Why Office 365 Data Loss Prevention DLP Rules Are Not Working

Data breach becomes one of the biggest fears to organizations today. As users are depending on cloud services to store their data, the solutions that limit data flow and access are also more important. Microsoft’s Office 365 renders a service for Data Loss Prevention (DLP) that is capable to identify the sensitive and critical information of any organization. The DLP applies a deep content analysis on the sensitive data without affecting users that are working with rest of the content.

With the help of Office 365 DLP policy, users can identify, track, and protect the crucial content such as financial documents, credit card numbers, health records, social security numbers and so forth. This DLP Office 365 service offers many security features to prevent confidential data that is stored in the cloud from intruders. However, sometimes, when a user composes a new email message that comprises sensitive information, the Exchange Online DLP policy tips are not displayed as expected. This implies that our valuable data is not secured even after applying Office 365 data loss prevention policy.
There are many things which can arise this issue that can cause Office 365 DLP rules not working. In this editorial, we have comprised some possible causes and resolutions for Office 365 Data Loss Prevention not working issue. Now, let us get started.

Cause 1 - Office 365 Policy Tips Not Working After Installing MS Outlook Separately


Users have to go through two major steps to enable Office 365 data loss prevention policy:
Step 1: Enable Policy Tips in MS Outlook
  • Hit a click on File >> Options >> Mail
  • Scroll down until you did not find Mail Tips section
  • Then, hit MailTips Options to enable DLP in Office 365
  • Verify that Policy Tip notification option is enabled from Select MailTips to be displayed selection box
  • Make sure that Display automatically when MailTips apply feature is activated from MailTip bar display options
  • If all the settings are accurate in MS Outlook then, navigate to the next step
Step 2 - Check Settings in Office 365 Account
Follow the below guidelines in Exchange Online tenant where Office 365 DLP not working:
  • Launch the DLP policy in Exchange Online protection
  • Navigate to Choose a mode for the requirements in this DLP policy tab
  • Here, check that Enforce or Test DLP policy feature is enabled or not

Cause 2 - Policy tips feature is not enabled by DLP Policy


If policy tips are disabled from Exchange Online data loss prevention then, follow below steps to enable:
  • Go to the Properties of DLP policy in Exchange Online Protection that is situated under Choose a mode for the requirements in this DLP policy
  • Here, verify that make Enforce or Test DLP policy either Policy Tips option is enabled or not

Cause 3 - Sensitive data threshold for the DLP policy is not met


If the sensitive data threshold for DLP policy is not met then, the associated Office 365 DLP not working or policy fails to display. Thus, follow down-mentioned steps to fix this:
  • Modify the states of the applicable data loss prevention policy by clicking on the EAC
  • Go to the Compliance management >> Data loss prevention
  • Hit double-click on any one policy that is displaying in list policies or you can highlight one item and hit the Edit button
  • Doing this will take you to DLP Policy page, here click on Rules

You can generate a new DLP policy and leave it in the non-activated or disabled mode. This mode does not enforce the policy and you can modify any predicates, activities, or values that are associated with rules of Office 365 DLP rules not working and before you test or begin the enforcing.

Concluding Lines

Office 365 Data loss prevention is one of the best practices that every individual should use in their accounts. However, what if the Office 365 DLP policy tips will not work properly? Well, users can loose their crucial information. For that, you can get Office 365 Security Measures that can be drawn their entire business. Hence, in this article, we have comprised some easy workarounds to resolve Office 365 DLP notworking issue,