DLP and keyword-triggered email encryption

Check Point's DLP (Data Loss Prevention) inspects outbound mail for sensitive data and can act on it. It is also how you set up keyword-triggered email encryption. Like everything in Check Point, DLP has two layers: an engine that detects, and a policy that enforces.

How DLP works: two layers

The DLP engine (Security Settings → Security Engines → DLP) detects sensitive content using prebuilt data types (classifiers) such as credit card numbers, social security numbers, PII, and health data.

A DLP policy then activates the engine, sets the mode, and scopes the users. Outbound DLP workflows (block, encrypt, notify) only run in Prevent (Inline) for outgoing and internal traffic.

DLP data types

Check Point ships with a large library of data types you can switch on: financial, PII, health, credentials, and region-specific identifiers. Enable the ones relevant to your organisation rather than everything at once.

Keyword-triggered email encryption

A common DLP use is letting users encrypt a message on demand by putting a keyword in the subject line.

• Create a DLP rule that matches the subject using a regular expression. Use (?i)\[encrypt\] so it matches the literal tag [encrypt] case-insensitively.
• Choose the workflow action. "Email is allowed. Encrypted by Email Encryption" uses Check Point's own secure portal. Alternatively, "Encrypt using Microsoft OME" hands the encryption off to Microsoft.

Square brackets are a character class in regex, so an unescaped [encrypt] would match any single one of those letters. You must escape them as \[ and \], and (?i) makes the match case-insensitive so [ENCRYPT] and [Encrypt] both work.

The recipient experience (Check Point encryption)

When Check Point encrypts a message, the recipient receives a notification with a link to a secure portal. They authenticate with a one-time code emailed to them, read the message, and can reply securely from the portal. The link is time-limited (around 10 hours).

Which encryption method, and what licence you need

Both methods are triggered by a DLP policy in Prevent (Inline) mode. The difference is who does the encrypting, and what licence that needs.

Check Point's own guidance: if the organisation already uses Microsoft encryption, trigger it through DLP so recipients get the same experience they are used to. Otherwise, use Check Point Email Encryption, which works on every mailbox without a Microsoft licence upgrade.

Microsoft encryption also needs a transport rule in Exchange, which Check Point creates when the workflow is first enabled. Contact us if the rule does not appear.

Detect vs Prevent for DLP

In Detect mode you can see what people are sending that matches your DLP rules, without acting on it, which is useful for baselining. But the encryption workflow only actually encrypts in Prevent (Inline), because it has to modify or route the message before delivery. In Detect, a match is logged but nothing is encrypted.

Outbound inline protection also needs the SPF include (include:spfa.cpmails.com). See the Deployment modes article before enabling it.

Next steps

Next: Anomaly Detection and impossible-travel logins

Previous: Creating a policy: a worked example with Click-Time Protection