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Server 2008 and Windows 7 End of Life: 3 Things You Need to Know

Microsoft has announced that they will no longer be providing security updates for Server 2008 and Windows 7 systems as of January 2020. This means that organizations have 6 months to implement a plan to address the increasing security vulnerability that these systems represent to your networks and data.

In this webinar, Community IT Innovators’ CTO Matt Eshleman covers three things you need to know to update your security and plan for this development.


photo of Matt Eshleman

As the Chief Technology Officer at Community IT, Matthew Eshleman is responsible for shaping Community IT’s strategy around the technology platforms used by organizations to be secure and productive. With a deep background in network infrastructure he fundamentally understands how technology works and interoperates both in the office and in the cloud.
Matt joined Community IT as an intern in the summer of 2000 and after finishing his dual degrees in Computer Science and Computer Information Systems at Eastern Mennonite University he rejoined Community IT as a network administrator in January of 2001. Matt has steadily progressed up at Community IT and while working full time received his MBA from the Carey School of Business at Johns Hopkins University.

Matt is a frequent speaker at NTEN events and has presented at the Inside NGO conference, Non-Profit Risk Management Summit and Credit Builders Alliance Symposium. He is also the session designer and trainer for TechSoup’s Digital Security course.

Matt lives in Baltimore MD with his wife, daughter and son. He is a member of the Baltimore Choral Arts Society and on the support committee of the Reservoir Hill House of Peace.

Slides Transcript – Server 2008 and Windows 7 End of Life: 3 Things You Need to Know

  1. Windows 7, Server 2008 and SQL 2008 End of Life Webinar Series July 2019
  2. About Community IT Advancing mission through the effective of technology. 100% Employee Owned
  3. Presenter: Matthew Eshleman CTO
  4. AGENDA What’s EOL &When Managed computers at CIT Approach to handling workstations Approach to handling SQL Approach to handling Server 2008 Steps to secure your organization
  5. Windows Server and SQL Server end of support is fast-approaching Extended support forWindows Server and SQL Server is ending – meaning Microsoft will no longer release security updates. This may expose you to security attacks and compliance risks with regulations such as GDPR. Extended support for SQL Server 2008/2008 R2 ended July 9, 2019 SQL Extended support for Windows Server 2008/2008 R2 ends January 14, 2020
  6. Environment at Community IT – Servers 2% 17% 49% 32% Windows Servers Windows 2008 Windows 2008 R2 Windows 2012 Windows 2016
  7. Environment at Community IT – Workstations 82% 16% 2% 0% Windows OS Windows 10 Windows 7 Windows 8 & 8.1 Windows XP
  8. Strengthen security End of support also means you will no longer have access to critical security updates, opening the potential for: Cybercrime will cost the world $6 trillion annually by 2021, up from $3 trillion in 20151 Business interruptions Protection against hackers and malware Loss of data, brand reputation, and customer trust
  9. Three things to know End of support is coming or is here You can get 3 more years of support in Azure Community IT’s recommendation is to replace
  10. Workstations • In place upgrade is possible • No longer free • Upgrade costs • $16-$87 toWindows 10 Enterprise through TechSoup • $60 – $190 to Windows 10 Pro List Price • ConsiderTCO • Computer replacement on 3-4 year timeframe • New Desktop $800, new laptop $1300
  11. Workstations • Recommend buy new computer • Windows 10 provides tight integration with Office 365 • Windows 10 has a reliable update mechanism
  12. SQL Server 2008 • End of Support as of July 9, 2019 • Migrate or Upgrade? • Upgrade if you can • Alternate is to migrate to Azure • Migrate to the Microsoft cloud and get three years security updates at no charge, with built-in features that protect your data
  13. Security Steps That should be Completed Disable SMBv1 Remove Public RDP access to any server Ensure that systems are up to date on patches
  14. Server 2008 Server 2008 R2 • End of Support as of Jan 20, 2020 • Decommission, Migrate or Upgrade? • Migrate from server to services • Look at your org’s IT Roadmap • Migrate to the Microsoft cloud and get three years security updates at no charge, with built-in features that protect your data
  15. Server 2008 Server 2008 R2 • Server 2008 didn’t include nativeTLS 1.2 support • Server 2016 can be joined to 2008 R2 domain. • DCPromo of 2019 Domain Controller requires upgrade from FRS to DFSR
  16. Migrate into Azure Azure Sponsorship for nonprofits Be Aware of Pricing Using Azure Site Recovery
  17. Typical Network Evolution • Azure AD Join, Azure AD Domain Services < 25 users: • Single Server, Domain Controller, Print 25-50 users: • Single HyperV Host: Domain Controller, Utility Server, Files, etc • Azure Domain Controller, Apps 50-200 users: • Multiple PhysicalVirtual Hosts on Premise • Cloud Servers 200 – 1000 users:
  18. Reference Links • Microsoft Announcement: • How to migrate from Server 2008 R2 Domain -> 2016
    If you still have 2008, then you need to do a swing migration • Support in Azure: • Discuss Migration Options:
  19. Upcoming Webinar 5 Steps to Create an Information Strategy forYour Organization Wednesday August 21st 1:00 – 2:00 PM EDT
  20. Next Steps Implementation Replace or Migrate Accurate Inventory
  21. cybersecurity at © 2018 Community IT Innovators, Inc. All Rights Reserved. THANK YOU!