Com Port Issue

Afternoon,
I have connected a tool into pc usb for an update.
Its currently connected to COM4
I have an updater tool on pc which i browse to the new file for update & select it.
I then click a button which scans pc to see which port the tool is plugged into.
I dont see anything happen here as COM1 is still shown "never had this fail before when pressing scan"
Using the drop down arrow i manually slect COM4.
I then press the update button and see a progress bar.
Now it should connect with the tool & start its 5 minute update.
This now doesnt happen as when the progress bar reaches the end i see a Communication fail message.

Never had an issue,do you see a work around or something i could try which might approach it a different way.

many thanks.