Microsoft grossly overestimated the loyalty of those it thought were its most steadfast customers when it asked for their help in getting friends and family members to dump Windows XP, a corporate communications expert said Friday.

"There's nothing wrong with asking your customers for help," said Gene Grabowski, an executive vice president at Levick, a Washington, D.C. firm that specializes in crisis public relations and corporate reputation messaging. "But you have to establish loyalty before you ask them, and even then you have to structure [the request] so there is a distinct advantage to the customer."

Microsoft neither had the customer loyalty it had assumed it had, nor a plan that made the effort attractive to those it asked for assistance. "Essentially, Microsoft was asking its customers to help it sell more product," said Grabowski.

Grabowski was referring to the appeal Microsoft made Feb. 7, when it implored its technically astute customers to help others who are still running Windows XP get rid of the soon-to-be-retired operating system.

Those same savvy users ridiculed the idea, saying that Microsoft's pitch -- which relied on upgrading Windows XP to Windows 8.1 or purchasing a new computer -- was unacceptable because they refused to recommend Windows 8.1. They also criticized Microsoft for not offering a discount on an upgrade, for not suggesting the older but more familiar Windows 7 as an alternative to Windows 8.1, and for not providing an upgrade path from XP to 8.1 that retained settings, files or applications.

"The problem here is that Microsoft is behaving more like the 'Sopranos' than a technology company," Grabowski said. "They're shaking down their customers."

Grabowski was scathing in his evaluation of Microsoft's long-planned, long-stated decision to stop providing security updates for Windows XP after April 8. That deadline -- Microsoft will officially retire the OS from support, although it will still run long after April 8 -- has prompted the company to urge customers to either upgrade Windows or buy new hardware.

Once Microsoft stops patching vulnerabilities in XP, users will be in the crosshairs of cyber criminals, Microsoft and security professionals have said.

"Microsoft's warning its customers that if you don't upgrade, which you have to put sweat equity into -- not only do you have to pay, but you have to put in the time -- you're probably going to be hacked," Grabowski said. "They're asking customers to buy an upgrade or suffer the consequences. That's a shakedown to a lot of customers."

While some, including industry analysts, have argued that Microsoft is obligated to secure its customers no matter how old the OS, a larger number have made the point that Microsoft has supported XP far longer than usual, for nearly 13 years rather than the usual 10, and because it's barraged customers with warnings for years, isn't honor bound to continue supporting the aged operating system forever.

To some extent, the argument is moot either way, because many customers have the perception that they're being exploited, said Grabowski. And customers who feel that way are very unlikely to help Microsoft without a quid pro quo.

"It's starting to irk a lot of businesses, let alone home users, that Microsoft's asking them to dig into their pockets and learn a new OS," said Grabowski. "That frustrates those customers. Rather than get closer to its customers, Microsoft is alienating them."

Those miscalculations revealed that Microsoft had neither a clear idea of its customers' perspective nor a realistic strategy to reduce Windows XP's global footprint, Grabowski maintained.

According to statistics released Saturday by analytics company Net Applications, 29.5% of the world's personal computers ran XP in February.