RS232 communications can be one of the most frustrating problems to troubleshoot. There's a lot of things to look for when you're having problems with file transfers.
With that said, make sure the settings on both the controller and the computer match identically. Including BAUD, Stop Bits, Data Bits, Handshaking etc.
After that's all confirmed to be correct, make sure the cable itself is wired correctly and make sure there's no hardware issues. Also make sure that you're using a quality, shielded cable for the transfers.
Try sending a file the other direction. If you're successful here, you've probably just got a wiring or settings or hardware problem. (narrows that down, eh? )
Make sure you're not next to any source of RFI, (Radio Frequency Interference). These sources can come from many places, like welding machines or other high voltage systems, they can come from live conduit, or even come from a (large) live extension cord that's coiled up on the floor.
HTH.
Matt
San Diego, Ca
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(Note: The opinions expressed in this post are my own and are not necessarily those of CNCzone and its management)