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While capital losses are problematic because they are only deductible against capital gains and then up to $3K of ordinary income per year, Section 1244 of the tax code converts some capital losses into ordinary losses. In order to take advantage of Section 1244, your stock must be Section 1244 stock, which is generally stock that represents the first $1M invested in a company. But Section 1244 is limited, to $50K for individual taxpayers and $100K for married couples filing jointly.