What USB-RS232 adaptors do y’all use and would it make any difference?
RS232 problems using a USB to Serial adapter cable - will a MAX232 help - Electrical Engineering Stack Exchange
Which USB-RS232 adapter to get?
How to choose USB-RS232 cable?
How do I install my USB serial adapter in Windows XP? (.exe method)
How do I confirm that Windows detects my USB device?
Serial communication is not working. Is the problem caused by the adapter or my serial software application?
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Most of RS232 to USB adapters are low quality and don't work for that reason. They also may not support semi-exotic features like oddball baudrates (those that aren't multiples of 2400bps) or hardware handshaking.
Here are some other things you can check as well:
The most classic RS232 problem is mixing up Tx and Rx. In which case you need a "null modem" type of RS232 cable/adapter. It is a device consisting of DE-9 male to DE-9 female (optionally with a cable between them) where Tx and Rx are flipped internally. Not to be confused with a gender changer, which only switches between DE-9 male/female without flipping the signals.
Continuity/resistance test with multimeter between RS232 DE-9 pin 5 and USB-A connector pin 4. This is signal ground and must be present. (Pin-outs of these are easily found on the Internet)
Are there any hardware handshaking signals used by the device? If so these might not get passed on over the USB adapter. Most common are RTS and CTS on pin 8 and 9.
COM port settings: baudrate, stop bits, parity.
If none of that helps, it is oscilloscope troubleshooting time from there on.
You may need to go into the Windows Settings and assign a COM Port number between COM1 and COM4 for the USB adaptor to be recognised by old software.
Also it could be the case that the Brother software is attempting to manipulate the hardware of a UART directly in the PC, so it will not work unless you find a motherboard with hardware UART connections - some industrial PCs come with all 4 COM ports for instance .