Outlook: Sending Sensitive Info using Email Encryption

At HFA, it's against company policy to send any sensitive information without first encrypting the email. Sensitive information includes PII such as Social Security Number, Credit Card Numbers, Drivers License numbers, and other information not meant to be consumed by the public.

Read below on how to send sensitive PDFs using expiring OneDrive Share Links for maximum security.

Sending Email Without Attachments

If you need to send sensitive information to a trusted partner, you must follow these steps:

In Outlook, open the outgoing message in a new window.
Write your reply
Click Options Tab > Encrypt > Encrypt-Only to set encryption on the message

Sending PDFs with Sensitive Information

If you are required to send a PDF containing sensitive information, you should first password protect the PDF before sending, then use OneDrive to create a sharing link (with a short expiration date) for the PDF you are sharing.

Save the sensitive PDF to your OneDrive and make sure it syncs
Open the PDF in Acrobat and encrypt the PDF with a password
On the next screen, choose Viewing to password protect viewing the file (most restrictive). Then type a password for the file. It's best to use a randomly generated password.
Once the PDF is password restricted, create a OneDrive Share Link to the PDF with a short expiration date following these steps:
1. Right-click the File in your File Explorer > Click Share
  In the popup window that opens, click the Gear icon at the bottom next to the Copy Link button:
2. On the next screen, check "People you choose" or "Anyone" depending on what is allowed for the file you are sharing. If you select People you choose, you'll have to provide email addresses on the main Share screen, along with the PDF password in the message.
  IMPORTANT: Fill in an expiration date that is no more than a few days in the future. You can also give the user permission to modify the document -- only applies to Microsoft Word/Excel documents.
3. Click 'Apply' button, then Copy Link button to copy the file sharing link to your clipboard.
Create a new email to recipient, paste the share link from previous step and also include the PDF password in that email - do not attach the PDF itself to the email
Encrypt the email using the instructions at the beginning of this article and send to recipient

Sharing sensitive files and info this way helps ensure that if the recipients (or your) email mailbox is compromised, the attacker cannot open the attached PDF to brute force their way in. Hopefully your Share Link's expiration date has passed, and the file is no longer accessible.

Reach out to HFATechHelp@hfahawaii.com with any specific questions about sharing sensitive information.