Email is the foundation of all business communications, both internal and external. For decades it has made workplace collaboration faster, easier, and more accurate. But its central position puts a target on its back. Threat actors are working harder than ever to intercept confidential data in transit. If they succeed, the consequences can be devastating – particularly for small and medium-sized businesses (SMBs).
How can you prevent this from happening to you? If you use Outlook, email encryption is one option that could protect your data and prevent cyber-attacks.
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Why Encrypting Emails is Essential
From intellectual property to transaction details, sensitive information is passed back and forth through email every single day. This data is often unsecured and vulnerable, giving threat actors a golden opportunity. In short, emails are the low-hanging fruit: Low risk, low-effort, and high-reward.
The consequences for your business, if this information is successfully stolen, may include:
- Ransomware: Cyber-attacks where data is held hostage until a fee is paid.
- Data Breaches: An event where large amounts of personal data is accessed and in some cases, sold.
- Legal Issues: Many countries, including Australia, have strict data protection regulations. Failure to comply can result in heavy fines, audits, and other penalties.
- Damaged Social Standing: If the data of individuals – particularly clients – is compromised, your reputation will be badly damaged.
The most effective way to avoid these negative outcomes is by protecting emails from interception.
What is Encryption?
Encryption is a process that changes data into an unreadable format, reducing its usefulness to threat actors. To restore it, users must have the correct encryption key. This strategy allows sensitive information to be held, and even transferred between locations, without fear of interception – as even if it is stolen, malicious actors won’t be able to use it.
For businesses using Microsoft 365, understanding how to encrypt mail in Outlook is a crucial step in securing data. Fortunately, Microsoft makes this fairly easy to do.
How to Encrypt Email in Outlook
In Outlook, encrypt emails using these steps:
Choose Your Encryption Method
Outlook supports two encryption options:
- Secure/Multipurpose Internet Mail Extensions (S/MIME) Encryption: A widely-accepted email encryption protocol.
- Microsoft Purview Message Encryption: Built into Microsoft 365, available to anyone with Purview.
Outlook Email Encryption Using S/MIME
- Ensure you have a digital certificate. If not, ask your internal or external IT team for assistance obtaining one.
- While your message is open, select Options/More Options.
- Choose your desired sensitivity level and protection options. Here, you can also request a receipt confirming that the email was received unaltered.
- Select “Ok”. At this stage, Outlook will warn you if certain recipients may not be able to decrypt the message.
- Compose and send your email.
Encrypting Emails Using Microsoft Purview
Note that Purview encryption should not be used if S/MIME is already applied. You will also only be able to use this form of protection if you already have access to Purview.
- Set up Message Encryption.
- While writing an email, select Options/Encrypt.
- Choose your desired encryption settings.
- Finish and send your email.
Common Challenges and Troubleshooting Outlook Email Encryption
When encrypting email in Outlook, you may experience issues:
Unable to Send Encrypted Emails
If you are unable to send encrypted emails, there could be a few culprits:
- Encryption not enabled: Double-check that encryption has been set up correctly, and that you chose the right option before sending a message.
- Missing or expired digital certificate (for S/MIME): If you’re using S/MIME encryption, you must have a valid digital certificate installed.
- Microsoft 365 licensing limitations: Some encryption features, like Microsoft Purview Message Encryption, require specific Microsoft 365 plans. Make sure your subscription supports the encryption tools you’re trying to use.
Recipients Unable to Open Encrypted Emails
Recipients may experience difficulty decrypting emails. Consider these possibilities:
- No access to the decryption method: Recipients who aren’t using Outlook or don’t have a Microsoft account may need to authenticate via a secure portal.
- Client Limitations: Certain email services may not support encrypted messages properly. In this case, little can be done except suggesting the use of a different client.
- Expired or Revoked Certificates (S/MIME): Your recipient is not the only one that matters. If the recipient doesn’t have one, S/MIME messages may fail to open.
Troubleshooting Tip: Inform recipients ahead of time if you are encrypting emails, particularly in cases where they may encounter issues (such as partners who may not use Microsoft products). Ensure they have the correct systems in place to receive and open these emails.
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Additional Tips for Effective Outlook Email Encryption
Knowing how to encrypt email in Outlook is only the first step. To ensure effectiveness, follow these best practices:
Train Your Team
Your encryption is only as strong as user behaviour allows. Provide employees with regular training on how to encrypt and decrypt emails, and explain why it matters.
Establish Encryption Policies
Clearly define which emails require encryption. You can also use mail flow rules to automatically encrypt certain messages, reducing the risk of human error.
Combine Encryption with Other Security Tools
Encryption should only be one part of a strong overall security posture. Combine it with access controls, endpoint protection, continuous monitoring, and network segmentation. If internal resources are limited, consider partnering with a managed service provider to ease the burden.
Verify Recipients
Always double-check recipient email addresses. Even when encrypted, misaddressed emails can still become a security risk.
IT Guidance That Helps You Reach Success
Email security cannot be left up to chance. The consequences of a breach aren’t worth the meagre amount of time saved by sending data in an unsafe manner, especially when platforms such as Outlook make encryption so simple. Putting the time in now will prevent a lot of wasted time, money, and effort down the line – making your business safer and more profitable.
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