Going for a check-raise in the wrong situation may end up costing you a lot (by way of missed bets) when you have the best hand. This is just as bad as losing money.
In the event that you are not sure whether it is correct to check-raise, I recommend that you bet. You're better off winning one call than none with a strong hand. The following are some subtle considerations and observations regarding check-raising, focusing on when it is a mistake to attempt a check-raise.
PERCEPTION OF THE CHECK-RAISEWhen you check-raise with a big hand, you must understand that you are basically giving your hand away. When a player bets a flop and you raise from a late position, your opponent still doesn't have the "complete picture" on your hand. This is because you may have one of two hands. Either you have a big hand or you are raising for a free turn card. Since your opponent doesn't know which, they will usually call and make another decision about your hand on the turn. If you check-raise a player on the flop, your opponent usually eliminates the possibility that you have a draw and puts you on a big hand. So the major consideration about the check-raise is deciding when you want to release this information about your hand.
If you are against a smart tight player and/or a player who will make good folds, a check-raise is pointless since they will suspect that they're being trapped and may fold at the next available opportunity, even if they have a good second best hand. They have the complete picture once you check-raise, but they may have paid you off if you simply bet the whole way because you didn't totally give your hand away. Of course, the above consideration doesn't apply when you are against players who will bet until they are raised and then call all the way after the raise. This is the ideal opponent to check-raise.
SOMETIMES, STRAIGHT-FORWARD PLAY IS MORE PROFITABLEThis is somewhat tied in with the previous topic: check-raising scares some opponents out of being aggressive against you, even with a big hand. When this is the case, consider that straight-forward play may be the most profitable. Let's say you have 6-6 and your opponent has K-Q. The flop is K-K-6. Let's say you check, as expected your opponent bets, and you then check-raise. Your play here will definitely put your opponent on the defensive, even though his hand is good. Now he will probably just call you down the whole way. Many opponents freeze up when check-raised in this situation and assume the worst: you have A-K, K-6 or 6-6. A check-raise always triggers concern in your opponents and they will rarely come back at you without the nuts.
Now let's replay the hand with straight-forward play. On the flop, you bet and he now calls. This opponent may now put you on a hand like 8-8 or maybe A-6. Maybe you have AQ and you are trying to pressure him out of the pot? In any case, your opponent thinks that he has you beat and simply calls the flop, intending to pump it on the turn. Surely enough, the turn is a blank, you bet again and he comes out with a raise. Now you can reraise. I guarantee that 99% of opponents will always call this reraise and a river bet with a hand like K-J in this spot. If you check-raise on the flop, you would have missed all this fabulous action when the bets are twice the size.
Many of you may be thinking that you would check and call this flop and check-raise the turn. If your opponent has K-J, he will bet all the way, so you won't have trouble getting in a check-raise. While you will only pick up two bets instead of three on the turn, you will still win a nice pot. The problem with check-raising here is that it will only really succeed if your opponent flops a big hand at the same time you flop an even bigger hand.
If this doesn't occur (which is most of the time), you should consider that a check-raise will not achieve the same result as straight forward play. Let's say your opponent has 10-10 on a flop of K-K-6 when you have 6-6. In this situation, many opponents will bet if you check (either the flop or turn), so the option for a check-raise is certainly open. But if you check-raise him at any point, he may accept defeat and fold too easily. If you simply bet into him the whole way, he may well call you the whole way because you aren't actually giving your hand away.
Further, if you did go for a check-raise, there is also the added risk that your opponent will not bet the turn after you called the flop, fearing (correctly) that you are setting him up for a check-raise on the turn. This would be disastrous as it causes you to miss out of collecting on a round where the bets are twice the size.
PLAYERS WHO ROUTINELY RAISE THE FLOP FOR A FREE TURN CARDCheck-raises are not appropriate for players who usually raise the flop for a free card on the turn. Here is an example. About 3 months ago, I had 8-9. The flop came J-10-7h. I bet and a player raised me. He is a bit of a tricky player and often raises the flop then checks the turn. But I momentarily disregarded this and called his raise, intending to check-raise the turn. On the turn, a 4h fell, I checked and to my disappointment, he checked behind me. On the river, a 10h fell, pairing the board and completing a possible back-door flush draw. I bet, he thought for a few moments and then called me. He had 10-8. He clearly thought that I may have caught a miracle flush or had a hand like A-10. This opponent was a little overwhelmed by the possibilities so he simply called me on the river and I won and mediocre pot. (Recommended to play Full Tilt Poker)
If I played this more up front, the player would have called me the whole way with 10-8. On the flop, he initially put me on a pair of jacks when I bet. If I reraised him on the flop, he would probably put me on a hand like A-J. Since he can catch an 8, 9 or 10 to win, he will call me the whole way anyway. On the river, when a repeat 10 fell, I would have bet again and he would probably consider raising me and I would win a big pot. In other words, you should be up-front against a player who usually puts in fancy free card raises.
NUT FLUSHThis is a very quick note, but important one. You should almost never attempt a check-raise with the nut flush. Not only do you COMPLETELY give your hand away, you also may force out players who are drawing dead. Why do you want to do that? Let's say you have Ad-8d and the flop is Qd-9d-4d. If you come out betting, your opponents will think that you either have the Ace of diamonds and you are therefore on a draw. They would never put you on an ace high flush. They may even think you have a queen with a strong kicker and don't want to give someone a free shot at a flush.
Let's say one of your opponents has J-10d, another has Q-J and a third has Kd-X. Virtually all of these hands will call the flop if I bet. Further, most will call the turn, even if another diamond falls. One or both will surely pay me off on the river too. As soon as I start check-raising, I'll give away my hand and these opponents may start folding. Since these opponents are effectively drawing dead, I want them to stay in the pot and call me. I don't want to start pushing them out with check-raises. I would rather bet and give them the impression I'm trying to protect a vulnerable hand - therefore they think they still stand a chance of winning the pot.
DANGER CARDSIf a danger cards falls, forget about check-raising. Let's say you have Kh-Qh and the flop is Ks-Qd-7s. You bet and an opponent raises you. You call thinking that you will check-raise the turn. On the turn, a Queen of spades falls. This card paired the middle card and completed a possible flush draw. If you check, even an opponent with AK may not bet the turn. So keep in mind that a turn card or river card may appear so dangerous to your opponent that they will fail to bet and you won't get a check-raise in if that happens. Even if you do check-raise in this situation, a player with enough gumption may fold AK!
YOUR ACTION ON PREVIOUS ROUNDSRecently, I played a game of Omaha in which a player made a very poor choice against me. He had 5-5-X-X and I had A-10-X-X. The flop came A-10-5. He bet and I raised. He then reraised and I called. On the turn, a 5 fell and he checked. This would have to be the most suspicious looking check I've ever seen in my life. In the circumstances, it is absolutely ridiculous to attempt a check-raise on the turn. He put in the last raise on the flop, so he should not attempt a check-raise me on the turn. When he checked the turn, I read that he was going for a check-raise and put him on A-A. The check looked very suspicious and what else could he have except AA or 10-10? I checked behind him intending to fold when he bet the river. On the river, a 10 fell giving me 10s full of aces. He bet and I had to make a silly crying call.
The important point to take away from this is that you cannot expect to get in a check-raise if you have already shown a lot of aggression on a previous round of betting. People will be reluctant to bet into you without a massive hand.