Is replying to emails a critical part of your profession? We made some recent changes to Outlook based on requests from clients in the financial and legal industries to make replying easier and safer.
In order to use these features, you will need to download and install ReplyGuard or SendGuard for Outlook. This Outlook addon installs inside Outlook and prompts you at the appropriate times as shown below.
Productivity: Clear Email History and Include Attachments
Once you have the ReplyGuard/SendGuard for Outlook installed and configured (setup instructions later), the following prompt will be displayed when you Reply to an email.

You can now remove the history (previous emails) from your replies simply by ticking the appropriate check box.
You can also automatically include attachments (from the original email) when replying to emails by ticking the appropriate check box. This is an extremely useful feature for legal communications, quotes etc when you need to refer to the original document.
Protection/Security: ReplyGuard also provides protection for the very common problem of inappropriate Reply-Alls
You will now be prompted to confirm recipients when doing a reply-all to an email with multiple recipients (if you want, this can be configured to only prompt when the email includes external recipients).

The prompt serves as a reminder that the email is going to multiple recipients and also allow users to quickly change recipients without having to go back.
Corporate Users: Reply Guard can be configured to log (to Windows log or text files) that the prompt was displayed and the user confirmed to send to the selected recipients.
Setting Up
Corporate users also have the option of customizing messages, deploying with preset and locked settings.
Follow the steps below to configure ReplyGuard/SendGuard.
Once you have downloaded and installed the Outlook addon, make changes to the settings screen as explained below.
Click on Standss Outlook Addin (on the Outlook Ribbon)
Click on the SendGuard button and then click Settings.
Select the ReplyGuard tab and change the Settings as shown below.

What is the difference between ReplyGuard and SendGuard?
ReplyGuard can be purchased separately or as part of the full SendGuard Outlook email security product.
ReplyGuard is an Outlook addon to provide productivity and protection related to replying to emails. SendGuard includes ReplyGuard as well as additional tools to provide more complete data leakage protection due to emails/attachments being accidentally sent to the wrong people.
You can download and install a fully functional trial of SendGuard by clicking on the image below. You can use the settings screen to only enable ReplyGuard or to enable the additional tools such as SendConfirm, SendRules and DLP protection that are part of the full SendGuard for Outlook.