With Reuters’ story last week that Blackboard is putting itself up for sale through an auction, one question to ask is ‘why now?’. As Michael has pointed out, Blackboard is in the midst of a significant, but incomplete and late, re-architecture of its product line.

Bottom line: If you think that Ultra is all about playing catch-up with Instructure on usability, then the company’s late delivery, functionality gaps, and weird restrictions on where the product can and cannot be run look pretty terrible. But that’s probably not the right way to think about Ultra. The best analogy I can come up with is Apple’s Mac OS X. In both cases, we have a company that is trying to bring a large installed base of customers onto a substantially new architecture and new user experience without sending them running for the hills (or the competitors). This is a really hard challenge.

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