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Bull Flag and Bear Flag Trading Strategy: Where to Enter, Where to Stop, When to Skip
By Spencer Li, CFTe · Last updated 17 October 2026
How to enter a flag, where the stop goes, how far to aim, and which flags to leave alone.

Free trading guide
By Spencer Li, CFTe · Last updated 17 October 2026
How to enter a flag, where the stop goes, how far to aim, and which flags to leave alone.

Spotting a bull flag is the easy part. The trouble starts when you have to decide where to buy it, where to admit it has failed, and how far it might run.
A bull flag strategy waits for the short pause after a sharp rise to end, then buys when the price breaks out of it, either on the breakout close or on the first pullback to the broken line. The stop goes on the other side of the flag, and the height of the move before the flag gives a rough target. A bear flag strategy is the same trade upside down: a gentle drift up after a sharp fall, traded when the price breaks down.
A fourth decision matters more than the other 3, and most guides leave it out: which flags to skip. In this guide, I'm going to walk through each decision with one worked example in round numbers, then the flags I leave alone.


Chapter 1 of 6
A flag is a short, tight pause after a sharp price move. The sharp move is called the flagpole, and the pause drifts slightly against it inside 2 roughly parallel lines, usually on falling volume. A bull flag follows a sharp rise and drifts down. A bear flag follows a sharp fall and drifts up. The full definition and the pole, pause, push check are in our post on what a flag pattern is.
A pennant is the same idea with converging lines, a tiny triangle hanging off the pole. Everything below applies to pennants too, and pennant vs flag vs triangle shows how to tell the 3 apart. The wider family lives in our price chart patterns guide.
So why trade flags at all? Because a flag hands you a small, clearly drawn risk. The breakout says the pause is over, the far side of the flag says where the idea is wrong, and the gap between the two is usually small compared with the move you are hoping for.
Further reading

Chapter 2 of 6
Imagine a stock that rallies from 40 to 50 in a week on heavy volume. It then drifts down inside a flag for about 2 weeks, with the upper line sloping from 50 to about 48 and the lows holding at 46, while volume dries up. Then it closes at 48.50, above the upper line, and volume jumps back in.
You now have 2 ways in.
Some traders buy inside the flag before it breaks. I don't, because a flag that has not broken out is just a pause, and pauses can end either way.
| Breakout entry | Retest entry | Buying inside the flag | |
|---|---|---|---|
| When you buy | the close outside the flag | the first pullback that holds | before any breakout |
| Where the stop goes | under the flag's low | under the retest low | under the flag's low |
| Risk per share | larger | smaller | small, if bought near the lower line |
| Main danger | a false break that closes back inside | the trade leaves without you | the flag fails before it breaks |
Personally, I enter most flag trades on the retest. When I had an AI sort through 734 of my own trade charts, the pullback to the broken level was the entry I used most often, and I kept the breakout close for breaks with unusually heavy volume behind them. Missing a trade costs me nothing, while a wide stop on a false break costs real money.
Either way, the candle has to close outside the flag. A wick that pokes through and closes back inside is a trap, and volume should rise on the break.

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Chapter 3 of 6
The stop goes where the pattern is proven wrong, which on a flag is the far side of the pause. If a bull flag falls back through its own lows, the resting buyers have left, and the flag no longer exists.
The breakout buyer at 48.50 puts the stop just under the flag's low of 46, at 45.50. The retest buyer at 49 puts it just under the retest low of 48, at 47.50.
Say both traders risk 1% of their account. The stop distance decides the position size, so the retest buyer can hold twice as many shares for the same 1%. The sizing arithmetic is in where to put your stop loss and take profit.
Edwards and Magee, in their 1948 classic Technical Analysis of Stock Trends, added a sharper idea. Volume inside a healthy flag should keep shrinking, so a day inside the flag with unusually heavy volume is a warning, and they placed a tight stop just under that day's close. If the volume meant failure, you are out at once. If it was the start of the breakout, the price usually runs away from the stop. In a flag, volume gives the early warning.
The stop belongs at a level on the chart, rather than at a comfortable fixed percentage that the flag's ordinary wobble can hit.
Further reading

Chapter 4 of 6
The traditional answer is the measured move: the pole's height, projected from the breakout. The idea is that the move after the pause tends to roughly echo the move before it, which is why the classic chart books say flags fly "at half-mast".
In the example, the pole runs from 40 to 50, so it is 10 points tall. Projected from the 48.50 breakout, the target is 58.50.
Where the pole starts matters. Edwards and Magee measured from the point where the move broke away from its previous range, usually marked by a burst of volume, up to where the flag began. Start at some low further back and you get a bigger number than the chart earned.
The next step is to check the target against the chart. Suppose an old high at 54 stopped the price twice last year. The measured target says 58.50, but the realistic first target is 54, because that is where sellers turned up before.
Same flag and same target, but the retest buyer gets nearly twice the reward for each point of risk. Had that old high sat at 51, the breakout buyer would be risking 3 to make 2.50, and that flag is a skip, however pretty it looks.
Further reading

Chapter 5 of 6
Edwards and Magee called flag breakouts "among the fastest" forms of market action. That gives you a free test. If the price breaks out and then goes nowhere for days, the urgency behind the flag has faded.
The first danger is the failed breakout, a close back inside the flag after you bought the break. In my own rules, that cancels the trade. I either get out, or I step aside and wait a few candles to see whether a clean retest forms, and I never chase the bounce.
Once the trade is working, I take part of the position off into strength, usually as it nears the target or a resistance level, and move the stop on the rest to break-even. The remainder rides under a trailing stop for as long as the trend holds. The exact numbers are part of my own system, and I leave them out here. The habit underneath them is to have the exit plan written down before entry, so that the fear and greed of a fast-moving trade do not make the decision for you.
Further reading

Chapter 6 of 6
Edwards and Magee warned their readers: "you will be tempted to buy on every consolidation pattern formed after a sharp rise." Their advice was to wait until the example is clear. Here are the flags I leave alone.
Flag trading is 99% waiting and 1% action. That stock which ran from 40 to 50 will throw up plenty of flag-shaped pauses in a year, and the job is to act on the few where the pole, the pause, the push and the arithmetic all agree.
So, the last flag you traded: did you buy the breakout or the retest? Where was your stop, and was the target ever realistic?
Further reading
Quick answers
The breakout entry buys the close above the flag, with a wider stop. The retest entry waits for a pullback to the broken line that holds, which gives a smaller stop but sometimes misses the trade.
Just under the flag's low for a breakout entry, or just under the retest low for a retest entry. A close back below the flag's low means the pattern has failed.
You measure the flagpole from where the sharp move began to where the flag started, and project that distance from the breakout. It is a rough guide, worth checking against nearby resistance.
The same way, upside down. The entry is a close below the flag's lower line, or a retest of it from below, with the stop above the flag's high and the pole's height projected down. Traders who do not short can read a bear flag as a reason to stay out.
A rare, extreme flag described by William O'Neil in How to Make Money in Stocks: a stock that rises 100% to 120% in 4 to 8 weeks, then moves sideways for 3 to 5 weeks while giving back only 10% to 25%. He rejected pennants, but he kept this one.
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