When should an individual file for unemployment benefits? July 21, 2021 22:10 Updated Once the individual is separated from work, they should immediately file a claim for unemployment benefits. Related articles How can I find out if I am eligible for unemployment benefits? How is eligibility determined? General Information It says I have a pending issue online. What does that mean? What is the best method to reset my userid for the UInteract system so I can file a claim?