So I haven't been able to get my engine to start. Tried everything (almost).

Noticed some smoke coming from the engine block and opened the oil cap. Smoke came out.

I had my friend crank the engine with the oil cap off and it looked like a steam engine puffing up smoke every revolution.

Is this normal or not?

Could something be wrong with the timing or valves?

Smoke shouldn't come out of the oil cap. A little air coming out (blow-by) is somewhat expected on higher mileage engines and can have varying significance. On the 616 sometimes the valve train can sling a little oil up out of the cap hole, too. But smoke is definitely not normal.

What engine? Have you done a valve adjustment?

__________________
1987 300D, arctic white/palomino--314,000 miles
1978 240D 4-speed, Euro Delivery, light ivory/bamboo--370,000 miles
2005 Jeep Liberty CRD Limited, light khaki/slate--140,000 miles
2018 Chevy Cruze diesel, 6-speed manual, satin steel metallic/kalahari--19,000 miles
1982 Peugeot 505 diesel, 4-speed manual, blue/blue, 130,000 miles
1995 S320, black/parchment--34,000 miles (Dad's car)

It is an 82 300sd.

I was going to do a valve adjustment but the car died.

Well, you probably want to wait for some of the more-experienced guys to chime in, but my inclination would be do a valve adjustment and see what you find out. You can do an adjustment as long as you can turn it by hand. Maybe an exhaust valve is way off or something. My guess is an exhaust issue of some type, but that is most definitely just a guess.

__________________
1987 300D, arctic white/palomino--314,000 miles
1978 240D 4-speed, Euro Delivery, light ivory/bamboo--370,000 miles
2005 Jeep Liberty CRD Limited, light khaki/slate--140,000 miles
2018 Chevy Cruze diesel, 6-speed manual, satin steel metallic/kalahari--19,000 miles
1982 Peugeot 505 diesel, 4-speed manual, blue/blue, 130,000 miles
1995 S320, black/parchment--34,000 miles (Dad's car)

Can you crank the engine with the valve cover off?

I could pin point where the smoke was coming from then.

If you're getting smoke out the oil fill cap when the engine is not running you have a problem. Holed piston(s)?

__________________
1977 300d 70k--sold 08
1985 300TD 185k+
1984 307d 126k--sold 8/03
1985 409d 65k--sold 06
1984 300SD 315k--daughter's car
1979 300SD 122k--sold 2/11
1999 Fuso FG Expedition Camper
1993 GMC Sierra 6.5 TD 4x4
1982 Bluebird Wanderlodge CAT 3208--Sold 2/13

I thought he meant there was only smoke as it cranked. Yeah I would say if it continues to smoke while it's just sitting there, it's something more serious than a valve. But again, I'll let the experts chime in and will be interested to see what you find out.

__________________
1987 300D, arctic white/palomino--314,000 miles
1978 240D 4-speed, Euro Delivery, light ivory/bamboo--370,000 miles
2005 Jeep Liberty CRD Limited, light khaki/slate--140,000 miles
2018 Chevy Cruze diesel, 6-speed manual, satin steel metallic/kalahari--19,000 miles
1982 Peugeot 505 diesel, 4-speed manual, blue/blue, 130,000 miles
1995 S320, black/parchment--34,000 miles (Dad's car)

Yes. If there is a hole in the piston cranking it over will sound obvious when the piston with the hole comes to the top it will sound and feel differently as that one will have no compression to resist.

__________________
[SIGPIC] Diesel loving autocrossing grandpa Architect. 08 Dodge 3/4 ton with Cummins & six speed; I have had about 35 benzes. I have a 39 Studebaker Coupe Express pickup in which I have had installed a 617 turbo and a five speed manual.[SIGPIC]

..I also have a 427 Cobra replica with an aluminum chassis.

Do you mean steam? Not sure how you can see "air". I'm just wondering for personal knowledge. I wonder if the OP means steam vs. smoke.

__________________
1982 240 D, 308,000 - 321,127 miles (sold)
1982 300 TD,166,500 - 226,000 miles
1998 E 320, 120,000 - 144,000 miles
2005 C 230 K, 26,000 - 77,000 miles (sold)

I think you would have oil shooting all over the place.

__________________
85 300D 75K Anthracite Grey 0-60 in 13 seconds **For Sale**
84 300D 333K Black (The Velveteen Rabbit) 0-60 in 14 seconds
00 Toyota Sienna 208K (Sold)
15 Subaru Outback 43K
11 Subaru Outback 67K
98 Ford Taurus 100K (Gertie - Was Grandma's - drove it to church and shopping - really) Daughter's car now.
30 Model A Ford 2 Door Sedan (Sold) 0-60 in . . . Never reached 60

Not so much Oil flings around if it does not start.

I am guessing a bad Head Gasket.

Might be time for a compression check.

__________________
84 300D, 82 Volvo 244Gl Diesel

Blow-by would be pressurized air ... you can't see it but you can feel it when you put your hand over the oil cap hole with the engine running. If there's smoke or steam coming out, there's something more than blow-by happening.

__________________
1987 300D, arctic white/palomino--314,000 miles
1978 240D 4-speed, Euro Delivery, light ivory/bamboo--370,000 miles
2005 Jeep Liberty CRD Limited, light khaki/slate--140,000 miles
2018 Chevy Cruze diesel, 6-speed manual, satin steel metallic/kalahari--19,000 miles
1982 Peugeot 505 diesel, 4-speed manual, blue/blue, 130,000 miles
1995 S320, black/parchment--34,000 miles (Dad's car)

Here is a video of the engine.

http://www.youtube.com/watch?v=a9QFfuHcP58

And here is the other thread about the engine.

Engine still won't fire???

GTK. I have some troubleshooting to do with the wagon. It's not as bad as the video posted by the OP, but similar.

__________________
1982 240 D, 308,000 - 321,127 miles (sold)
1982 300 TD,166,500 - 226,000 miles
1998 E 320, 120,000 - 144,000 miles
2005 C 230 K, 26,000 - 77,000 miles (sold)

From the video, I don't think there's much question but that is combustion gas coming out of the oil fill hole. The engine is not turning at a consistent speed with the starter either, leaving me to think that there is something funky going on (as Tom pointed out). If it were one holed piston, I think the combustion gases would be more rhythmic.

__________________
1977 300d 70k--sold 08
1985 300TD 185k+
1984 307d 126k--sold 8/03
1985 409d 65k--sold 06
1984 300SD 315k--daughter's car
1979 300SD 122k--sold 2/11
1999 Fuso FG Expedition Camper
1993 GMC Sierra 6.5 TD 4x4
1982 Bluebird Wanderlodge CAT 3208--Sold 2/13