Meaning
Troublesome, difficult, or vexing — used of a person, a child, or a situation that brings hardship and will not behave. A 'cross' pickney is a difficult, fractious child, and a 'cross' matter is one full of trouble. As a noun, a 'cross' is a burden or affliction one has to bear, as in carrying one's cross, and 'crasses' (troubles) grows from the same idea. So the word gathers up the whole sense of something heavy, awkward, and hard to manage that weighs a person down.
Examples
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Dat pickney cross, eeh.
That child is difficult, you know.
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Mi deh inna cross wid dis car.
I'm having no end of trouble with this car.
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It cross fi get a work dese days.
It's hard to find work these days.
Origin
From English 'cross' — a burden to bear, and being 'cross' (ill-tempered) — narrowed in Jamaican to mean troublesome or difficult.
How it’s used
Closely tied to 'crasses' (troubles). Describes something that gives constant trouble, whether a person or a situation.