How to Encrypt Outlook Email Without Microsoft 365 or Purview

Wondering Why You Can't Find the Encrypt Button in Outlook.com?

You're not alone, my friend. We know this for real because we, too, looked for it... and, for way longer than we care to admit. It's especially confusing because Microsoft’s Kafkaesque (sorry to use, but it's totally the right word) maze of help pages kept mentioning this magically elusive encrypt button.

And we even seem to remember it definitely used to be there, right? Did we wake up on some alternate timeline? Is the Mandela effect real? Wait, didn't Mandela have two "l's?"

Anyway...

Quick Summary

• Free Outlook.com accounts do not include email encryption
• Microsoft 365 Personal/Family plans add encryption, but it’s not end-to-end
• If you want to encrypt custom domains or email addresses from other providers, Microsoft requires expensive plans and complex setup
• SecureMyEmail offers true end-to-end encryption for free for Outlook.com and other legacy Microsoft addresses
• Setup takes about 5 minutes, and recipients don’t need to do anything to read or reply securely when you use SecureMyEmail to encrypt outlook emails.

Does Outlook.com Email Encryption Even Exist?

Many Outlook.com users are surprised to discover that encrypting email isn't something Microsoft includes with a standard free account! They keep wondering how to encrypt an email in outlook. 

That's not the real crime here, though. Email encryption can often be pretty expensive. The real crime is how Microsoft is always changing...everything. Product names. Features. Policies. Rules. We'll get back to that in a minute.

Wait — So You Can Encrypt Outlook Email?

You can indeed enable encryption for Outlook.com emails by purchasing a Microsoft Personal or Family subscription — which comes with lots of other Microsoft goodies (fun for the whole family!). But, here's the thing: we're not sure you should use Microsoft's email encryption.

There's Another Way — That Also Happens to be Free

SecureMyEmail will let you encrypt your Outlook.com (including Hotmail.com, Live.com, and MSN.com) emails for free. And if you have other emails, personal or business, you can encrypt them too with a paid plan, which is a quite reasonable $2.50/month per user with annual subscription.

SecureMyEmail is also more modern and private than Microsoft’s email encryption because it offers:

• End-to-end encryption
• Zero-knowledge architecture (Microsoft, nor anyone else — including SecureMyEmail — can read your emails or see attachments)
• A delightful experience for your recipients where they don’t have to download anything, register, or deal with passcodes or passwords

Microsoft’s Got Some History with Email Encryption

Let’s get back to why we are not sure if you should choose outlook email encryption. With Microsoft, although the cost is reasonable and it works “aw-ight,” things may change and you could find all your encrypted emails marooned on Microsoft Island.

Unfortunately, this sort of thing has happened before. Microsoft, up until kinda recently, offered reasonably priced add-ons to Microsoft 365 (formerly Office 365) accounts to encrypt email. Then they reorganized, renamed, and repriced everything — and forced business users (and many MSPs who support them) to buy much more expensive Business Premium and Enterprise licenses.

Once You're In, You're a Bit Stuck

If you ever upgrade with Microsoft, and maybe bring over a business account, or want to encrypt other emails from different providers (which, again, they used to allow under Outlook.com personal but don't anymore), you're possibly locking yourself into an upgrade path with a lot more technical complexity — and no off-ramp.

Microsoft 365 Encryption: Not Quite What You Think

That’s because real encryption is locked behind different Microsoft 365 tiers, policy toggles, and sometimes legacy UI constraints. And even then, it’s limited and a bit clunky, especially for recipients. Read more about the chaos in our full breakdown of Microsoft 365 encryption.

Microsoft Makes Great Products. Often. But...

We're not trying to be haters here. Microsoft is a great company and can certainly build great products.

The Catch: It's Always Changing

Again, it’s just that their products, plans, branding, and support documents change so often and contradict each other so much that the entire experience starts to feel like a job. And not a fun one.

In fairness, their licenses come with a bunch of other things — perhaps things you need or want. We're just saying you might want to keep your outlook email encryption separate so you don't get surprised later. Or if you simply don’t want Microsoft having access to all your encrypted private email and attachments forever.

Who's Holding the Keys?

Not saying they’re snooping. Actually, they were quite emphatic a ways back that they don't. Remember when Microsoft proudly told us they don’t scan your email for ads like Google? That was true — and honestly, props for that. But the access is there and could be exploited by a bad actor, even without Microsoft's knowledge.

The big difference between SecureMyEmail and Microsoft email encryption — unless you set up something called S/MIME (which requires a computer science degree to figure out and your recipients need one too) — is that, with us, YOU control the encryption and access. Not Microsoft.

If they get breached or have a rogue employee who decides to sell your data or identity on the dark web you are out of luck.

With SecureMyEmail, it’s different. We use Zero Knowledge Architecture. That means if you encrypt outlook email with us and Microsoft (or even we) get breached, your encrypted email is still protected. Only you hold the keys. Only you can unlock your content.

Here’s the Good News

You can get real, end-to-end encryption for your Outlook emails — no Microsoft 365 required.

And it’s totally free forever for Outlook.com, Hotmail.com, Live.com, and MSN.com addresses. SecureMyEmail for the win.

Why SecureMyEmail Offers It for Free

We get this question a lot. Why would anyone offer strong encryption for free?

Simple: It spreads the word. 

When you use SecureMyEmail, recipients can see that you used us. Don't worry. It's subtle branding. Not an obnoxious ad. We would never embarrass you like that. This grows awareness organically. Some users upgrade to paid plans to encrypt their Gmail, Yahoo, iCloud, business email, or HIPAA-compliant messages. Some of your recipients might sign up too. It all works out. But if you’re just encrypting a personal Outlook.com address? Totally free.

What Will Your Recipients Experience?

This is maybe the best part.

No registrations. 

No passwords. 

No downloads. 

Recipients are emailed a clean, secure link to view and reply to your message on a very nice looking interface — fully encrypted both ways. Attachments too.

Microsoft vs SecureMyEmail: Encryption Showdown

How to Get Started

1. Download SecureMyEmail
2. Set your secret password to create your encryption keys
3. Sign in with your Outlook.com, Hotmail, Live, or MSN address
4. Start encrypting — no plugins, no portals, just privacy

TL;DR: Want Outlook Email Encryption That’s Free, Fast, and Private?

It’s called SecureMyEmail, and yes, it’s free for Outlook.com users and more.

• Real end-to-end encryption for Outlook.com and older Microsoft addresses
• Works on iOS, Android, Mac, Windows, and in browser
• Easy for senders and recipients
• No Microsoft 365 required
• Have your own domain or multiple emails to encrypt? No credit card needed for trial — $2.50/month after that

Make your Outlook.com email private today. And, for free!

Want More?

• How to Encrypt Gmail Messages for Free
• How to Encrypt Yahoo Mail
• ProtonMail, Tutanota, StartMail… or Just Encrypt Your Current Email?