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Windows Server 
2003 Migration 
Opportunity for transformation 
Scott Curtis 
11/11/2014
2 
End of support for Windows Server 
2003/R2 
245 Days Remaining 
Optimistic Estimates 
Server migration: 200 days 
Application migration: 300+ days 
11/10/2014
What end of support means 
Now 
is the time to act 
No 
compliance 
No 
updates 
Start planning your migration and transforming your datacenter toDdaisycontinued 
support for many 
applications 
Increased 
operations costs 
Impact on 
Microsoft Small 
Business Server 
2003 
Impact on both 
physical and 
virtualized 
servers 
No 
safe haven 
Windows 2003/R2 servers will not 
pass a compliance audit 
37 critical updates released 
in 2013 for Windows Server 
2003/R2
Datacenters are being transformed 
70% 
of CIOs will embrace 
a “cloud first" strategy 
in 2016 
-IDC 
45% 
of total IT services will 
be spent on cloud 
services by 2020 
-Forrester 
71% 
of companies see 
rising demand for IT 
projects in 2013 
-InformationWeek 
Sources: “Outlook 2013,” InformationWeek Report, 12/06/2012; “Worldwide CIO Agenda 2013 Top 
10 Predictions,” IDC, doc #238464, December 2012; “Prepare For 2020: Transform Your IT 
Infrastructure And Operations Practice,” Forrester Research, Inc., October 24, 2012;
What about the cloud?
Migration process 
1 Discover 2 Assess 3 Target 4 Migrate
Discover & Assess your inventory 
By type 
Microsoft 
server roles 
By criticality 
Microsoft 
applications 
Custom Third-party applications 
applications 
Mission critical Important Marginal Can be retired 
By complexity and risk 
Low Medium High 
1. Discover 2. Assess 3. Target 4. Migrate
Assess your inventory 
1. Discover 2. Assess 3. Target 4. Migrate 
ID Application Owner 
Discover Assess 
Server role 
Microsoft app 
Third-party app 
Custom app 
Retire 
Marginal 
Important 
Critical 
Complexity (1–3) 
Risk (1–3) 
00001 Exchange 
Denise 
Smith 
X X 1 1 
00002 Web Server Qiong Wu X X 2 2 
00003 Shipping Services Naoki Sato X X 2 1 
00004 Quick Quarter Close Daniel Roth X X 2 2 
00005 
Lucerne Publishing Document 
Converter 
Andrea 
Dunker 
X X 3 2 
00006 Trey Research Lookup Tool Eric Gruber X X 2 3 
00007 A. Datum Index Oliver Kiel X X 3 3 
00008 Inventory Key 
Robin 
Counts 
X X 2 2
Target your destination 
Windows Server 
Evaluate options for each 
application and workload 
2012 R2 Cloud 
1. Discover 2. Assess 3. Target 4. Migrate
Windows Server roles 
1. Discover 2. Assess 3. Target 4. Migrate
Windows Server 2012 R2 
Hybrid applications 
Enterprise-class scale and 
performance 
VMware virtualization 
Low-cost, highly available 
file-based storage 
Windows 
PowerShell 4.0 
Work Folders 
1. Discover 2. Assess 3. Target 4. Migrate 
>_
Windows Server 2012 R2 Editions 
1. Discover 2. Assess 3. Target 4. Migrate
Hybrid Cloud 
For your hybrid datacenter solution 
Access your data and apps anywhere 
Hardware as a service 
Priced per user 
Flexibility 
1. Discover 2. Assess 3. Target 4. Migrate
Cloud tools 
Powerful, simple enterprise-class email. Cloud file syncing and sharing 
1. Discover 2. Assess 3. Target 4. Migrate
Migrating applications 
+1 
Application must be 
upgraded to latest 
version 
Use technology to 
counter 
incompatibilities 
Modify application 
to work on new 
platform 
Use different app or 
SaaS offering to 
achieve same 
business result 
Application can be 
migrated without 
change 
1. Discover 2. Assess 3. Target 4. Migrate
Microsoft applications 
1. Discover 2. Assess 3. Target 4. Migrate
Target your destination 
Choose your journey 
ID Application Owner 
1. Discover 2. Assess 3. Target 4. Migrate 
Discover Assess Target (destination and journey) 
Server role 
Microsoft app 
Third-party app 
Custom app 
Retire 
Marginal 
Important 
Critical 
Complexity (1–3) 
Risk (1–3) 
Windows Server 
2012 
Microsoft Azure 
Hosted Exchange 
Migrate as is 
Upgrade version 
Switch app vendor 
Virtualize or shim 
app 
Repair, rewrite, or 
refactor 
00001 Exchange 
Denise 
Smith 
X X 1 1 X X X X 
00002 Web Server Qiong Wu X X 2 2 X X X X X 
00003 Shipping Services Naoki Sato X X 2 1 X X X 
00004 Quick Quarter Close Daniel Roth X X 2 2 X X X 
00005 
Lucerne Publishing Document 
Converter 
Andrea 
Dunker 
X X 3 2 X X X 
00006 Trey Research Lookup Tool Eric Gruber X X 2 3 X X 
00007 A. Datum Index Oliver Kiel X X 3 3 
00008 Inventory Key 
Robin 
Counts 
X X 2 2 X X X
Migrate your workloads 
1. Discover 2. Assess 3. Target 4. Migrate
Next steps 
Explore resources 
mapletronics.com/server2003eol-resources 
Experience innovations 
Take advantage of innovations in 
Windows Server, new hardware, cloud 
operating system, and application 
platform 
Get started today 
A smooth, successful server migration 
takes time to plan and execute, so start 
today to make sure you meet the 
deadline

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Windows Server 2003 End of Life Webinar - 11/11/14

  • 1. Windows Server 2003 Migration Opportunity for transformation Scott Curtis 11/11/2014
  • 2. 2 End of support for Windows Server 2003/R2 245 Days Remaining Optimistic Estimates Server migration: 200 days Application migration: 300+ days 11/10/2014
  • 3. What end of support means Now is the time to act No compliance No updates Start planning your migration and transforming your datacenter toDdaisycontinued support for many applications Increased operations costs Impact on Microsoft Small Business Server 2003 Impact on both physical and virtualized servers No safe haven Windows 2003/R2 servers will not pass a compliance audit 37 critical updates released in 2013 for Windows Server 2003/R2
  • 4. Datacenters are being transformed 70% of CIOs will embrace a “cloud first" strategy in 2016 -IDC 45% of total IT services will be spent on cloud services by 2020 -Forrester 71% of companies see rising demand for IT projects in 2013 -InformationWeek Sources: “Outlook 2013,” InformationWeek Report, 12/06/2012; “Worldwide CIO Agenda 2013 Top 10 Predictions,” IDC, doc #238464, December 2012; “Prepare For 2020: Transform Your IT Infrastructure And Operations Practice,” Forrester Research, Inc., October 24, 2012;
  • 5. What about the cloud?
  • 6. Migration process 1 Discover 2 Assess 3 Target 4 Migrate
  • 7. Discover & Assess your inventory By type Microsoft server roles By criticality Microsoft applications Custom Third-party applications applications Mission critical Important Marginal Can be retired By complexity and risk Low Medium High 1. Discover 2. Assess 3. Target 4. Migrate
  • 8. Assess your inventory 1. Discover 2. Assess 3. Target 4. Migrate ID Application Owner Discover Assess Server role Microsoft app Third-party app Custom app Retire Marginal Important Critical Complexity (1–3) Risk (1–3) 00001 Exchange Denise Smith X X 1 1 00002 Web Server Qiong Wu X X 2 2 00003 Shipping Services Naoki Sato X X 2 1 00004 Quick Quarter Close Daniel Roth X X 2 2 00005 Lucerne Publishing Document Converter Andrea Dunker X X 3 2 00006 Trey Research Lookup Tool Eric Gruber X X 2 3 00007 A. Datum Index Oliver Kiel X X 3 3 00008 Inventory Key Robin Counts X X 2 2
  • 9. Target your destination Windows Server Evaluate options for each application and workload 2012 R2 Cloud 1. Discover 2. Assess 3. Target 4. Migrate
  • 10. Windows Server roles 1. Discover 2. Assess 3. Target 4. Migrate
  • 11. Windows Server 2012 R2 Hybrid applications Enterprise-class scale and performance VMware virtualization Low-cost, highly available file-based storage Windows PowerShell 4.0 Work Folders 1. Discover 2. Assess 3. Target 4. Migrate >_
  • 12. Windows Server 2012 R2 Editions 1. Discover 2. Assess 3. Target 4. Migrate
  • 13. Hybrid Cloud For your hybrid datacenter solution Access your data and apps anywhere Hardware as a service Priced per user Flexibility 1. Discover 2. Assess 3. Target 4. Migrate
  • 14. Cloud tools Powerful, simple enterprise-class email. Cloud file syncing and sharing 1. Discover 2. Assess 3. Target 4. Migrate
  • 15. Migrating applications +1 Application must be upgraded to latest version Use technology to counter incompatibilities Modify application to work on new platform Use different app or SaaS offering to achieve same business result Application can be migrated without change 1. Discover 2. Assess 3. Target 4. Migrate
  • 16. Microsoft applications 1. Discover 2. Assess 3. Target 4. Migrate
  • 17. Target your destination Choose your journey ID Application Owner 1. Discover 2. Assess 3. Target 4. Migrate Discover Assess Target (destination and journey) Server role Microsoft app Third-party app Custom app Retire Marginal Important Critical Complexity (1–3) Risk (1–3) Windows Server 2012 Microsoft Azure Hosted Exchange Migrate as is Upgrade version Switch app vendor Virtualize or shim app Repair, rewrite, or refactor 00001 Exchange Denise Smith X X 1 1 X X X X 00002 Web Server Qiong Wu X X 2 2 X X X X X 00003 Shipping Services Naoki Sato X X 2 1 X X X 00004 Quick Quarter Close Daniel Roth X X 2 2 X X X 00005 Lucerne Publishing Document Converter Andrea Dunker X X 3 2 X X X 00006 Trey Research Lookup Tool Eric Gruber X X 2 3 X X 00007 A. Datum Index Oliver Kiel X X 3 3 00008 Inventory Key Robin Counts X X 2 2 X X X
  • 18. Migrate your workloads 1. Discover 2. Assess 3. Target 4. Migrate
  • 19. Next steps Explore resources mapletronics.com/server2003eol-resources Experience innovations Take advantage of innovations in Windows Server, new hardware, cloud operating system, and application platform Get started today A smooth, successful server migration takes time to plan and execute, so start today to make sure you meet the deadline

Editor's Notes

  1. Mainstream support from Microsoft for Windows Server 2003 ended in July 2010. Windows Server 2003/R2 has been on Extended Support since then, which means only security updates are released. July 14, 2015 is the End of Support for Windows Server 2003/R2.
  2. End of support means: No updates 37 critical updates were released in 2013 for Windows Server 2003/R2 under Extended Support. No updates will be developed or released after end of support. No compliance Lack of compliance with various standards and regulations can be devastating. This may include various regulatory and industry standards for which compliance can no longer be achieved. For example, lack of compliance with the Payment Card Industry (PCI) Data Security Standards might mean companies such as Visa and MasterCard will no longer do business with you. Or, the new cost of doing business will include paying catastrophic penalties and astronomically high transaction fees. No safe haven Both virtualized and physical instances of Windows Server 2003 are vulnerable and would not pass a compliance audit. Microsoft Small Business Server (SBS) 2003 servers are also affected. Staying put will cost more in the end. Maintenance costs for aging hardware will also increase. Added costs will be incurred for intrusion detection systems, more advanced firewalls, network segmentation, and so on—simply to isolate Windows Server 2003 servers. Many applications will also cease to be supported, once the operating system they are running on is unsupported. This includes all Microsoft applications. Now is the time to act You must start planning migration now. Servers may still be running Windows Server 2003/R2 for a number of reasons. You can use these reasons as a discussion point: Perceived challenges of upgrading applications Presence of custom and legacy applications Budget and resource constraints Additional information: “Making the case for upgrading from Server 2003” (http://www.theregister.co.uk/2013/06/23/windows_server_2003_reasons_to_upgrade_analysis/)
  3. Windows Server 2003 provided IT with an amazing operating system for the past 10 years, but IT has changed a lot since then. The industry is moving forward and so has the operating system. It’s important to understand why your peers are making the transformation. Let’s talk about the advantages and pitfalls of The Cloud…
  4. Cloud Advantages: Low capital expense Improved accessibility (any time, anywhere access) Easier upgrades Less onsite IT support needed Potential Pitfalls: Totally dependent on internet connection You have no control over uptime/downtime Who owns your data? Changing to another provider can be painful Still need onsite server for file storage/user management (active directory)
  5. The migration process will follow four key steps. We will cover them briefly here.
  6. Once you have a catalog, you will need to assess what is in that catalog. This means categorizing your applications and workloads in several ways and doing a thorough analysis of what is there. We suggest you consider categorizing your applications and workloads in four ways: By type: Microsoft Server Roles, Microsoft Applications, Custom Applications, and Third-party Applications By criticality: Can Be Retired, Marginal, Important, and Mission Critical By complexity: Low, Medium, and High By risk: Low, Medium, and High With this categorization complete, you can begin to understand the scope of the problem and can prioritize your workloads and applications. The categorization will also reveal some potential opportunities, as well as potential issues. The criticality category, for example, might raise concerns about what to migrate when and in what order. The complexity and cost categories will indicate which migrations might be the easiest and quickest to accomplish. A cross-category analysis provides even more insight. For example, an important application with low complexity and only medium risk might be a good candidate for early migration.
  7. At this point, the process may have provided additional information that looks something like this.
  8. You must choose a migration destination for each application and workload. There are four destinations for migration: Windows Server 2012 R2 Applications to The Cloud Email to Hosted Exchange or other email service Cloud Cache for collaboration/file sharing Different workloads and applications will logically lead to certain targets. Others could offer the possibility of migration to one or more of these destinations. The choice will be driven by factors such as speed and ease of migration, cost, and desired functionality in the migrated solution.
  9. There are five key server roles to consider for migration from Windows Server 2003/R2: File Server Web Server Active Directory Domain Controller Terminal Services Server roles are the some of the easiest (File Server) and potentially some of the hardest (Active Directory) migration scenarios. Only a thorough analysis of what exists today and what the desired end state is will show exactly what effort is needed to migrate these roles off Windows Server 2003/R2. For an interesting perspective, see http://social.technet.microsoft.com/Forums/en-US/42070a54-a907-4526-b35c-6d6837f37a4e/migration-plan-for-windows-server-2003-to-windows-server-2012
  10. Windows Server has seen many advancements in the past 10 years, and today the current version is Windows Server 2012 R2. Enterprise-class scale and performance Windows Server 2003 R2 Scales to 64 logical processors and 1 terabyte of memory (x64 versions) Windows Server 2012 R2 Scales to 320 logical processors and 4 terabytes of physical memory (x64 versions) Scales to 64 logical processors and 1 terabyte of memory on a virtual machine Supports up to 64 nodes and 8,000 virtual machines in a cluster Vmware Virtualization Ability to combine several servers into a single server chassis and allocate resources to each server. Servers run as independent virtual machines with separated roles. Lower cost of ownership Low-cost, highly available file-based storage Windows Server 2003 R2 Not available Windows Server 2012 R2 Offers new SMB 3.0 protocol enhancements and low-cost, “commodity” hardware with new File Services for storing server application data such as SQL databases and VHDs for Hyper-V on file shares Automatically rebalances Scale-Out File Server clients Tracks SMB client connections per file share, and then redirect clients to the cluster node with the best access to the volume used by the file share Enables leveraging of commodity storage into virtual storage pools, which can then be provisioned as Storage Spaces Provides virtualized drives that can be formatted and accessed just like a physical drive, which can also be dynamically resized with the addition of more physical drives to the storage pool Includes storage tiers, write-back cache, parity space support for failover clusters, dual parity, and the ability to automatically rebuild storage spaces from storage pool free space Work Folders: Work Folders add to the functionality provided by Workplace Join and allow users to sync files on a Windows Server 2012 R2 file server with folders on their own device, and provide administrators with the ability to centrally manage the files and folders. Essential for mobile users and BYOD. Hybrid applications Windows Server 2003 R2 Requires virtual private networks (VPNs) or other form of point-to-point connectivity for communication among geographically separated parts of an application Windows Server 2012 R2 Protects existing investments in on-premises applications Unifies application management Provides flexibility to build and deploy hybrid applications on-premises and in the cloud Provides a common development environment for .NET developers to build cloud (Azure) and on-premises applications Windows PowerShell 4.0 Windows Server 2003 R2 Provides more than 100 cmdlets Windows Server 2012 R2 Provides more than 3,000 cmdlets in over 100 modules and includes several significant features that enable easier and more comprehensive control and management of Windows-based environments Enables the deployment and management of configuration data for software services and the environment in which these services run through Desired State Configuration (DSC)
  11. Links on Windows Server 2012 R2 Editions Comparison: http://www.infralib.com/2014/02/windows-server-2012-r2-products-editions-comparison/ http://www.microsoft.com/en-us/download/details.aspx?id=38809 http://windowsserver2012.itpro.co.uk/business-benefits/72/which-version-windows-server-2012-should-i-choose
  12. Sales hat: MT owned and maintained equipment TorQ 41 Data Protection with failover Access from anywhere/any device Grows with your company Pricing per user Low capital expense
  13. Hosted Exchange: Fully featured email Share calendars/contacts/tasks Any device access (Standard & above) Email protection & continuity Disaster recovery Outlook Web Access Cloud Cache: Instant collaboration Easy access to shared files Secure sharing with third parties Simple setup and administration
  14. The three key Microsoft applications and technologies likely to be considered for migration are covered in this section. We will look at options and considerations for each.
  15. Your plan might look something like this now. And now it’s time to make some decisions and get moving.
  16. Now is the time to migrate. These resources can help you get started: Migration website Windows Server 2012 R2