Some programs hang with offline shield enabled

I've noticed that a few programs hang for a long time or indefiitely when the ofline shield is enabled, even though my computer is connected to the internet. It is undpredictable when this happens and I can release the hang by starting a Webroot scan, which seems to "kick" Webroot into action and cause to release its blockage on the program.
 
I am running Webroot on Windows 7. Some examples of the affected programs are:
1) Using the rm program from Gnuwin32 to recursively delete the contents of a directory: rm -rf dir*
2) Lauching Microsoft Excel by typing the name of a .xls file into a command window
 
The program doesn't occur if I disable the offline shield but I would prefer to run Webroot in "green" mode rather than "brown" mode.
 
If I use Windows Process Explorer to analyse the blocked thread in case 1 above, I see the following stack trace:
 
0   ntdll.dll!KiFastSystemCallRet
1   kernel32.dll!GetBinaryType+0x23
2   rm.exe+0x116dd
 
What might be causing this problem and how can I prevent it from happening?