@EricDavelaar: Do the files not upload even after you have re-started Insync? Please send to us the logs.db file at support@insynchq.com
Re: missing context menu, are you running Insync under the default administrator account? If yes, please install it under the non-default admin or non-admin account (but with admin rights) to get the Insync context menuitems. Please read the explanation here: Insynch menu not showing when right click on folders