Reply with Attachments in Outlook

By: standss , Aug 20th, 2019

Many of the emails that you receive in Outlook contain attachments. If you forward the email to someone else, the attachment stays with the new email. However, when you hit Reply or Reply-All on the email, the attachment from the original email is not attached to the new email.

A client recently asked us: What can we do to keep the attachments with the replies?

You can obviously attach copy the emails manually to the new email but this is not what the client needed. As a large multi-national law firm, their lawyers needed a way to automatically attach the original files to the emails (so that they could refer to them in the replies).

The good news: This feature is available inside Outlook for users of ReplyGuard for Outlook and SendGuard for Outlook.

SendGuard for Outlook (which includes ReplyGuard, SendConfirm and SendRules) is used by thousands of Outlook users to ensure that emails get to their intended recipients.

The Reply with Attachments Prompt

You can configure Outlook to display the following prompt whenever you Reply or Reply All to an email with attachments.

Include attachements with response message box

Now all users have to do is click Yes to create a Reply with the original attachments to it.

Configuring ReplyGuard/SendGuard to prompt for attachments

ReplyGuard is one of the components included in SendGuard. If you haven’t done so already, you can download and install SendGuard from here.

Click Standss Outlook Addins (on the Outlook Ribbon)

Click on SendGuard –> Settings.

Click Reply Guard to go to the relevant settings.

Reply/Forward Special Functions

Change the Settings to Prompt and then click OK

The prompt will displayed automatically on emails with attachments when you click Reply.

Deploying the Outlook Attachment Prompt to Many Users in Your Organization

SendGuard is designed for single users as well as large enterprises. Settings can be preconfigured and deployed out to users using a customized MSI  or ADMX file. The settings screen can also be locked/hidden so users cannot change or disable settings made by admins.

Please contact us for more information on network deployment.

You can also try a fully functional demo of SendGuard (which includes ReplyGuard) by clicking below.

SendGuard for Outlook

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