Provide Remote Assistance to Your Off-Network OS X Users

It’s forecasted that 202 million laptops will be sold in 2016, compared to 127 million desktops.  As we all know, laptops are mobile and often off of the corporate network.  Not only does that mean the device should have proper encryption to protect the private data, it also means that standard administrative tasks such as patching a machine, distributing software and having access to the device to perform a remote control session can be much more problematic – or even down right impossible with the current management tools.

For LANDESK Management Suite customers, however, off-network access is completely feasible. An administrator can essentially follow the exact same workflow to patch, distribute software or perform a remote control session when properly configured with a LANDESK Cloud Service Appliance.  No VPN is necessary and no end-user interaction is required!

If you need to know how to install a Cloud Service Appliance in your environment, see Best Known Method for Configuring LANDESK Cloud Service Appliance (former Management Gateway) version 4.2 and newer

Better yet, in LANDESK Management Suite 2016, the certificate approval process has been significantly simplified by switching the certificate approval process to the core server. Essentially every agent install will create certificate for the Cloud Service Appliance and present itself to the LANDESK Core Server.  The administrator just needs to approve or block the per device certificate on the LANDESK core to grant or deny that device off-network access.  For more detail around this process, see this LANDESK Community article.

Once the certificate is approved on the core server for the device, an administrator can deploy patches and software distribution via a policy delivery method and perform an on-demand remote control session to the device off the network.  The client will also continue to send in it’s scheduled inventory and security scans assuming it has internet connectivity.

How to Perform a Remote Control Session to an Off-Network OS X Device

  1. Launch the LANDESK Management Suite Console
  2. Expand the Network View and find Devices > All Devices
  3. Find your desired machine from the list or use the search bar at top
  4. Right click on your OS X device and select ‘HTML remote control’ and the machine’s default browser should launch
    • If nothing happens and you don’t see a browser launch, it means the machine is not connected to the CSA and may either be powered off or without internet connectivity.
    • To verify, you can go to the remote control page on the CSA by using the URL: https://cloudserviceappliancename/rc. Not only this an alternative way to remote control a machine, but it will show you a list of all available clients that have an active internet connection.
  5. Enter your LANDESK username, password and the domain associated with the user that has access to perform a remote control session. If you’re using a local account, you can leave the domain blank.
  6. Note: Not only does the user need to be a remote control operator, but the machine must be enabled for remote control as well. Furthermore, the machine may be setup with user permissions that would require someone physically present on the device to grant access.

How to Deploy Software to an Off-network OS X Device

 When a LANDESK agent is deployed to a client device, is creates a scheduled task to call back into the core server to see what policies it has been targeted for.  For machines that are going to be off-network you may want to set policy check in to be every 2 hours. There is obviously a trade-off between over burdening the core server with requests and knowing a machine only checks in once a week, so find what the right balance is for your environment.

  1. Open the Distribution Packages tool within the LANDESK console
  2. Right click on the Mac software distribution package to deploy and select Create Scheduled Task
  3. Right click on the scheduled task that was generated and select properties
  4. Add your desired targets to the Targets menu
  5. Set the Task type under Task Settings as a policy
  6. If you’re targeting a group of machines that may have some of them on the network and some off, you may want to use a policy-supported push
  7. Set the radio button in the Portal Settings to either Recommended or Optional if you desire to put the package into Workspaces.  If you’d like to automatically deploy the app, select Run automatically
  8. Change the Reboot Settings or Distribution and Patch settings if desired
  9. Set the schedule task settings with the appropriate start time

How to Deploy Patches to an Off-network OS X Device

  1. Open the Patch and Compliance tool within the LANDESK console
  2. Ensure your desired content is in the Scan folder
  3. Right click on the definition and select Repair
  4. From the Add targets select on the Repair settings task panel, select Add all affected computers
  5. Set the Task type under Task Settings as a policy
  6. If you’re targeting a group of machines that may have some of them on the network and some off, you may want to use a policy-supported push
  7. Ensure the Display in portal option for the portal settings panel is set to Run automatically (unless you want your users to update their own apps, in which case you can select Recommended or Optional)
  8. Schedule the task to start when desired from the Schedule task panel
  9. Save the task

Does Your Mac Patch Process Rely Solely on Hope and Prayer?

The Hope and Prayer of a Contractor

My family and I love to play pickup basketball games together in our backyard. We do however, live in Texas, and as you probably know, Texas summers are hot. Due to the heat, we decided it would be wise to install an overhead light on the basketball court so we could play hoops when the sun goes down. Since I’m not electrician, we contracted out the work in early February.

Well, it’s now the middle of August and we’re still waiting for the electrician to finish his job. Last week I was pressing the general contractor for a commitment for a specific day for the work to be done. Let’s just say his response was not exactly what I was expecting.

“He said next week for sure. Praying that happens.”

Now, I am a very religious individual and strongly believe in the power of prayer. I even believe prayer should be invoked on behalf of our businesses and livelihood.

However, I believe prayer is a tool to be used after we’ve done everything possible on our end to bring about our desired outcomes. I do not believe prayer should be a tool used as a crutch to overcome our own lack of effort and planning (James 2:20). A general contractor, in my opinion, should be able to effectively work with his team and his subcontractors to gain commitments and delivery dates without doing anything more than throwing it onto the wings of hope and prayer.

How Does this Relate?

So what does this story have anything to do with patching processes for Macs?

To that, I say, good question. In response, I’ll answer your question with a question. Are you secretly relying solely on hope and prayer that the Macs in your environment will simply be self-managed by the savvy users that employ them? After all, Mac users want to be treated differently, right?

I was on a phone call again on Friday and asked the IT administrator if they have just Windows devices employed in their environment, or if they have anything else such OS X devices and/or Linux devices that he would need to manage. His response is about as common as it gets.

“We have some Macs, the total number of which is growing, but it’s mainly just our marketing team and several of our executives. At this time, we don’t manage them.”

You don’t manage them? Wow! How often do we hear the idiom “a chain is only as strong as its weakest link?” Why do organizations invest so much time and money in their infrastructure when they’re only going to patch a percentage of the total attack vectors, leaving the remaining portion to chance…or was that to hope and prayer?

The Vulnerability Data

Common Vulnerabilities and Exposures is reporting that OS X has 178 new security vulnerabilities published in 2015 alone. To compare, that’s more than 2013 and 2014 combined and we still have a third of the year to go – this data only includes vulnerabilities released up until the first week of July. It doesn’t account for the latest zero-day vulnerabilities being reported this week here and here. Furthermore, of the 178 vulnerabilities, 25 of them allow the attacker to gain additional privileges on the compromised system. To put that into perspective, 25 new privilege vulnerabilities is greater than all previously reported exploits of the same type over the last eight years combined!

NumberofVulnerabilities GainPrivileges

Hoping and praying an attack doesn’t surface, through the management process of “look the other way”, is incredibly risky and could potentially cost you millions. Infosec Institute is reporting that in 2013 “the average annualized cost of cybercrime incurred per organization was $11.56 million, with a range of $1.3 million to $58 million.”

So What Do I Do?

Sounds like it’s time to quit relying on just hope and prayer and to put forth some action. So where do you start? First and foremost, obtain a tool that allows you to scan your managed machines against a known vulnerability list that you can control, and ensure your machines scan on a frequent basis and then centrally report up their results.

Just knowing where you stand against the 178 new vulnerabilities is a great start. It will also give you the information you need to make intelligent business decisions.

Notice that I mentioned you will now have the data to make intelligent business decisions. Blindly patching all 178 vulnerabilities without properly testing them, while better than completely ignoring them altogether, is not moving forward intelligently. If you were to blindly patch everything, there’s a good chance you could break a critical business process which in turn could potentially affect your organization to the tune of millions of dollars as well. So be careful and use caution.

Many security pundits will encourage you to test and evaluate new patches in phases. Apple doesn’t have a “Patch Tuesday” so you’ll need to be constantly vigilant about when Apple releases new security updates. Hopefully the tool you use to scan your machines can notify you of new content. If not, keep on an eye on Apple’s Security Updates page found here.

I personally like to break down my patch process into five distinct phases:

  • The lab test phase
  • The smaller, more controlled initial test pilot phase
  • The larger, greater reach secondary pilot phase
  • The mass rollout phase
  • The exception handling phase

The size of your organization and the resources available may force you to adapt, and that’s alright. It’s the checks and balances part that is critical.

The Lab Test Phase

Inside the lab test phase, you should have replica environments for the different types of configurations you have deployed in your environment. Keep them up to date with reality. Make sure when you update your critical business applications in production that you also update your test lab machines. Almost as important, make sure you downgrade the business critical applications to the current release version when testing new security content. Don’t think just because the Apple security update works with version 2.2.x of your business app that it will also work with version 2.1.x.

In order to advance out of the lab test phase, ensure that your exit criteria has been defined and that it meets your success metrics. These metrics may be as simple as defining a machine has been patched, it still can be logged into and that the critical business applications can still be opened. You may also decide to get much more granular, that’s up to you and your organization’s tolerance for risk. What’s important is that a set of defined exit criteria has been established. You can’t be successful if you don’t know what success looks like. Once you have success, document the status of your exit criteria with times and dates and move on.

In regards to timing, when new content comes out, you should be immediately testing against your lab machines.

The Smaller, More Controlled Initial Test Pilot Phase

Once you’ve validated the content against your lab machines and have met your successful exit criteria, move on to a focused pilot group. This is stating the obvious but members of this pilot group need to be using machines that match the type of devices deployed to your entire corporation. That may mean you’re going to need to find dozens of different types of users to match finance, engineering, marketing, etc. Understanding your different user types is critical. Furthermore, these individuals need to be flexible and must be willing to communicate when things don’t work. Build feedback channels into your process that are easy to use. If something breaks, the pilot test group user should know exactly how to contact you with the information you desire.

The next obvious step is to notify the pilot group that patches are coming so they know to be alert and aware.

Just like with the lab test phase, define your exit criteria and document it. Not everyone in your pilot group is going to be available 100 percent of the time. You may have to settle with a 100 percent approval rating from your test group, or up to seven business days. Define what success is, establish the process, and once you can quantify whether you’ve hit your metrics, move on. If you can’t meet your success metrics due to issues, single out the offender and proceed with the rest while you move the offender into the exception handling process.

Ideally, you should be able to wrap up this phase within three to 10 business days from the initial content publication date.

The Larger, Greater Reach Secondary Pilot Phase

The larger pilot phase is nearly identical to the first, only this time increasing the amount of participants. Maybe you move from 2 percent of your machines to five to 10 percent of your machines. Due to the greater number of participants, you may need to be more lax in your exit criteria. You may decide that if 75 percent of your participants approve, or if seven business days have transpired, you have sufficient information to move on. When things break, people complain. When it comes to patch, no news is often good news, that’s why we can put time down as a successful metric. It’s not perfect, there are always those applications that are run on a periodic basis, but it’s a start. Just document were you stand and move on.

Again, just make sure the proper notification is going out to your pilot group so they know to be aware and provide them with dates they need to respond by. Ensure the proper channels are in place so the pilot users can communicate the good and the bad.

This phase should put you two to three weeks out from the content’s publication date. Remember, time is not on your side. The key is to be disciplined, yet focused on getting the content released.

The Mass Rollout Phase

Here comes the fun part, let’s roll out the patch updates to the rest of the organization. While no process will prevent every potential bad outcome, enter into the mass rollout phase with confidence. It won’t hurt to hope and pray at this point either, but at least you’ve done your part.

The key to this portion is to capture the feedback and learn. If a certain individual or group is adversely affected, understand how he/she/them differ from your pilot test groups. Consider adding in this individual or a member from the group into your pilot phase for future testing. The outspoken, high-energy individuals are usually willing to participate in such programs, so bring them in.

Make sure you’re using your patch tool to track the progress. You should be able to hit a pretty high success criteria within days of release.

Where I see most companies struggle here is with off-network devices. Ideally your patch tool should be able to handle the delivery of a patch regardless of where it sits, whether on or off the network. If it doesn’t, you may want to re-evaluate your tool. Machines are always going to be offline or off network, sometimes for days, weeks, months or even indefinitely. Build your process around the exceptions and you’ll be successful.

The Exception Handling Phase

Use this phase to deal with all of the one-off scenarios. It may be a single system that causes you grief. It may be a patch that will not apply. It may be hardware that fails months after patches have been applied, making you vulnerable to items you thought you had patched months ago.

Every scenario is going to be unique and require a different set of steps to troubleshoot. Figure out what you can and then re-insert it back into your patch workflow when it’s ready to be re-evaluated. For me, what’s important, is to document, learn and use what you can to enhance your established patch process so that with each iteration it gets better and better.

Conclusion

Using your patch tool, you should be able track the trends and understand how quickly you can turn around a patch. What may take 35 days can be gradually improved to 30 days, then into the 20s, the 10s and maybe even into single digits. The size of an organization will have such an impact on turn around that comparing against others is not as important as comparing against yourself.

Now, after implemented your newly minted and customized patch process, continue to hope and pray what you’ve done is enough. Zero-day threats will always be with us, having 100 percent prevention is nigh impossible. But having done all that you can do and covering what is in your control, you can now use that prayer and hope  to overcome what is outside your control.