Prompt users when emailing external recipients in MS Outlook

By: Standss Contributor , Jul 18th, 2023

Double-checking your email recipients before sending your emails is important because it can help you avoid data breaches and simple human errors. According to the Office of the Victorian Information Commissioner (OVIC), the main reason for emails being sent in error is simple human error. So, while it may sound simple, the main way to prevent data breaches when using email is to be careful and pay attention. For example, when checking the recipients of an email, double click on a recipient’s name as displayed in the ‘TO’, ‘CC’ or ‘BCC’ fields so that their full email address is visible.

However, people seldom double-check their emails before sending them. Our brains are wired to rely on heuristics and take mental shortcuts to process information quickly.

We automatically assume we have entered the correct recipient’s address without verifying it. This cognitive bias can make us overlook the need for double-checking, as we trust our initial perception to be accurate.

Besides, in our fast-paced digital lives, we often operate on autopilot, performing routine tasks without conscious awareness.

Composing and sending emails can become an automated process, allowing us to overlook the importance of scrutinizing the recipient field. As a result, we may click the send button without giving it a second thought.

In this post, we will show you how you can use an Outlook-addin called SendGuard to confirm recipients (internal and external) and attachments in outgoing emails in just two simple steps.

Step 1: Get SendGuard for Outlook

Download SendGuard from our website. Close Outlook before installing SendGuard. Follow the instructions on your screen to install SendGuard on Outlook. Once the installation process is complete, navigate to Standss Outlook Addins and click SendGuard.

You can trial SendGuard for 30 days without the need for a credit card.

If you need to use SendGuard in your organization, please contact us at to access test licenses. We will help you deploy the trial version of SendGuard to your pilot users.

Step 2: Configure SendGuard

Click SendGuard > Settings > SendConfirm. The following screen will open up. It is in this window that you can configure SendGuard to prompt users for confirmation on external and/or internal emails.  Confirmation of Recipients and Attachments are features of the SendConfirm module of SendGuard. You can choose to prompt external recipients or internal recipients.

External domains are color-coded for easy identification.

You can also force users to view attachments before ending. This prevents the leakage of any sensitive information that can be unknowingly included in attachments.

Uncheck the Internal email address box if you need to prompt for confirmation on external recipients.

You will receive the following prompt if you are going to send an email.

Depending on your configuration, the recipients and attachments can be pre-ticked, or you can individually check the box next to each recipient and attachment to confirm their validity.

You can also change the recipients in the “To”, “Cc” or “Bcc” from the SendConfirm prompt.

Other Email Security Features in SendGuard

Reply Guard- view and confirm recipients when reply or reply-all is clicked on an email with multiple recipients.

Reply Guard can also:

  • Get you to confirm recipients in a distribution list.
  • Prompt/remind you to call or chat via Microsoft Teams with the person you are emailing after you have replied to them a specific number of times.
  • Warn you if you are about to reply-all on an email you are bcc’d on

Delay Guard- delay sending of your emails for a certain interval. This will provide you with a brief period for reflection and a chance to retrieve a message from the Outbox folder before it goes out.

SendRules- create customized rules to detect sensitive data unique to your organization. SendRules contain a richer set of conditions, exceptions, and actions, which provides you with the flexibility to implement many types of messaging policies such as adding additional recipient(s).

Data Loss Prevention- define and apply DLP polices to scan for sensitive data. You can create a list of client keywords and approved domains to prevent client data from being sent to an unauthorized domain. Users can be alerted when they are sending client data to a non-approved domain.

You can also apply your own branding/corporate logo to the prompt SendGuard displays. The advanced tab in the SendGuard menu allows you to log sent or declined emails.

Logs maintain basic details of the email as proof that the user was prompted for confirmation before an email was sent. These logs are in a standard format and can be used with PowerBI/Splunk etc for compliance reporting, impact assessment etc.

Speak to us today!

Send an email to if you are interested in implementing the SendGuard Outlook add-in your organization or need any additional customization before using SendGuard.

SendGuard for Outlook

Image Credit:

Photo by Austin Distel on Unsplash

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