Did all these symptoms start at the same time? So to be clear: you have coolant in the diesel, potential diesel in the coolant, and oil draining into the cylinders?

My first instinct would be at/in the injectors. When I had a cracked cup, my coolant (green) smelled like paint thinner and had a visible clear layer floating on top. Is the coolant cap hard to remove? Diesel will swell the plastic tank and make cap removal difficult - it should spin easily by hand. Usually diesel will push into the coolant as it's under a higher pressure at the cups, so I'm leaning away from this. Injector orings could contribute though usually you get oil in the fuel and it would show as black specs in the fuel filter. Is it harder to start when warm? Check your IPR and ICP numbers if you can. IPR duty cycle should be 14% when you turn the key on, and when you crank it, duty cycle should go up to no more than 35% and ICP jump up to 500 psi or more. When it starts, ICP should be around 450 psi and IPR duty cycle between 11-12%.

You can pull the valve covers and look for oil coming out the base of any injector - that would indicate a bad upper o ring. Also try unplugging each injector while it's smoking to see if that clears it up. Could be an injector sticking open (gray smoke). Wouldn't hurt to do a compression test while you're there.

i plan on doing a compression test, i bought the harbor frieght one but i am having a hard time tracking the fitting down (m10x1.0 male to 1/8 npt). plan on pressure testing the cooling system(going to rent the tool) and the cylinders. looks like the part wont be in till Thursday if i order it on amazon tonight. AUTOMeter 2265 if any one wants to build one,
Homemade Compression Adapter - PowerStrokeNation : Ford Powerstroke Diesel Forum


the smoke started through out the winter getting bad, the other symptoms where recently, longest trip i did was in November(out t to idaho)wit any problems besides the smoke in the cold.

i just started it today after it sat all weekend(been in the 60s) and it fired right up and was lumpy for a minute and cleared up, i had the p/s valve cover off but i didn't notice any of the injectors leaking by at the base, going to pull the D/S cover tommarrow or wendsday.( the paint thinner smell is a good description in the coolant)

So far my plans
Compression test and cooling system pressure test(see if i can push it back up into the bowl)
CUPS
Oil Cooler Reseal/inspect
Injectors(probally upgrade to stage ones, only if i fell confident on what the problem is after i do some more diagnoses
heater core(might as well with 226k on mine)

well i couldn't do a compression test.... arg couldn't get the compression tester to fit any way i tried., so i pulled the injectors , all the seals where perfect..... just how i installed them 100k miles ago.... the cups where still shinny, and i couldn't see any visible cracks. going to pressurize the cooling system tommarrow and see what i can find.

Very doubtful you'd visually see a cracked cup, but the pressure test will show them.

I forgot about the oil cooler as a mixing source - I'd prioritize a reseal on that and see if that helps with the coolant issue.

welll this is wierd, 3 cups on cyclinder 4, 6, and 8 are all leaking in the same spot, kinda looks like the sealant has maybe failed? still not a 100% sure how its getting all the way up to the fuel bowl


and i am thinking of just spending the extra $200 and putting a new one on + a new heater core(getting tired of draining the coolant LOL)

Get it ifixed OP?

www.cncfab.us

well i put it back together on sunday, loving the stage 1 injectors from full force, no more coolant in the fuel filter and the coolant is staying clean so far, so knock on wood i have it figured out.

ive put about 200 miles on it, seems to be loosing a little coolant when it cools down, but my filter housing on the coolant is seeping/i am hoping some of the air is just bleeding out , so i am going to close it off and see if that is it, if not im going to open the heater core up and inspect it?(didn't end up replacing it because the system held 16psi for a while).


but the cloud of smoke is gone and straight diesel is coming out of the fuel filter, and besides a little residual from doing the oil cooler and cups the coolant is staying clean, so i am happy so far and appreciate everyone's help