Announcement of New DLP Policy Tips Masked by Unclear Text

As described in message center notification MC894577 (21 Sept 2024), Microsoft plans to make some changes to the Data Loss Prevention (DLP) policy tips exposed to Outlook users. Regretfully, the text of the notification raises several questions that deserve clarification. This might happen as Microsoft rolls out the update in late October 2024. At least, let’s hope so.

The first issue is client support. The notification specifies the new Outlook for Windows but doesn’t mention OWA. Typically, any new feature now introduced for the new Outlook also turns up in OWA, if not in Outlook classic.

Microsoft has committed to support Outlook Classic until at least 2029). Enterprise customers are not rushing to adopt the new Outlook due to its functionality deficit want to see new features being delivered, especially anything related to security. What’s curious here is that Microsoft’s documentation for conditions that support policy tips for Outlook explicitly include Outlook classic in the clients due to support the new conditions. According to the documentation, you can expect to see the policy in production version 2303 & Build 16.0 16216.10000 or higher, and semi-annual channel version 2302 & Build 16.0.16130.20478 or higher.

Groups, What Groups?

The documentation also mentions that the Sender is a Member of condition is supported by Azure-based dynamic distribution groups. The other two supported group types are distribution lists and mail-enabled security groups. The three group types are Exchange Online objects and dynamic distribution groups are not found in Entra ID (or Azure AD as it was). I have no idea what Microsoft means by Azure-based dynamic distribution groups.

The Advent of Premium DLP Policy Tips

The larger issue is revealed in the warning that “any existing conditions outside this updated list, which may currently trigger Policy Tips in New Outlook, will stop working after October 18th, 2024.”The updated list is the set detailed in MC894577 and the documentation, so that’s clear. What’s not known is what existing conditions (Figure 1) will suddenly stop working on October 18.

Figure 1: Defining conditions for a rule in a DLP policy

Until now, there hasn’t been much differentiation between the DLP policy tips displayed in Outlook to accounts with Office 365 E3 licenses and those with Office 365 E5 licenses (or equivalents). This is unlike Teams, where DLP support has always required Office 365 E5 licenses.

The warning might mean that from October 18, 2024, Microsoft will differentiate between Office 365 E3 and E5 licenses when DLP decides what policy tips to display in Outlook. Even if a policy match dictates that a specific policy tip should appear, it won’t show up in Outlook unless the account has an appropriate license. The way the documentation is laid out and the clear separation of sets of policy tips into basic (E3) and premium (E5) conditions support this interpretation, as does the bald statement that “Features mentioned above are enabled based on Licenses.”

Premium DLP Policy Tips Are Another Reason for Customers to Upgrade

The text of MC894577 is unclear and misleading. Discovering that Microsoft wants to introduce premium DLP conditions isn’t surprising because it aligns with the general direction throughout Microsoft 365 to find places to introduce new functionality that requires high-end licenses. As I have noted many times. Microsoft wants to grow the annual revenue per user (ARPU) they generate from the Office 365 installed base to increase cloud revenues and profits. Increasing the ARPU by selling add-on licenses or convincing customers to move from low-price to higher-price bundles has been happening for years, but it is becoming increasingly obvious.

Updating DLP to increase the set of conditions that can indicate potential data leakage issues to users through policy tips is a good thing. Making the new conditions a premium feature is OK too, even if it makes management of DLP policies a little more complex and potentially more expensive, if you decide that the new conditions are a must-have.

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