How to check raise the river
To check raise on the River you need to be in early position and the player behind you must bet when you check to him. Unless you are in a no limit game and your check raise on the River is extremely large, it is very likely that your check raise on the River will either be called or re-raised. Because of this you should rarely consider using a check raise on the River as a bluff. As you can see, I did not say always because based upon all of your observations there may be situations where you believe that check raising on the River will win you the pot. No matter what decision that you make on the River, it needs to be based, in large part, upon the previous betting action and the knowledge that you have gained in previous hands of the other players that are in the pot.
Advantages of check raising on the River
If you have either been slow playing a monster hand or you made a monster hand on the River card and you have a player behind you in the hand that has been aggressively betting the whole hand, then a check raise on the River can earn you a much bigger pot.
Disadvantages of check raising on the River
Probably the biggest disadvantages of check raising on the river are that the player behind you just checks to your check and you miss an extra bet and that your check raise on the River is followed by a re-raise or 3 bet and you are put in a decision position. You may find yourself in a position where it does not even make sense to call the 3 bet and had you just called the initial bet instead of check raising it, then you would be showing down cards right now.
Good times to check raise on the River
The factors that make for a good situation to check raise on the River are when you have a really good and well concealed hand and you are playing against a very aggressive player. If you are trying to buy the pot the best time for you to check raise on the River is when it brought a very scary card, one that could have made you a really good hand. For it to be a good hand to check raise on the River with a bluff, you must feel that you have developed a pretty conservative table image.
Bad situations to check raise on the River
Bad situations to check raise on the River are when the player that has been betting behind you is a player that you normally know to be a very conservative one. In this situation you better have the nuts to check raise on the River. Another bad situation to check raise on the River is when your hand is not strong enough to call or re-raise a potential 3 bet.