"He left it with Teamsters". I assume that is he got a 1099-R, then he received the money and did something with it (buy you dinner, take the grandkids out to a ball game, whatever). The 1099-R is sent to you to show how much the plan administrator sent him over the year (once a month, once a year, whichever).
If you literally meant that he left it with the Teamsters, then not only do I not understand what this means, but they would not have sent him the 1099-R.
When you withhold federal income tax on a distribution, this withholding is only an estimate of how much tax you would owe. The plan administrator has no idea how much tax you are going to owe, because it depends on other income items, other deductions, and other items that are known to you but not to the administrator. That is, the withholding on the 1099-R is not the tax due on the income from the 1099-R. Instead, all your income items are added together and applied to your return, and all the withholdings are added together and used to pay the tax due.
Normally, the plan administrator asks you how much you want to withhold. If you don't have an answer, then the plan administrator might choose some set percentage as a default. In this case, the withholding is right at 15% of the income, so I would think that the plan administrator defaulted to that.
I don't understand the second set of questions? Are you saying that TurboTax asked you these questions? And where did the $553.61 come from? Was it on the 1099-R?
Normally, you report the amount of the distribution as taxable income, the withholding is withheld by the administrator and sent to the IRS, and the difference is sent to you. Is that not what happened to you?
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