By 'check for the originalEstimate.sum()' do you mean when an issue is created or updated? Or something else?
I think that setting up a listener, a fast-track transition, or a post function would be your best bet, depending on what you want to do exactly. You should read the doucmentation on those features and see if any of them fit your needs. If you need help writing any code, let me know.
Hopefully this helps!
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