By: Karrie Westmoreland
Let’s start simple: patching is the process of applying software updates that fix bugs, close security holes, and occasionally add new features. Vendors like Microsoft, Adobe, Apple, and countless others release these patches regularly — sometimes on predictable schedules (“Patch Tuesday”), other times as emergency fixes for newly discovered threats (“out-of-band” updates).
When it comes to cybersecurity, patches are your front-line defense against known exploits. If a vulnerability is a broken lock, a patch is the replacement key — except the burglars also have the old key, and they’re already trying it in your door.
Why it matters:
In nearly every single penetration test I’ve performed — across industries from finance to manufacturing to creative agencies — outdated, unpatched software is a recurring theme.
Sometimes it’s servers running years-old operating systems. Sometimes it’s applications like Adobe Reader or Illustrator left unpatched because “it still works fine.” Other times, it’s forgotten web apps on old frameworks quietly collecting dust (and vulnerabilities).
Here’s the uncomfortable truth: patching issues aren’t just “tech debt” — they’re open invitations for attackers.
Think of patching like fixing a leaky roof: first you spot the drip, then you patch the hole, test to make sure the rain stays out, and finally check the ceiling for new water stains. Only in this case, the “rain” is hackers, and they don’t wait for a storm to pay you a visit.
The last two years have been a reminder that patch timelines matter. We’ve seen cases like:
Attackers watch vendor bulletins as closely as defenders do. The difference? They act immediately with a vengeance.
1. Payroll’s Patch-Free Paradise
The Situation:
During a 2024 assessment, a company’s payroll portal was running a three-year-old Apache Struts version with a known remote code execution flaw. The patch had been out for 18 months.
Why no update? “It might disrupt payroll week,” said HR.
What Happened Next:
I ran a known exploit script and got shell access faster than you can say “direct deposit.” Within an hour, I could see employee data and internal finance records.
How to Avoid This:
2. The Designer’s Dangerous Plugin
The Situation:
In 2025, a creative agency’s design team loved their Adobe Illustrator plugin… from 2018. IT flagged it for a known privilege escalation bug. Designers refused to update, fearing broken workflows.
What Happened Next:
I “gifted” them a compromised version of the plugin on their shared network. Once installed, it gave me admin rights on multiple workstations, letting me stroll into their client IP repository.
How to Avoid This:
It’s easy to assume patch delays are just laziness, but in reality, they’re often the result of competing priorities and operational friction. In many organizations, patching has to compete with revenue-generating activities, and since a vulnerability doesn’t look like a burning fire (until it is), it tends to slip down the priority list.
Ownership confusion adds to the chaos. If no one clearly “owns” patch management, updates get stuck in limbo. IT might think Security is handling it; Security might think IT is on top of it; both might assume it’s not urgent because there’s been no visible incident — yet.
Then there’s Shadow IT — those forgotten servers in the corner rack, abandoned SaaS accounts, or the “temporary” VM that became a business-critical system. If it’s not in the inventory, it’s not getting patched, and that’s exactly where attackers go hunting.
Approval processes can also be a killer. In some companies, pushing a patch to production requires more signatures than adopting a new corporate logo. By the time approvals are in, attackers may have already exploited the vulnerability elsewhere.
Finally, legacy systems bring their own headaches. These are the brittle, business-critical tools that haven’t had a major update in a decade and may break if you so much as install a security patch. Instead of patching, some teams take the “let’s not touch it” approach, which works… right up until the day it doesn’t.
The bottom line? The reasons for slow patching are often understandable — but attackers don’t care about your organizational chart, your quarterly goals, or your “we’ll get to it” list. They care that the door is open.
For actively exploited vulnerabilities, aim to update within 24–48 hours. These should be treated as emergencies, with a hotfix deployed as soon as possible and a rollback plan ready in case something goes wrong.
For a security patch that isn’t yet under active attack, a seven-day turnaround is a solid target. Roll the update out to staging first, verify that everything works, and then deploy to production.
Major version upgrades usually require more planning, so a quarterly schedule works best. Allocate time for testing, coordinate across teams, and plan these updates in advance so they don’t get buried under day-to-day work.
For minor and patch updates, a monthly cycle is a good rhythm. These can often be automated, allowing your team to approve and deploy them with minimal manual effort.
Keys to Making It Work:
The truth is that patching doesn’t have to be a headache. With a little planning, some clear ownership, and a dash of automation, it can become one of the easiest wins in your security playbook.
Think of it like locking your doors at night — it’s a small habit that becomes second nature, and over time, you stop even thinking about it. The difference is, in the digital world, you might have a few hundred “doors,” and patching is how you make sure each one stays locked.
If you treat updates as routine maintenance rather than emergency repairs, you’ll save your team stress, save your business money, and sleep a lot better knowing attackers will have to work a lot harder to get in.
In security, you might not get a shiny award for keeping your systems up to date — but you do get the quiet confidence of knowing your company’s name won’t be splashed across the news for the wrong reasons. Leaving client data exposed because of an unpatched system is more than a technical oversight; it’s a trust problem that can damage your reputation in ways money can’t easily fix. Cybersecurity doesn’t have to be complicated, but it does have to be a priority — not something that gets pushed to the bottom of the to-do list, or worse, left off entirely.
Coming Up Next…
Patching your main software is only half the battle. The other half? Making sure the building blocks of that software — the libraries, frameworks, and hidden bits of code it relies on — are kept just as fresh.
In my next article, I’ll talk about updating dependencies:
Because no matter how shiny your application’s front door is, if the hinges are rusting away behind the scenes, you’re still at risk.