I just rolled over a 401K from a previous employer. The cost basis of the holdings was greater than the sales price. How and when do I handle the loss? You already have. Since your 401(k) contributions were deducted from your taxable income, you've never paid tax on them. You'll never have to pay tax at all on the amounts you lost, since you're only taxed when you withdraw from the 401(k).IOW, you don't get any deduction for losses in a 401(k).Phil MartiVITA Volunteer
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