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Tips for Remote Troubleshooting Mac, Windows, and Linux Systems



Troubleshooting end users’ computer issues doesn’t have to be tedious or time consuming. The right combination of tools and soft skills can help you isolate issues quickly, reducing the time it takes to close individual tickets and freeing you up for more exciting IT projects. You may even be able to leverage existing tools in your organization — like your directory service — to homogenize the process across Mac®, Windows®, and Linux® operating systems. Let’s walk through some of the ingredients of a stress-free approach to remote troubleshooting.

Efficient Troubleshooting Starts with Soft Skills 

The temptation is always there to just dive into a system and start testing educated guesses, but a more reliable approach starts with effective communication with the end user and concrete answers to the right questions. A little extra time up front can help you fix the issue (or escalate it to the manufacturer’s support team) without too much trial and error. Here’s how to get the most out of your initial conversation:

  • Ask a series of bite-sized, yes-or-no questions. This can be more efficient than having the user describe the issue in long-winded abstract terms. Each successive question should help you decide to either pursue or dismiss a given root cause.
  • Avoid jargon wherever possible. Even though a technical term might be the most accurate and efficient way to indicate something, non-technical users often respond more constructively to language that’s focused on outcomes. Talk about what something does rather than what it’s called.
  • Repeat your understanding of the issue back to the user in your own words. It’s amazing how much information can be lost in translation, leaving you to pursue the wrong solution. Ironically, this tends to happen more often with users who see themselves as relatively tech savvy — they may try to use technical terms and concepts without fully understanding them, or offer a red herring solution instead of accurately describing the problem.
  • Work proactively to form positive relationships with end users. This piece of advice comes from an interview with our own IT admin, Ryan Bacon, who is a strong advocate for treating users as customers and eliminating the us vs. them mentality that sometimes surfaces in the IT world.

With clear information from the user, diagnostic tools can then help further isolate the problem and identify its root cause.

Isolating the Problem with Remote Diagnostics 

It can be helpful to rule out a variety of low-level issues at the outset. This part of the conversation with a user can be frustrating because the user might assume you’re just going through the motions or you don’t think there’s a real problem. But the truth is, a simple reboot sometimes works wonders, and it’s probably worth a try.

A remote system reporting tool can save some of this frustration, enabling you to quickly check a machine’s vitals at the beginning of every troubleshooting session. Ideally, you can do this securely from any location, without borrowing the user’s laptop. And if the system is configured to consistently send telemetry to a central database like your directory, you may not even need to bother with screen sharing. Here’s some of the info you’ll want to retrieve up front:

  • Error codes and logs — even if a code doesn’t point directly to a solution, information as basic as its timestamp could help point you in the right direction by correlating the issue with some other event like an OS update or a change to your environment’s network infrastructure.
  • OS version and installed patches / updates — rule out compatibility issues and make sure auto-update functions aren’t hogging CPU in the background.
  • Last reboot time — ensure that the system isn’t stuck in the middle of an update or that caches aren’t overloading RAM.
  • Network connections — make sure that the user is connected to the fastest and most secure network available.
  • Hardware usage — check available memory and CPU, along with storage capacity, battery health, mounted volumes and their format(s) and partitions.

Fixing the Issue 

Given most manufacturer terms these days, if you identify a hardware issue, you’re more likely to send the whole machine back than replace a component yourself. Still, when it comes to filling out warranty cards and other service forms, it can be helpful to pull a machine’s serial number and other configuration info remotely, before you get the box from the user.

If the problem is related to a software install, a configuration issue, or something else you can take care of in-house, ideally you can do that remotely too. Tools like a remote command runner come in handy, along with a way to push system policies from a central control point. For larger issues, you’ll want to take the data you’ve collected and turn to a full-fledged remote troubleshooting tool.

Essential Remote Troubleshooting Tools 

Your troubleshooting arsenal should include a powerful and secure remote desktop and screen sharing tool. Apple® and Microsoft® have offered different versions of these products for their operating systems over the years, but updates have been somewhat inconsistent and each offering comes with its own bugs and quirks. Instead, we recommend finding a third-party option that’s OS-agnostic. 

With most solutions, you’ll need to have the user log in and grant remote access, preferably with multi-factor authentication for added security. Advanced products will let you access a system that isn’t logged in or powered on, though these can get expensive and you may need to take extra security precautions. Preferences around cost and functionality will vary depending on the size of your organization and the volume of tickets you receive.

Retrieving System Telemetry With a Cloud Directory Service 

One component that’s often overlooked in the context of remote troubleshooting is the directory service. Your directory’s primary function may be to store user identities, managing authorization and authentication to IT resources. But a modern directory service, designed to replace Active Directory® and LDAP, can do more.

JumpCloud® Directory-as-a-Service® integrates deeply with a broad spectrum of modern IT resources, including Mac, Windows, and Linux machines. Its available System Insights™ feature maximizes the directory’s system management capabilities, which also include GPO-like policy control and a remote command runner. System Insights reports hundreds of critical data points from all three major OSs in near-real-time, so it can help you get a head start on remote troubleshooting without clicking around in a screen-share tool.
To see what it’s like having core system data available as part of a modern cloud directory service, try JumpCloud with full functionality for free.


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