Hi Richard. Thanks for the report. Python's working as designed (and as documented and tested) here. IOW, the behaviour is deliberate - this isn't a bug.

Any change in behaviour would have to target 3.10 at the earliest (and it's already quite late in the release process for 3.10). A couple of questions: (1) what would you want the comparisons `datetime_in_sgt <= datetime_in_utc` and `datetime_in_utc <= datetime_in_sgt` to give? (2) How would you propose to change the behaviour without breaking existing code that makes use of the current behaviour?

> This is confusing and non-intuitive.

That's a rather subjective judgement. I'd personally find the behaviour you suggest non-intuitive (and I find the behaviour of Java's order comparisons on ZonedDateTime to be highly non-intuitive). We'd need something a bit more objective and/or widely supported to justify a behaviour change.