Longhorn has already survived several major delays, intense scrutiny from the industry and a radical redesign of its features.
But the toughest test for Microsoft's next release of Windows is still to come: Will anyone buy it?
Even though its been five years since Windows XP's debut, Microsoft could still face a tough sell when it releases Longhorn next year. With past updates, users had clamored for more stability and security, but analysts say people are pretty happy with Windows XP.
"Microsoft for the very first time is going to be faced with the challenge of being the player whose (operating system) is 'good enough'" as is, said Jupiter Research analyst Michael Gartenberg.
The challenge is one Microsoft has tackled for years with its Office software, but it's a relatively new problem for the Windows side of the house.
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