“Dear John…” how to breakup with your old infrastructure

From:         SysAdmin
Sent:          Friday, August 29th, 2014 11:38 am
To:             JOHN-WS2003R2.CONTOSO.COM
Subject:     I really don’t know how to say this in person…

Dear John (a.k.a. Windows Server 2003)

I wish I were writing you for other reasons, but I just can’t continue supporting our relationship feeling the way I feel right now. I’m writing this email instead of logging into the console because I have so much to tell you and this seems like the best way to say it without getting distracted.

What can I say – it has been fun.  You have worked hard all these years keeping our old mission critical applications running, long after others have abandoned you. You stood by me as we transitioned Active Directory away from you and over to the bright shiny new systems running a “more modern” flavor of Windows Server.  It must have been difficult to see those services migrated away after the planning and pilot deployment. This has gotten me thinking – I’ve realized I need to sit down and take stock of where our relationship stands today and I realized that we’ve grown apart.  I’m ready to move to a more mature relationship but I don’t think you and I are on the same page. After reading this – I definitely believe you are not able to continue fulfill my needs.

I want to make this as easy as possible for both of us – so I started exploring other options.

First off, I need to discover what exactly we’ve been doing over the last 11 years. I mean really – you never cease to surprise me when a site visit turns up yet another one of your relatives running some application or print server that is critical to someone’s daily routine. This concerns me – it really does. You’ve obviously gotten around a lot and have been very popular with the IT staff.  This has got to stop. I’ve contacted a couples councilor who has recommended I try “The Microsoft Assessment and Planning Toolkit” in order to get a view of just how far reaching your deployment has grown over the years and what workloads you still maintain.

Next – it’s time for me to set aside some “alone time” to plan and Assess just how much work lies ahead.  I know it will be tough and there will be lots of work to come – but knowing what lies ahead and prioritizing is half the battle.  I still have a lot to learn about what my options are, so I started a personal learning path as part of this Tech Journey of Modernizing the Datacenter.

As much as I don’t like to say it – after taking the time to Assess and reflect on things, it’s time for me to Target exactly what needs to get done to painlessly end our relationship without another nasty fight. I’ll be honest, some things will need to be replaced because the old way isn’t working anymore. Other things will require some assistance to migrate to new solutions. I am going to keep an open mind and explore my options.  I plan on making some hard decisions in the months to come.

Finally – when all is said and done, I’ve got to be strong and stand firm to our deadline of July 14th, 2015. With it fast approaching, I’ll prepare myself to Migrate things on my own or get some additional help from partners who are better equipped to get me through this stressful time.

I know I will revisit our time together and remember the happy times – successful Service Packs, new CD-ROM updates and Sneakernet deployments. I’ll forever hear your disks whirring and see your lights blinking in my minds eye for a long time to come. I’m going to miss all of this, more than you can imagine.

…but it’s time for me to move on.



Your SysAdmin

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11 CommentsLeave a comment

  • Yeah, come out into the real world where you have to convince the business to spend a quarter mill on new Portal software because the OS that it runs just fine on is going unsupported. Or try to track down someone who wants to claim ownership of the 300 intranet web sites and convert the VB6 code to something supportable. And then find a programmer to support it because the original guys are long gone. And while you’re at it, let’s get Microsoft to change the user interface a few more times so that when I have 15 RDP sessions going I can play Where’s Waldo on every server. Nyaaah, nyaah, guess where we put logoff in this release!!!!!

    • Thanks for your thoughts Dave. Lots of resources out there to get the task underway for migrating to a more recent server OS. You aren’t alone, lots of customers are in the position you mention – lots of IT guys/gals that are also stuck figuring out what’s next. My personal opinion is to get at ‘er and figure out what’s ahead. Microsoft Migration Planning Assistant is the starting point http://www.microsoft.com/en-us/server-cloud/products/windows-server-2003

  • I so much love this..I have handled some 2003 servers that has served for 10 years and making a decision to take that away from the rack is like losing some from the family 🙁

    But yes, It has to happen and we have to move on..

    • I remember pulling the plug on my last Banyan vines 4.11 server with StreetTalk way back when…

  • Oh Boy! do i feel out of touch. as time moves on and others entice me to risk my client base, i am not compelled to risk my client base, or force client data infrastucture to be rendered. i only speak of clients still working seemlessly with server platforms running server 2000. it works. pure and simple. besides, it is not the clients burden, that server 2008 or server 2012, do not support the programs needed to run day to day ops of these clients. my job is to deliver customer service and support, not bad news and a sales pitch. how do i explain to a client, to spend resources, and a significant amout amout of grief on a new server platform that does not support them or thier needs? (i am truly stuck between a rock and a hard place)

    • I hear you on the support side – I was in the trenches as a consultant / hired gun as well.
      While you can continue to run OSs that are no longer supported, you are exposing yourself and your clients to risk that they might not be aware of. Some of this risk includes loosing certification or upkeep of their various legal requirements (think PCI compliance for payment processing as an example – although it varies by country, sector and scenario). Apps that your customers run on the out of support OS need to be identified and re-examined as to what their options are for app upgrades or app virtualization on a newer platform.
      Check out the Migration Planning Assistant to see what all the options are. http://www.microsoft.com/en-us/server-cloud/products/windows-server-2003 sometimes knowing what the options are is all you and the customer need to start that hard conversation.

  • I need to thank before I could express the view.

    As all to work together to a find way to over come the fast growing change and need to adopt strategy. It is a must need to share the technical views in terms of all the adaptability and migration. There should be a road map defined atleast for next 10 to 15 years.

    The portability and adaptability need to be stressed in the technology.

  • I really wish I could get the discovery tool to work in my browser.
    Tried IE 8 and 9 Those are the only two IE’s available on my corp. network. When I go to the site, the sections:

    “Select your Windows Server 2003 workloads
    Choose one more categories of workload that you need to migrate.”

    Both show large white boxes with what appears to be check boxes inside. But cant check them and no data around them to indicate what the heck I would be selecting.

    I am on a team dedicated to this issue. Is there an independent tool?


    • Very strange… The UI is not the most intuitive (IMHO) but I was able to get it to work with previous versions of IE. Tried adding it to trusted sites?

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