But David Evans, a cryptography expert and professor of computer science at the University of Virginia, is skeptical about the usefulness of the Tresorit contest.
"Anytime you have software run by them, you are trusting them with all that data," Evans said. "It's a murky security proposition that they are offering you."
Evans said that many firms actually pay professional hackers to attempt to break into their systems and expose various weaknesses.
"If they really cared about doing a security assessment about their design they wouldn't be doing this kind of challenge," Evans said. "The problem is that hiring someone good is going to cost a lot more than $25,000 and won’t get them any publicity."
For his part, Tresorit's Nagy says the hacker challenge is a valuable exercise, no matter who takes part.
"We want to make sure our system is safe," he said, "but most of the time vulnerabilities exist in unlikely places."
Whether or not Tresorit's effort works, the value of such contests isn't lost on the NSA either. The spy agency joined Carnegie Mellon University in April to sponsor "Toaster Wars," challenging high school code geeks to play a online game of "capture the flag" by hacking a make-believe space-traveling robot.