The new SendSafely Outlook add-in

The SendSafely Outlook add-in is now available for install from Microsoft AppSource. Once installed, the SendSafely add-in is automatically activated when composing a new email message or a reply to an existing message. To configure the plug-in, browse to your inbox and compose a new email message. On the “Message” ribbon at the top of the screen you should see a section labeled “Apps”. Within that section you should have a SendSafely button.

After pressing the button, the SendSafely Task Pane will open on the right side of the screen. The Task Pane is the primary interface for interacting with SendSafely when composing a message.

The first time you load the SendSafely add-in you will need to log in with your SendSafely account by pressing the “Login to SendSafely” button on the Task Pane.

SendSafely customers that are isolated to a specific region or have multiple SendSafely portals, it may be necessary to expand the “More Options” section of the login page to specify the hostname of the portal you want to connect to.

When you press the “Login to SendSafely” button, a new login window will open and load the login page for your SendSafely portal. If prompted to display a new window, choose the “Allow” option.

After you complete the login process, the login window will close and the plugin should display your login information at the bottom of the Task Pane.

At this point you are ready to use the SendSafely add-in. To attach files to the message you are composing, drag files onto the upload icon in the top center of the Task Pane or choose the option to browse your device for files. 

After attaching one or more files, the files along with their upload progress will be displayed in the Task Pane. It is important to leave the task pane open while any uploads are in progress otherwise the upload may not complete.  A “Secure File Transfer” dialog will also be inserted at the top of the draft email message, which is how your recipients will access the link to download the files.

Recipients for your file transfer are determined based on the recipients in the To and Cc fields of the draft message. As each recipient is added or removed, they will appear in the SendSafely Task Pane along with the option to enable SMS verification. Users that are added via the Bcc option will not be able to access the attached files.

To enable or edit the phone number used for SMS verification on each recipient, use the karat on the left hand side of each recipient’s email address. Make sure to press the blue check mark button to save the phone number. Recipients who have previously received items from you using SMS verification will automatically be added with this option enabled.

When you press Send, the SendSafely add-in will mark the package containing your files as available for download by your recipients. You may briefly see a status notification above the send button while the process completes.

When sending from a slow internet connection, this process may take more than a few seconds. When this happens, outlook may prompt you with a dialog indicating that SendSafely is taking longer than expected. If this happens, you should wait for SendSafely to finish processing the message. Do not press the “Don’t Send” button. 

When processing is complete, the dialog will automatically update and indicate that SendSafely has finished processing. At that point you should press the “Send” button and the email will be sent.