Installing the Outlook Plug-in



The SendSafely Microsoft Outlook Plug-in lets you send encrypted files and email messages directly from Outlook. The SendSafely Outlook Plug-in is available with our Basic, Pro and Enterprise subscriptions.

System Requirements: 

  • Windows 7 or later
  • Microsoft Outlook 2007 or later 

NOTE: These instructions assume that your Outlook installation is already configured to send and receive email using the same account that is registered with SendSafely.

Using the Online Installer (recommended)

Step 1 - Download and run the installer

To get started, go to and download the installer. A pop-up will ask you to either Run or Save. Click Run and follow the steps to complete the installation. (If no pop-up appears, locate the installer in your downloads folder and double click to start the installation process).


Depending on your system configuration, the installer package may also prompt you to install additional prerequisite components on your system (these include the .NET Framework Client Profile v3.5 and Visual Studio Tools for Office Runtime). You may need to right-click the installer and choose the “Run as Administrator” option in order to install the prerequisites correctly.

If the installation fails, it may be due to a problem installing one of the pre-requisite packages listed above. If this happens, you should download and install the VSTO runtime and then attempt to install the SendSafely Plugin again.  

VSTO Runtime Installer:

Step 2 - Restart Outlook

After installation, Outlook must be closed and restarted for the Sendsafely plugin to activate. Make sure all Outlook windows are closed or click File and click Exit to close Outlook. Once Outlook restarts you should see a pop-up window with Quick Start instructions.



Step 3 - Configure the Outlook Plugin

Click Configure Now from the Quick Start Pop-up to to launch the SendSafely Plug-In Console and start the configuration process. The first step is to provide your SendSafely credentials. From the SendSafely Plug-in console, go to the Connection Info tab


For new user’s that don’t already have a SendSafely account, click Register Now for Free and follow the prompts. If you are already registered for SendSafely, then log in using one of the following options:

  • if you have a SendSafely password, enter email address and password and press Verify Credentials, or
  • if you are using your Google Account to log in, press the Login using Google link, or
  • if you are an enterprise Single Sign-On user, press the Use Single Sign-on link

Once your credentials are configured, the Policy Configuration tab can be used to update preferences around when the SendSafely plug-in is automatically used (Attachment Policy) and expiration settings (File Availability Policy)


Attachment Policy

By default, files are only sent via SendSafely when the “Attach Encrypted File” button is pressed in the email editor window. You can also optionally configure the plug-in to automatically override file attachments using the following options:

  • Every Time I Attach a File – All files attached to any email message will be sent using SendSafely.
  • When Sending Files to Users Outside of my Domain – All files attached to any email that includes at least one recipient in an email address outside of your email domain will be sent using SendSafely.
  • When the Attachment is Bigger than X MB. - Files that are larger than the configured file size (in MB) will be sent using SendSafely.
  • Ask me Before Using SendSafely – You will be prompted to confirm whether files should be sent using SendSafely every time any of the configured policy conditions are met.

File Availability Policy

This setting controls the default number of days that files sent using the SendSafely Outlook Plug-in will be available for download. Please note that the Outlook Plug-in uses its own expiration setting that is not bound by the Default Expiration setting in your SendSafely user profile in the SendSafely Web Portal.  We recommend updating BOTH values to the same value to avoid any confusion. Your web portal profile can be accessed by logging in to and following this menu path: Account Menu > Edit Profile > Account Profile.

This Recent Packages tab shows recent SendSafely activity for your current Outlook session. This tab is cleared every time you restart outlook and will remain blank until you send at least one package.

Using the Offline Installer (MSI) 

The MSI installer provides an offline option for installing the SendSafely Outlook Plug-in. We only recommend the MSI installer be used when necessary, as it does not auto-update like the ClickOnce version does. 

Step 1 - Uninstall the ClickOnce version

Before installing with MSI, double check any versions installed using ClickOnce have been uninstalled (i.e. from within Outlook, navigate to File->Options->Add-ins)

Step 2 -  Download the MSI Installer from SendSafely

Below is a link to a SendSafely Workspace containing the latest MSI installer. When prompted, use the email address associated with your SendSafely account to authenticate. If you do not already have access to this workspace, you can email and request access.

Step 3 - Extract and Run installer

Once downloaded, extract the ZIP archive to a folder and Run the MSI installer. Follow the prompts on the screen to install the plug-in, then restart Outlook to confirm it is working. Refer to the Online Installer section above for instructions on how to configure the plug-in once it is installed. 



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