Returned error code 255 on one machine

I have an application that I wrote that I have deployed on my network.  I have approximately 105 PCs to deploy this to, and PDQ Deploy works perfectly on all but one machine. This one machine I get a message saying "returned error code 255"  I have no idea what is going on.

I ended up just pushing the file to the machine, then remoting in to the machine to install it with my user credentials (the same ones used in PDQ Deploy).  This application is a work in progress, and I have found myself updating it roughly once to twice a month when I have the time to work on it.  I would like to know what might be causing this issue on just the one machine, so that I do not have to keep doing this work around for it.

Does anyone have any ideas what causes error code 255?  I just recently updated to .net 4.8, as the scanner said it needed it, but that did not help my issue with this error code.