In a couple of days we will be saying goodbye to 2014 and ringing in the New Year 2015. Simple math should show you that if you are still running Windows Server 2003, it is long since time to upgrade. However here’s more:
When I was a Microsoft MVP, and then when I was a Virtual Technical Evangelist with Microsoft Canada, you might remember my tweeting the countdown to #EndOfDaysXP. That we had some pushback from people who were not going to migrate, I think we were all thrilled by the positive response and the overwhelming success we had in getting people migrated onto either Windows 8, or at least Windows 7. We did this not only by tweeting, but also with blog articles, in-person events (including a number of national tours helping people understand a) the benefits of the modern operating system, and b) how to plan for and implement a deployment solution that would facilitate the transition. All of us who were on the team during those days – Pierre, Anthony, Damir, Ruth, and I – were thrilled by your response.
Shortly after I left Microsoft Canada, I started hearing from people that I should begin a countdown to #EndOfDaysW2K3. Of course, Windows Server 2003 was over a decade old, and while it would outlast Windows XP, support for that hugely popular platform would end on July 14th, 2015 (I have long wondered if it was a coincidence that it would end on Bastille Day). Depending on when you read this article it might be different, but as of right now the countdown is around 197 days. You can keep track yourself by checking out the website here.
It should be said that with Windows 7 there was an #EndOfDaysXP Countdown Gadget for the desktop, and when I migrated to Windows 8 I used a third party app that sat in my Start Menu. One friend suggested I create a PowerShell script, but that was not necessary. I don’t remember exactly which countdown timer I used, but it would work just as well for Windows Server 2003 – just enter the date you are counting down to, and it tells you every day how much time is left.
The point is, while I think that migrating off of Server 2003 is important, it was not at that point (nor is it now) an endeavour that I wanted to take on. To put things in perspective, I was nearing the end of a 1,400 day countdown during which I tweeted almost every day. I was no longer an Evangelist, and I was burnt out.
Despite what you may have heard, I am still happy to help the Evangelism Team at Microsoft Canada (although I think they go by a different name now). So when I got an e-mail on the subject from Pierre Roman, I felt it important enough to share with you. As such, here is the gist of that e-mail:
1) On July 14, 2015 support for Windows Server will come to an end. It is vital that companies be aware of this, as there are serious dangers inherent in running unsupported platforms in the datacenter, especially in production. As of that date there will be no more support and no more security updates.
2) The CanITPro team has written (or re-posted) several articles that will help you understand how to migrate off your legacy servers onto a modern Server OS platform, including:
- Step-By-Step: Migrating The Active Directory Certificate Service From Windows Server 2003 to 2012 R2 (by Dishan Francis, Microsoft MVP)
- Step-By-Step: Migrating DHCP From Windows Server 2003 to 2012 R2 (by Dishan Francis, Microsoft MVP)
- Step-By-Step: Active Directory Migration from Windows Server 2003 to Windows Server 2012 R2 (by Anthony Bartolo)
3) The Microsoft Virtual Academy (www.microsoftvirtualacademy.com) also has great educational resources to help you modernize your infrastructure and prepare for Windows Server 2003 End of Support, including:
4) Independent researchers have come to the same conclusion (IDC Whitepaper: Why You Should Get Current).
5) Even though time is running out, the Evangelism team is there to help you. You can e-mail them at cdn-itpro-feedback@microsoft.com if you have any questions or concerns surrounding Windows Server 2003 End of Support.
Of course, these are all from them. If you want my help, just reach out to me and if I can, I will be glad to help! 
(Of course, as I am no longer with Microsoft or a Microsoft MVP, there might be a cost associated with engaging me )
Good luck, and all the best in 2015!
The World According to Mitch 
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