How to NEVER send a sensitive email to the wrong person

By: standss , May 14th, 2024

Relying solely on autocomplete when composing emails can increase the risk of sending misdirected emails.

Firstly, it may suggest email addresses similar to the intended recipient’s, resulting in the user selecting the wrong suggestion without verifying the recipient’s identity. Secondly, autocomplete relies on the user’s past interactions, so if the contact list is outdated or contains incorrect information, obsolete email addresses may be suggested.

Additionally, autocomplete may suggest the wrong recipient when multiple contacts have similar names or addresses.

In this blogpost, I will show you how you can still use Outlook’s Autocomplete and still protect yourself from this kind of mistake.

Preventing confidential email from going to the wrong email address

This technique works particularly well if there are certain people from whom you need “better protection” e.g. if you’re a lawyer, you need to be extra careful that you don’t send sensitive information to opposing counsel… or you send information to a report in the media.

Our Outlook addin SendGuard for Outlook has a feature called SendConfirm. If you enable this feature, Outlook will prompt you before it sends out any email.

You probably don’t want a prompt for every email you send out but…

You can configure Send Guard so that Outlook will prompt you only when you send out emails to particular people (e.g. your boss, opposing counsel, reports from the media etc.)

Setup when you want to see SendConfirm Prompt

Here’s how to configure Send Guard to do this (please note that if you are not already a user of SendGuard, you will need to download and install the Outlook addin before you can do this)

  1. Open Outlook.
  2. Click on the Standss Outlook Addins tab on the ribbon.
  3. Click on SendGuard and then click Settings to open the Settings screen.
  4. Click on the SendConfirm tab.
  5. Enter the email addresses for which you want the SendConfirm prompt to be displayed.

Now anytime you click Send to send an email to anyone on the list, Outlook will ask for confirmation before the email is sent out.

If you’re a SendGuard user, I hope that this tip helps you get even more out of your software.

Other Email Security features in SendGuard

Detect Confidential Information: Scan outgoing emails for sensitive information such as social security numbers, credit card numbers, health identification numbers, etc.

Reliable recall for sent emails: Delay emails in your Outbox to give you a brief window to safely recall emails.

Client-side rules for automated actions based on email content and properties: Warn users, block emails, automatically mark emails for encryption, CC or BCC managers or compliance managers.

Achieve Compliance with International Data Privacy Laws: GDPR (EU), CCPA (California Consumer Privacy Act), HIPAA for the US healthcare industry, FINRA for the US financial sector, Australian Privacy Act, POPIA (South Africa), PIPEDA (Canada).

For more information, contact

SendGuard for Outlook

Image Credit:

Photo by Tima Miroshnichenko

4 Replies to “How to NEVER send a sensitive email to the wrong person”

  1. Hi

    Does this plugin work on non outlook client e.g. the webmail access interface.

    Please confirm.


  2. @Tony, currently SendGuard only works with Microsoft Outlook. It does not support non-Outlook email clients

    Update: Our addins run on all platforms including New Outlook, Classic Outlook (Windows), Legacy Outlook (Mac), OWA

  3. Are you able to enter a list of email addresses it WON’T alert on sending, instead of putting in a list that will?

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