Need help getting started with Safeguard Send Core or Safeguard Send Core Plus? This guide explains how to use the Outlook add-in. This modern web app helps you to avoid mistakes by putting up a warning prompt whenever you go to send an email outside your company, or if there’s a certain number of recipients, or a certain number of attachments (or any combination of these conditions).
Note that this app is similar to the Microsoft 365 specific version of Safeguard Send for Microsoft 365, except that it presents a different prompt. However, just like Safeguard Send for Microsoft 365, it also works in desktop Outlook on Windows (both classic and new), Office on the web, and on Macs. However, this version does not support phones (yet!) due to a Microsoft limitation.
This article assumes that you or your IT Admin has installed the add-in into Outlook. If not, please consult this article on how to install Safeguard Send Core and Safeguard Send Core Plus.
If you are using Safeguard Send Core, then by default a rule is created that simply displays a warning prompt similar to this:
In the sample above, the outlook.com address is external to the company, and so is called out in the warning prompt. Up to 5 external email addresses can be shown in list. After that, an “…and others” line will be shown, indicating that there are other external recipients. Internal recipients, that is, those that are in the same company as you, are ignored.
Note that the individual recipient’s email addresses are displayed, not just their email “display names”. This helps to prevent mistakes by allowing users to examine the email addresses carefully to be sure that this is what is intended.
And that’s it! A super simple path to a more secure environment.
At this point you might be asking how you can change the warning prompt, say the words used, or possibly something bigger like only have the warning prompt show when there is also an attachment (like we’ve shown above), or even if one of the recipients has a domain ending in gmail.com or hotmail.com, etc. To do this, you need Safeguard Send Core Plus or even Safeguard Send for Microsoft 365, both of which use one or more rules for greater flexibility when checking outgoing emails.
Note that it’s possible that either you or someone in your company opted for Safeguard Send Core Plus, which is just like Safeguard Send Core, but with additional rules and other customizations. Generally, the prompts are similar to the one shown above and the buttons always offer Send Anyway or Don’t Send. However, one question that frequently arises is how Safeguard Send Core Plus handles multiple rule conditions. The answer is that the add-in evaluates all the rule conditions first, then presents a window that displays all the warnings all at once:
In the above image of a typical Safeguard Send Core Plus prompt, there are 3 rule violations. The sender is sending to more than 3 recipients, there are also 3 attachments being sent to a restricted recipient, and there are 3 attachments being sent to more than 5 external recipients. The above is just a sample – the actual rule violations that you will see in your prompts will depend on which rules your administrator or manager opted to implement.