I have two problems with Offline Files in Windows 7 that maybe you can shed some light on. I have narrowed these problems down specifically to Offline Files in Windows 7 and have manufactured some workaround solutions, but they are not great. This is a really long forum post, I apologize. I broke it up into sections so it would be easier to reference in replies. Setup background: everyone in my company has mapped our file server share as “X:” and within that folder there is a “Company” and “Employees” folder. The Employees folder has a folder with each employee’s name, which they then have available offline. No other folders are made available offline. For example, I have the X: drive, and only “X:\Employees\Elizabeth” is available offline to me. As expected, files that aren’t available offline are accessible only through a VPN if working off our network. Problem 1: Working remotely with VPN, even when not slow, yields an “Offline: Not Connected” status. This happens quite often with coworkers that work remotely. NOTE: This is different than the “Offline: Slow Connection” status. No matter how many times I refresh, try to access the X: drive, it still shows as “not connected.” Reconnecting the VPN only results in a split-second of the X: drive showing as “online” and it immediately goes back to “not connected.” However: I know it is connected since I can access other folder shares on the same file server and in fact it has pretty good speed and no problems doing so. Having Offline files enabled has created some sort of confusion in Windows. A workaround solution that we made has been a huge pain: If we create a different share on the file server for the “company” folder and the individual “employee” folder, then map them as different drives (Y: and Z:, respectively), then the user can access the “Company” folder with no problems (since this way there are no Offline files available at all on the Y: drive). This is a terrible solution since it doesn’t solve the connection problem – remote users need to sync and Z: will still not show as being online (again, even though Y: connects with no problems). Have any of you encountered this? Is there a permanent solution out there rather than the workaround solution we had to use? Problem 2: Having Offline Files enabled somehow causes a “file path does not exist” error when trying to save a document while working online (on our network/not using VPN). This is a strange one and I have only seen it with one coworker so far. He was getting a “file path does not exist” message when going to File > Save in any program (Notepad, Office, anything – it didn’t matter) and trying to save to a “Company” folder location. He was working online at the time. If he saved it to his desktop and dragged it into the desired location, it copied over with no problems. We found that we had to go into “View your offline files” and “Delete offline copy” of the Company folder (even though no offline files in that location were enabled at that time) to get the error to go away. This worked for a while, but then the problem reoccurred and the only way to get it to disappear for good was to disable Offline Files altogether. In this case it seems like Windows was getting confused again. The path obviously existed since we could use Explorer to find the path, and navigate to the folder location in the Save dialog. Has anyone seen this error? How can I get offline files to stop messing with Windows’ idea of valid file paths? Any help with these problems is appreciated. If you have some other forums to suggest as well please share them. I am at wits end and am not finding much in the ways of Google search.