This has been a recurring situation ever since we started with Vista and Windows 7. Basically when the user logs in, if verbose login messages are disabled (a GPO setting), they just see “Please wait”. If verbose messages are enabled, they see a number of different messages about policy processing, but the one that is most relevant here is that about Group Policy Printer Preferences (I forget if that is the exact words used). It is not at all unusual to see this taking up to an hour or even more to get past this message. In this instance there is not a print services log on the terminal server (which is the computer being logged onto in one case, by a thin client).
At the moment it is most likely I will have a look at the settings of each printer in Group Policy Preferences because the GPP printer item settings now work better if the option to “run in the local user’s security context” is selected as I referred to not very long ago in another context.
UPDATE: I have spent a bit of time working on this today, and it’s still not resolved. The particular situation that is especially relevant is logging on to a terminal server using a thin client. Not only are these delays continuing to occur, but if the user has disconnected from the terminal server session and then tries to reconnect later, they get a message saying that the terminal server can’t log them on because it is currently processing a connect, reset, delete or <something> operation. This operation apparently lasts forever because they keep getting the message even days later. And the Terminal Services Manager doesn’t have their username listed in its list of disconnected sessions.
The next step will be to try changing the login to a RDSH server that is running a different edition of Windows to see if this is related to particular editions of TS, and looking to see whether this problem is specific to TS. However I have seen similar sessions of delay involving other computers lately, it is a Windows Vista/7 specific happening. Like the Windows 7 print problems we had recently, this is turning into a very complex multifaceted problem with no clear answers that will end up taking an inordinate amount of my time to solve. As operating systems get more sophisticated and have more features added, they are also getting more complex and we end up spending a lot more time solving problems on them.
The RD server is currently installing 2008 SP2 to see if this helps the situation.