Hi, this was fixed by downloading the update directly instead of using HELP > CHECK FOR UPDATES. So if anyone has a similar problem please download the update direct from:
// STAMPMANAGE DELUXE 2016 *** ONLY *** if you are using and paid for StampManage DELUXE 2016
http://s3.amazonaws.com/LSSDownloads/StampMngUp2016.exe
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// STAMPMANAGE USA 2016 *** ONLY *** if you are using and paid for StampManage USA 2016
http://s3.amazonaws.com/LSSDownloads/StampMngUSAUp2016.exe
DONT DOWNLOAD THESE files if you are using an older version of the software 2015 or older