If you attempt to install the Reserve Outlook add-in into a folder within C:\Program Files\… the information provided on the command line such as URL is NOT copied into the user’s outlook.properties file. However, if you select any other folder in the computer as an install location, then the details are updated into the outlook.properties file.
The problem with using any other location is that those locations are not trusted by Windows. As such, the application when invoked forces a popup which, due to the expired application signing certificate, is not pretty. This is quite scary and is likely to result in many of the users declining the installation.
Because the files are sent to the users’ computers silently, they will not be aware that the add-in has been deployed into their machine. Any popup around email is worrying, so it is easy to see people taking the Don’t Install option.