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For much of my IT career, cybersecurity training has looked exactly the same. Once a year, IT forces everyone to watch a few videos and take a multiple-choice quiz. This training does check a box, but it rarely changes actual user behavior or provides a ton of new insights. However, AI will begin to completely flip how training is done. A new integration announced recently by Dashlane and KnowBe4 gives us a clear view of how AI and real-time automation will change cybersecurity training for the good.

About Apple @ Work: Bradley Chambers managed an enterprise IT network from 2009 to 2021. Through his experience deploying and managing firewalls, switches, a mobile device management system, enterprise-grade Wi-Fi, 1000s of Macs, and 1000s of iPads, Bradley will highlight ways in which Apple IT managers deploy Apple devices, build networks to support them, train users, stories from the trenches of IT management, and ways Apple could improve its products for IT departments.

The visibility gap in macOS

According to Dashlane, one-third of all corporate logins use weak or compromised credentials that fall outside SSO coverage and are unprotected by any official password manager vault. If an employee auto-fills a compromised password from their Safari’s iCloud Keychain into a corporate portal, IT never knows it happened. The security team cannot train a user on a mistake they cannot see. All things considered, SSO integration for all corporate apps should be the ultimate goal.

“Employees are the first line of defense against attackers, making it critical that enterprises take the opportunity to turn users’ risky behavior into a learning moment,” said John Bennett, chief executive officer, Dashlane. “Dashlane’s unique vantage point in the browser paired with KnowBe4’s wide-array of training content creates a vehicle for organizations to automatically instill a more proactive security posture across their workforce.”

In-context training is the future

This is where the Dashlane and KnowBe4 integration is pretty interesting to me. Dashlane’s Omnix platform sits at the browser level, giving it visibility into credential risks across all employee passwords in the browser, even if they are stored outside the company vault.

When an employee attempts to enter their password on a phishing page or uses a compromised credential, Dashlane intervenes. But instead of just blocking the action and creating an alert for an IT admin to review later, it actually triggers a targeted training through KnowBe4.

This automated and targeted approach is exactly how AI and automated systems will handle human risk going forward. If an employee makes a mistake, the system will detect it, blocks it, and immediately delivers a micro-training module that explains exactly what the user did wrong, while the context is still fresh in their mind. It’s not meant to be a gotcha, but a correction with explanation.

“Integrating KnowBe4 with Dashlane Omnix took the friction out of improving employee security habits—a significant part of our security posture. It also keeps accountability with the user,” said Scott Holleran, senior vice president of technology, Vertex Service Partners. “My team gets to spend less time on password security and more time focused on building our security program.”

9to5Mac’s take

After 20+ years in IT, I believe security awareness training is only truly effective when tied to a specific event. Calendar-driven training simply does not work for modern cyber threats. As IT teams deal with an increasingly complex threat landscape and the rise of agentic AI risks, they do not have the time to manually analyze individual alerts and assign follow-up training. It’s similar to how correcting the behavior of your small child or pet is really only applicable in the moment.

The integration of real-time threat detection with automated, contextual education removes the friction that prevents employees from improving their security habits. By turning a risky click into an immediate training moment, IT teams can spend less time creating training that people are just happy to click through and focus more on addressing issues in the moment. KnowBe4 is a leader in this space, and it makes sense for Dashlane to partner with them.

Apple @ Work is exclusively brought to you by Mosyle, the only Apple Unified Platform. Mosyle is the only solution that integrates in a single professional-grade platform all the solutions necessary to seamlessly and automatically deploy, manage, and protect Apple devices at work. Over 45,000 organizations trust Mosyle to make millions of Apple devices work-ready with no effort and at an affordable cost. Request your EXTENDED TRIAL today and understand why Mosyle is everything you need to work with Apple.

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