VIPRE SafeSend is an Outlook add-in designed to prevent data leakage caused by misaddressed emails and autocomplete errors. The tool requires users to confirm external recipients and file attachments before emails are sent from the organization. The product scans outgoing email content and attachments for personally identifiable information (PII) and other sensitive data. Users can build custom DLP rules to define sensitive data using keywords, data patterns, and regular expressions to detect structured data. SafeSend provides pre-send warnings to minimize data leakage incidents. The tool includes configurable triggers based on domains, attachments, classifications, DLP rules, and other email-based variables. It can detect when emails are being sent to non-approved domains and warn users accordingly. All settings are configurable using Windows Group Policy and can be specified on a per-group basis. The product supports customizable branding with corporate logos and styling. It includes recipient highlighting with color-coded alerts for BCC and CC recipients. The tool provides a full audit trail with advanced user action logging to files or Windows Event Log. Logs can be ingested into SIEM platforms for analysis and reporting. SafeSend is localized into 30 languages to match Outlook's display language and is available on Microsoft Azure Marketplace.