I have a problem with a validation rule not being triggered.
Object A trigger updates Object B Object B has a validation rule. Will the validation rule fire?
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Yes whenever there is an insert/update on any object from trigger the validation rule will fire You can read more on order of execution in the official documentation here
Whenever you create or update the record on object B, its validation rule will fire. It dosnt matter from where this creation or update is happening.
You can just think from object B's perspective, why it would let anyone create or update a record on it unless the data on that record is correct. If it happens then it is going to corrupt your database so, it dosnt matter from where the event is firing; it can be from data load , workbench, annonymous window or test class dosnt matter to it.
I hope I was able tk answer your question.