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Andrew Milich / 1.13.2023Home / Email Security
How to encrypt an email in Outlook, and is that the best encryption solution?
A well-configured encryption design is the cornerstone of safe email communication, but Microsoft Outlook doesn’t offer it by default. Whether you’re using Microsoft Office 365 or Outlook on the Web, you have to take additional measures to enable encryption, which can be tricky.Follow this guide to navigate encryption on the platform confidently. We will explain:
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- What is an encrypted email in Outlook?
- How to encrypt an email in Outlook (you’ll learn the two available methods)
- How to automatically encrypt emails on the platform
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What does it mean to encrypt an email in Outlook?
Encryption, in email terminology, refers to the process of making your digital communication (messages and attachments) unreadable to unauthorized parties. It is necessary because of the way emails are transferred from the sender to the recipient. A typical email travels through several network and web application servers, which means a hacker or malicious actor could infiltrate your communication at any node on the route.Encrypting an email is like putting it in a padlocked box—the message will be accessible only to someone with the decryption key. Know that encryption can be executed using different designs, and manually encrypting an email in Outlook is based on a combination of cryptography setups, such as:- Data-in-transit encryption—This design encrypts the communication exchanged between two nodes in the network, but only during transmission
- Data at rest encryption—Your message is encrypted while stored in a database
How secure is an Outlook email without encryption?
Outlook, like Gmail and Yahoo, is a Big Tech email service provider (ESP) that follows the bare minimum in terms of securing your communication. The industry standard for popular providers is to use basic spam filtering and Transport Layer Security (TLS) protection, which is an in-transit encryption protocol. Your data could remain unprotected because of TLS’s vulnerability to raccoon attacks and other network-level threats.Microsoft Outlook’s in-house encryption features enhance the privacy of your online communication, provided you’re using adequate software and security techniques.How to send a secure email in Outlook—available methods
Outlook enables encryption via two methods:- Office 365 Message Encryption
- S/MIME (Secure/Multipurpose Internet Mail Extensions) Encryption
| Outlook encryption | Description |
| Office 365 Message Encryption | This method allows Microsoft 365 (M365) clients to use the platform’s in-built encryption system for secure communication. The outbound messages are protected by in-transit and at-rest encryption protocols (forwards and replies are also encrypted). You can access this method on desktop and web clients using Enterprise E3 or E5 licenses (costs $32–$36/month) or Azure Information Protection add-on license (in case you have a Business Standard or lower plan) |
| S/MIME | S/MIME is an end-to-end encryption (E2EE) method, which means the message remains encrypted from the time you send it until it is decrypted by the recipient. E2EE is considered the strongest format of cryptography as it combines the benefits of in-transit and at-rest encryption. You don’t need a special Outlook subscription to use S/MIME, but you and the recipient(s) must obtain Individual S/MIME certificates from a certifying authority (which is usually the digital admin of your company or organization) or S/MIME control software |
How to send an encrypted email in Microsoft Office 365
Office 365 Message Encryption is designed according to the organization’s Information Rights Management (IRM) policy. The idea is to keep your confidential and personal info encrypted within the Microsoft ecosystem and protected when traveling to other email networks like Gmail.Follow these steps to send an encrypted message from your Office 365 client:- Click on New Mail to create a message
- Go to the Options tab
- Select the Encrypt button from the ribbon—you’ll find a drop-down menu containing up to five Sensitivity Labels (depending on the software version you’re using):
- Encrypt-Only
- Do Not Forward
- Confidential\All Employees
- Encrypt and Prevent Forwarding
- Highly Confidential\All Employees
- Select Encrypt-Only—a message will appear under the ribbon explaining what the option entails (you can select other Sensitivity Labels as well to see what they do)
- Create and send the message like usual
- Are using Outlook 2016/2019
- Want to encrypt all outgoing emails
How to encrypt an email in Outlook 2016 and 2019
If you’re using Outlook 2016 or 2019, here is how you can deploy encryption on a single message:- Open the new message window
- Go to Files and click on Properties
- Navigate to Security Settings from the options box
- Check the box beside the Encrypt message contents and attachments label
- Exit the settings to compose and send your message
How to automatically encrypt all emails in Outlook
If you frequently send encrypted emails, encrypting all outbound messages makes sense, but know that the recipients must have your digital ID to access them. This is how to set it up:- Click on File and go to Options
- Navigate to the Trust Center option on the side panel
- Choose the Trust Center Settings button
- Select Email Security
- Check the box beside Encrypt contents and attachments for outgoing messages (under the Encrypted e-mail section)
- Select OK to exit
How to set up an encrypted email in Outlook with S/MIME
Microsoft Office 365 encryption isn’t foolproof because your data still remains vulnerable to server or insider attacks (and the company’s servers are always a hot target). A skilled hacker can find the decryption keys on the server and access your messages, so many users rely on S/MIME’s end-to-end encryption design for stronger protection.S/MIME users have a public and private key pair—the former encrypts the message, and the latter (which is in possession of the recipient) is used to decrypt it. No one on the network can infiltrate the message because they can’t access the key.To enable S/MIME encryption, you must first acquire the certificate from your IT admin—your key can be stored on a smart card or your PC. Once you have the certificate, do this:- Go to Settings to install the S/MIME control or extension
- Navigate to Mail and select S/MIME
- Click on Run or Save as prompted
- Create a new message
- Go to More Options (using the three ellipses “…” button)
- Scroll to Message Options
- Select Encrypt this message (S/MIME) and exit
Drawbacks of Outlook’s encryption features—and alternatives
Outlook’s encryption features are somewhat underwhelming because they are either insufficient or difficult to use. Office 365 encryption hardly gives you peace of mind—in the past, a major security breach led to the leakage of sensitive data like email metadata (subject lines, timestamps, etc.), contact lists, and even email content.While S/MIME’s E2EE setup is more secure, implementing it is a laborious process prone to errors. There have also been cases of missing encryption buttons and confusing licensing policies.Following these drawbacks, many users have started using third-party encryption software or, even better, completely migrated to a reliable end-to-end encryption email service—like Skiff!Skiff is all you wish for in an ideal privacy-first email service. It offers:- A stable and robust E2EE setup
- Modern, intuitive, and user-friendly interface
- Complete product suite (drive, calendar, and more!)
- 10 GB of free storage
Ensure total email encryptionSkiff Email offers top-notch end-to-end encryption, providing utmost confidentiality
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Skiff makes end-to-end encryption easy and accessible to everyone!
Skiff is built on the concept of simplifying email privacy. You don’t have to jump through hoops to enforce encryption or keep hackers at bay, as the platform’s end-to-end encryption setup is easily available once you sign up. Write any message, with or without attachments, and it will be encrypted in a few simple steps—refer to the whitepaper to see how it is done.Skiff makes end-to-end encryption easy and accessible to everyone!
While you enjoy complete encryption, the account control is 100% yours. Skiff is designed on a zero-trust policy, so no one but you has access to your inbox, encryption keys, calendar, or the content of your messages. While your emails are always safe on Skiff’s network due to E2EE, we have devised additional security protocols to prevent hacking, spamming, and phishing attacks.Here are some other highlights of Skiff’s E2EE email and collaboration platform:- Email subject encryption—Most E2EE services do not encrypt email subjects, but Skiff is meticulous about keeping it encrypted as well (as it carries info that can reveal sensitive information)
- Multi-platform access—Skiff is available via browsers, desktop clients, and mobile apps. You can check out the download options here
- Zero-knowledge login—Skiff doesn't want its servers to contain vulnerable user identifiers, so the signup/login process doesn’t require or collect any personal info. You can add two-factor authentication (2FA) if you want additional login security
- E2EE collaboration tools—Skiff is one of the few product suites that are fully encrypted. Your content and uploads, including notes, wikis, and calendar entries, are only visible to you and your chosen collaborators. Sign up and get full access to everything Skiff!
Skiff’s product suite caters to your business and personal needs
Users stick to the outdated encryption setup in Outlook and Gmail because of these platforms’ productivity suites—but not anymore. Skiff brings together all the essentials you’d need to organize and upgrade your online correspondence. It also offers easy document import features so that you have it all in one place.Here’s a bird’s-eye view of Skiff’s four primary products—Skiff Mail, Skiff Pages, Skiff Drive, and Skiff Calendar:| Product | Features |
| Skiff Mail | Skiff Mail provides all the necessary functionalities, such as email aliases, custom domains, labels and folders, import and migration, scheduling emails, customization, email search, multi-device sync |
| Skiff Pages | Create documents in Skiff’s end-to-end encrypted workspace or collaborate with people in real time. You can also make use of multi-language support |
| Skiff Drive | Upload all types of files (like images, PDFs, spreadsheets, and PPTs) on Skiff Drive and sort, preview, or share them as you please. You get 10 GB for free, but you can expand it up to 1 TB. Skiff also offers optional IPFS (InterPlanetary File System) integration if you prefer decentralized storage |
| Skiff Calendar | Skiff Calendar (integrated with your email) is your one-stop solution for organizing meetings, sharing invites, and keeping track of your daily chores |
Sign up to upgrade your privacy standards!
Get your Skiff account running in a few easy steps:- Visit the signup page
- Enter your chosen username
- Set up a strong password—and your account keys will be generated!
Skiff’s team constantly develops new, impressive features, so join its Discord server or Twitter to keep up with the latest updates.
