There are too many hypotheticals in this question for anyone on this forum to provide an accurate response.
The only person who can answer this is the individual that prepares the company tax return. It is that person who needs to get comfortable with the facts since they are signing the tax return.
Not sufficient understanding of the facts in a forum setting such as this.
Based on the limited facts, I think the IRS would challenge this deduction, unless of course the company included this cost in your wages.
*A reminder that posts in a forum such as this do not constitute tax advice.
Also keep in mind the date of replies, as tax law changes.
