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The real challenge is to ensure it .If the resistance holds then you can make a trade in that direction.

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You will have to wait if the resistance will hold, the prices will retest this area, and and try to break through it, and then possibly a pullback, then as it breaks out again, you can prepare to make a trade in the direction.

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IMHO. (assuming there is no news) When Support becomes Resistance; yes, there is a high probability of a near future breaking down (not always). I agreed it would be a good logical choice to enter a short after retest the new resistance however I probably won't short it yet because we don't have a clear direction where it will goes next up or down. Sometime it could retest the new resistance many many times before it decide to go in one direction either way. What I am more concern about is where your Stop Loss and Take Profit Target if you actually entered a short after it retest the new resistance (Broker normally like do a head fake to takes out the stops first and give fault signal to traders before continue in the real trend).
I personally will consider to wait until after it broke down first and short after the 1st pull back with the confirmation of down trend of 30M and 1H chart.

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At the time the support becomes resistance, there will be a breakout, the first breakout will have a pullback, you can trade the second wave.

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when support become the resistance, this trading pattern work in open of london market very well Untill after 7:30 to 8:00. but you most check if there is any news at that time or not, in this kind of system you most be sure that market as broking the old swing low and that place may turn to resistance which give you more confirmation that market is going down you can enter when the market make a retracement to that level which as been broking.

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The entry point when support becomes resistance or vice versa is when it retest the point. However whether this points will hold you will need other indicators to confirm it.

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When the Support becomes the resistance, you can enter a short position below the resistance.

However, the real challenge is to ensure that the resistance will hold the price below it.

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If the market formed a good resistance at the previous support levels, it should definetly try to retest the newly formed resistance area. Try to trade after the retest, that gives more confident in your entry. In some cases it may not happen. no problem forget this one try to point in another time

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When support becomes resistance if can use an indicator like the Bollinger Band expandtion to time your entry.

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The short version would be, when it moves back to retest that level.