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Server 2008 and Windows 7 EOL

by Louis Barker | Oct 16, 2019

Windows 7 and Server 2008 being phased out in January 2020 – How to best prepare your business before the New Year


Microsoft has a 10 year cycle for its operating systems. On January 14th 2020, Windows 7 and Server 2008 (R2) will be phased out and classified End Of Life (EOL). Once this date rolls over, Microsoft will stop supplying any updates or security fixes, signalling to everyone it is no longer valid. Over time, everyday programs like web browsers, Antivirus/Security products and other internet based programs, such as Skype or Spotify, will also stop supporting Windows 7, potentially leaving computers unprotected and not able to access some services. Even if these services are not being utilised, just by having unsupported systems running on a network does present some major security holes that have been exploited in the past. A major attack, WannaCry, in May 2017, managed to cripple the NHS in the UK and Nissan for several days, causing billions worth of losses worldwide. The success of this attack will ensure further attacks are likely in the future.


Windows 7  


For desktop computers and laptops, Windows is still unofficially offering free upgrades for all Windows 7 and 8.1 users to bring them up to Windows 10. The Windows 10 Update Assistant will evaluate your current system and, if there are no known compatibility issues, download any further updates and run the upgrade to Windows 10. For most, this has been a very simple process and may not require any assistance to complete. However for other computers that are having issues upgrade, Dorchester might require a further inspection to evaluate the issue and offer a solution. When upgrade does complete, there is a 30 day window if unforeseen issues do occur for a roll back to the previous version of Windows if required. Every step of the way, Dorchester IT is happy to help and guide you through the process.


Server 2008 R2


Upgrading is a little more difficult for servers. In a majority of the cases, we recommend running a newer version of the system that upgrades to the 2016 version. Servers are normally running business critical services. Having one go offline after a bad migration or another issue from the upgrade means down time and lost productivity. Our technicians are readily available to assist with this process, ensuring the transition goes as smoothly as possible. With the NBN rollout and advancements in internet speed and capacity, there are more options to choose from when looking at a replacement. Accounting, email, communications and business-line apps (Leap/Attache/RMI Master etc.) have tried and tested Cloud based offerings, reducing the need for in-house servers hosting the information. However, for companies still requiring/using Terminal Servers, a locally based server is still our preferred option.


For a large amount of our customers, planning and budgeting are necessary before moving forward with any replacements. Over the coming weeks, our technicians will be contacting our customers that we know are using Server 2008, in order to organise an evaluation on the current roles performed and ensure a plan is started on any systems that will be affected or if additional work is required. If you would like us to evaluate any systems you may have a concern with, please contact us and we will be able to perform an audit to identify the risks and offer solutions. Early action will ensure that Christmas and New Year’s is spent celebrating and not worrying about whether your systems are protected or not. Dorchester is open throughout this period to help with any last minute requests that might need to be made.


For further information on the phase out, or for a technician to advise on your current system and what options are best suited to your business, please contact us on 1300 796 788 or email us at

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