Why Your Business Should Regularly Upgrade Operating Systems, Computers and Software

To upgrade or not to upgrade? That is the conundrum. You hate seeing those pop up notifications saying “A Software Updates is Available” and want them to go away. Then again, you don’t feel like taking the time to run and update and reboot. Many businesses struggle to stay up-to-date on their operating systems, apps, and hardware usually out of lethargy, lack of compliance, or personal preference. Sometimes it’s out of fear (“I heard there’s a bug in the new update!”).

Worst of all might be the almighty mental sin of “If ain’t broke, don’t fix it.”

This is where businesses and business owners get themselves into trouble. Often times, companies that started decades ago are using a particular database or application that works just as they need it to. The database or app works as intended for the business, the business expands and grows, and things become very routine and rigid. The problem arises when that database or app is so archaic that it does not work with new operating systems or hardware.

For example, your shipping company founded in the 1990s uses a database we’ll call “A+ Shipping.” Your business grows, you’ve got hundreds of trucks and employees, but the company that made A+ Shipping went out of business or got bought out by a competitor who stopped providing support for A+ Shipping. Because it was developed in the 90s, A+ Shipping doesn’t work on any OS beyond Microsoft Windows XP (or the dreaded Windows Me). Microsoft has stopped offering extended support for XP seven years ago — and that includes security patches and updates. It’s now 2021 and your entire company has hit a wall: the software won’t run on anything available today, the computers employees are using are so outdated they can’t send emails or use web browsers anymore.

And you’re system is wide open for attack. The mentality of “If it ain’t broke, don’t fix it” has now had serious consequences.

Sometimes it’s not that dire; it can just be annoying. We’ve seen businesses use a computer for so long that it’s not even compatible with new printers meaning that even simple protocols for sending jobs to a printer on the network is impossible. A printer breaks, you replace it and suddenly find yourself unable to use workstations in your business.

Upgrading is a simple thing, as long as you do it consistently and regularly. The cliche moaning and groaning from business owners about upgrading computers and equipment comes from past experiences where they waited too long and it became a nightmare. Imagine upgrading from A+ Shipping and Windows XP to a new database software and Windows 10 (or macOS or Linux). One day everything looks different! Not to mention the dangers of upgrading a 25 year old database to something new, risking data loss or corruption.

And if the risk of serious pain or disruption of business isn’t enough to convince you to upgrade regularly, consider the following reasons below.

Enhanced Security


In May 2017, sixteen hospitals across the UK were hit with a massive ransomware attack. If you’re unfamiliar, a ransomware attack consists of breaking into a network, accessing computers and locking users out. Usually, the attacker leaves a message on screen stating the contents of the hard drive have been encrypted and if you want to ever see your data again, you have to pay up. One could imagine the chaos caused by hospitals unable to access computers for client information, schedules, test results, etc. Being the victim of a ransom attack is such a mess, the FBI advises to just pay the ransom if attacked. But back to the UK: the ransomware attack was a Windows security exploit publicly published by a group called TheShadowBrokers in April 2017. The real rub? Microsoft issued security patch before the exploit was published and it’s believed the computers ransomed in UK hospitals didn’t install the update.

If you’re in any kind of business, it’s likely you’re handling sensitive data. At the very least your employees personal information is stored somewhere in HR files. There’s also banking credentials and tax information. Plus client data. The point is, there’s a lot at stake. This makes running security updates and patches crucial to protect your business. Software manufactures continue to monitor for security flaws and zero day exploits in their code. When they find one or are made aware of one, they write a string of code to patch the hole. This patch is issued to all owners. So if you don’t install the new patch, you’ve still got the hole in the code.

It also goes beyond just latest security patches. Hackers and computer thieves seek out old operating systems on the internet to attack. Why? Because companies have finite resources. As new operating systems are written and released, there isn’t enough bandwidth to support antiquated ones. Moreover, an operating system that’s six versions back is being used by very few people to where the costs to the company to continue to support just isn’t worth it (and these few users will likely be reminded to upgrade). That means that old operating systems aren’t getting security patches any more. And no one from the company is monitoring threats to the OS.

A house is only as secure as the weakest door or window locks.

And if you’re running Microsoft Windows, remember to keep your antivirus software up to date!

Increased Employee Productivity and Satisfaction


First and foremost, employees just want to be able to do their job without headaches; and nothing creates bigger headaches than technology not working. As userlane.com puts it: “The one thing that all bad software has in common, though, is that it has a negative impact on employee productivity and makes your employees’ job harder than it needs to be.”

Remember the PC Load Letter gag from Office Space?


According to a 2019 survey by G2, more than half of surveyed employees are unhappy at work because of the software tools they are using. Worse still, a quarter of all surveyed employees claimed the software they have to use at work has made them “consider leaving their jobs.” The same G2 survey also showed that 95% surveyed either agreed or strongly agreed that software “makes them more productive at work.”

So what software you are using directly plays into both the productivity and happiness of your employees. It should also be mentioned here there is a distinction between updates and upgrades. Both are equally important in the context of this article and employee satisfaction. An update is a newer version available of existing software (or firmware). If you’re running macOS, for example, the software update is usually a higher number after the second dot as in macOS 10.15.7. If you have macOS 10.15.1, you update to 10.15.7, incorporating the associated security patches, bug fixes, and improvements of all versions between .1 and .7. An upgrade is the process of replacing an older version of software or hardware with something newer. Going from macOS 10.15.7 to macOS 11.0 is an upgrade; you’re replacing your entire operating system. Replacing your Gateway PC running Windows XP for a Chromebook is an upgrade. Ditching your check reader for an iPad and Square card reader is an upgrade.

Software updates can protect your business by providing security patches and bug fixes. Upgrades can keep your equipment compatible and employees happy.

Improved Network Performance


What’s one piece of technology in your home or office that should be updated the most frequently and almost never is?

Here’s a hint: It’s not your computer or iPhone.

You may be good at keeping your Chromebook up to date, or getting rid of all the annoying software update badges on your iPhone gone, but when is the last time you updated your wireless router?

In 2018, a sophisticated botnet broke into half a million routers. Your wireless router is a single gateway to all networked devices in your home or office. NETGEAR regularly issues firmware updates for their routers to keep protection up to date. In addition to security, network performance and speed can also be tied to updates. Firmware updates can fix bugs or even update the router for faster network speed.

Not only could you be leaving the door open to hackers, but you could be costing yourself precious network speed. Don’t worry though, it’s not just you: a 2014 Tripwire research study found that fewer than half of IT professionals bothered to install firmware updates to wireless routers in their own homes.

Router updates are simple to do and can be done just before going to bed so you don’t suffer the agonizing wait time for your network to come back up. Visit the website of your router’s brand to find out how check for firmware updates.

Prevent Future Complications and Compatibility Issues


Compatibility is the name of the game when it comes to technology for your business. For years, Mac and PC compatibility was an issue when sharing files, installing software, and Microsoft Office sat right in the middle of it. Now, with the widescale adaptation of cloud computing and hosting, operating system compatibility is pretty much a thing of the past. Microsoft Office 365, for example, works on everything under the sun including mobile devices.

But that doesn’t mean you should neglect to do your homework on your company’s technology. Mobile apps, for example, aren’t always available on both Android and iOS platforms. Android app development and submission for Google Play is pretty much wide open while Apple maintains a rigid obstacle course to approving apps for the App Store. You don’t want to upgrade your business software to an app that only works on one platform, alienating your employees who use the alternative.

Updating the software you have also maintains compatibility with the surrounding world. The internet continues to evolve and update at warp speed. If you attempt to keep an old computer on the internet you’ll eventually find the web browser can’t open some, then any, webpages. The first problem outdated browsers encounter is with web codecs, and video or multimedia no longer play or load on sites. As the internet continues to pull away from your archaic browser, less and less of the page loads then finally the dreaded “unable to load webpage” error occurs.

Peripheral accessories almost always require the latest updates on your computer or mobile device. Bluetooth and iOS updates are hyper common when trying to utilize wireless devices with your iPhone or iPad. If you’re using Windows, there’s usually driver updates that need to be installed to use (or continue using) accessories with your computer. Most importantly, these little updates keep you futureproofed as best as possible, allowing you to incorporate the ever-growing Internet of Things (IoT) more into your business down the road.

Update and upgrades are usually nuisances during busy business times. The best approach is to schedule regular update times — most businesses do overnight or weekend updates. A good IT professional will never attempt to do updates during business hours AND leave time for troubleshooting or problems to pop up following updates. This is why Friday evenings are popular update windows for large companies; it gives the entire weekend to fix problems that occur.

The same goes for your home or home office. Run software updates before leaving the house or going to bed. Keep current backups using Google Drive, OneDrive, or iCloud so if a software update erases something you can recover it. Get in the habit of staying up to date with software versions or upgrading when the time comes. If the company that makes your business software no longer offers support, that’s a sign it’s time to upgrade or switch software. Keeping with the old analogy of technology is like a car: the brakes and tires need to be replaced from time to time. Because if you don’t do it, it’s not going to end well.

Understanding Remote Work Security and IT Support in a Post-COVID World

Empty cubicles. Polished cafeterias serving no one. Offices absent of company officers. What seems like the opening of The Walking Dead is how many businesses left their offices at the close of a very challenging 2020. In the wake of COVID-19, business workforces mass shifted to remote work.

It has presented what is certainly a daunting challenge – making the necessary technological and infrastructural adjustments, including everything from boosting network throughput and VPN capacity to implementing remote-in software like Splashtop to access computers at the office. Companies around the world embraced Microsoft Teams and Zoom to continue the new “business as usual” model of teleconferencing. Over the course of 2020, businesses adapted and made it work.

So where does that leave us for 2021?

According to Reuters, the number of permanent remote workers looks to double this year as businesses found that workers are more productive working from home. Businesses (and employees) have embraced working from home. In fact, prior to COVID-19, companies were already shifting to more remote-workers. Four years ago, Dell and UnitedHealth Group were already embracing remote work and, just recently, Forbes believes that an estimated 70% of global workforce will be working remotely at least five days a month, putting it succinctly: “While 2020 may be considered the year of remote work, it is just the beginning as we see the trend continuing in 2021.”

But for many companies, the remote worker model is not without its challenges. First and foremost is cybersecurity — Cisco’s recently published Future of Secure Remote Work Report shows cybersecurity is “extremely important” or “more important than before the pandemic” to 85% of 3,000 IT decision-makers in both small and large businesses. And why shouldn’t it be? Employees aren’t bottled up behind company firewalls anymore; they are sending and receiving multitudes of company data over their home networks. As Cisco’s report put it:


“The global COVID-19 pandemic has forced digital change on organizations at high speed and certainly faster than many had dealt with before the pandemic,” Durbin said. “It meant that senior IT and security managers have been called on to refocus efforts and help their organization re-orientate around secure remote working practices.”


What’s interesting is IT and security are, of course, focusing on protection measures for company communications and data. What are not being discussed enough are the simple protection measures that every remote worker can and should be taking at home. A 2018 User Risk Report from Proofpoint found that, out of 6,000 surveyed technology users in the U.S. and Western Europe, a whopping 44% of respondents say they have not added a password to their home Wi-Fi networks! “In addition,” the report goes on, “that despite widespread FBI warning earlier that year about router vulnerabilities, 66% of users have not changed their router’s default password and 79% have not updated firmware.” Cybersecurity extends beyond the company’s IT — remote workers need to take it upon themselves to make sure their home networks and technology are secure.

In addition to home security, companies should be wary of whether end users’ home technology is up to the challenge of a permanent workload beyond passwords and router firmware. Are a company’s end users using older routers with outdated 802.11 type networks? An old router can severely crimp load speeds, a potential headache for end users dealing in large files and zoom calls. It’s not just speed — Wi-Fi range can also be impacted, limiting a remote worker to a particular room or corner so they don’t lose connection. Maybe they also live in an area with limited cable internet coverage. As Vox puts it, “remote work requires reliable, secure at-home broadband connections that can power video conferences. Because much of rural America lacks broadband internet, remote work is restricted to areas with access to that tech.”

Shifting Toward an All-Remote Model

Here are some of the greatest challenges that companies with an all-remote model are facing and how best to overcome them:

Remote Support

Prior to COVID, most IT support teams were on site and resolving end user tickets either over the phone or at the users’ desk. A faulty keyboard or charger needing replaced was a simple fix: stop by the cube or office and swap the item out. It kept customer support personal.

In the realm of all-remote support, everything must be done by phone, computer, or mail. Desktop support teams quickly adjusted to resolving issues by walking customers through processes or procedures over the phone, or remoting in and taking control of an afflicted users’ device. For physical device replacements, the operations side of things has gotten busy shipping and receiving product to and from end users.


New hires are beginning their first day of work at home, and may not even venture into the office for weeks.  This makes efficient deployment critical so the new worker has their company asset at the home on the first day and pre-installed with all necessary software to access the company network, files, and email.  In some cases, a company may send out a pre-provisioned asset.  FedEx or UPS drops the laptop or mobile device off at the user’s home, the user logs in and finds everything they need to get started.

Challenges remain in doing this to scale because large numbers of assets need to be pre-installed with company software, updates run, network or VPN configurations  setup.  Then someone has to ship and track all the shipments up to delivery.  This is where MDMs really shine, particularly with zero-touch deployment.  By utilizing Apple Business Manager or Microsoft Azure, brand new devices can be shipped from the seller to the end user, bypassing the company altogether.  The asset connects to the user’s home network and “checks in” with the Mobile Device Manager.  The device then begins to download all the predetermined software and configuration.  Even in a post-COVID world, companies that need to deploy large amounts of new assets to users, zero-touch simplifies things enormously.  As 9to5mac.com puts it:


“When the world gets back to ‘normal’ in the post-COVID–19 world, I think the workplace will be changed forever. That means that IT policies will change forever. If a large subset of employees is working remotely, how will you do device deployment when your IT policies and procedures are all built around in-the-office employees? This fact is why zero-touch implementation has to be central to your future device deployment plans.”


Inventory Management

In “the before time” of pre-COVID, inventory might have been more manageable. The end user was usually working in their cube or office, where their company-issued asset was. If you needed access to a computer, or if a user left the company, it was easy to track down an asset. With remote work, company assets are scattered to the wind. Collection of terminated or retired end users become critical, as does securing an asset with company data on it. This would also include collecting assets that need to be serviced or repaired and getting a working computer back to the user with absolute minimum downtime.

Consider creating a dedicated operations manager role that is responsible for all inventory coming and going. With workforces going remote, it is imperative to figure out how best to manage the new way physical devices and accessories are being handled. If not properly monitored, costs could quickly rise for a company with poorly managed inventory; lost assets and accessories would have to be replaced much faster.

File and Documentation Access

This area of focus is critical for all businesses, small and large. Sometimes, when working remotely, business owners or employees need to access company information or even company computers left in the office. Sometimes a user needs to be able to access devices at their desk and print something at the office without ever going in. Software like Splashtop comes in handy for small businesses who need to remotely access an office computer (and fulfill tasks like printing elsewhere from home). For larger businesses, a VPN is usually required to safely join the company network for access to shared network drives.

Also included in this group is sharing documentation among end users. In the past, users could gather in a meeting room or stop by one another’s desk with a laptop to share presentations or spreadsheets. Now, these documents are almost exclusively shared amongst each other virtually, requiring the ability to edit, comment, and make notes and pass back. Microsoft Teams and Google Docs offer easy solutions for sharing and collaborating on documents.

The other point to make here is the absolute necessity of Mobile Device Manager (MDM) software. MDMs allow for more automation, ensure security and software version compliance, and provide real-time status of physical location and device status. They allow a company’s end users to work from anywhere in the world and still receive updates, track location and provide security (imagine losing your laptop full of company secrets on a crowded bus or train — an MDM allows it to be tracked, locked down, and even remotely erased if necessary).

A proper MDM setup helps resolve the challenges I listed above. By utilizing JAMF, a company’s fleet of devices can be easily managed wherever they may be. Updates are sent out regularly to prevent any potential security holes with out-of-date or unpatched software. Deployment is greatly simplified, even to the point of “zero-touch” where a new hire can receive a brand-new device, and watch as the device “checks in” with the MDM and sets itself up. And, of course, inventory management — with an MDM, we can track and “see” every device, as well as lockdown systems and remote erase.

What Your Business Can Do to Adapt

Remote workforces and remote support is here to stay in 2021. Companies that were caught off guard by COVID need to embrace remote support and transition their IT to manage workers offsite. Even if the COVID vaccine brings a ‘return to normalcy’, employees have adjusted (and come to enjoy) working remotely. Therefore, employers should be prepared to welcome and support a remote workforce.

For business owners and IT managers, the following steps are recommended to begin the journey to a healthy remote support environment:

  1. Embrace an MDM – Whether it’s JAMF, In-Tune, MobileIron, WorkspaceOne, make a Mobile Device Management system a welcomed addition to your company. It will only help with management, deployment, and support.
  2. Give Your Employees Guidelines for At-Home Setups – A simple guide for employees to review their home setup. Chances are, it hasn’t changed since they moved in. Help your end users identify out of date routers, secure Wi-Fi networks, and check network speeds. Are they using surge protectors? Do they have roommates? Should their company asset still be cable locked even at home to prevent theft? You can even consider in-home consultation to end users, reviewing their setup and making suggestions and upgrades.
  3. Bolster Your Desktop Support – For Mac systems, conventional “Windows IT” is usually left to handle MacOS and LinuxOS support. This is a situation that would be easier to navigate in person as the IT support specialist could usually fiddle with the Mac or use trial-and-error to resolve an issue. Now, Mac and Linux support is even more critical because it’s being done over the phone or at a distance; it pays to have knowledgeable people ready to assist to prevent downtime or user frustration.
  4. Consider the Cloud – A lot of big company architecture is unwieldy and outdated; e.g. not suited for a totally remote workforce. On prem servers require security and firewall credentials, as well as proper access if being contacted from off-site. This can make MDM deployments tricky. Hosted on prem email or file sharing can also bog down a company