After reviewing the WLW log file there was an error every time WLW was started when it tried to create a temporary folder.
The error in the log looked like the following:
System.IO.IOException: Not enough quota is available to process this command.
According to this foum post this can happen when 'Offline Files' quotas are too small or there are too many temporary files. These files can be deleted through the control and the quotas can be adjusted as well. The problem was fixed after Nigel9999 followed these steps.