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What forms are sent with regards to the following so I know where everything would be reported?

401K & IRA withdrawals
Monthly pension payouts
social security

As far as I know (and I'm going to check with the one company) he never contributed to any of his pension plans.

Form 1099R is used to report pensions and 401K or IRA withdrawals. Form SSA-1099 reports Social Security payments (including deductions for Medicare B). You should receive the forms about mid-January.

On the 1099Rs, block 1 reports the gross distribution. If the taxpayer hasn't made any after tax contributions then block 2a (taxable) should be the same as block 1, or be left blank or $0. Typically, a distribution from an IRA will check box 2a, Taxable Amount Not Determined (because the payer doesn't know whether you made any after tax contribution). Block 7 will contain a code (explanations on the back of the 1099) indicating the type of payment. If payment is made from a Roth IRA than the box in block 7 is checked.

Note that you can ask the payer to withhold federal and state tax. This can save you from having to make quarterly payments. Be sure to have enough withheld to equal the total tax paid in the previous year. This is "safe harbor" and protects you from having to pay a penalty if not enough tax is withheld or estimated tax paid during the year.

Hope this helps.

Karl (Tax-Aide volunteer)
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