Detecting Personally Identifiable Information (PII) in Outlook 365

Do your organization’s users need to send potentially sensitive personal information, such as credit card numbers, personal health details or any other personally identifiable information (PII) through email communications?

You can safeguard both your users and your organization by configuring Outlook to detect emails containing sensitive data.

Outbound email data breaches are prolific and email environments like Microsoft Outlook don’t come with the necessary native controls to eliminate the risks associated with people’s behavior as they use email.

In most cases, these breaches happen due to human error. This includes adding the wrong recipient to an email, attaching an incorrect file or not using tools like Bcc correctly.

Organizations in specific sectors—like law firms, banks, and healthcare providers—handle highly sensitive information. While data breaches pose a significant risk to all businesses, the repercussions can be particularly severe for these heavily regulated industries.

In this post, we will show you how you can use a data loss awareness tool called SendGuard to detect personally identifiable information in outgoing Microsoft Outlook emails.

Sending Confidential Information via Email

Organizations manage various types of sensitive information, including:

  • Financial data
  • Proprietary data
  • Credit card numbers
  • Protected Health Information e.g. health records
  • Social security numbers


SendGuard for Outlook is an Outlook add-in designed to help protect these type of sensitive data and prevent users from inappropriately sharing sensitive data with people who shouldn’t have it.

It typically provides features such as email attachment scanning for potential errors, prompting for confirmation before sending sensitive emails, and ensuring compliance with email policies.

It’s often used in corporate environments to mitigate the risk of data breaches and ensure that employees adhere to email security protocols.

Users do not need to do anything extra! A prompt similar to the following will be displayed if potentially sensitive information/personally identifiable information is detected.

Setting up SendGuard to Detect PII in Outgoing Emails

There are two main versions of SendGuard tailored to your Outlook environment:

  1. SendGuard Web Add-in: Ideal for New Outlook, OWA, Outlook for Mac, and also compatible with Outlook for Desktop.
  2. SendGuard COM Add-in: Specifically designed for Outlook for Desktop.

Installation Methods

  • COM Add-in: Download the 30-day free trial directly from our website.
  • Web Add-in: Contact our team at sales@standss.com to receive the installation file.


For this blog post, I will demonstrate the web add-in version of SendGuard, which is compatible with all versions of Outlook. It is easy to configure, deploy, and manage settings via the SendGuard License Management system.

I will guide you through configuring SendGuard to detect PII using this system. The COM-addin works in a similar way.

Create DLP Rules in four simple steps

For the purpose of this blogpost, I will create a DLP rule to detect a Master Credit Card number in emails.

I can do this under the Data Loss Prevention tab in the SendGuard License Management System.

The steps are outlined below to create DLP rules.

Step 1: Set your DLP Rule

Give your rule a name. You also need to choose a Rule Type. The following rule types are available:

Custom Rule: Allows you to perform customized checks on outgoing emails.  For example, you can set up custom rules to scan attachments, detect potentially inappropriate messages (eg. profanity) display prompt or block emails according to Microsoft Sensitivity labels.

DLP Rule:  DLP offers predefined policy templates to help you get started, or you can create a custom policy. These rules utilize regular expressions that can be adjusted to accommodate various data formats. This post will guide you through creating a DLP rule.

Step 2: Configure your DLP Rule

SendGuard includes ready-to-use policy templates that address common compliance requirements, such as helping you to protect sensitive information subject to the General Data Protection Regulation (GDPR), U.S. Health Insurance Act (HIPAA) U.S. Gramm-Leach-Bliley Act (GLBA), or Payment Card Industry Security Standard Council’s Data Security Standards (PCI-DSS). You can customize these DLP policy templates to meet your specific requirements. We recommend that you contact us and we would assist you in modifying the DLP policies.

In the above screen you can see some of the DLP policy templates available in SendGuard.

In the next step, you get to choose what happens when a Master Credit Card Number is detected.

Step 3: Set DLP Rule Actions

In this step you will need to choose what will happen when a credit card number is found in emails. You have three options:

  • User must tick checkbox to send
  • User must type “SEND” to send
  • Block sending of emails

Step 4: Review and finish setting up

Click Finish if you are okay with the way the rule is configured.

After configuring the rule, you can view it as shown below:

You can see that the rule I created to detect credit card numbers in outgoing emails is enabled, along with the other rules I previously set up. You can create other DLP rules in a similar manner as shown above.

The next time you send out an email, SendGuard will scan it based on your settings.

SendGuard is Microsoft Certified Software

SendGuard is a Microsoft 365 Certified email protection software.

Throughout the certification process, SendGuard underwent rigorous penetration testing and assessments related to data handling, privacy, and security features.

During this process, SendGuard was thoroughly evaluated against security controls based on industry standards, including SOC 2, PCI DSS, and ISO 27001.

Learn More – SendGuard is now Microsoft 365 Certified

Easily Install and Manage Settings using License Management System

The easiest and simplest way to deploy the SendGuard addin is through the Microsoft 365 Admin Center.

There are other deployment options available such as Group Policy, customized MSI installer, Group Policy Preferences or Template (ADMX) and Microsoft Intune.

SendGuard License Management System allows IT admins to effortlessly manage user subscriptions and settings without the need for re-installations or redeployments. Whether you upgrade or change plans, everything is handled seamlessly via the Standss SendGuard License Management system.

Speak to a Sales Specialist

Interested to learn more about how SendGuard can help prevent accidental data loss and maintain regulatory compliance in your organization? Reach out to a sales specialist on sales@standss.com.

SendGuard for Outlook

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