Hello Derek,
Can you try to run recorder with elevated privileges? Maybe there is some issue with an automation of recorder due to permissions and UAC. If that does not help, we would like to check logs from recorder.
You can use LogAdjuster (Start->SolarWinds Orion->Documentation and support->LogAdjuster), set log level for WPM section "Recorder - *" items to VERBOSE and click apply. Then restart recorder, record transaction and play it back. Grab log files from "c:\ProgramData\Solarwinds\Logs\SEUM" that start with "WebRecorder" and open a support case where you attach these. Reply with case number here and well look at them.
After you have the logs, you should set log level back to INFO for the recorder.