I think the closest fit to dukkha in English is the word 'discontent'. The essential idea behind dukkha is a mismatch between what is and what ought to be. To use the classic examples, we think we should have been born into a better condition; we think we should always be healthy; we think we should always be young and vital; we think we should live forever.....
As i understand it Dukkha can be derived from the Sanskrit kha, one meaning of which is some sort of opening, ie 'the axle-hole of a wheel', and the antithetic prefix Duk. Meaning that if you were given a wheel to try for a fit and having tried putting it on your chariot axle you would see that the wheel's 'kha' is a bad fit. Someone would then ask you if ...
I'm not sure who wrote the short introduction at the top of the Dukkha page of AccessToInsight.org but it is a very appropriate comment to your question:
No single English word adequately captures the full depth, range, and
subtlety of the crucial Pali term dukkha. Over the years, many
translations of the word have been used ("stress,"
I hope you don't mind if I give you an answer through different angle(Islamic angle).
'Sukkha means good news and dukkha means warnings'
We have sent you ˹O Prophet˺ only as a deliverer of good news and a
warner to all of humanity, but most people do not know - Quran 34:28
In Islam, every messenger which was sent by God came with Sukkha and dukkha.
Additional site for sutta crossreferencing.