How about the manual shutoff on the side of the IP? If that is having an issue, is sticky, or if you have a vacuum issue that could probably lead to the same symptoms. I was having a random vacuum issue for a while that would cause the shutoff to act like it was being actuated, which of course killed fuel delivery. Just a thought.

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1987 300TD 231,000
#22, afterglow, plastic fan, euro lights, alternator upgrade, cluster housing update

What is this manuel shut off that you speak of?! Is it acutally vaccume controlled?

HitManX had the same problem that you're describing. I won't say that his cause was yours, but try starting the car with the fuel cap on the tank removed. If it runs, then you have a cloged tank breather.
Yes, a small amound of fuel should squirt out an high pressure. If id doesn't, something in the fuel system is clogged or not working.
When the lift pump is working, there is a massive volume of fuel coming out of it. IIRC, the volume the lift pump sends is about 3 times greater than the fuel that car needs. It's just cycled through the filter, and sent back to the tank.
If the car isn't smoking the blueish/white smoke that smells like antifreeze, the head is fine. There are a lot of #14 heads that last the life of the car. The problem is probably not nearly as bad as many people make it out to be. Just like there will be a lot of 3.5 L rod benders that will never bend rods. The rest of the car will die around the engine.
If you want to be safe and sleep better, just ask your mechanic to do a compression test while it's in the shop. (The price he'll ask is probably a lot cheaper than the loss of sleep due to worrying about the engine failing) IIRC, the cylinders should be in the 27-32 bar range, with a maximum of 3 bar difference. I'll look it up later as the WIS is on another computer that I have to drag out.
I hope this helps.

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'95 S320 LWB
'87 300SDL
'04 E500 wagon 4matic

It may be the tank vent.

It sounds like the car is starving for fuel, or has an air leak. Maybe the lift pump is failing?

I'd start by removing a fuel line and replacing it with a clear hose, in order to see if you have an air leak.

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1999 SL500
1969 280SE
2023 Ram 1500
2007 Tiara 3200

I will test the clogged tank breather idea when I get off this aftenroon. That would sure be amazingly simple if that is all it is...

I did try disconnecting the line to the IP and cranking the engine. This caused a foutain of diesel fuel, meaning that the lift pump appears to be functioning normally. Yet when i reconnect the line and try it, bam, same problem...starts for about 3 seconds and then dies.

One thing that is weird...despite having fuel, I don't see the 'squirt' of diesel when i take the lines off the injectors... This leads me to believe there is some sort of a fueling issue still....even though it seems to be getting a lot of fuel, initially at least, from the lifter pump. I will bypass the small white filter this afternoon as well and see if that is the culprit.

Anyone know for sure if i should see a jet of diesel when i crack the lines to the injectors? I'm finding mixed answers on other posts...

Great news....the car runs fine... I turns out the return fuel hose that runs from the final injector back to the return was loose on the nipple. I pulled it off, cranked a few times, and bam, started right up.

Thank god it wasn't a cracked head...

Thank you all for the input.

Thanks for posting the resolution.

Frustrating when folks come in here for solutions and then disappear.

You should hang around a while and take your licks from the oil burner Sturm Abtelung about your greaser.

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1998 E300 +310,000K
1996 E300 +460,000K