Eric, that reference is for Windows so not a lot of help on Debian.
Sorry if this is egg sucking territory, but the first thing I'd try would be:
sudo owserver -d /dev/ttyS0 --foreground
to be able to see any error messages displayed. Next would be to look at the
--error_level command line switch.
It'd also be worth checking the port mapping - strange things can happen with different system's interpretations of obscure little tables in the BIOS. If you don't have any other serial devices you can try conveniently then you could put the port in raw mode, I have a script called raw-serial to do this:
#!/bin/bash
PORT=${1:-/dev/ttyS0}
SPEED=${2:-9600}
stty -F $PORT $SPEED raw pass8 -cstopb -crtscts clocal -echo
then send a big file to it:
cat somebigfile > /dev/ttyS0
If you have a serial break-out box then look for data with that. If not a meter (20 V DC range) on the transmit data line (pin 3 on a 9-pin connector, 2 on a 25-pin) vs ground (pin 5 on a 9-pin, pin 7 on a 25-pin) should show different readings while the cat is in progress.
An alternative would be to wrap pins 2 and 3 together (either size connector - just touching the two pins with a key or something should do) then in two separate terminal windows do:
cat /dev/ttyS0
and
the same somebigfile cat as above.
I don't have a proper serial port to hand but have just checked the above on a USB-to-serial adapter (/dev/ttyUSB4 in my case, 0 through 3 being my mobile broadband dongle).