I have a custom field of type Multiple Issue Picker which I had set required in the field configuration which is associated with a field configuration scheme which is associated with the Project itself and the correct issue.
For some reason it functions correctly requiring the user to select an issue during the create screen, but during edit/view screen even though it is required and has the red asterisk next to it people can delete the issue selected.
Interestingly enough when I try editing the issue again, the custom field starts yelling at me about how its required.
I will note I use a behavior such that the Issue picker only appears and becomes required when another custom field of single select list has specific values selected in that list. This shouldn't impact things though as the value chosen is one that makes the multi issue picker required and appear, and it isn't being edited after creating the issue.
During some testing it seems that after deleting the issue picker fields contents and submitting said changes, and editing the issue again, although it says I must enter an issue in as it is required (as mentioned previously above) If I enter an issue in the issue picker and then delete it, the issue picker custom field doesn't care anymore that it is empty and will allow me to update even though it has the red asterisk next to it.
This is a very long question but if someone could please help It would be greatly appreciated. I can't begin to understand why this single custom field is behaving so weirdly