Retirement tax questions

"How do I enter the information for Box 5 of Form 1099-B? "

The literal answer is "you don't", at least if you're asking where is that Box 5 checkbox in the TurboTax "Stocks, Mutual Funds, Bonds, Other" interview.

The way you "signal" to TurboTax that there's a checkmark in Box 5 of the official 1099-B is you select the correct "sales category" from the drop down list of sales categories that's on TurboTax's 1099-B input form.

So you'd either select sales category B if the holding period of the security is short term (a year or less) and select sales category E if the holding period of the security is long term (over 1 year).

Tom Young

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