SendSafely Outlook Plug-In

SendSafely Enterprise and Pro users can use our SendSafely Outlook Plug-in to send files directly from within Microsoft Outlook. This page will provide you instructions on how to get the plug-in set up and configured on your Windows desktop computer.

System Requirements:  In order to use the plug-in your must have a Windows XP, Windows 7 or Windows 8 PC that runs Microsoft Outlook 2007, 2010 or 2013. These instructions assume that your Outlook installation is already configured to send and receive email using the same account that is registered with SendSafely.

Step 1 - Download and Run the Add-In Installer

Download and run the add-in installer (SendSafelyOutlookSetup.exe) on the Windows desktop where Outlook is installed. Outlook should already be configured to send and receive email using the same email address you have registered with SendSafely Enterprise.

Follow the prompts provided by the installer until you receive a message indicating that the SendSafely Outlook Plug-in was successfully installed. 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). Typically a reboot is not required however if the .NET Framework Client Profile is installed a reboot may be required (you will be prompted accordingly). Both of the prerequisite packages are developed and signed by Microsoft and certified to run on all supported versions of Windows.

Step 2 – Close and Re-Open Microsoft Outlook

Once the plug-in is installed, you will need to close and re-open Outlook if it was running prior to the installation process. If the plug-in was installed correctly, you should be prompted with a “Quick Start” interface that provides a high-level instructions on how to use the plug-in.

Step 3 – Configure your API Key and API Secret

In order to authenticate your account with SendSafely, the plug-in uses an API Key and API Secret. The API Key and API Key Secret are essentially software-level credentials that allow a program to access your account without the need for sharing your username and password with the software. The API Key and API Secret can be configured by pressing the SendSafely icon button from the main menu bar in Outlook, which will open the SendSafely Plug-in Console. The first tab of the console, labeled “Connection Info” is where you can provide the API Key and API Key Secret.

To obtain a new API Key and API Secret, log in to your SendSafely account and go to the Edit Profile page. From there you should see an API Access Keys section that allows you to manage your API Keys. Provide a unique description of what the key will be used for (i.e. “Outlook 2010 Plug-In”) and press the “Generate New Key” button. The newly created API Key and API Key Secret will be displayed on the page.

Please note that for security reasons, the API Secret will never be displayed again. Never share your API Key or API Secret with ANYONE. These values can be used to access all of your account data and should be treated the same as a username and password.

You should copy and paste the API Key and API Secret directly into the Connection Info tab on the Plug-in console. Once entered, press the “Validate Credentials” button to verify the information and store it securely within the plug-in.

Step 4 – Configure Plug-in Policy Settings

In addition to the Connection Info tab, the plug-in console has two other tabs:

  • Policy Configuration – This tab controls preferences around when the SendSafely plug-in is automatically used and other configurable settings. The options on this tab are disabled until a valid API Key is configured for use by the plug-in.
  • Recent Packages – This 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.

Once a valid API Key has been verified by the plug-in, you can customize the policy settings used by the plug-in. 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 Plug-in will be available for download.

Step 5 – Start Sending Files

Once the plug-in is configured you are ready to start sending files. Any time you are composing or editing a message, you should see the “Attach Encrypted File” button with the SendSafely logo in the outlook menu bar. This button can be used to add files to an email message that will be sent using SendSafely. Much like a traditional email attachment, you will see the original filename with a .SendSafely file extension attached to the message. Each file associated with a message will have a .SendSafely file attached. These attachments will be removed once the real file is encrypted and uploaded to SendSafely. Files are not encrypted or uploaded to SendSafely until you press the “Send” button. You can remove each .SendSafely file from the message before sending to prevent the file from being sent with SendSafely.

When you attach one or more files with SendSafely, you will also see a link placeholder and text appended to the top of the message. The link placeholder will be replaced with the actual secure link needed to access the files once the message it sent. If you wish to move the link or edit the automatically inserted text you may do so as long as the placeholder link remains intact somewhere in the message.

Once you press “Send”, the message will be moved to the SendSafely Outbox and queued for processing by the plug-in. Before encrypting the files, the plug-in will present a list of recipients and ask if you would like to enable SMS verification for each recipient. After confirming these settings, each .SendSafely file will be processed by the plugin, which consists of encrypting the file and uploading the file to SendSafely. You will see a dialog that shows the overall progress of each file associated with the package. This dialog can be closed and your files will still continue to be processed in the background.

Once all files have been successfully uploaded to SendSafely, the email message will be released by SendSafely and sent to each recipient. Note that while files are uploading, the message will remain in the SendSafely outbox and will not be sent until the upload is complete. If for some reason you exit outlook prior to the upload completing, any pending messages will remain in the SendSafely Outbox and will be resumed the next time you run Outlook.

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