I have a life insurance policy for a non-smokers rate, and I like a good cigar every once in a while (I'm not a frequent everyday smoker). Should I be worried about having them come in and randomly test me for tobacco use?

No, there's nothing random about it. They test 100% of the time when you apply for life insurance.

However, Life insurance companies do not do "random" testing on policyholders. If you are approved for the non-smoker rate for life insurance, and then you start smoking after you have purchased your life insurance, your rate remains the same.

However, I believe if you lied about your smoking when you purchased your life insurance, and you die as a result of smoking, the insurance company has a 2 year period of contestability from the time the life insurance policy started providing coverage, to deny any claim based on misrepresentation of material facts on the application.

But, life insurance companies do not randomly test you for tobacco use after the life insurance coverage is "In Force" and you have been approved for your policy.