Apple Inc.’s (APPL) success in tossing out a $625.6 million award won by VirnetX Holding Corp. (VHC), security technology licensing company, the same week the computer giant reached a licensing deal with The Kudelski Group, a much smaller cyber security company, suggests patent owners might fare better if they dramatically lowered their expectations.

Cupertino, California-based Apple has been fighting with Zephyr Cove, Nevada based VirnetX since 2010 and has now twice tossed out large awards won by VirnetX including the $368 million awarded in the first trial. Apple also succeeded in throwing out a $533 million award Smartflash Inc. won in February. Apple also is of course still fighting a $234 million award to the Wisconsin Alumni Research Foundation (WARF).

Officials from Apple and VirnetX didn’t return several emails seeking comment for this article.

“The overturning of a large damages award seems to be common place these days,” said Chandran Iyer, a partner in the Washington, D.C. office of Sughrue Mion PLLC. It’s not an Apple specific thing. The strategy for companies these days is that if the patent owner’s case is meritorious and the money sought by the plaintiff is reasonable (i.e., a very few million dollars), the patent owner will pay. Any damages award that is over 8-10 million dollars, the defendant has nothing to lose by appealing. It feels like a near certainty that the Federal Circuit will revise the award amount down in some ways. Also, the days where an NPE is going to be able to get a large damages award affirmed by the Federal Circuit seems to be gone.”

To be sure, Apple has shown a willingness to settle when the demands are relatively reasonable, hence the $24.5 million it agreed to pay Marathon Patent Group Inc. (MARA) and its partner Rensselaer Polytechnic Institute and the $25 million it agreed to pay to Network-1 Technologies Inc. (NTIP).Even so, Los Angeles-based Marathon noted that RPI was unhappy with the $24.5 million settlement and held up the final approval. The deal with Kudelski

Group is likely to be in the range of these two deals.

Lee Cheng, the general counsel of Newegg LLC, the online computer retailer known for fighting so-called patent trolls to the mat, predicted in March that Apple would never pay a dime to Smartflash and even offered to bet $1,000. He said on Tuesday, in an email commenting on Apple’s victory against VirnetX, “No one took me up on my bet. Wah. Comment: I quote Nelson Muntz: ‘Ha. Ha.’”

Nelson Muntz refers to the fictional school bully in the animated TV series The Simpsons.

But even some patent licensing company executives believe some companies have gone too far in their demands.

“I always thought $625.6 million was a really big number” to pay to VirnetX, a security technology company, said a former patent licensing company executive, who requested anonymity. “I’d be surprised if WARF was overturned. WARF is a research institute. You’re effectively getting a license for all they do. I don’t think they’ll end up paying $234 million. They’ll pay a fraction of that maybe a quarter to a half.”

A quarter to a half of $234 million is $58.5 million to $117 million and still quite sizable.

“It all comes down to settlement expectations,” said Mark Gober, a senior director at 3LP Advisors in Silicon Valley. “VirnetX’s stock would tank if it settled for $25 million. Look what happened to Vringo’s stock when it settled with ZTE for under $25 million after years of battling and lofty investor hopes.”

The former Vringo now known as Form Holdings (FH) saw its stock drop more than 10% the day it announced a $21.5 million settlement with ZTE Corp.

“No one’s going to pay hundreds of millions of dollars for technology they’re already using unless they are absolutely forced to,” Gober said. “Why not fight it out for years if you’re Apple and have the funds to do so? The litigation costs are small on a relative basis.”

In the meantime, this creates an existential problem for patent monetization companies who are facing recalcitrant defendants and impatient investors.

“The real investor problem is that you don’t know when you have the potential for a deal,” said a patent market observer who spoke on condition of anonymity. “When you talk with large companies their strategies aren’t logical or I should say they’re logical for a large company with unlimited resources.” He said it’s impossible to have a rational discussion with someone sitting on that much cash.

“It doesn’t matter whether you win an award or if you survive an appeal because eventually it will be overturned. If big technology companies can overturn every award, how do you judge a deal? VirnetX is only the latest example.”

Big companies like Apple used to worry about huge damages awards and injunctions, but not since the U.S. Supreme Court became concerned that patent law had diverged from traditional jurisprudence and that non-practicing entities had somehow subverted that divergence for their own interests.

First in eBay v. Mercantile Exchange, the high court made it all but impossible to win injunctions. Second, the high court in Mayo and Alice established new limits on what it considered patentable subject matter, effectively making it much harder to win enforcement actions involving patents that are based on abstract ideas such as software and medical concepts or discoveries. Third, as Sughrue Mion’s Iyer noted the Court of Appeals for the Federal Circuit has showed an increasing skepticism of large damages awards based on inexact calculations of the value of the patents infringed.

Complicating matters further is the America Invents Act of 2012, which created the Patent Trial and Appeal Board to oversee inter partes review (IPR) and covered business method (CBM) review challenges of patents. The PTAB has invalidated some 80% of patents challenged in IPRs and CBMs, though the percentage has shown signs of falling as the number of lower quality patents dwindles.

“The legal system in the U.S. allows someone to procrastinate paying for a license without downside,” said the former patent licensing company executive. While he said he expects the pendulum to swing back toward patent owner rights in the long term, he sees few signs of that currently.

The high court’s recent rulings on willful infringement and enhanced damages Halo and Pulse may be a hopeful sign, though it is much too early to say how far reaching the rulings will be.

“The U.S. is a couple hundred years ahead of the rest of the world in our technological capabilities. But when you allow others to copy your technology without consequences you’re discounting what the U.S. is known for. The long term consequences of that will be catastrophic.”

In the meantime, Apple, as the biggest public company in the world, appears to be unconcerned about how the erosion of patent rights could hurt U.S. competitiveness.

The computer giant is fighting an enforcement action over a patent covering smartphone design filed by Shenzhen Baili Marketing Services Co. in China. A Beijing IP court handed the struggling Chinese startup an injunction against the American giant’s sales of iPhone 6 and iPhone 6 Plus in China.

Even so, Apple has spent heavily in China to gain a foothold in the world’s biggest consumer market. The company even used a small chunk of its $40 billion in cash or $1 billion to acquire a stake in Didi Chuxing, the Uber of China. The investment drove Uber to sell its Chinese unit to Didi.