Windows: Sharing Sensitive Information - Internally

When you create, view or contribute to the content of files as part of your daily workflow, many times you’ll be working with data that’s considered sensitive and therefore should be protected.

There are several reasons why information is considered sensitive and as a result, should be protected. When determining if a file should be protected before it’s saved or shared with others, you should consider the following:

  • The content of the file – Files that contain personal of financial data like social security or credit card numbers are always considered sensitive, therefore should always be protected.
  • Rules around sharing data with others – In order to preserve the secrecy of sensitive information organizations often have policies that designate information shared with certain users, should always be encrypted.
  • Organizational policies around email attachments – Depending on the organization and configuration of Smartcrypt, policies could mandate that all email attachments must be encrypted.   

Most often these files are also relevant to other’s job functions, informational needs and/or stored for future use or reference. As a result, they need to reside on file shares or other common repositories that others in the organization can access. Smartcrypt provides a simple way to secure the file using encryption to ensure wherever it resides in your environment, it’s protected.

Encrypting Files into a File Share

Concept: When users are working with sensitive files and need to securely share the information with their colleagues, a common approach is to encrypt the file and save it to a share, for others to access. Smartcrypt functionality can be accessed directly from the right-click menu allowing users to easily secure and save files in the appropriate locations.

Process:

  1. Locate the desired file on your desktop or in Windows Explorer.
  2. Right click on the file to reveal the ‘right-click context menu’.
  3. Position your cursor on ‘Smartcrypt’ to reveal the Smartcrypt sub-menu.
  4. The following encryption options are presented:
  5. Select ‘Encrypt to’:                               
    1. This option will display the ‘Save Archive As’ window, for you to name the file and select the destination into which the encrypted file will be placed.
    2. The name of the original file will be shown in the ‘File Name’ field, do not modify this; so the encrypted file will retain the name of the original.
    3. Select the files share or other destination into which the encrypted file will be placed.
    4. Click Save.
  6. Choose the desired method of encrypting the file. The ‘Choosing the Method of Encryption’ section describes the key selection options
  7. Click Encrypt
    1. An encrypted version of the file will be created, named as specified and placed in the selected destination folder. 

NOTE:  The original, unencrypted file still exists in its original folder. Depending on your security concerns and corporate policy, you may want to delete the original file leaving only the encrypted file.



Sharing Smartcrypt Files as Email Attachments

Concept: When sending files via email, Smartcrypt interacts with Outlook to prompt users to take the required protection actions before the file is sent; you will see different prompts based on whether the attached file is already encrypted or not encrypted.  

Things to consider:

  • Is the file already encrypted?
  • Which key is it encrypted with?
  • If so, is the file encrypted with a key the recipient has access to?

Before you send the file, you should ensure it’s encrypted with the appropriate key or method, accessible by the recipients.

Attaching Files that are NOT Already Encrypted

Process:

  1. Open Microsoft Outlook and create new message.  
  2. Attach the desired file, using ‘drag and drop’ or the ‘Attach File’ button.
  3. Compose your email message and press the ‘Send’ button.
  4. You will be presented with the ‘Encryption Options’ page.
    1. As per policy, only the ‘Encrypt Attachments’ option is enabled.
    2. Click Next.
  5. Choose the desired method of encrypting the file. The ‘Choosing the Method of Encryption’ section describes the key selection options.
  6. Click Encrypt

An encrypted version of the file will be sent to the recipient identified in the email message. 

Attaching Files that are Already Encrypted

Process:

  1. Open Microsoft Outlook and create new message.
  2. Attach the desired file, using ‘drag and drop’ or the ‘Attach File’ button.
  3. Compose your email message and press the ‘Send’ button.
  4. The email will be sent with the attached, encrypted file.

NOTE:  Before you attach and send a file that’s already encrypted, ensure you check the Smartkey it’s encrypted with, is a key the recipient has access to.

Please see the ‘Viewing and Editing Smartkey Access’ to learn how to check and edit what users have access to which Smartkeys


Attaching Files that are Non-Sensitive

Concept: You may be working with files that do not contain sensitive information and therefore you don’t desire and are not required to protect it. In these situations, Smartcrypt allows you to attach and send non-sensitive files without encrypting them.

Process:

  1. Open Microsoft Outlook and create new message.
  2. Attach the desired, non-sensitive file, using ‘drag and drop’ or the ‘Attach File’ button.
  3. Compose your email message and press the ‘Send’ button.
  4. You will be presented with the ‘Encryption Options’ page
  5. Select ‘Send message without any changes’.
  6. Click Next

The non-sensitive file attached to them message will be sent, and not encrypted.

My Attached File Exceeds the Maximum Size Limit

Concept: If you’ve attempted to share a file with others via email and experienced a failure due to the size of the file, you can use Smartcrypt to address the issue.

Smartcrypt allows you to compress files, thereby reducing its size and allowing you to share them through email without encountering file size limitations.

Process:

  1. Locate the desired file on your desktop or in Windows Explorer.
  2. Right click on the file to reveal the ‘right-click context menu’.
  3. Position your cursor on ‘Smartcrypt’ to reveal the Smartcrypt sub-menu.
  4. The following encryption options are presented:
  5. Select the ‘Compress to’ option:                       
    1. This option will display the ‘Save Archive As’ window, for you to name the file and select the destination into which the compressed file will be placed.
    2. The name of the original file will be shown in the ‘File Name’ field, do not modify this; so the compressed file will retain the name of the original.
    3. Select the files share or other destination into which the compressed file will be placed.
    4. Click Save.

If the File is Still Too Large

If the default compression doesn’t reduce the size of the file below the permissible limit, you can attempt to increase the compression using the following method.

Process:

  1. To access the Smartcrypt application’s Options menu, right-click on the Smartcrypt icon running in the system tray.
  2. Select “Options’
  3. Under ‘Compression’, navigate to the ‘Compression’ drop-down menu, and select from the following compression settings
    1. Fast – Will compress the file using the method that will result in the fastest time to completion.
    2. Maximum – Will compress the file into the smallest possible file size. This method should only be used if all other methods don’t result in a file size that meets the size limitations, because this could take a measurable amount of time.
  4.  Select ‘OK’ to exit the Smartcrypt application options menu.

  5. Locate the file you desire to share.

    1. Execute the compression using the steps outlined earlier.

    2. After the compression has completed, attempt to attach it to your email message and send.