Author Archives: Chris Filippi


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.

Windows 10 – Revisited

July 12, 2016
Chris Filippi
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It’s been nearly a year since my previous article regarding Windows 10 (Should We Upgrade to Windows 10 Now?, 7/27/15), and by popular demand, it seems time to revisit the Windows 10 issue in its entirety.  Though my position on Windows 10 for the vast majority of Windows 7 and 8 users remains unchanged, I’d like to offer a little insight from our involvement with Windows 10 as IT professionals and my own personal experience.

First off, we are not recommending upgrading to Windows 10 on systems currently running Windows 7/8/8.1 with the following, extremely limited exceptions:

  1. You’re using a Microsoft Surface that shipped with Windows 8.1 and your software is 100% compatible
  2. You need 3D printing capability
  3. You have an Xbox One that you need to interface with
  4. You have a handicap and can significantly benefit from Windows 10’s new accessibility features like Cortana
  5. You just bought a computer that shipped with Windows 8.1, is Windows 10 ready, and you’ve done little to the machine other than take it out of the box

Second, if you’re purchasing a new machine, we fully recommend getting Windows 10 preinstalled provided:

  1. All the programs you intend to install are Windows 10 compatible (e.g. you’re not going to install QuickBooks 2014 or earlier, Office 2007 or earlier, etc.)
  2. If you’re setting it up yourself, you understand the security options and the implications of signing in with a Microsoft account instead of a conventional logon

Now, let’s go to the “why” of the Windows 10 equation. Windows 10 is indeed a relative improvement over its predecessors and is invariably the de facto standard for new PCs.  That said, it’s not without its foibles and potential consternation with users.  To exemplify, I’ll resort to my own personal transition from Windows 7 to 10 on one of my primary machines.  I’ll then review the results and put it in a more general context.

Let us begin…

About 9 months ago, I performed a clean install (not an upgrade) of Windows 10 on my personal laptop – a Samsung Series 7, circa 2011, which shipped with Windows 7.

I’ll begin with the positives:

5 Things I Love About Windows 10

  1. Boot speed – Windows 10, like Windows 8.1, offers remarkably faster boot and wake speed than Windows 7 (albeit when it’s working right – see below).
  2. Better search capability – Again, like Windows 8.1, the search capability in Windows 10 is dramatically improved: searches are faster and more intuitive across the board.
  3. Window snap – I’m constantly moving data from one program to another (e.g. copy/paste from Excel to Outlook) or need to see two programs at once, and have become truly enamored with how well windows can be shuffled in 10. The side-by-side feature is so beautifully intuitive and efficient I often prefer it to my 3 monitor desktop still running Windows 7.
  4. Multiple desktops – As a proverbial “Power User” I frequently have a lot going at once. Multiple desktops (a feature Linux users have enjoyed for years), is a solid way to keep computer tasks visually organized – even when the workflow is chaotic.
  5. Notification Center – The Action Center of Windows 7 is a complete joke compared with the new Notification Center in 10. Besides being able to immediately adjust my system environment (e.g. Airplane Mode), I get a full read on what’s waiting for me (e.g. unread messages in Outlook)

Next, the regrets:

5 Things I Miss From Windows 7

  1. Jump lists – The ability to “pin” frequently used documents and folders to the taskbar in Windows 7 via a “Jump List” (i.e. right-clicking on a taskbar icon) was a huge performance boost: instead of repeatedly navigating through the same folders, commonly used files and locations were instantly accessible from anywhere. For whatever reason, this functionality is limited to only 10 items per jump list in Windows 10.
  2. Windows Media Player / Media Center – Since the tragic loss of my beloved iPod many moons ago, I elected to put my music collection on a Windows media server, shrugging iTunes in favor of a more flexible solution that would sync music to everything. The Windows 10 replacement “Groove” is little more than a sadistic portal to buy music rather than enjoy what you currently have and put it on your devices.
  3. Wireless Network Management – the ability to retrieve the wireless passkey for a network you’ve previously connected to (even though you’re not connected right now) or searching / removing said previous wireless networks is fundamentally impossible in Windows 10 without using a cryptic command prompt interface.
  4. Single Control Panel – While Windows 10 effectively eliminated the schizophrenia of the app (aka Metro) vs. program (aka Desktop) world that plagued Windows 8, the ability to control basic computer settings remains wholly disjointed.
  5. VPN – Configuring a VPN in Windows is a pain (akin to configuring a dial-up connection in Windows 95), yet Windows 10 makes it even more laborious, requiring two completely isolated interfaces.

And finally, the ugly:

5 Things That Drive Me Nuts with Windows 10

  1. Start Menu – As much as I appreciate Microsoft’s efforts to combine the Windows 7 and 8 Start Menus, I truly pine for the pure simplicity that was in Windows 7 – while tiles are pretty, they’re generally useless, and “grouping” programs by alphabet letter just means more scrolling.
  2. Firefox breaks – There is little doubt, despite Mozilla’s advertising, that Windows 10 is a hostile environment for Firefox: be warned.
  3. WDS printer installation – Windows 10 loves to find stuff on your network that you can use, even if it prevents you from using it after it’s found it. Such is the case with WDS printers that Windows 10 seems fit to install; then don’t work, whereas the conventional installation of the printer works fine.
  4. Libraries – Libraries allow an amalgamation of multiple document repositories in one place. Thus, users with data on multiple servers or drives could search for files and content across numerous locations in one shot. While Library capability persists in Windows 10, it must be manually enabled, and the “Documents” link in the File Explorer points only to local documents, not the Documents Library.
  5. Edge – To say “Microsoft Edge was not ready for the world” is arguably the understatement of the year. Less than a month after it was released, hijackers had already figured out how to compromise it, and it took Microsoft over a year to provide a viable plug-in architecture. By contrast, Google Chrome has evolved leaps and bounds over the last year (version 51 as of this writing) and has garnered massive adoption despite not needing to crush Netscape.

Keep in mind, all the above conclusions were formed after I got Windows 10 working as it should – and getting there was no small matter.  Despite the fact that the Microsoft Compatibility Checker reported no issues with my 4-year-old hardware and I was performing a clean installation on a brand new, totally blank hard drive, I ran into two major issues:

  1. My laptop, like many high-end machines of its era, featured hybrid (aka “switchable”) graphics – essentially an integrated video card that uses low power for regular 2D work combined with an dedicated video card for games and video playback. Despite the latest drivers and updates, my laptop took a full 45 seconds to “awake” from sleep – previously instantaneous under Windows 7. After a few hours of research and countless restarts, I managed to resolve the issue. However, if I was paying for my time, it would have made more sense to get a new machine.
  2. To combat the poor performance of conventional laptop hard drives without the decreased capacity and excessive cost of a solid state hard drive, my laptop employs a small, high-speed solid state hard drive to cache regularly accessed data on the significantly slower though massively larger conventional hard drive. After Windows 10 was installed, the solid state drive was effectively useless – lying idle while my laptop chugged away grasping for data from the slow mechanical spindles. Again, I was ultimately able to get the cache functionality working again, but not after a significant amount of time and frustration.

All told, I have fully functional Windows 10 laptop at the cost of a new hard drive plus several hours of my time – but while I get my time for free, my clients do not. Ergo, this “upgrade” would be a complete loser for a customer – especially if their system was working just fine under Windows 7, as mine was.

Nearly one year ago I said:

Since Windows 7 will be supported by Microsoft until 2020, it’s reasonable to assume that all Windows 7 computers currently in the field or purchased this year be supported for their service lifetime. By the time Windows 7 is no longer available preinstalled for new system purchases (probably within 6 months), we will likely be recommending Windows 10 as opposed to Windows 8.1. At that point, new systems will have hardware specifically designed to work with Windows 10 and the majority of common software/hardware ailments should be sufficiently vetted and solved.

Granted, Windows 7 will still be available on new systems for at least 2 months at this writing, possibly 5 (the crystal ball was apparently less optimistic a year ago), but new systems shipping with Windows 10 are indeed built with Windows 10 in mind – and we recommend them heartily – provided your software is compatible.

As for the upgrade question, I again quote from nearly one year ago:

  • From a productivity standpoint, Windows 10 has little improvement to offer the modern desktop. Users aren’t going to start barking orders to Cortana and the replacement of Internet Explorer is likely to create more problems in the business world than it’ll solve.
  • Changing the user experience is never a good idea unless there’s an immediate benefit. While Windows 10 certainly starts faster than Windows 7, offers superior touch-screen support, etc., there’s very little the average user will be able to take advantage of vs. the frustration of adapting to a new working environment.
  • There are a number of privacy concerns with the Windows 10, the bulk of which have yet to be understood. As the nature, manageability, and intent of the data collection Microsoft has implementing is largely unknown (and highly reliant on third-party research), we cannot assure users their information nor computer use is safe.

Given that nearly 7 out of 10 laptops and 3 out of 10 desktops in our experience suffer from one or more significant, negative impacts after “upgrading” to Windows 10 leads to one invariable conclusion: with little to gain and a lot to lose, “upgrading” to Windows to 10 is simply a gamble you shouldn’t play. Unless you’re in one of the few categories mentioned above, please ask yourself why you would want to upgrade other than:

  1. It’s new, so it’s better
  2. It’s gotta be better than what I have now
  3. I’m gonna miss out because my “free” upgrade ends this month
  4. Microsoft wants me to
  5. Microsoft keeps pestering me to
  6. Microsoft pestered me again and then totally f***’d me by “upgrading” my system without my consent and now I’m stuck with the f***’n thing!

Now Google Windows 10 Upgrade Sucks – I got 984,000 results in 0.4 seconds the last time I tried; you score may vary.

There’s zero doubt that Windows 10 will be improved and become more ubiquitous over the next few years. Software designers will be forced to embrace it and hopefully Microsoft will repair what ails it.

Nevertheless, our general answer to the Windows 10 “upgrade” question remains the same a year later: Don’t.

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