Michael Cherry said the move would counteract Microsoft's failure to deliver on the promise of 'Windows Vista Ultimate Extras'.
"I'd like to see a free upgrade [to Windows 7] for Vista Ultimate users. It would buy them a lot of good will, and I don't think it would cost them much."
Ultimate Extras was one of the features Microsoft cited in the months leading up to the early-2007 release of Windows Vista Ultimate to distinguish it from lower-priced versions.
According to Microsoft's marketing, Extras was to regularly provide "cutting-edge programs, innovative services and unique publications" only to Ultimate users.
But users quickly took Microsoft to task for too few add-ons and a too-slow release pace. Five months after Vista's launch, critics began complaining and Microsoft said that it would do better.
Two months later, users again blasted Microsoft as the company's self-imposed deadline for delivering more add-ons came and went without any new downloads. The last time Microsoft delivered Extras was in September 2008, when it released a puzzle game, some sound effects and three screensavers.
In February, Microsoft announced that it would drop the concept from Windows 7's Ultimate edition.
"Our new approach to planning and building Windows doesn't have the capacity to continue to deliver features outside the regular release cycle," a company spokeswoman said.
Microsoft has not yet disclosed the pricing for Windows 7's editions, although the company will reportedly offer free or discounted upgrades to users who buy Vista PCs after July 1. According to those reports, people who buy Vista Ultimate after that date will be upgraded to Windows 7 Ultimate.
"Pricing is always the last thing for them to decide," Cherry said.