May 18, 2015

Why have so many businesses postponed migration with Windows Server 2003 approaching end of life?

I understand in theory why a lot of small businesses would have resisted moving away from Windows XP, if for no other reason than the “if it’s not broken, don’t fix it” attitude. There is a lady at my wife's office who has XP on her laptop, for example, and she refuses to even update to the service packs out of fear that "it will mess something up." Presumably Windows Server are a somewhat more sophisticated user group, so why have they put off the migration from Windows Server 2003 to this point? It doesn’t make a lot of sense to me, but I assume it makes sense to someone.
Andy has a great answer. I'd add that sometimes companies are just like people: they procrastinate forever until they are absolutely forced to make changes.
Surveys of people not making the move have found a few reasons:

1) They just plain didn't know. Bit9 did a survey where it found 57% of respondents didn't know it was coming in July.

2) Many who heard didn't believe it. Server 2003's EOL had been pushed back once and like with XP, a lot of folks said "eh, they won't do it."

3) No money. Some companies had their IT budgets already set for the year and if they learned late about the EOL they couldn't do anything about it because their budget for 2015 was already allocated.

4) App dependencies. Maybe they had an app that was really tied to Server 2003 services and was not easily ported. Maybe they had 16-bit apps, which won't run on Server 2008/2012. Both of these scenarios will handcuff you to Server 2003.

5) Assessment. Many firms aren't just replacing their old Server 2003 boxes, they are taking the time to do a complete assessment of their IT infrastructure and deciding what else to replace/update. That's taking time because a lot of firms are finding stuff and having an "oh, we have that?" moments. So it's taking longer to go through everything than planned/expected.

By the way, that office worker who refuses the service packs? Who's in charge there anyway? IT should put it foot down and make her update to SP3.
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