Confidential email in Outlook—what it is and how much protection it offers

Sending a confidential email in Outlook? Learn about the level of protection this feature offers and discover how to secure your online correspondence.
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Outlook is a comprehensive email service provider (ESP) offering numerous features that enable effective digital correspondence. The problem is that some of those features might be a bit misleading, especially to new users.Sending a confidential email in Outlook is a great example of such a misconception—it implies privacy and security, but the reality is slightly different. This guide will shed some light on this option and how it works so that you can take the appropriate action to protect your emails. You’ll also learn how to send a private email that nobody but the recipient can access.
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What is the Outlook confidential email feature?

Paid Microsoft 365 users can change the sensitivity level of their emails. This feature is mainly aimed at businesses, and you’ll only see it if the admin has enabled that option.There are four sensitivity levels to choose from:
  1. Normal
  2. Personal
  3. Private
  4. Confidential
Keep in mind that the sensitivity level doesn’t impact the email’s security or limit the actions recipients can take. It indicates your intentions without posing any restrictions, so the recipient can download and forward the message as they normally would.

How to mark an email as confidential in Outlook?

Changing the sensitivity level is simple and can be done directly from the draft. The process involves three steps:
  1. Go to File > Properties
  2. Click on the default option next to Sensitivity under the Settings section (it will be Normal in most cases)
  3. Choose Confidential from the drop-down menu
Note that the sensitivity level is different from a sensitivity label, a separate option letting users mark an email or file as:
  • Non-business
  • Public
  • General
  • Confidential
  • Highly confidential
Like sensitivity levels, labels don’t affect the recipient’s action or offer extra protection to your emails. When sending private data or attachments, you’ll need to go the extra mile to ensure adequate protection.

How to send a private email in Outlook

Sending a private email with any provider is possible only with encryption. It scrambles the contents of your emails into strings of unintelligible characters so they can’t be read by anyone other than the recipient.By default, Outlook uses the TLS (Transport Layer Security) standard, which offers basic and incomplete email protection. It provides security while your email is traveling to the recipient but not while it’s sitting on Microsoft’s servers.This wouldn’t be such a significant issue if Microsoft wasn’t a frequent target of cyberattacks. There have been numerous security breaches, often resulting in the exposure of users’ private details and email contents.The safest way to communicate online is to protect your emails with end-to-end encryption (E2EE). It keeps the contents of your emails secure from the moment they leave your device until they reach the desired recipient, and only they have the decryption key to decipher the message.This doesn’t mean that you should go with any email service provider offering E2EE, as encryption standards and implementations can vary greatly.Outlook offers two E2EE options to users:
  1. Microsoft Purview Message Encryption (MPME)
  2. S/MIME (Secure/Multipurpose Internet Mail Extensions) support
Both solutions suffer from significant drawbacks, as you’ll see in the below breakdowns.

MPME—effective, but not for everyone

MPME is the revamp of Microsoft’s Office 365 Message Encryption (OME). It uses end-to-end AES-256 encryption, a solid security standard offering considerable privacy and safety from unauthorized third parties.While it can keep your emails secure, MPME isn’t suitable for all users. The first reason for this is the cost—this level of encryption is offered under the two priciest Microsoft 365 tiers:
TierCost per user
Microsoft 365 E3$36/month
Microsoft 365 E5$57/month
Both plans have an obligatory annual commitment, so you’d have to splurge quite a bit to secure your emails with MPME.Even if you do, you might not be able to set it up unless you’re a tech pro, as the process is quite complex. It requires the knowledge of PowerShell, Microsoft’s network and system administration program—if you’re not familiar with it, you’ll need help from a Microsoft specialist.

S/MIME—a solid alternative?

MPME is a robust encryption method mostly aimed at business users, so individuals can leverage Outlook’s S/MIME support. It is a widely-used protocol offering decent protection, though it has demonstrated significant vulnerabilities.S/MIME is easier to set up than MPME, but the process is not without complications. The first step is buying the certificate separately, forcing you to bear significant expenses. Then, you’d need to install and configure the S/MIME in your Outlook settings, which is a bothersome process.The effort might not be worth it, as Outlook only offers S/MIME support for their web app, and even that is limited to Windows desktop devices. You can’t use S/MIME with iOS, Android, or macOS Outlook clients or even the web version.
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Want to send emails securely? Drop Big Data providers and choose privacy-first solutions

As widespread and convenient as they may be, Big Tech providers like Gmail and Outlook don’t pay nearly enough attention to privacy. From data mining to exposing users to security risks, their practices have made people skeptical about sharing private information online.Luckily, several privacy-first email services have surfaced in the past few years. If you want full control over your data, you should use a provider like Skiff.Skiff Mail delivers unparalleled end-to-end email encryption and covers two key aspects of online correspondence:
  • Data ownership and safety
  • Ease of use
The following comparison shows how Skiff Mail is different from a typical Big Data solution:
FeatureBig Data providersSkiff Mail
Data ownershipThe email service provider creates and stores decryption keys on its servers. While encryption implemented by mainstream email services can protect you from online attacks to some extent, your emails are still accessible to them The user creates the decryption key, which is stored on their device. The email leaves the sender encrypted and can’t be deciphered by anyone but the recipient—even Skiff’s team can’t see it
Ease of useMore advanced E2EE is often costly and involves complex setupSkiff Mail comes with built-in protection standards and can be used by anyone regardless of tech skills
Besides the fundamental differences, a few features set Skiff apart from the competition:
  1. Generous free plan
  2. Robust product offering
  3. Crypto integrations
  4. Open source code

Free without time limits

Skiff Mail offers a comprehensive free plan instead of a limited trial. Users can enjoy various features:
  • Free unlimited email search
  • 10 GB of storage
  • 4 aliases
  • Confidential signup without leaving any personal information
Skiff’s beautifully-designed user interface provides a smooth experience by ensuring every feature is clearly laid out without distractions. You can maximize your efficiency and rest assured your correspondence is completely private.If you need more storage, aliases, or extra features like custom domains, you can check out the Essential, Pro, or Business plan.

Everything you need to maximize your productivity

Besides the E2EE email service, Skiff offers three privacy-first products to help you take your workflow to the next level:
  • Skiff Pages—Secure alternative to popular file management and collaboration software. Leveraging the power of decentralization, the platform lets you create and share private documents without privacy concerns
  • Skiff Drive—Supports all file types and lets users seamlessly share, upload, download, and preview files across supported devices. Skiff offers optional InterPlanetary File System (IPFS) integration, so you can store and share your files securely through a peer-to-peer network
  • Skiff Calendar—Lets you manage events and appointments without the risk of third parties uncovering their details
Skiff products are available for browsers, iOS, Android, and macOS devices. Visit the download page to check the availability of each platform.

Integration with various crypto wallets

The platform supports true anonymity and confidentiality by facilitating integrations with:

Fully transparent codebase

As an open-source solution, Skiff welcomes code reviews and contributions. You can examine the cryptography and UI libraries to determine how the platform’s encryption method and privacy practices work. Check out the whitepaper and join the Skiff discord channel to learn more and become a part of the platform’s growing community.

How to get started with Skiff and secure your correspondence

You can sign up for Skiff Mail in three quick steps:
  1. Go to the signup page
  2. Create your free account
  3. Start using Skiff Mail and other products
If you’re coming from Outlook or other providers, you can migrate your inbox and files with ease. Your threads and data will be end-to-end encrypted from the get-go, so you can start sending private emails without extra steps.

Don’t forget to secure your device and accounts

Solid E2EE gives you privacy and confidentiality, but online security goes beyond your digital conversations. No encryption can fully protect you if:
  • Your device is compromised by malware
  • Your passwords are weak
Malware can come from anywhere on the web, so be careful when downloading files or visiting websites you aren’t 100% sure about. Invest in comprehensive malware protection to deal with threats swiftly or avoid them altogether.You should also stay away from public Wi-Fi as much as possible. You’ll sometimes have no other choice if you need to do urgent work, but don’t connect to unsecured networks if not absolutely necessary. In such cases, users typically rely on a VPN to encrypt the connection and minimize the chances of an attack but remember that it doesn’t provide absolute protection.As for passwords, they are the simplest yet one of the most effective ways to avoid getting hacked. To ensure proper safety of your files and data, set complex passwords for your:
  • Online accounts
  • User accounts on shared devices
  • Wi-Fi network
  • Devices
Password management software can help you create and store passwords so you can fortify your accounts without locking yourself out. Most devices have built-in password management features, but various third-party options can also do a solid job.

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