I am a software engineer and have seen the problem first hand.
Me> The software on this box is out of date and not supported
PHB> We must have the lastest and supported and ra ra ra
Me> We need three weeks of development time and a couple of days of sysadmin time
PHB> Oh don't do that sales wants X
PHB> OMFGBBQ the shit has hit the fan
Me> Yes that is because we are running out of date software. Now our customers are pissed
PHB> No time for that, just keep it running