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My boss proposed I should pirate Photoshop, as documented here. I would not do that.

However, a coworker proposed that I could just use virtual machines to re-use the trial version of that software over and over. I feel that this is probably just as illegal as using a pirated copy from a legal point of view.

Do you know more about this?

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Read the EULA . –  reinierpost Oct 12 '10 at 8:10
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Ask your boss a written order. Or suggest to use Gimp instead of Photoshop –  mouviciel Oct 12 '10 at 9:23
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Not exactly an answer, but: what exactly do you need Photoshop for? If you have to quickly edit something beside your usual work, but aren't a professional artist, cheaper or free alternatives like The GIMP probably offer more functionality than you know how to use, I guess The GIMP is about as powerfull as a Photoshop CS3. If your job requires you to professionally edit images on a regular basis, and you absoulutely need a tool more complicated than GIMP, but your boss refuses to buy a photoshop licence, you are working for the wrong company. –  rumtscho Oct 12 '10 at 9:29
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@mouviciel is right, The GIMP rocks. Rather donate the cash to GIMP dev :) –  invert Oct 12 '10 at 9:36
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I'm tired of reading "Photoshop = GIMP". Here are the first things that comes to my mind (and if I think a bit more I could list hundreds more): (1) GIMP doesn't handle CMYK at all which cuts it 100% appart from professionnal printing. Professional printing = CMYK. (2) Photoshop has different font antialasing types, which makes it possible to do small and nice buttons. It's not possible at all with GIMP (= one antialias). (3) Scripting: Photoshop has a JavaScript step by step integrated machine. And so on. Thus you can't do 1/100 th the good job you can with Photoshop. –  Olivier Pons Oct 12 '10 at 10:31
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up vote 21 down vote accepted

It's not ethical and it's not legal to circumvent licensing methods. Trial software is meant to allow you to experience the software before you buy it, not to give you free software. I sometimes understand (though never condone) such behavior when done by a poor, private person. But if it's done by a company or for commercial reasons (i.e. you're making profit from someone else's work without paying) it's down right criminal.

And to finish my argument: I suppose you work in a software company. How would you answer if I ask you whether it's OK for me to install your software on a new VM every month to avoid paying for YOUR software?

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Please tell your boss that last sentence, @Paperflyer! And let us know his response. –  invert Oct 12 '10 at 9:36
    
I did. He agrees. But there is a Chinese TehBigBoss, and he does not agree. He is the problem. –  bastibe Oct 12 '10 at 13:08
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Definitely not ethical. The obvious intent of a demo/trial is that it be available for an evaluation period, then disabled or crippled until it is purchased.
Note that a trial version's EULA might prohibit it from being used for commercial purposes anyway.

As @reinierpost commented, you can't know if it's legal without reading the EULA - they may mention reinstallation explicitly.
Even if it does look like there's a loophole because virtualization or reinstallation aren't explicitly mentioned, it may just be that the EULA's legal language hasn't caught up with the technological landscape yet. In that case, if it goes to court, it'll be up to someone else to decide if it's legal or not - and unintentional loopholes are not likely to stand up to serious scrutiny.

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Often trail-versions are explicitly for non-commercial use, just for trying it out, if it does fit your needs. If that is the case using it in everyday company work is illegal anyway, even on first install / usage. (Again, this may differ from app to app; see EULA.)

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It surely is circumvention, but whether it is strictly legal or not, I don't know. It sounds less bad than blatant piracy.

(l) "Trial Version" means a version of the Software, so identified, to be used only to review, demonstrate and evaluate the Software for a limited time period.

Source: http://www.adobe.com/products/eula/server/

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