Insurance Frustration!

Uh, they keep tabs on your driving record all the time. They don't wait for you to file a claim before checking on your record.

No, insurance companies don't "regularly" check someone's driving record/history.

There may be a "periodic" check (something in the range of once every 2-3 years, but usually the only time they really check is when you add/change a policy. When it comes to auto insurance, the underwriting teams do not have the time to check millions on policies on a weekly, monthly, or even yearly basis.
 

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