In a computer-implemented method for managing tax withholding liabilities, a notification of a non-standard compensation transaction is received. The non-standard compensation transaction is initiated during a time period covered by the notification. A resulting tax withholding liability is automatically calculated. A directive is automatically generated for directing a calculated tax withholding payment to be made and applied against the calculated tax withholding liability. The calculated payment is to be made to a tax authority on or before a calculated due date of the tax withholding liability.
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