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 ...