Not sure if this is a comment or an answer. But as per you now being a contractor, all your tools are now tax deductible expenses. And you can get cheap licenses from eBay. But being a contractor also opens a can of worms as you have a completely different set of responsibilities. See Changing from (Retired) PT W-2 to 1099 for example, and Freelancing Stack exchange

You know that the people who work to create and produce the software you're pirating want to earn a living too, right? Just like you, right? You want to be payed for your work, right? Well they want to be paid for their work too. When you pirate software you're stealing from the men and women who work to create and produce that software. They have rent, mortgages, utility bills, grocery bills, etc., etc. just like you. So stop stealing their work. There's nothing that can excuse or justify doing that.

@joeqwerty I needed it for school and couldn't afford $400 for Windows + Office (in fact it's hard for me to still afford it). It's even harder to justify considering free alternatives that work just as well but because someone insists on using a proprietary format it must be used. I wasn't aware of cheaper alternatives and am skeptical if buying from someone off ebay is much different.

Whats the difference between buying off amazon or ebay or anywhere else and walking in to a shop and buying except convenience and sometimes price? Some of these have sold thousands of units and have top ratings ebay.com/b/Microsoft-Office-and-Business-Software/3768/…

@Kilisi just because Ebay sells it and it works doesnt mean you get a valid license - keygen sellers have been around since Ebay was brand new. Typically, all you bought was convenience - you dont have to go find the keygen yourself, someones already done it for you and sold you a generated key. If you get audited, “I have a license key” holds no weight when you cant actually provide the license, which is a separate thing.

@Moo there are legit keygens for MS products that validate and stay validated? I didn't know that.... I'm a bit worried about how you know it. But you can also buy the whole product on ebay and get the physical cd at a fraction of the cost. In the original unopened packaging if you want. It's just what people have for sale. I've bought 12K UPS for 2k because a business went broke and it was being sold asap.

Saying that you needed it for school and couldn't afford it neither justifies it nor excuses it. If I steal your wallet because I need the money, does that excuse or justify my actions? Pirating software is illegal. Stop doing it.

@Kilisi Physical packaging doesnt matter either - Ive seen some rather excellent counterfeit examples come out of China where you couldnt tell the difference. Pretty much all the cheap stuff you see on Ebay where MS licenses are concerned is illegitimate and dont give you a valid legal license - there are a few outlets selling liquidated stock, sure, but they dont sell thousands on an ongoing basis, they sell tens or hundreds every now and then. How do I know? I worked with the Metropolitan Police around this area for a few years. The saying “if its too good to be true” definitely applies.

@Moo the metro cops are investigating ebay? Sounds unlikely but feel free to downvote my answer. I buy hardware, software, clothes, jewelry and pretty much everything else on ebay as I can't get stuff locally. Ebay seems a legitimate business to me. In any case I'm not about to investigate everything I buy.

@Kilisi feel free to keep justifying it to yourself, its obvious you arent listening.

@Kilisi civilian contractor working for the largest police force in the UK (no one calls them “metro cops” so I dont think you know what you are talking about in their case - its the Metropolitan Police, or The Met) is far from “fantasising Im a cop”. But nice troll.

@Moo whatever floats your boat, have a great day

@joeqwerty if you really think stealing someone's wallet is the same as not having a license to software you use, you should probably talk to a councilor (or a lawyer)

@JoeStrazzere the question is how do I get the company to pay for a license for me. Or is this unreasonable?

Theft is theft in whatever form it takes. Software piracy is theft.

@joeqwerty my point is stealing someone's wallet is a lot different than using unlicensed software. I seriously hope you can understand that.

@wipeoututopia - It's your professional reputation, but I guess you can ask the company to find out if they would pay for it. As I indicated, if I wanted to be a contractor, I'd make sure I had a legal copy of Windows installed first. Without that, it's kind of a bad "look" for a contractor.

I understand that you have no malicious intent, but the fact is that software piracy is a crime. You can try to justify, excuse, or differentiate it any way you like but the fact of the matter is that you're breaking the law and you're stealing from the people who create and produce the software you're pirating. Stop doing it.