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7’s Up: Goodbye Windows 7

November 7, 2018
Chris Filippi
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7’s Up: Goodbye Windows 7

Support for Microsoft’s Venerable Windows 7 Operating System Ends January 14th, 2020

-Chris Filippi, November, 2018

After an incredible 10+ year run, the sun is finally setting on Windows 7.  Regarded by many as the finest operating system produced by Microsoft to date and still in widespread use today, Microsoft will end support (and more importantly stop issuing security fixes) for it in 14 short months.  As with the end of Windows XP back in April of 2014, this is a HUGE deal: it literally means it’s a bad idea to keep using this stalwart product after January 14th, 2020.

Consequently, if you have any Windows 7 machines, you should plan on replacing them in 2019.

Released in July of 2009, Windows 7 was an eagerly anticipated replacement of Windows XP and its lackluster successor, Windows Vista.  Compounded with the public’s general rejection of Windows 8 in 2012, Windows 7 remained the preeminent business operating system on new computers long after 2015 when Windows 8 was replaced by the current Windows 10.  Despite a massive (and widely criticized) effort by Microsoft to move users to Windows 10, it is currently estimated that over 40% of Windows-based PCs in use today are running Windows 7.

Thus, it’s quite likely that you have (and rely on) one or more Windows 7 systems in your office right now.  If you’re unsure, take a quick look at your start button in the lower-left corner of your screen: if it’s a blue ball with a 4-color Windows logo on top, odds are you’re running Windows 7.

So, why such a huge deal?  Simple: end of support means Microsoft will no longer fix any security vulnerabilities in Windows 7 after January 14th, 2020.  Furthermore, software and hardware manufactures will begin requiring “Windows 8 or above” for their products.  This can become a big headache as businesses frequently replace hardware (such as printers) and rapidly evolving products (such as web browsers) are perpetually updated.  The latter becomes a “double-whammy”: if you can’t run the latest version of Chrome or Firefox, you’re exposed to all the security flaws that are now public knowledge in the version you’re running.  Consequently, we strongly advise against keeping Windows 7 in play after the sunset date.

Does this mean you need to buy all new computers to replace your fully-functional Windows 7 systems?  Unfortunately yes, especially in the small business space because:

  1. Upgrading from Windows 7 to Windows 10 is not recommended, as I’ve discussed extensively in the following articles:
    1. Should We Upgrade to Windows 10 now?
    2. Windows 10 – Revisited
  2. In the modern age of ransomware, identity theft, and state-run cyber-terrorism, using an “unpatchable” operating system is way too big of a risk for even the most modest of businesses to take.
  3. Unlike larger companies with lots of identical PCs, small businesses usually buy computers on an as-needed basis; resulting in significant hardware disparity (e.g. Bob has an OptiPlex 5040, while Jim has an OptiPlex 720, and Sarah has an HP EliteDesk 800). This disparity makes a “refresh” virtually impossible to roll-out (i.e. replacing the hard drive in each machine with a pre-imaged, clean installation of Windows 10) due to the physical differences of the hardware.  Thus, the cost of labor involved in upgrading a single, 5-year old machine is generally put to better use towards new hardware with Windows 10 already installed.

On the bright side, a new computer with Windows 10 has countless advantages over your aging Windows 7 systems.  To name a few:

  1. Most new systems ship with solid-state hard drives, providing faster load times, quicker reboots, and longer system life.
  2. Windows 10 has been widely adopted as the de facto operating system for Windows PCs, with wide support from hardware and software manufacturers.
  3. Searching, multiple monitor support, and system security are vastly superior in Windows 10.
  4. Newer hardware means more speed, which translates to more productivity.

With 2019 rapidly approaching, now is a good time to plan putting your Windows 7 machines out to pasture.  To that extent, we strongly recommend:

  1. If you don’t have one, get a Windows 10 machine online soon and make sure your business-critical applications and hardware will work. If they don’t, factor in the cost to upgrade/replace those products
  2. If you have several relatively new and identical machines running Windows 7, consider a hardware refresh if the systems will be less than 4 years old by the end of 2019
  3. If you’re currently using a server running Windows Server 2008 or 2008 R2, plan on replacing your server at the same time as your workstations. See our related article Exchange to the Cloud – Why the End of Support for SBS 2011 Marks the End of In-house Exchange for Small Business

There’s no questions that Windows 7 has had a good run, and there’s no reason you can’t continue to use it up to its expiration date on January 14th, 2020.  Just remember, that expiration date is not a “manufacturer’s suggestion” – it’s a funeral bell and should be treated accordingly.

End of SBS 2011

November 7, 2018
Chris Filippi
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Exchange to the Cloud

Why the End of Support for SBS 2011 Marks the End of In-house Exchange for Small Business

-Chris Filippi, November, 2018

It’s hard to believe it’s only been 6 years since I was urging customers to replace their Windows 2003 Small Business Servers with the 2011 version to keep their Exchange data in-house.  Back then, I warned “Microsoft wants you to put everything you do in Outlook on their servers, not yours.”  This threat will come to fruition on January 14th, 2020.

This poses two immediate challenges to SBS 2011 users in 2019: migrate all your Exchange data and replace your SBS 2011 server.

As mentioned in my previous article, Microsoft stopped including Microsoft Exchange Server in their Small Business Server package with the release of Windows Server 2012 Essentials.  Thus, if wanted to keep using Exchange, you had three choices:

  1. Get Small Business Server 2011 before time ran out
  2. Migrate your Exchange data to the cloud
  3. Get full-versions of Windows Server and Exchange

Back in 2013, option 2 was significantly more expensive than option 1, due to increased bandwidth requirements and high per-mailbox hosting costs.  Option 3 was, and remains, radically more expensive, due to licensing costs plus additional hardware and maintenance.

Microsoft appears to be keeping their promise of ending support for Windows Server 2008 R2 and Exchange 2010 (the foundation of Small Business Server 2011) on January 14th, 2020.  Thus, continuing to use these servers beyond that date poses a major security liability no business should take on.  Furthermore, new versions of Microsoft Office will likely no longer support connectivity to Exchange 2010 and mobile devices are likely to follow.

Make no mistake – if Microsoft still offered Exchange bundled with a small business version of Windows Server, I would likely endorse it.  If Microsoft was extending support for Exchange 2010 and Server 2008, I’d say keep it.  If G-Suite or XO Office measured up to the capability and compatibility of Exchange, I’d say move it.  The harsh reality is they haven’t, they won’t, and they don’t.  Thus, unless ending your reliance on Exchange is a change you’re ready to make, Office365 and Exchange in the cloud is now your best option.

So, in essence, Microsoft has won.  However, there is a bright side: due to massive competition in the Exchange hosting market, Office365 hosting costs less than half what it did in 2013.  Additionally, internet bandwidth offerings have exploded in most areas, dramatically reducing the ancillary bandwidth requirements of hosting Exchange data outside your organization.  Finally, the popularity of Office365 has spawned affordable and comprehensive migration tools to get your Exchange data to Office365 with minimal downtime and IT expenditure.  These three critical factors make the move from your in-house Exchange on SBS 2011 to the cloud a lot more palatable.

To that end, there’s still the overlying reality that your Small Business Server needs to go (or be severely relegated) before the January 14th, 2020 deadline.  This effectively means you should consider replacing your existing server with either Windows Server 2016 Essentials or Windows Server 2016 Standard.  At this time, we cannot recommend Windows Server 2019 Essentials as it lacks client backup and Remote Web Access.  Fortunately, your new server will likely cost less to buy and maintain than your current SBS 2011 server did.  Despite the added cost of an Exchange hosting subscription, you will likely no longer need:

  1. Email antivirus and anti-spam software subscriptions
  2. Specialized backup software for Exchange
  3. Backup email accounts for when your server or internet connection is down
  4. Additional server resources for Exchange data
  5. SSL certificate renewals to keep Exchange securely accessible
  6. Potential vulnerabilities associated with hosting your own mail server
  7. Labor required to install Exchange patches and updates

In conclusion, the end of support for the key components of Microsoft Windows Small Business Server 2011 marks two impending changes you need to make before 2020:

  1. Migrate your Exchange organization to the cloud
  2. Replace your SBS 2011 server

Additionally, if you still have computers running Windows 7, please see my other article 7’s Up: Goodbye Windows 7 as you’ll likely want to replace your Windows 7 workstations in conjunction with your server.

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