Microsoft Windows: End of the World (Support)


Companies like yours need to keep up with strict business, compliance and industry regulations. New threats have made it harder than ever to secure data and applications. With end of support for Windows Server 2008 (including R2) and Windows 7 operating systems approaching, the time to prepare is now, not in December.  Waiting will not make it go away.

Although you can certainly make logical arguments upgrading and modernizing applications should and will lead to improved capabilities and efficiencies for end-users, in this case not upgrading introduces significant risks to the company.

End of support means the end of critical security updates, opening the potential for business interruptions. Worse still, without regular security bulletins it is impossible to guarantee protection against hackers or malware.

Unfortunately, the technology world still communicates in technical terms not easily understood by the business community.  This is still the case with Microsoft’s announcement regarding the end of support for products.  Simply stating an end of support date looming for Windows Server 2008 (including R2) and Windows 7 doesn’t mean it resonates with the business community using those software applications.

The first question often is…

What do I need to do about the end of support?

… when the first questions should be:

What products are impacted by end of support?

What do these products do?

Do we currently run or use any of these products?

So let’s take a step back and answer those questions.

What products are impacted by end of support?

  1. Windows Server 2008/R2 January 2020

  2. Windows 7 January 2020

  3. SQL Server 2008/R2  July 2019

What do these products do?

  1. Windows Server 2008/R2 – is the foundational software used by most companies to manage their users, assign security permissions to users and groups, and support other software sitting on top of this foundation.  The scope and impact is company-wide.

  2. Windows 7 – is the operating system software used by end users on their individual desktops/laptops and support other software sitting on top of this foundation, for example, Outlook, Microsoft Office.  The scope and impact is the end user.

  3. SQL Server 2008/R2 – is the database software other software uses for database functionality, for example, Great Plains, industry specific software.  The scope and impact is company-wide.

Do we currently run or use any of these products?

To know if you are using any of the solutions impacted by end of support, you should rely on your technology department or provider to conduct an assessment of all the systems currently in use and provide a report showing the current versions and usage of those products.

Once you have a report, whether you have 1 or 100 systems impacted, you should then use the information to develop a plan for addressing each one.  Some systems may take months to address, so having a plan sooner than later will save management potential stress and sticker shock.

What to expect.

Let’s assume you’ve had an assessment done and determine you have 4 servers running Windows Server 2008 R2 and 25 workstations/laptops running Windows 7 Professional.  Developing a plan for addressing them should be tailored to your specific business, budget and system use.  Workstations may be replaced quickly, where servers may take months.

Cost is not the only factor.

Using our example, a ‘refresh plan’ should be defined for every workstation running Windows 7 Professional.  If the workstations are 4 years or older, it may make more fiscal sense to replace them with new machines running the latest Windows 10 operating system.  If the machines are still acceptable from a performance specification standpoint, it may make sense to upgrade the machines to Windows 10 Pro from Windows 7 Professional.  Aside from the costs related to these options, consideration should be given to how employees are using those machines and what potential improvements might be gained from a machine replacement versus upgrading only the software.  To avoid a large capital expenditure (CAPEX) cost at the last minute in December, you may want to spread out the purchase of replacement machines over the next 5-6 months.  A simple method is to take the number of machines, 25 in our example, and divide by the number of months remaining before you want them all replaced.  It is now June, so assuming replacement needs to be completed by January 1, 2020, purchasing 4 machines a month July through November and 5 in December would have them all replaced by year end, spreading the cost over time.

Migrating servers from Windows Server 2008 R2 requires more analysis and planning because typically servers are running mission critical software applications for the business.  It is not best practice to upgrade a Windows Server operating system as you typically would with a Windows end-user operating system and in most cases, it would be recommended to migrate to a new installation.  Some standard questions to consider during planning include –

  1. What business software is running on the server?  Will that software run ‘as-is’ on a new version of Windows Server 2016 or will it require an upgrade as well?

  2. Is business software running on Windows Server 2008 R2 that is NOT supported by later versions of Windows Server and will not run on later versions?  Should the business software be replaced with software more current and supported?  Should we continue to run the software on Windows Server 2008 R2 knowing the significant security risks?

  3. What impact will downtime have on the business related to migrating servers?

  4. Can they all be migrated during a single timeframe (likely a weekend) or does it need to be a phased approach?

  5. Does the server hardware need to be replaced along with the Windows Server software?  If so, what are the options now available that may not have been available 2-5 years ago?

  6. Will our customers and vendors be impacted by any of these changes?  What notices should be sent prior to the changes?

Don’t wait.  Get help.

If all this seems overwhelming, you’re not alone.  Many companies read the headlines and do nothing about it because it’s just too much to contemplate and is a major distraction to normal business duties.  Because of the very real security risks, this is one of those times procrastination can really hurt the business exponentially more than the cost associated with addressing the issue. 

You don’t have to do it alone.  Fluid has been working all year and will continue to through the end of the year to do the heavy lifting for companies.  From the assessment, planning, recommendations, obtaining necessary quotes, working with third-party vendors, and implementation, we try to do as much as possible to keep the business running.  We will take on the tasks management and operational staff don’t have time to deal with.  The additional benefit is knowing it will be done with technology proficiency and discipline many companies simply don’t have in-house.

If you do not know if ‘end of support’ will impact your company, you are at risk.  At a minimum, knowing your exposure should be a top priority.  Waiting until December may make the holiday season more stressful than it needs to be.  If you need help, we’re here to do so. 

You can reach Fluid at 866-802-9848 or via email at secure@fluiditservices.com


Does anyone really understand Office 365?


I was recently asked to provide training for Office 365.  This innocent request is like asking for training on airplanes.  The wide variety in types along with new releases with new features is a moving target.

Just when you think you’ve finally turned the corner to understanding Office 365, Microsoft releases half a dozen new products in a flurry to get them in the marketplace.  This has been a recurring theme over the past three years, seeming with no end in sight.  Trying to keep up is a daunting task, Microsoft itself often can’t answer questions about their own products.  They certainly lack any consistency.

This puts a tremendous strain on companies like ours who recommend, implement and support Office 365 products.  If our experts have a hard time keeping up and understanding the products, imagine what is like for a business trying to determine if Office 365 is right for them.

To make my point, let’s just scratch the surface of Office 365.  There are roughly seven bundled versions of Office 365 license types for business use.  Within each of these license types are “included applications”.  This is where it really gets interesting.  The Office 365 E3 license includes the following applications and services:

  1. Outlook

  2. Word

  3. Excel

  4. PowerPoint

  5. Access

  6. Publisher

  7. Exchange

  8. OneDrive

  9. SharePoint

  10. Teams

  11. Yammer

  12. Stream

Many of these applications and services may be recognizable and some completely foreign.  Understanding and using some of the more obscure applications and services are a luxury only attainable with an internal IT staff dedicated to Office 365.

This list is not near the end of it, not even close.  There are hundreds of additional add-on products and services to Office 365 for specific purposes.  Here is a very short sample:

  1. Visio

  2. Project

  3. Phone System

  4. Audio Conferencing

  5. Advanced eDiscovery

  6. Advanced Threat Protection

  7. Kaizala

  8. Intune

  9. Cloud App Security

  10. Meeting Room

  11. Enterprise Mobility + Security

  12. Dynamics 365

  13. Power BI Pro

  14. PowerApps

  15. Azure Active Directory

  16. Flow

  17. Windows 10

  18. Microsoft 365

Each of these products has multiple options and features to choose from.  In addition, there is an entire Office 365 Marketplace with thousands (over 2500) add-on third-party applications.  You get the picture.

Here’s a link to see for yourself: https://bit.ly/2JpXKkK

Adding frustration, many of these products change names (as with the Skype for Business change to Teams) and are released without, in my opinion, being fully vetted for any problems or bugs.  The general public ‘doesn’t know what they don’t know’ and may try deploying solutions that don’t meet the business need, don’t work reliably, or both.

It’s not all negative

Office 365 has provided a wealth of valuable productivity solutions at very affordable prices making them now attainable for the smallest of businesses.  When understood and used properly, business productivity and value can increase dramatically.  But there’s the rub.  The products must first be understood and then implemented properly with adequate training to take full advantage.

Consider again the original request: provide training for Office 365.  To train for Office 365 there must first be training on the Office 365 family of products and ecosystem to determine what is relevant for the business.  Care must be taken to understand and delineate mature and robust products from recently released ‘bleeding edge’ products.

It’s our job to understand and keep up with Office 365.  Internally, we must continually deploy and test new products to understand them, learn what works well, what doesn’t, and where they fit within business use cases.  Teams and Voice is a great example.

Skype for Business changed to Teams and added voice plans last year.  Teams is included in many Office 365 licenses and Voice is included with the E5 license or as an add-on.  We migrated from Skype for Business to Teams and from our previous voice provider to Microsoft Voice last year.  Transitioning voice services to Microsoft was not for the faint of heart.  Will our number transfer (port) correctly?  Will the voice quality be acceptable? Will the auto-attendant have the features we need?

Surprisingly, the migration of our voice services to Microsoft was easy and the quality has been excellent.  A pleasant surprise.  The migration to Teams was not as smooth.  Teams is a great application with an abundance of really great features consolidated in one place.   It has improved our collaboration and productivity while allowing us to shed products.  Answering a call within Teams and then sharing files, sharing screens and instant messaging during the call is awesome. 

The ‘gotcha’ with Teams has been SharePoint.  Transitioning our files to SharePoint was very time consuming and the change in ‘look and feel’ and how files are accessed has been difficult.  There have been painful performance and accessibility issues, including some downtime.  But we now know the details to better advise our clients through real world use.

Providing education and advice on Office 365 products prior to purchase and implementation will reduce the amount of surprises and frustration.  Ensuring every user understands the capabilities proactively will also reduce the amount of support requests related to the roll-out.  Time spent up front will pay dividends towards a smoother implementation.