Relying on end users for security is difficult, but securing enterprise systems doesn't have to be. For a system to be valuable, it must be accessible and beneficial to end users. Organizations have improved security awareness training for employees, but the training has limited value until the underlying systems are secured. Securing a system removes an attack vector that funnels the attack up to the end user (such as phishing). This is when training shows its value.

Remove the Attack on the System + Train End Users on Most Likely Attacks = Thwart the Attacker
Secure life cycle management sounds difficult, but it isn't. The approach starts with identifying the systems that are running in the enterprise. If you have an inventory of these assets, great! If not, then start scanning your networks for hosts, look at Active Directory or LDAP, ask around, and create an inventory list. (Your last resort is pulling the plug to see who screams.) If you work in the cloud, check the invoice for systems.

Once you have an inventory, prioritize everything according to what's important to the enterprise. Anything hanging off the external network is a priority because it is accessible from the Internet. Internal systems with sensitive information are a high priority (personally identifiable information, financial info, customer, backups, etc.). Prioritizing is important because resources to secure the systems are always constrained.

Now it's time to find out how bad things are. It's impossible to manually check each system for patch levels or security settings, so don't even try. Use a benchmarking tool like the Center for Internet Security's CIS-CAT, Microsoft's Baseline Security Analyzer, or a vulnerability scanner. These tools will take your inventory list, compare items to known good security configurations, and provide a gap report for each system.

Review the recommendations and decide which ones make sense for your enterprise. Benchmarks have different levels of recommendations, and the highest-level security recommendations may not work for your enterprise (because they're too restrictive). If your enterprise has regulatory requirements, now is the time to align with them.

Come up with a strategy to get systems secured according to the recommendations. All new systems should receive the approved recommendations by default. Existing systems will need to be scheduled according to their priority. Now is a good time to decommission unnecessary or legacy systems (for example, the dusty machine under the desk), and don't forget about development systems. Even though a system may not be in production for end users, if it is on the network then it can be a weak link in the overall security of the enterprise.

The full life cycle of the system is from when it's turned on until it's turned off. It must be secure during the entire life, so deploy it based on the secure configuration and keep it maintained until it is powered off. Maintenance is critical because a lot of time and effort was spent getting the enterprise secured up to this point. Keep on top of the latest benchmark releases, and scan the enterprise environment with a vulnerability tool (such as OpenVas, Tenable Nessus, Rapid7 Nexpose, etc.). Benchmarking and vulnerability scanning should be integrated into the enterprise patch management program. This will ensure that a system is initially deployed securely and is kept up to date until it's powered off and securely disposed.

There is a great feeling in the secure life cycle when subsequent reports show how much progress has been made in securing systems. No enterprise can be made 100% secure; the goal is to reduce the risk to an acceptable level and give end users the best chance at thwarting attackers through the training they receive. Most breaches occur because of insecure configuration or lack of system patching. Ponemon Institute's 2018 State of Endpoint Security Risk states that the average time to patch is 102 days. This provides attackers with a large window to find weak points to exploit. Unless your enterprise is specifically targeted, keeping secure configurations and patches up to date is a great way to not end up in the news.

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