I read through the cold starting thread but couldn't find anything that seemed particular to my problem plus it is quite old now.
I have a Mk6 2005 2.0 Duratorq with 110k miles on the clock.
It was recently purchased and the previous owner has changed the glow-plugs recently. He also had a bleeder squeezer hard plumbed into the fuel filter for some reason, possible to try and cure this problem.
You have to use the starter for up to 10 times in bursts of 5 seconds before it grudgingly starts but once started for a few minutes it restarts like a dream. Indeed, sometimes the merest hint of starter motor and it bursts into life and never misses a beat but leave it overnight and back to square one.
I can encourage it to start a bit easier by turning the ignition on for 5 seconds without the starter motor and repeating 5 times but is this just pressurising the system?
Another thing, while it's churning the starter motor, there's a load of black smoke that smells to me like unburnt fuel so my thinking was could be injectors or low pressure on the pump but that's just a guess.
Any ideas?

