Furthermore, Microsoft markets its Open License program to small companies, which often don't have dedicated staff on hand to examine licensing contracts, DeGroot said.
While it's true signing up for the Open License program might be easy for them, customers get only 20 percent discounts on products versus 40 percent, which is what some other programs offer, he said. But neither Microsoft nor a reseller would want to explain to a small customer that isn't spending a lot of money on software how they can save more with a different license.
"The customer is not getting the best deal," DeGroot said. "The complexity of the thing makes both Microsoft and the reseller disinclined to explain to the customer how they can save more money."
DeGroot said he doesn't believe Microsoft is willfully trying to mislead customers with its licensing, but since the company itself has never been in the position to have to license its own products, the people in charge don't really understand what customers are going through.
Unfortunately, the situation is likely only to get worse as Microsoft begins combining subscriptions to hosted services with its traditional per-CPU licensing models, he added. "My very distinct impression is that licensing is getting more complicated," DeGroot said.
And despite Microsoft's rosy view of things, he said that some enterprise customers have chosen not to renew their contracts this year because "the customer doesn't understand the value of what they bought or how they bought it," DeGroot said.
"If you're in a company and you don't understand why you're paying someone money, you're inclined to stop paying," he said. However, until a critical mass of customers comes to the same conclusion, Microsoft will not be motivated to change its course, DeGroot added.
In an e-mailed statement through Microsoft's public relations firm Wednesday, Stacie Sloane, a director of licensing at the company, said Microsoft has made "significant strides over the past few years in balancing customer choice with flexibility" to simplify its licensing agreements and reduce the number of programs from 74 to nine.
She said the company also has provided new tools to help customers navigate the complexity of its licensing, including Online PUR, a way to search on the Web to find out about software use rights in Microsoft's licensing programs.
"We continue to look for ways to make the purchasing experience simpler for customers, including our current multi-year investment to ultimately shift the customer experience to one purchasing platform and a single agreement for any type of offer," Sloane said.