February 15
All businesses. Give annual information statements (Forms 1099) to recipients of certain payments you made during 2018. Payments that are covered include (1) amounts paid in real estate transactions;(2) amounts paid in broker and barter exchange transactions; and (3) substitute payments and gross proceeds paid to attorneys.
Employers. For Social Security, Medicare, withheld income tax, and nonpayroll withholding, deposit the tax for payments in January if the monthly rule applies.
Individuals. If you claimed exemption from income tax withholding last year on the Form W-4 you gave your employer, you must file a new Form W-4 to continue your exemption for another year.
February 16
Employers. Begin withholding income tax from the pay of any employee who claimed exemption from withholding in 2018 but did not give you a new Form W-4 to continue the exemption for 2019.
February 28
All businesses. File paper versions of most annual information statements (Forms 1098, 1099, and others) for certain payments you made during 2018 (due date is April 1 if you are filing electronically).
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