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Income Tax
9 Months Ended
Oct. 31, 2019
Income Tax Disclosure [Abstract]  
Income Tax Income Tax

 Autodesk had income tax expense of $29.7 million, relative to pre-tax income of $96.4 million for the three months ended October 31, 2019, and income tax expense of $35.2 million, relative to pre-tax income of $11.5 million for the three months ended October 31, 2018. Autodesk had income tax expense of $88.8 million, relative to pre-tax income of $171.5 million for the nine months ended October 31, 2019, and income tax expense of $69.8 million, relative to pre-tax loss of $75.7 million for the nine months ended October 31, 2018. Income tax expense for the three months ended October 31, 2019 decreased and nine months ended October 31, 2019 increased primarily due foreign earnings and withholding taxes.

Autodesk regularly assesses the need for a valuation allowance against its deferred tax assets. In making that assessment, Autodesk considers both positive and negative evidence related to the likelihood of realization of the deferred tax assets to determine, based on the weight of available evidence, whether it is more likely than not that some or all of the deferred tax assets will not be realized. In evaluating the need for a valuation allowance, Autodesk considered cumulative losses as a significant source of negative evidence and maintained a valuation allowance against our deferred tax attributes in the U.S. and certain foreign jurisdictions as of October 31, 2019.

As of October 31, 2019, the Company had $215.8 million of gross unrecognized tax benefits, of which $198.4 million would reduce our valuation allowance, if recognized. The remaining $17.4 million would impact the effective tax rate, if recognized. It is possible that the amount of unrecognized tax benefits will change in the next twelve months; however, an estimate of the range of the possible change cannot be made at this time.