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Remote Desktop RemoteApp .exe (icon) Causing RDweb to crash with Runtime Error

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Ok guys, I have been chasing some weird issues with RemoteApp deployment.  I had abandoned the GUI to deploy RemoteApp as the session collection would fail every time when deploying the apps.  I have it narrowed down to a specific program that has an issue.  When trying to setup the new RemoteApp via Powershell without specifying an -IconPath this app fails with this error:"New-RDRemoteApp : Could not find the specified icon:"

 If I try to deploy this app with the -IconPath parameter the process will complete.  However, as soon as this hits the RDweb, IIS crashes out with a generic runtime error.  I have tried to place the icon in the same root folder as the executable, no luck.  I have even opened the exe with Resource Hacker and created a new Icon and exe.  Same problem every time.  I can use powershell to remove the app from the collection and IIS immediately gives me the working RDweb interface after a refresh.  I am at a loss as to why this one application refuses to allow a successful deployment.  Any help is greatly appreciated.

Windows Server 2016 Datacenter

Running on VMware ESXi6.5

****-License01.corp.contoso.com = RD License, Broker, Gateway and Web Access (Also handles application licensing)

****-APPS01.corp.contoso.com = RD Session Host (houses the applications and data)


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