Checklist: 10 Must-Ask Questions to Evaluate Cloud Email Security Solutions

Email remains the most common entry point for cyberattacks, and AI is reshaping how those attacks unfold. Today’s threats to cloud email use AI to impersonate trusted contacts, mimic real workflows, and blend seamlessly into day-to-day communication.

To stop these attacks, security teams require solutions that use AI the way attackers do—strategically, contextually, and at scale. That means platforms grounded in behavioral intelligence, built to understand your organization’s relationships, language, and patterns well enough to detect anomalies.

To help you identify whether a solution meets the standard, we’ve created a 10-question checklist based on expert insights from The Essential Guide to Cloud Email Security. While the full guide outlines the key challenges facing security teams, this vendor-neutral checklist helps you quickly evaluate whether a solution can stand up to today’s most advanced attacks.

A few key questions to shape your strategy:

• Can the solution detect payload-free attacks like BEC, impersonation, and VIP fraud with behavioral AI rather than static indicators?

• Does it remediate malicious emails in milliseconds across all mailboxes, or rely on time-consuming manual triage?

• Can it convert real attacks into timely simulations to deliver context-specific security awareness training, without manual content management?

• Does it understand normal behavior across employees and vendors, including message style, invoice frequency, and recipient patterns?

• Can it suppress graymail and reduce digest fatigue, so users stay productive without drowning in low-value alerts?

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