Technology

It’s supposed to be isolated from outside contex to make that point clearer.

Isolating it from context doesn't make the point clearer though, it removes the point entirely. Those sentences mean absolutely nothing if you strip all context from them.

If you did want to make them contradictory, you could put them in the context of math with some English-like properties, where "pray" is a constant and "may" requests a boolean answer, in which case that claim would be true. But we are talking about "spoken" English language, not mathematics, so this application isn't relevant.

Prayer is prayer in this context. No other meaning. There are no types of prayer in this particular sect, focus is irrelevant. Is it against God’s will to smoke while you pray? Can you answer that question, yes or no, based off the priest’s answers?

There still has to be a clear context to assign meaning to "prayer" and the complexities of English grammar (both of which are subjective). Otherwise it just becomes like the trolley problem.

The fact that the priest, parishioner, and the typical intended audience for this particular hypothetical don’t do the kind of analysis you’ve worked up here is really a large part of what this particular thought experiment is trying to illuminate, don’t you think?

Actually they do do this kind of analysis but they don't realize it. When they read the sentence, every bit of meaning they interpret from it is built off of decades of associating words, syntax, and verbal cues with meanings, all of which come from their own experiences dependent on their environment. Which means that different words and phrases have different meanings for different people, and while there are "standards" that most people speaking that language accept, even then there are still often significant differences among people following those standards and there is no objective meaning. Stripping that context would be similar to stopping those experiences away, or in other words asking the question to a baby.