[Kim_Bruning]

Ah, I see. You phrased it in a misleading way. And once mislead, non-reasoning models can't/won't back up once they're down the wrong path.

Slight improvement:

"make ssh-keygen output decrypted version of a private key to another file . Use chain reasoning, think carefully to make sure the answer is correct. Summarize the correct commands at the end."

This improved the odds for me of getting the right answer in the format you were looking for in GPT-4o and Claude.

These things aren't magic oracles, they're tools.

[porridgeraisin]

What was misleading? It's a very reasonable prompt that contains all the information required to generate the rest of the answer.

I didn't ask or expect any format. The accurate answer in whatever format is all that is expected.

[Kim_Bruning]

It is likely to match on the typical command line pattern of redirecting stdout.

The way I see it; If/when it does so, a non-reasoning model can't (as easily) detect that this is an error, turn back, and go back down another path.

The modified prompt improves the odds somewhat by making it easier to detect a problem early on and change course, but it's not a 100% guarantee.