According to a study by the United States Postal Service, 58% of millennials have less privacy concerns about snail mail than about digital communications, which they are worried may be less safe. So if you’re working with clients in a legal or business capacity, how can you assure them that your communications will be safe if you prefer to communicate digitally? 

The fact is, emerging technologies have made digital threats only more prevalent, so it makes sense that some may be wary of sending important information or documents via email. So if you’re dealing with sensitive information like contracts, case files, or medical records in your day-to-day, making sure that file security is top of mind can help you not only avoid legal or compliance trouble but can also build trust with your clients.

You can help make yourself, your clients, and/or your customers feel more comfortable with digital communications by taking steps to make sure you use a secure process to send documents online. 

In this article, we’ll explore how to send a secure email. 

1. Password Protect Your PDFs

Perhaps one of the simpler methods of encrypted document and message sharing is to make it so the recipient has to enter a password to access it. Just like you add a password to an email or banking account, adding a password to your PDF attachment adds an extra layer of protection that keeps unwanted eyes off the document. 

The most prominent PDF-sharing tool, Adobe Acrobat, has this feature baked in, so you can add a password to your PDFs without having to navigate to a different tool. 

To password-protect a PDF in Adobe Acrobat: 

1. Open your file
2. Select “Tools” 
3. Select “Protect a PDF” 
4. Enter your desired password
5. Select “Apply” 

Cost: Free within Adobe Acrobat
‍Pros: This feature is simple to use and is already included in many PDF-hosting tools.
‍Cons: You’ll have to give the recipient the correct password to enter – which, if you’re sending the document digitally and the password digitally, may also become compromised. When possible, try to tell the recipient the password in person or over the phone to mitigate risk.  

2. Encrypt Your Emails

Encryption is a process that obscures text and makes it unreadable for anyone who doesn’t have the correct encryption key. It’s similar to password-protecting a document like a PDF, but instead, it protects the entire email so it can’t be read by anyone who shouldn’t have access to it. 

You can encrypt emails yourself in platforms like Gmail (if you have a Google Admin account) and Outlook. 

‍To encrypt an email in Gmail with an Admin account: 

1. Open your user settings
2. Select the “Accounts tab” 
3. Select the account you want to enable encryption for
4. Check the “Enable S/MIME encryption for sending and receiving emails” box
5. Select “Save” 
6. Compose your email
7. Select the lock icon
8. Set your passcode
9. Select “Save”
10. Send the email 

Cost: Free
‍Pros: This feature is intuitive and is already included with most email accounts.
‍Cons: Encryption won’t also encrypt attached documents, so you’ll still have to take that extra step. 

3. Use a Secure Cloud-Based Platform

A cloud-based platform like Dropbox or Proton Drive allows you to upload your documents to the cloud and lock them behind a secure passcode that users will need to enter in order to see your content. Then, you’ll just have to include a link to the secure folder rather than attaching your documents directly to the email. 

This can be extremely helpful for those who need to send a large volume of files, as emails have a cap on the size of attachments that can be added. So for lawyers, for example, opting to send documents through the cloud means it’s easy to send large files like contracts, case notes, and interview transcriptions. 

‍Cost: Varies by platform.
‍Pros: Allows you to send a lot of files at once or files that are large sizes safely and without having to send multiple emails.
‍Cons: Moving your documents into the cloud opens up the possibility of data breaches or leaks.

4. Hire an Encrypted Email Service

If you need to send a lot of encrypted emails, it may make more sense for you to hire a service that will send encrypted emails for you, like StartMail or ProtonMail. With these services, you won’t have to go through the motions of encrypting the email yourself and coming up with the encryption key. The mail service will do the encrypting for you, and then help your intended recipient access the email. 

‍Cost: Varies by platform.
‍Pros: It is a surefire way to make sure your encrypted emails are safely delivered and can save you some time during the encryption process.
‍Cons: Puts a price tag on something that can be free. 

5. Manually Encrypt Attachments

Only encrypting an email won’t encrypt the attachments, so if you want to protect those, you’ll have to do it manually. It isn’t hard to add attachment encryption to an email you’ve already encrypted. You’ll just have to adjust the settings.

To add attachment encryption in Gmail: 

1. Enable encryption
2. Select “Compose”
3. Select the lock icon
4. Select “View details” 
5. Select that you want to encrypt the attachments

Cost: Free
‍Pros: Adds an extra level of security to your encrypted emails in a simple way.
‍Cons: May be slightly more time-consuming than other encryption methods.

What Is the Most Secure Way To Send Documents via Email?

The most secure way to send a document via email is to send it using end-to-end encryption services, which usually requires hiring an encrypted email service that will ensure that only the sender and recipient can gain access to an email’s contents. If you’re looking for confidence that your files will be delivered secretly, outsourcing to an encryption service may help give you more peace of mind. 

Email Security Risks + Warning Signs

Like any digital format, sending an email puts you at risk of a specific kind of attack — a cyberattack. Cyberattacks like phishing and malware can sometimes be hard to spot, but good training can make sure you don’t fall victim to a scam.

While phishing attacks typically are sent to the user's email, malware (a portmanteau of “malicious software”) may target an email you send. Malware attacks can do things like intercept your emails and steal your information.

While it might be hard to spot an intercepted email until you get a complaint from a client or customer, there are a few things you can look out for. These include things like a changed password, suspicious sent emails, and a slow or lagging computer. 

Good cybersecurity practices can help negate the risk of a cyberattack, especially for vulnerable professions like legal firms, which may be targeted because of the sensitive information stored on your hard drives. 

Email Security Best Practices

Those wondering how to securely send emails for legal purposes (or any other industry, for that matter), won’t have to reinvent the wheel. Keeping your emails safe is all about staying vigilant and taking necessary precautions when dealing with sensitive information. 

A few best practices for email security include: 

• Using two-factor authentication to secure your email account
• Encrypting sensitive data and documents
• Changing your password occasionally (and make sure each one is unique)
• Filtering spam and potential malware messages
• Never open or respond to an email from a suspicious sender or containing a suspicious link
• Follow Health Insurance Portability and Accountability Act (HIPAA) guidance when sending emails with medical information to avoid legal fees

Get Encrypted 

Those working with sensitive information should put cybersecurity at the forefront. That’s why our transcription services here at Rev prioritize security by being HIPAA-compliant*, encrypted, and secure. 

Learn more about how Rev can help those working in the legal field keep information safe.

**HIPAA compliance is available for Enterprise plans only.