Should a cold hand crank compression test work?

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I'm not sure which part of my setup is failing me but something doesn't seem right.

First of all, this is on my 87 300SDL that was running good and not smoking before I started to remove components.

I have the starter, intake manifold, radiator, and several other components removed so I cannot start the engine to warm it up.

I went and got my Harbor Freight 93644 compression tester this morning.

Removed all of my GP's and selected the correct adapter.

I tested the number 1 cylinder first and after about 5 crankshaft rotations I had almost no pressure, nothing reading on the gauge, just a bit of air when I hit the release valve.

I then moved to the number 2 cylinder and turned the crank about 10 times. This time I got nothing at all, no reading on the gauge, no air when I hit the release valve.

Then I got side tracked before getting to the other cylinders but I'm guessing that the engine either needs to be warmed up prior to doing this or I need to crank it around alot more than 10 times. According to the instructions it needs to be turned 8 times but I'm thinking that might mean 8 compression strokes, not just 8 revolutions of the crank.

What do you all think?