Same behavior is happening to me. Using the latest build (992000006) of SmartEndpoint, on both Windows 10 and Windows Server 2008 R2 machines, upload crashes. If I try to upload the entire folder with the installers, the initial client MSI uploads successfully, but then it crashes. If I try to upload individual MSIs, it crashes. I'm also a vSphere open server, R80.20.M1 take 14. Chatting with TAC right now to try and come up with something. Spoke with a friend who required a new build of R77.30.03 SmartConsole in his environment for the E80.86 clients to upload properly - wondering if there is a similar issue in the R80.20.M1 train that needs to be fixed.