1. A method of providing help information for a tax software application having a plurality of user interface screens, the method comprising: determining, by a hardware processor and during a current session of the tax software application, an application context of the tax software application displayed to a user, wherein the application context comprises a user interface screen of the plurality of user interface screens; retrieving, by the hardware processor and during the current session, a plurality of database entries corresponding to the application context and identifying a plurality of help files accessed by the user during a previous session of the tax software application; assigning, by the hardware processor and during the current session, a plurality of priority values to the plurality of help files, wherein assigning the plurality of priority values comprises: accessing a user profile in the tax software application for the user, identifying an itemized income tax deduction of the user from the user profile, identifying a first help file of the plurality of help files corresponding to the itemized tax deduction of the user, and assigning a first priority value to the first help file and a second priority value to a second help file of the plurality of help files, wherein the first priority value exceeds the second priority value in response to the first help file corresponding to the itemized income tax deduction of the user; and presenting, by the hardware processor and during the current session, the plurality of help files to the user according to the plurality of priority values.