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At what point does it "make sense" to continue developing and supporting APIs for a product? Arguably, Skype has a huge user base and thus huge "custom application potential energy". But here we see them shaking off any ties, without mention of possible future offerings.

So, what metrics should they be aiming for to prove viability?

They're probably just looking to make it as profitable as possible as quick as possible. They probably aren't looking long-term.

There also exists the possibility that this is a way to try and drive up share prices by looking like they are doing something.

"We're dropping off unprofitable parts of the business! Look at us! We're doing something. Skype's outlook is improving!"

"Skype's outlook is improving!"

by dropping Outlook integration

Queue rimshot...
Wow, I didn't even know about Skype Extras until today! I could have been using Skype Extras to record calls, send faxes, and do all kinds of other great stuff with Skype.

I think Skype (and, by extension, eBay) really dropped the ball on this one.

You never used it (along with basically EVERYBODY ELSE) and you think they dropped the ball? :-)
Yes: if none of their users knew about it, that's a marketing failure.
That stinks. I rely on Skype + plugins for my remote interviews.

Everyone else from cell phone makers to TVs to Twitter sees value in being a platform. I don't understand why Skype can't make it work.

Maybe it goes back to what Eric Ries told me about his experience with IMVU. He said his product didn't take off until the co stopped making it an IM plugin because most people don't understand what an IM plugin is.

I use the Skype plugin for Pidgin. If new Skype won't make it work, I won't upgrade ever.
It is really sad to see Skype, which is incredibly popular, still doesn't know how to leverage its platform. I hope they learn that to build and leverage a product successfully, you absolutely need to help developers make money off your product. If developers don't feel invited, neither will end users in the long run (well, they will have the user base until the next Skype killer comes along).