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Carry-forward of individual losses, with late-filed past taxes [US]
Is Jim right to be worries? Yes, since the statute of limitations for refunds for 2012 is close and he might lose any tax refunds he might be entitled to for that year. Also, the pattern itself may raise some flags of suspicion and trigger audits, both because of such a variance in income and because of the medical expenses (which are generally considered a red flag). So he might get audited. However, if all the income and expenses are properly documented, audit itself should not be a problem.