection to his desktop PC which means he may lose access if his PC loses power due to a building power problem (which occurs from time to time) - it's better for us to maintain a terminal server for connections than have to purchase a whole bunch of UPS equipment.

Thanks in advance.

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