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Lumension Guide to Patch Management Best Practices

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With the sophistication and sheer volume of exploits targeting

major applications and operating systems, the speed of

assessment and deployment of security patches across

your complex IT infrastructure is key to mitigating

risks and remediating vulnerabilities. Here are the

Lumension-recommended steps to cure your

patch management headache.

Patch Management Best Practices

WP-EN-04-17-12

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Introduction

Laying the Groundwork

1. Discover Assets 3 2. Agent Maintenance 4

3. Classify Value and Risk 8

4. Establish Workflow and Groups 8 5. Identify Test Groups 12 6. Staff Training 14

Before Patch Tuesday

7. Schedule Resources 15

8. Reserve Down-Time for Servers 15 9. Watch for Pre-Announcements 15 10. Confirm Reporting Up-to-Date 16

11. Deploy missing updates and prerequisites 17

On Patch Tuesday

12. Study Vendor Information and Patch Tuesday Security Briefings 19 13. Prioritize Potential Patches 19

14. Change Control 20 15. Staged Testing 21

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Introduction

Patch and vulnerability management is a core component of your risk mitigation strategy. It is the first and last line of defense against existing and new exploits – laying the foundation from which your AV and other security technologies work. As the sophistication and sheer volume of exploits targeting operating systems and major applications increases, the speed of assessment and deployment of security patches is key to mitigating risks and remediating vulnerabilities – and reducing costs.

In this best practice guide, we are going to take a deep dive into a best practice process for patch and vul-nerability management, developed by Lumension over thousands of customer engagements. This process – which is flexible and simple enough to be adapted into your environment – revolves around the well-known monthly release of security updates from Microsoft known as Patch Tuesday, and includes:

» Laying the Groundwork for a Successful Patch Process

» Before Patch Tuesday

» On Patch Tuesday

» After Patch Tuesday

Every company’s Patch Management process is going to be a little bit different, but what’s important about these best practices are: It’s a repeatable cycle. It’s based on calendar events – in this case Microsoft’s Patch Tuesday. It’s iterative – it can be tweaked based on what’s learned from previous patch cycles. It’s measureable.

Documenting a process for the organization is really the best way to communicate the importance of patch-ing your environment to the rest of the organization. In this best practice guide we chose to base the process on the well-known Patch Tuesday event, but you can align your patch process with other recurring IT tasks – with equally effective results – that works best for your organization.

Laying the Groundwork

This section is about gaining an understanding of the machines under management and preparing the Patch and Remediation process. At a high level, this means identifying the systems to be managed, defining the patch-roll out plan, and training the organization on the Patch and Remediation process.

1. Discover Assets

Within Lumension® Endpoint Management and Security Suite (L.E.M.S.S.), identify all hardware and software on the network and categorize them

by platform, applications, department, etc.

Practical Steps:

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» Follow the Discover Assets wizard to set up an Asset Discovery job.

» As a best practice, administrators will want to schedule a more frequent recurring scan to identify new endpoints that enter the network, then a less frequent scan as the number of machines under management stabilizes

2. Agent Maintenance

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Practical Steps:

» You can either set up a recurring Asset Scan or an Asset Scan/Install Agents job.

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» We also recommend verifying agent availability and last check-in via LRS:

• Run the Asset Management report “Endpoint Check-in” in LRS.

• Select the desired date of last endpoint check-in (“Last Contact Date on or before”) – typically your current date.

• The report displays the list of endpoints that have not checked-in with the server in a given timeframe.

• Ensure that agent communication is established with all the endpoints in your environment.

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» It may also be useful to verify the agent versions and operating systems of your endpoints through LRS, especially if you are planning to perform an upgrade to a newer version of L.E.M.S.S.:

• Run the Operational Report “Agent Version and Operating System Distribution” in LRS

• The report displays the mix of agent versions and operating systems in the endpoint environment, along with a detailed endpoint count.

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3. Classify Value and Risk

Determine which systems are most critical to protect based on the assets housed and/or the function they provide. Define the level of risk by criticality of system and how prone it is to attack.

Practical Steps:

» Review your network topology and classify your assets by level of criticality.

4. Establish Workflow and Groups

Determine ownership, permissions needed and responsibilities for threat identification, testing and reme-diation across security, IT and business units. Define correlating system groups. L.E.M.S.S. will predefine system groups based on desktops, servers, physical or virtual hardware, as well as operating systems. If more granular management is required, IT managers can create additional groups based on specific re-quirements, e.g. if servers are internet-facing, they may be grouped as high-risk but also as limited down-time. Use RBAC controls and set up permissions for desktop patch admin, server patch admin, as well as individuals who have reporting access only.

Practical Steps:

» Determine system ownership, uptime requirements, and patch windows for these machines. Define the patch cycle for different managed systems.

» Define users and roles within your organization and who needs access to which systems.

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9 • Next, assign users to the selected role(s) from the Users tab.

» Set up your categorized assets in custom groups in L.E.M.S.S.

• On the Manage Groups page, click on Custom Groups. Navigate to View in the upper right corner and select Group Membership to create a custom group.

• Navigate to View in the upper right corner and select Endpoint Membership to assign endpoints to that group.

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» Set Hours of Operation (HOP) for managed endpoints that require a specific patch window.

• On the Manage > Agent Policy Sets page, create a new agent policy and define the hours of operation.

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» For machines managed over the WAN, it is recommended to set up a caching proxy per remote location to cache the package content.

• Deploy “Lumension Caching Proxy 2.7 for Windows” to a target machine in the remote location

• Create Agent Policy and set FastPath Servers – Both Interval and Define Servers

• Manage > Agent Policy Sets > Select Create and Save when completed

• Apply Agent Policy to your custom group

• Manage Groups > Right-click on the group > Select Policies > Select Add > Select Agent Policy and click Save

◦ Note: Policy will not set until the next check-in to L.E.M.S.S.

• For more information on setting up a caching proxy please review the following resources:

◦ Best Practices Fast Path: KB article 523

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5. Identify Test Groups

Build a representative sample set of each type of machine based on steps 2 (Agent Maintenance) and 3 (Classify Value and Risk), in readiness for patch testing step 15 (Staged Testing). Make sure your test group includes a representative sample of platforms under management and includes a representative sample of applications in the environment, especially machines that have custom, in-house developed applications. As a best practice, at least one machine from each major group in the organization should be included in a test group.

Practical Steps:

» Once test groups have been identified, create custom groups for those test groups.

• On the Manage Groups page, click on Custom Groups.

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13 • Navigate to View in the upper right corner and select Endpoint Membership, then click on Manage,

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6. Staff Training

Train applicable staff on vulnerability monitoring and remediation techniques. At a minimum, administrators responsible for deploying Patch updates need to be trained in the Patch and Remediation application. As a best practice, there should be an internal resource for all employees to learn more about why it is important to keep machines in the organization fully patched.

Practical Steps:

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Before Patch Tuesday

This section is about preparing the environment for the monthly patch deployment, including industry re-search on what is expected to be released by Microsoft and other application vendors and assess the impact of those planned releases to your managed machines.

7. Schedule Resources

Allocate IT resources for Patch Tuesday while also integrating additional patch release schedules from third-party software, such as Adobe, Apple (ad hoc), Java and so forth. In addition, review the patching needs of any internally-developed applications and/or custom patches and consider deploying these patches as part of the monthly patch cycle.

8. Reserve Down-Time for Servers

Reserve time slots to be able to deploy patch updates to any mission critical servers within 72 hours of the Patch Tuesday release.

9. Watch for Pre-Announcements

Monitor security sites for pre-announcements of patches and discussion of vulnerabilities and possible zero-day exploits that they may address from sources such as Lumension Endpoint Intelligence Center

(LEIC), Microsoft Security Response Center (MSRC), SANS Internet Storm Center, National Vulnerability Database (NVD), etc.

Practical Steps:

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10. Confirm Reporting Up-to-Date

Review last deployment reports via Lumension Reporting Services (LRS) and make sure all computers are being regularly scanned. Validate the L.E.M.S.S. application server is actively communicating with the global subscription service (GSS).

Practical Steps:

» To confirm recent deployments and ongoing scanning in LRS:

• Run the operational report “Deployment Detail”

• Select the group(s) that you are monitoring

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17 • Go to the Tools > Subscription Updates page.

• Confirm that the “Successful” column shows “true”, indicating successful replication.

• If “false” is shown in any of the rows, troubleshoot to ensure replication.

11. Deploy missing updates and prerequisites

Determine if your software is fully updated or if there are any missing Service Packs, hotfixes or rollups from prior months that are still outstanding. Remember that some patches won’t install if you have miss-ing prerequisites. Check that each machine in the defined group has received the latest Service Pack or update needed.

Practical Steps:

» To verify if your software is fully updated:

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are still outstanding.

» Deploy missing updates:

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On Patch Tuesday

This section outlines the steps to prioritize the Security Patches released by Microsoft and other application vendors and to deploy those patches out to the machines managed in your environment.

12. Study Vendor Information and Patch Tuesday Security Briefings

Microsoft and other vendors provide webinars, email alerts and comprehensive online information on all new Patch Tuesday updates.

Lumension offers a monthly Patch Tuesday Security Briefing as well as other patching guidance on the

Lumension® Optimal Security Blog, the Lumension® Patch Tuesday Alerts webpage and in the Patch Tuesday newsletter.

Important information to consider when understanding the impact of Patch Tuesday on your environment includes:

» What is the bulletin severity rating?

» Is the vulnerability known / publicly disclosed at the time of release?

» Does the vendor know of any active exploits at the time of release?

» How easily can the vulnerability be exploited once the bulletin is been released?

13. Prioritize Potential Patches

With the vendor information gathered in step 12 (Study Vendor Information and Patch Tuesday Security Brief-ings), use patch impact (Critical, Important, etc.), asset risk and value to prioritize your systems for patch testing and deployment. Understand the applicability and impact of deploying these patches to your environment, espe-cially critical machines. When making this assessment, consider:

1. Threat Level;

2. Known Active Exploits in the Wild;

3. Risk of Compromise;

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Practical Steps:

» To review the released Patch Tuesday patches and their applicability in your endpoint environment, we recommend you use LRS and run the report “Patch Release by Vendor”

• The report provides a high-level overview of the applicability of the released bulletins to your managed endpoints and groups. It reflects the severity of and expected workload for that month’s Patch Tuesday release and the organization’s patch status.

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15. Staged Testing

Testing each patch is vital; automated deployment is very risky and not advised. Be certain to test the patch in each environment of your previously defined groups and deploy the patches in phases. In addition, be-fore remediation, and especially if there is a lack of time or resources to perform a test on the patch bebe-fore deploying it on a production system, there is great benefit in joining patch user forums and learning what experiences others have had in installing or using the patch.

Practical Steps:

» Deploy applicable bulletins to test groups configured in step 5 (Identify Test Groups) above.

» Ensure successful deployment before rollout to additional groups in the environment.

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16. Installation of the Patches

Stage deployments by system groups and prioritization. Start with smaller, low-risk groups, and validate that no problems occur, and then work your way to larger and higher-risk areas of the network. As a best prac-tice, and especially if your servers have a limited maintenance window, it is recommended to cache all the patch content before deployment. If deployments are scheduled off-hours, take advantage of Wake-on-LAN settings to wake up any powered-down endpoints and ensure that they receive the content.

Practical Steps:

» In L.E.M.S.S., go to the Review >

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» Go to the Manage Groups page under the Vulnerabilities view and filter for new critical bulletins. Deploy bulletins that are applicable to that target group.

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After Patch Tuesday

This section is about assessing the success of the Patch and Remediation deployments in your environ-ment.

17. Deployment History

Maintain accurate records of all patches deployed. Validate that any necessary reboot(s) occurred and/or that your endpoints don’t require a reboot.

Practical Steps:

» To confirm recent deployments in LRS:

• Run the operational report “Deployment Detail”

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18. Calculate Time to Deploy

Measure how long it takes to get all servers, desktops and laptops fully patched in your organization. This is a great metric to measure against. Remain vigilant for laptops and VPN-connected systems that may con-nect days (or weeks) after the initial deployment.

Fully patched and time to deploy success metrics may be defined differently for different organizations de-pending on the mobility of the machines being managed, how often the machines are online, or the type of machines under management, such as desktop or server.

Practical Steps:

» To strategize and organize patch deployments to the appropriate endpoints and endpoint groups, use LRS as follows:

• Run the report “Patch Tuesday Monitoring Report”

• Select the group(s) that you are monitoring

• The report provides a summary of the patch status for a selected group of machines for the critical patches released in the selected Patch Tuesday cycle.

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19. Monitor for Compliance

Make certain that new or rebuilt systems are “base-lined” for their appropriate systems group. Monitor for removal of patches. Create or update an existing mandatory baseline for future deployments.

Practical Steps:

» Upon successful deployment of bulletin content, add bulletins to mandatory baseline policies.

• Go the Manage > Groups page

• Select the Mandatory Baseline View

• Click on the “Manage” button

• Select bulletins to add to the mandatory baseline

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20. Checks and Balances

Review the Effectiveness of Patch Tuesday Remediations report in LRS to validate the deployment.

Practical Steps:

» To review the patch progress and effectiveness of deploying Patch Tuesday remediations and to understand the security posture and vulnerability compliance of the enterprise for Patch Tuesday patches released by Microsoft for the selected patch cycle, use LRS as follows:

• Run the report “Effectiveness of Patch Tuesday Remediations Report”

• Select the group(s) that you are monitoring

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21. Metrics Improvement

Modify system settings, distribution parameters and so forth to further optimize the system for next month’s updates. WAN optimization, polling frequency and minimizing the patches being detected can all help further optimize performance. Look for computers that did not receive updates at all or those that took unusually long to receive updates.

Practical Steps:

» Go the Manage > Groups page

» Identify any endpoints that are offline and/or have not been remediated.

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About Lumension Security, Inc.

Lumension Security, Inc., a global leader in endpoint manage-ment and security, develops, integrates and markets security software solutions that help businesses protect their vital infor-mation and manage critical risk across network and endpoint assets. Lumension enables more than 5,100 customers world-wide to achieve optimal security and IT success by delivering a proven and award-winning solution portfolio that includes Vul-nerability Management, Endpoint Protection, Data Protection, Antivirus and Reporting and Compliance offerings. Lumension is known for providing world-class customer support and servic-es 24x7, 365 days a year. Headquartered in Scottsdale, Arizona, Lumension has operations worldwide, including Texas, Florida, Washington D.C., Ireland, Luxembourg, Singapore, the United Kingdom, and Australia. Lumension: IT Secured. Success Opti-mized.™ More information can be found at www.lumension.com.

Lumension, Lumension Patch and Remediation, Lumen-sion Vulnerability Management, “IT Secured. Success Op-timized.”, and the Lumension logo are trademarks or reg-istered trademarks of Lumension Security, Inc. All other trademarks are the property of their respective owners.

Global Headquarters

8660 East Hartford Drive, Suite 300 Scottsdale, AZ 85255 USA

phone: +1.480.970.1025 fax: +1.480.970.6323

www.lumension.com

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