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Here are 2 trades from the same day. The first purple trade Mack skips because it is blocked by a possible short term up trend though the context is very good in my opinion (unless I'm missing something?) The second red trade is also blocked but Mack marks it red even though the context is not as good as the first (again, I might be missing something.) I'm now confused on when it is okay to take a trade despite a possible or confirmed short term trend in the way?

The one is a matter of a few factors.

First, many have difficulty in understanding exhaustion and believe something "has to happen". Nothing has to happen. . . ever. It is just that enough elements align to put probability in one's favor.

In the first situation, it is a matter of counting. You want to be long, so you will attempt to count your way to success. But what is being counted there? That isn't a second entry long is it? NOPE! To want to take that you are taking a Failed Second Entry Short -> aha! Going to trap them ------ NOPE!

1. Is the entry towards the beginning of the move -> NO. In fact, Mack correctly points out it is towards the high isn't it.
2. Is this a good higher low? No, this is the same movement, which makes it a Failure Attempt.

Please stay away from failures.

If you compare this to the second case, the elements are reversed now aren't they.

It is an entry to go short, when you want to go short.
It is towards the top of the move.
It is towards the beginning of the move.

In both cases note how the trade type count selection affects your biasing. Staying away from traps and trap counting is always recommended.

Work through 100 charts to differentiate counting, failures, and higher lows.

Hopefully helpful and good trades to you!

Hey Eric, I think you misunderstood the pictures. The first purple trade is a second entry short looking to also go short, not a failure looking to go long. I know Mack was also looking to go short at the purple bar because he says it is very tempting but he skips because it is blocked by a short term trend. He then also marks a trade a few bars later going short. The second trade which is marked red by Mack looks to be in worse context and is also blocked by a short term trend but Mack takes it anyway. I'm asking why he's willing to ignore the short term trend in the second case but not the first.

Whew!

Well, please review the overall contexts for strength:
a. Strength of market state (how do you evaluate?) Early 4 lectures
b. Strength of pullbacks
c. Expectations of targets.

The first one I would not take. It is a micro move upwards and look at the strength of rejection of the signal bar. The second one is much, much, much, much stronger for that isn't it?

Also, the strength of bearish bias is much stronger in the second case too (allowing for more leeway).

Consider what the bars represent with regards to strength, and when strength is broken. It isn't just the bars, but what the bars represent (which has to be seen because it isn't a linear translation). In the first case, it may be in an infinite pullback, but that is a very different context than a full outright bearish move.

Hopefully helpful & good trades to you!