The easiest way to verify the file is available is making sure the attachment is present in the IPS_Positioning table of your WebMap. Also, simply the fact that you can access Test Mode with IPS Setup app on that WebMap also indicates that the positioning file is available and provides a position. The existence/availability of the positioning file is the prerequisite for the creation of Quality Recordings.
Descriptions of the issues you seem to be experiencing indicates the positioning file is in place, but I am still not sure what the reason behind the unsuccessful upload might be.
Could you maybe export your WebMap data locally and share a zipped-up .gdb with me for more detailed inspection?
