The Patching Problem Every IT Team Knows Too Well (And How to Actually Fix It)

Let's be honest: patch management in 2025 feels like trying to drink from a fire hose while juggling flaming torches. You're managing thousands of devices, dealing with constant vulnerability announcements, and somehow expected to keep everything secure without driving your users (or yourself) completely insane.

If you're feeling overwhelmed, you're not alone. We recently teamed up with our friends at Tines to dig into the biggest patching headaches IT teams face today—and more importantly, how to solve them without working weekends.

Here's what we learned, and how you can turn your patch management from a constant scramble into something that actually works.

Why Traditional Patching Falls Apart at Scale

The volume problem is real. Microsoft alone published over 1,300 CVEs in 2024. If you're managing 5,000 endpoints (which, let's face it, is pretty standard these days), you're looking at potentially tens of thousands of exposures to track. And that's before you even think about macOS, iOS, Linux, or all those third-party apps your users love.

But here's the thing that really gets IT teams stuck: it's not just about the numbers.

The Four Patching Pitfalls That Kill Productivity

1. The CSV Shuffle

You know this dance well. The security team generates a spreadsheet of vulnerable devices, passes it to the device management team to patch, then gets back a spreadsheet of what was updated. By the time that's done, new CVEs appear and the process repeats.

This back-and-forth doesn't just waste time—it creates gaps where critical vulnerabilities slip through the cracks.

2. Tool Fragmentation Hell

One tool for installing applications, another for scanning vulnerabilities, a third for managing updates. When your patch management spans multiple platforms, you end up with duplicate effort, inconsistent results, and blind spots you didn't even know existed.

3. Manual Processes That Don't Scale

With the volume of CVEs and assets today, manual tracking and intervention is nearly impossible. Especially when audits demand proof of complete patch lifecycles. Mistakes, inconsistencies, and delays pile up faster than you can fix them.

4. End-User Resistance (The Silent Killer)

Your users see updates as the enemy. Slow reboots, broken workflows, popup notifications during important presentations—it's no wonder they click "Remind me later" until the heat death of the universe.

But here's what most IT teams miss: this isn't about stubborn users. It's about friction in your process.

The Real-World Solution: Orchestrate and automate patch management

We built a live workflow during our recent webinar that solves these exact problems. Instead of just talking theory, let's walk through how it actually works.

The Scenario: Critical CVE, Non-Compliant Users

Picture this: A new critical vulnerability drops. Your security team identifies it as high-priority (CVSS score above your threshold). But three days later, you've still got users who haven't restarted their machines.

Here's how the Tines workflow handles it:

Step 1: Intelligent Triage

Fetch vulnerabilities from Kandji automatically
Filter by CVSS score (you set the threshold)
Create audit records for compliance
Generate cases for each vulnerability

Step 2: Device-Level Tracking

Identify all affected devices
Create linked cases for each device
Map devices to users through your identity provider
Handle edge cases (like devices without assigned users)

Step 3: Smart User Communication

Send personalized Slack messages explaining the risk
Use AI to generate clear, non-technical explanations
Include specific instructions for their device
Set up automated follow-up reminders

Step 4: Progressive Enforcement

Restrict access to critical systems if needed
Escalate to managers for team-wide issues
Create self-service restoration options
Track everything for audit purposes

The Magic: Conditional Access using intelligent workflows

Here's where it gets really powerful. The workflow can automatically restrict a user's access to critical systems until they patch. But instead of just locking them out, it:

Sends a clear explanation of why access was restricted
Provides step-by-step instructions to fix the issue
Offers self-service restoration once they're compliant
Escalates to IT only when necessary

Real example from the workflow: "Hi Tim, we've temporarily restricted access to some systems because your Mac has a critical security vulnerability. Please update to macOS 14.3 or later, then click here to restore access."

Handling the Edge Cases

The workflow also accounts for all those messy real-world scenarios:

Orphaned Devices: When devices don't have assigned users, the system automatically tags them and sends IT a consolidated list instead of spamming individual alerts.

User Changes: If someone moves roles and no longer owns a device, the workflow detects this and routes it appropriately.

PTO and Exceptions: Built-in logic to handle when users are out of office or need emergency access.

Manager Override: Allows managers to restore access for their entire team once everyone's patched.

The Technical Details That Matter

Apple-Native Advantage

As an Apple-first platform, Kandji integrates directly with Apple's security frameworks like Endpoint Security. This means:

Real-time vulnerability detection
Native OS update management
Seamless connection with Apple's security architecture
Better user experience during updates

AI-powered Workflows with Tines

The Tines workflow platform delivers enterprise-grade orchestration:

Developer friendly, but not developer reliant: No coding required, but you can always code in Python if you prefer
JSON-based event handling: Every action creates auditable records
Solution-agnostic: Connects to your existing security stack, no limitations
AI-driven context: Agents generate clear, actionable outputs, from human-oriented summaries to tangible next steps it can act on
Error handling: Deterministic workflows that keep humans in the loop as needed

Audit Trail by Design

Every action gets logged with:

CVSS score that triggered the workflow
Timestamp of initial detection
User notifications sent
Remediation actions taken
Compliance status changes

When auditors ask "Why did you patch this CVE on this date?" you can show them the complete workflow history.

Getting Started: The Five-Step Framework

Identify and Prioritize Pull vulnerability data from scanners, patch tools, or MDMs. If you're using Kandji, this is all in one place. Set CVSS thresholds that make sense for your risk tolerance.
Structure Your Data Segment by device type, team, or user. Map devices to owners through your identity provider. Account for edge cases like shared devices or contractors.
Orchestrate and Automate Patch Execution Execute updates during low-traffic windows. Send clear notifications before and after. Build in user-friendly scheduling that respects time zones and PTO.
Track and Report Confirm patches worked. Maintain compliance audit trails. Create dashboards that show progress to leadership.
Iterate and Improve Add features like emergency patch approvals, manager overrides, or integrate with ticketing systems. Optimize based on user feedback and compliance requirements.

The Questions That Tell You If You're Ready

Before diving into intelligent workflows, ask yourself:

Do you have good visibility into devices, apps, and vulnerabilities across your entire fleet?
Can you automate the repetitive steps your team currently does manually?
Can you audit what's been done and prove compliance to leadership or regulators?
How do you handle exceptions like devices without assigned users or emergency access needs?
Do you have fallback plans when automation doesn't work as expected?

If you're answering "no" or "sort of" to these questions, you're not alone. Most organizations struggle with at least a few of these areas.

Why This Matters More Than Ever

Recent headlines tell the story: a key software supplier for the UK's NHS was hit by ransomware, disrupting emergency services and exposing tens of thousands of personal records. The root cause? A two-year-old Microsoft vulnerability that hadn't been patched.

The supplier was fined over $3 million. But the real cost was in patient care disruption and lost trust.

This isn't isolated. Ransomware increasingly targets healthcare, government, schools, and enterprises of all sizes. The stakes include financial risk, reputational damage, and regulatory fines.

The Cultural Shift: From "IT Police" to "IT Enablers"

Here's something we hear a lot: "How do we do all of this and still be seen as the good guys?"

IT and Security teams often struggle with their internal reputation—seen as the people who slow things down instead of keeping everyone safe. But when patch management is done right, it actually improves productivity.

Why? Because users can work confidently knowing their IT team has their back. If they lose their device, IT still has control. If there's a security incident, systems are already hardened. Remote work becomes truly secure work.

The key is building processes that feel helpful, not punitive. Clear communication, respect for user schedules, and self-service options go a long way.

What Success Actually Looks Like

When orchestration and automation are working well, you'll see:

Faster response times: Critical vulnerabilities patched in hours or days, not weeks
Better compliance: Continuous audit trails and automated reporting
Happier users: Clear communication and respect for their workflow
Focused IT teams: Time spent on strategic work instead of manual patching
Confident leadership: Real-time visibility into security posture

Ready to Stop Playing Catch-Up?

Patch management doesn't have to keep your team up at night. With the right combination of tools and intelligent workflows, you can move from constantly reactive to genuinely proactive.

Here are some resources to help you get started:

Watch the Complete Demo

Full webinar recording - See the live workflow demonstration and Q&A session

Learn More About secure patch management at scale

Case Study: How a fundraising platform cut unpatched vulnerabilities by 83%
Complete Patch Management Guide - Deep dive into orchestration and automation strategies and best practices

Ready to Get Started?

Import the Kandji x Tines Patch Management Workflow - Start with the exact workflow demonstrated in this post