>The whole 64-bit Adobe CS for OS X debacle comes to mind, it took them about 5 years too long to transition from Carbon to Cocoa, even though it was clear from the very first OS X version that Carbon was going to be replaced and would never have a 64-bit version.
I think Adobe really believed they could strong-arm Apple on that. I think they were spoiled by Microsoft's dedication to backwards compatibility at all costs[1], and thought that surely it would hurt Apple more than Adobe to let PS languish. I think they were so sure of this, in fact, that they made few arrangements for the contingency that Apple might just call their bluff. So when that happened, they had an uphill battle to fight.
I think Adobe really believed they could strong-arm Apple on that. I think they were spoiled by Microsoft's dedication to backwards compatibility at all costs[1], and thought that surely it would hurt Apple more than Adobe to let PS languish. I think they were so sure of this, in fact, that they made few arrangements for the contingency that Apple might just call their bluff. So when that happened, they had an uphill battle to fight.
[1] This story comes to mind: http://ceklog.kindel.com/2012/04/18/dont-build-apis/