<prompt> Human: So, for obvious reasons microsoft office specifically, Word is useful to create and constantly manipulate my resume then enter into PDF or word format for my job search. For more obvious reasons, Microsoft would like to charge me for the use of their product. Can I itemize and deduct this purchase under publication 529? found here on page 5: Edit: about half of you passed and half of you didnt. I can itemize.  <response>: Yes, if you itemize, and if your unreimbursed employee expenses are greater than 2 of your AGI, you could deduct the amount over 2. So in reality, no. 