Thanks a lot guys, turns out it was a poor cable connection.... anti-climactic I know...
I am going RJ11 to RJ45/Ethernet to DB25... I was treating the RJ11 cable as a straight through, but it was in fact a crossover which I didn't realise.
I don't like the application to begin with, sending an RS232 signal to an old dot matrix printer is a little archaic for me but I got it going so thats the important part!
Thanks a lot for the feedback everyone.