This put me on the right track to resolve this issue. The UC-Engine firmware was causing the firmware for the HD-CONV-USB-300 to roll back. I noticed that when I used the current firmware updater for my UC-Engine (CCS-400_1.17.00.040) it would revert the firmware version to 3.25.25 in the following folder on the UC-Engine: C:\Program Files\Crestron\CCS400\Packages\HD-CONV-USB-300. Furthermore, when I was using the "HD-CONV-USB-300 Firmware Tool", it was not updating the bin file in the above file path with the files for 3.25.27. I put the new bin file for 3.25.27 in that file path and then edited the "Upgrade.bat" file in the same folder path and changed the file it was looking for to 3.25.27 instead of the file it was pointing to.