Sending Files Securely using SendSecure for Outlook

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This article explains how to create a SafeBox from SendSecure for Outlook in order to securely send files. It also provides additional information about managing recipients and performing basic actions on open SafeBoxes.


To send secure messages via SendSecure through Outlook, you need to have SendSecure for Outlook installed on your PC. If it is not installed yet, you can get it here: SendSecure for Outlook.

Creating a New Secure Message

To create a new SendSecure message from Outlook:

  1. Start Outlook and locate the SendSecure group in the Outlook menu:
  2. Click New Message.
    Note: You need to enter your SendSecure credentials before creating your very first secure message.
    Remember: Although the opening SendSecure window looks like an email composition form, the content (message and attachments) you will put inside will never be sent by email to the recipients. Once sent, this form will ensure the creation of a temporary SafeBox that will securely store your content and make it privately retrievable by your recipients.
  3. Add a recipient, either by entering an email address via the To field/button, or by using the Add Recipient or Address Book buttons.
    You can add as many recipients as you need, considering the following:
    • The minimum required information is an email address.
    • A phone number (direct line only) may be required according to the selected Security Options.

    For more details, see Managing Recipients.

  4. Compose your message:
    Subject This is the only information (in addition to your identity) that will be disclosed in the notifications sent to the SafeBox participants (you and your guests) in order to summarize the purpose of the exchange. Adding a Subject is however optional.
    Message The text you enter here will be only visible by the participants accessing the SafeBox. The Message is optional if you add at least one Attachment.
    Attachments The files you attach here will be only downloadable by the participants who are accessing the SafeBox. Attachments are optional if you write a Message.
  5. Optionally:
    1. Adjust the Security Options according to the context/content of your message and the way the resulting SafeBox will be further used/processed.
    2. Change the Language in which your recipients will be notified and will access the SafeBox once it is created.
  6. Click Send.
Your message and attachments are securely sent to a new SafeBox in order to be also securely retrieved by the intended recipients. As such:
  • The recipients will be notified by email to access the SafeBox as Guest Participants.
  • On your side, as the Owner of the SafeBox, you can access its content and further manage it: see Managing SafeBoxes.

Converting an Email into a Secure Message

If you started writing an email but finally feel the need to secure your communication by using SendSecure:

  1. Stay in your email composition window.
  2. Locate and click the SendSecure Convert button in the menu of your email window (usually at the right):
    All the content of your email – including its recipients, subject, message and attachments – is transferred into a secure message composition screen.
    Note: As SendSecure messages can only be written in raw text, any formatting (e.g. bold, italic, bullet lists...) and embedded images from your original email will be ignored.
  3. Continue the secure message composition and send it as described in Creating a New Secure Message.

Managing Recipients

Once recipients are added to the To field, you can easily remove them, or edit their information and optionally add them to your Outlook address book.

Recipient Information

Overall, the recipient information that is required or at least relevant in the context of SendSecure includes:

An email address Mandatory.
A phone number At least one direct line number may be required depending on Security Options, otherwise it is optional.
A contact's name For display (optional), to better identify the person in email notifications and Web interfaces.
A company name Also for display (optional).
Other phone numbers Other optional direct line numbers of any type (Cell, Office, Home...) that will be potentially usable by the recipient to receive SafeBox authentication code.

Managing Non-Compliant Recipients

If a recipient is displayed in red, it means that some required information (email address or phone number) is missing. You will not be able to send your message as long as this recipient is left in that state. Here are guidelines to solve this issue:
  1. To get more details on the issue, simply put the mouse pointer over the affected recipient.
  2. From there, you can also edit the recipient to enter the information that is missing.
  3. At worst, if you do not have a phone number for the recipient while it is required, you may need to adjust the Security Options – if you are allowed to and if you can assume moderating the intended authentication methods for all recipients according to your secure exchange context.

Editing Recipients

To edit recipient information, put the mouse pointer over the recipient and click on Edit – or double-click on the recipient.
  • If the recipient was manually entered, or if the recipient was added from a corporate Outlook Address Book (which you do not own by definition):
    • The Recipient Properties window will open.
    • The information entered there will be only used for the current message.
    • If you need to save the recipient information for later reuse, click on Add to Outlook Contacts.
  • If the recipient already belongs to your personal Outlook Address Book:
    • The Outlook Contact window will open.
    • All modifications you will perform there will then be directly saved in the Outlook contact.

Adding a Recipient to your Outlook Address Book

To add a recipient as a contact to your personal Outlook Address Book:
  1. Put the mouse pointer over the recipient and click on Add to Outlook Contacts (or choose this option when editing the recipient).

    The Outlook Contact window will open, including all the information you may have already entered in the Recipient Properties.

  2. To complete the operation, you still need to Save & Close the contact from the Outlook Contact's menu.

Managing SafeBoxes

Opening a SafeBox in SendSecure Web Application

The Open in Browser option, always available in the Outlook menu, redirects you to your SendSecure Web Application, from which you can access and manage all your SafeBoxes and your user account (see Managing SafeBoxes in SendSecure Web Application).

Viewing a Summary of the Sent Message

When a secure message is sent from Outlook, a summary may be automatically saved by default in Outlook Sent Items – if your SendSecure settings were configured for it.

This summary:
  • Provides minimal information on the content that was sent:
    • The attachment list (file names/types and sizes only).
    • The message (or its length for information if the message was encrypted).
  • Provides information on the created SafeBox:
    • The SafeBox unique ID, for reference.
    • The Decryption Key (if Double Encryption was enabled in security options and if your SendSecure settings are configured to include it in the summary).
    • The scheduled closing date of the SafeBox.
  • Provides a link (button) to directly access the SafeBox in your SendSecure Web Application.

Manually Closing a SafeBox from Outlook

When you assume that a secure exchange involving one of your own SafeBoxes is done, you can manually close the SafeBox directly from Outlook (i.e. without having to do it from your SendSecure Web Application).

Just select one of the email notifications you received about the SafeBox (for example, the latest one reporting that a participant downloaded a file from the SafeBox), and select Close Now in the drop down menu located below the Open in Browser button.
Note: The availability of this option depends on the Security Profile that was used to create the SafeBox.

Other Options

From the drop down menu located below the Open in Browser button:
  • The Settings allow you to define all your local SendSecure settings, such as the way to manage the summaries of your sent messages and the language used by default when composing a new message.
  • If you Sign Out, you will need to re-enter your SendSecure credentials to be able to send a new secure message and access your SendSecure Web Application from Outlook.
  • You can also Check for Updates (when available), and get information About your current version of SendSecure for Outlook.
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