most similar posts get stuck on port initialise fail - you have got past this stage - so your software has found and negotiated data transfer with the port on your pc and the usb-serial converter
now, the data it is sending is either not handshaking with the register ie. wrong port set up for pc comms or incorrect cable pin out configuration. or the register is in the middle of a transaction.
don't change anything on the pc end, it sounds like you have got that bit sussed - i would start with the cable from the db9 to the till - check that it has the correct pinouts and that the port that you programmed on the register is actually the port that you plugged the cable into [i have been caught out with that before
let us all know how you get on