Description
It’s a problem when you pick the wrong recipients by mistake, and then send the email. And in the legal world, if you or a user accidently emails opposing legal counsel or other recipients it can be disastrous. This can sometimes happen by having two names listed for one person, where one is a work email address and the other is a personal email address. Then when composing the email and using the tab key to pick and choose recipients, the wrong “John Smith” is inadvertently chosen. This mistake has happened many times, including as far back as 2014.
Safeguard Send for Microsoft 365 helps to solve this and other issues when going to send emails by checking outgoing email, looking for incorrect recipients and other potential violations, for example examining email subjects, bodies and attachments, etc., to make sure they are in compliance with your business rules. If not, then it provides an external email warning prompt.

Notice that email addresses, not display names, are used in the external email warning prompt for better clarity.
While there are many outgoing email checks that can be performed, by far the most popular rule is an external email warning, that is, to prompt the user whenever sending an email outside the company. The image on the right shows what a typical prompt looks like, along with 3 fictitious email addresses. If there were any attachments or offending (i.e., sensitive/classified) keywords, they would appear here as well.
In addition to scanning the recipients underlying email address (and not just the display name), there are a number of different conditions that can be checked as an email goes out the door.
For instance, you can…
- …act on an email if sending an external email (i.e., outside the company (this is the most popular condition))
- …act if the number of attachments is equal to or greater than N
- …act if number of recipients is equal to or greater than N
- …act if sending to 2 or more recipients in different external domains
- …act if sending to recipients in one or more specific domains (e.g., @gmail.com, @hotmail.com, etc.)
- …act if sending an email with account numbers (credit cards, SSNs, drivers license numbers, bank account numbers, etc.)
- …act if the email subject contains or does not contain your keywords
- …act if the email body contains or does not contain your keywords
- …act if the attachment name contains or does not contain your keywords
- …act on every send
In addition, to call attention to the exact problem, the text of the warning prompt can be changed as well, or the email can be prevented from sending altogether. The latter is useful to prevent sensitive keywords or credit card numbers from ever being sent (to comply with either corporate or national privacy policies (like HIPAA) or company security compliance policies).
The Free tier includes includes a visible task pane along with the first three conditions (act if sending outside the company, act if the number of attachments is equal to or greater than N, and/or act if the number of recipients is equal or greater than N). There is effectively only one “rule”, the one visible in the task pane:

The task pane on the right is where each user configures their settings (in the free version that is).
The Standard tier includes the ability to make this task pane invisible for your users. And, in addition to including the first three conditions that are included in the Free tier, also allows the “act if sending to 2 or more different external domains”. Furthermore, up to three rules can be created, each with their own warning prompt text. In addition, it supports access to a dashboard for centralized control over your users and their rules.
The Pro tier includes all the conditions listed above, allows an unlimited number of rules, and provides further customization of the warning prompt (see the Screenshots tab above for details), including allowing for custom fonts and support for white labeling in general. This tier also automatically includes access to the dashboard for centralized control that allows you control over your rules for your entire organization.
Here is a complete comparison of all three tiers:
Features
COMPARE TIER FEATURES
Total number of rules
Prompt if sending an email outside the company
Prompt if the number of attachments is greater than N
Prompt if the number of recipients is greater than N
Prompt if sending to recipients in two different domains
Prompt if sending to specific recipients or domains
Prompt if sending an email with a SSN, credit card or other account number
Prompt if subject contains/does not contain specific keywords
Prompt if email body contains/does not contain specific keywords
Prompt on any send
Tech support included
Can hide task pane from users
Centralized managment dashboard
Corporate branding
Onboarding Concierge Service
Free Tier
$0.00
per month
1
Standard Tier
$8.00
per month
(Note: Bill Annually
AND SAVE 20%)
3
Professional Tier
$12.00
Per Month
(Note: Bill Annually
AND SAVE 20%)
Unlimited