Security & Compliance Systems: The Backbone You Can’t Afford to Ignore

Paul Riley – April 11, 2025  – 6 mins read

Most legal tech blogs focus on the shiny stuff — new case management platforms, slick integrations, AI-this and cloud-that. But in my world, the things that matter most don’t make noise when they work. Security and compliance systems are silent until they aren’t — and when they fail, they tend to fail loud, fast, and publicly.

As IT Director in a global litigation firm, my job is to keep the lights on, the regulators happy, and the clients confident that we’re not the weak link in their supply chain. It’s less about silver bullets and more about stitching together a fabric that holds — under pressure, scrutiny, and the inevitable curveballs of hybrid work.

Here’s what we’ve learned — often the hard way — about what actually works when building legal security and compliance systems that stand up to real-world use.

SSO: Great… Until It Isn’t

We’re heavily invested in Microsoft Azure AD for identity — it underpins our SSO strategy across email, PMS, DMS, HR, even our collaboration tools. For the most part, it’s been a win: fewer passwords, tighter control, and better visibility.

But here’s the catch: not all legal tech vendors are SSO-ready — even when they say they are.

We hit a wall during an implementation of a third-party client portal platform. Their marketing screamed “SSO Compatible,” but in practice it was a fragile front-end bolted onto legacy auth. Sessions timed out unexpectedly, tokens wouldn’t refresh, and worse — when a user left the firm, access didn’t always revoke instantly.

We had to roll it back, escalate, and ultimately chose a different platform altogether. The takeaway? SSO is only as strong as your weakest vendor. Don’t take “compatible” at face value — test, break it, retest, and push vendors on roadmap transparency before you commit.

What’s Working (Now)

After a few scars and some near misses, we’ve landed on a security stack that’s mature, manageable, and built with real-world legal workflows in mind. Key components:

• CrowdStrike for endpoint threat detection — light footprint, fast response
• Proofpoint for email filtering — catching spoofed domains better than anything else we’ve tried
• MFA with Conditional Access through Azure AD — tough but fair controls based on risk signals
• DLP Policies in Microsoft Purview — nudging users when they mishandle sensitive info, not punishing them after the fact

We also conduct regular third-party penetration testing — and we don’t just file the report. We treat it like a quarterly sprint review for security. No shelfware.

Lessons From the Trenches

1. You Need Fewer Tools, Configured Better

Tool sprawl is real. At one point we had four different alerting systems with zero correlation. Now we use a centralised SIEM and structured response playbooks. Simpler is safer.

2. Policy Without Practice is a Liability

You can write all the policies you want — data handling, BYOD, retention — but if your systems don’t enforce them, they’re just hopeful fiction. We’ve shifted focus to automation: if a policy exists, it needs teeth.

3. Security Isn’t One Project — It’s a Parallel Track

We used to treat security like something you “implement” and tick off. Now, every tech project has a compliance checkpoint — before a tool goes live, it gets a data mapping review, access audit, and regulatory impact check. Slower, yes. But a lot cheaper than a breach.

What’s on Our Radar

• Insider threat monitoring with behavioral analytics — especially important with growing contractor use and hybrid work
• Automated ISO compliance dashboards — we want to stop chasing evidence manually every audit cycle
• Enhanced retention tooling across DMS and email — making sure our archive strategy doesn’t become a liability

Final Thoughts: Compliance is a Muscle, Not a Badge

Security and compliance don’t get applause, and they probably never will. But they’re foundational. They’re the reason you get to keep your clients.

If you’re in a legal IT leadership role, my advice is simple: treat your security stack like a core system, not just an insurance policy. Don’t trust vendor labels at face value. And invest as much in understanding how your tools behave together as in what they say they can do on their own.

Because in this space, it’s not what you deploy — it’s what you enforce.

If you’ve had your own “SSO nightmare” or a compliance win worth sharing, I’m always keen to swap stories.