With multi months or multi year breakouts, ideal strategy is to buy at or as close to breakout as possible. But sometimes, if that opportunity is missed, there are other chances when stock price retests breakout levels. Sometimes these retests go slightly below breakout zones also and in these instances, it is better to wait for these dips to finish and buy on first sign of reversal from these minor downtrends, especially on daily or weekly charts. This can take form of candle stick reversal, or bar chart reversal, or divergence on indicators, or preferably all of these put together.
For more details, u can go through 52 weeks high thread on VP, or other relevant technical analysis threads. Or read the book How to make money in stocks by William ONeil.
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