Last night I was in late stages of a SnG. 2 of us have around 6k in chips, shortstack has under around 2500. Shortstack had been very passive on the bubble, waiting out a shorter stack, and had continued passive for a number of hands after we got to 3-handed. Blinds are 400/800 at the time.

I got burned in a similar situation twice.

Other stack has the button and folds.
I'm in the SB with an OK hand - J9 once and QT the second time.
Shortstack is in the BB. After ante and BB has less than 2BB

I raise 1BB.
SS reraises all-in.
I'm getting almost 5-1 to call, so I do.

Both times SS went all-in with little to nothing ... First time with 76o.
Both times SS outdrew me.

Here are some questions I'd like opinions on:

Was a raise the correct play? Seemed to me like it was, given SS's passive play.

If raise, should I have raised more to put SS all-in? This would have eliminated the thought that a re-raise might get me to fold.

After the first re-raise, should I have played the 2nd differently?

I'm a bit bugged by this. I had SS all-in 3 times with the best hand, and got outdrawn every time. Eventually I was SS, went all-in post-flop with top pair against 2 undercards, and got outdrawn runner-runner.

I don't see why you are forcing an all-in confrontation with a marginal hand. He is the one who is desperate, not you. As a steal attempt you want to make a bigger raise than 1BB. But, the fact that he is so shortstacked makes a steal unlikely to work. With a marginal hand he is calling and you have the all-in. I'd smply call the BB, hope to see the flop and then make a decision based on the flop. Steals work better against the mid-stacks then the shortstacks.

Why have a race (which is all you can hope for), when you have no need?

I just don't like this play.

Even with your 6K in chips, your M is only a 5! Fancy plays are going to get you in trouble.

I think it would be better to do a stop n go, than to try and steal preflop with J9, QT is good enough though.

According to PokerStove, J9 is a favorite over a random hand, so the push isn't bad given stacks.

You have to do some gambling when the blinds are this high.

Raising 1 BB is pointless though, you are giving the guy 3:1 odds. Don't be a puss. Either limp or push him all in.