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The correct response to this challenge will be in the form of a statement that shows that you actually see what happened; it will not be in the form of a conjecture. The answer must express certainty: "This is how this sutta works; it is explained this way."

This is the Buddha's First Sutta. You do not have any other knowledge of the Dhamma. There are no commentaries. Don't reach outside the realm of this sutta.

Do not waste your time speculating about what Anna Kondanna might or might not have already known. Think of a "generic" Anna Kondanna; better yet, put yourself in his place, role-play the role of Anna Kondanna. Another way of saying this is: how would you get to the DhammaCakkhu with only what was given in this sutta?

The Buddha taught in a manner that was always accessible to the intelligent from ground zero.

The Buddha was at this point "A Buddha" he could know that this sutta would be remembered right down to this time and he would make it effective for all time.

Again, this was his first sutta; he would have known that it would be given special attention in the future, and he would make it a masterpiece, a signature piece.

Read a couple or even all the versions of this sutta and refer to the Pāḷi to distinguish what is being translated as what. Do this just to the point where you see that the few minor differences in translation do not alter significantly the information being transmitted in the sutta. Then put the texts aside and use only your recollection to look into the sutta. Review again as necessary.

Distinguish between what the sutta is saying and what you think the sutta is saying; what you think it means as opposed to what it is actually saying.

Concentrate!

And remember who the Buddha is speaking to: five fellows who doubt his accomplishment; he has got to overcome that in some way.