It’s not really when to bluff. It’s when not to bluff!
Don’t bluff early and often. There are always exceptions but early in a game or a tournament you probably don’t have a good sense of who you are playing against, what their tendencies are and – just as importantly, who they think you are. If you play it tight early on, when and if you choose to bluff the other players will give you a little more leeway.
How many are you up against? Forget who you are playing against for now, just count heads. It’s always easier to bluff one or two, than five or six. The point of bluffing is not to fool some of the people some of the time: it’s to fool one or two people every time. If you bluff early and before too few have folded, the odds are against you.
The Flop. Don’t bluff if the flop has given too many people a shot at a good hand (unless of course, it’s given you a great hand. Then again, that’s not bluffing..) When you bluff after a ragged flop your chances are better, because their chances aren’t too good to begin with.
Down and Outs! Smart players don’t often bluff without some chance at a decent hand. A good time to bluff is often when you are hoping to draw to a straight or flush from an otherwise undistinguished hand. You still have a few outs that could bail you out if your bluff fails.
Odds are ‘Stacked’ Against You. Don’t bluff if your heads-up opponent can afford to lose. If he or she buys the bluff, you’re probably not going to be winning a large pot and, if you lose, you are probably going to be headed home.
Take Your Medicine. Luck often overrules skill. Odds are a great bluff will run head-on into a great hand every so often. When that happens hit the re-set button. Don’t change tactics, or drop bluffing from your repertoire. If you work at bluffing as hard as you work on the other aspects of the game, it will serve you well.