How to Enable Email Encryption in Microsoft Outlook Using Encryptomatic OpenPGP Add-in

We live in a moment where cyber threats and privacy breaches are increasingly common. Safeguarding our digital communications has never been more important. One effective way to protect sensitive information is through email encryption. Microsoft Outlook, a widely used email client, offers an array of tools to enhance the security of your emails. One such tool is the Encryptomatic OpenPGP add-in, which provides seamless email encryption within Outlook using the highly secure OpenPGP protocol. In this article, we will guide you through the process of enabling email encryption using the Encryptomatic OpenPGP add-in.

Understanding OpenPGP Encryption

Before diving into the specifics of using the Encryptomatic OpenPGP add-in, let's briefly understand what OpenPGP encryption is. OpenPGP is the open source implementation of the "Pretty Good Privacy" protocol,   a widely adopted standard for encrypting and decrypting data, including email messages and email file attachments. It uses a combination of public and private keys to secure communications. The sender uses the recipient's public key to encrypt the message, and the recipient uses their secret private key to decrypt it.

Step-by-Step Guide: Enabling Email Encryption with Encryptomatic OpenPGP

1. Install the Encryptomatic OpenPGP Add-in

 To get started, you need to install the Encryptomatic OpenPGP add-in for Microsoft Outlook. You can find this add-in on the developer's website, https://www.encryptomatic.com/openpgp/ . Once installed, it seamlessly integrates into your Outlook interface. You'll see the Encrypt button when you open a new email message in Outlook.

2. Generate Your Key Pair

  Before you can start encrypting emails, you need to generate your own key pair: a public key and a private key. These keys are at the heart of the encryption process. Launch the Encryptomatic OpenPGP add-in and follow the prompts to create your key pair. Make sure to keep your private key safe and secure, as it's essential for decrypting messages.  

Share your public key with anyone.  Other people can send you encrypted emails using your public key.  Only your private can decrypt and open a message that is encrypted with your public key.  This is different from, and much more secure than simple "password" encryption, where the same password is used to protect and open a secret message.  With OpenPGP,  very complex math is used to generate a key pair. The relationship between the public and private key is such that anyone can encrypt a message using your public key,  but only your private key can subsequently decrypt the message.

3. Import Recipients' Public Keys

As you may have guested by now, to send encrypted emails to someone, you'll need the public keys of the recipient. You can request their public keys and import them into the OpenPGP add-in. There are also public key servers where people sometimes publish their public keys.  We do not recommend using public key servers, as they often lead to spam and its not always clear that the published public key is associated with the recipient.  Best to get the public key directly from the recipient.  Encrypting a message with the recipient's public key ensures that only the intended recipients can decrypt and read your messages.

4. Compose Your Encrypted Email in Microsoft Outlook

When composing a new email in Outlook, you'll notice a new "Encrypt" button in the email toolbar. Clicking this button enables encryption for your email. The add-in will automatically select the recipients who have shared their public keys with you.

5. Add Attachments and Text

 Compose your email as you would normally, including any attachments. The OpenPGP encryption will secure both the body of the email and any attachments you include.

6.  Send Your Encrypted Email

Once your email is ready, hit the "Send" button. The add-in will encrypt the message using the recipients' public keys before it leaves your outbox. Your recipients will then use their private keys to decrypt the message on their end.

7. Decrypting Received Emails

 When you receive an encrypted email, the OpenPGP add-in will prompt you for a password to unlock your private key.  In some secure situations, it may be desirable to automatically have Encryptomatic OpenPGP decrypt the message for you. This can be done by allowing the add-in to access your private key for an extended period of time. Once decrypted, the message will appear in Microsoft Outlook like anyone message, and you will be able to read the decrypted message and any attachments seamlessly.  

8. Revoking or Updating Keys

 Over time, you might need to update your keys for security reasons or revoke access for certain recipients. The OpenPGP add-in offers options to manage your keys effectively, ensuring your encrypted communications remain secure.

Benefits of Using Encryptomatic OpenPGP Add-in

1. Enhanced Security

 By using the Encryptomatic OpenPGP add-in, your emails are protected from unauthorized access, adding a strong layer of security to your communications.

2. User-Friendly Interface

The Encryptomatic OpenPGP add-in integrates seamlessly into Outlook's interface, making the encryption process user-friendly and accessible.

3.  Selective Encryption

   You have control over which emails to encrypt and which recipients to include, allowing for selective application of encryption.

4. Cross-Client and Platform OpenPGP Compatibility

 OpenPGP is a widely recognized standard, meaning your encrypted emails can be decrypted using various compatible tools and email clients.

5. Data Integrity

 OpenPGP encryption not only secures your messages but also ensures the integrity of the data. Any tampering with the encrypted message would render it unreadable.

In conclusion, protecting sensitive information in our digital age is a top priority, and email encryption is a powerful tool in achieving this. The Encryptomatic OpenPGP add-in for Microsoft Outlook offers an effective way to integrate OpenPGP encryption seamlessly into your email communications. By following the step-by-step guide outlined in this article, you can enable robust email encryption, ensuring that your confidential messages and attachments remain private and secure.

Encryptomatic OpenPGP is free for personal use, and affordable for business and government use. Learn more at https://www.encryptomatic.com/openpgp/

What is the OpenPGP Protocol?

The OpenPGP protocol is a widely used standard for secure communication, specifically for email encryption and signing. It is an open-source implementation of the Pretty Good Privacy (PGP) standard, and it provides end-to-end encryption for emails and files. OpenPGP utilizes public-key cryptography to ensure that messages are only read by the intended recipient.

OpenPGP makes use of several encryption algorithms to secure the data being transmitted. The most widely used encryption algorithm is the RSA (Rivest–Shamir–Adleman) algorithm. RSA is a public-key encryption algorithm that is widely used for secure data transmission. It is based on the mathematical problem of factoring large numbers, and it works by generating a public and private key pair. The public key is used for encrypting messages, while the private key is used for decrypting messages.

Another encryption algorithm used by OpenPGP is AES (Advanced Encryption Standard). AES is a symmetric-key encryption algorithm that is used to protect sensitive data. It works by using a key to encrypt and decrypt data. The key used for encryption is the same as the one used for decryption, making it a symmetric-key algorithm.

OpenPGP also utilizes SHA (Secure Hash Algorithm) for generating message digests. SHA is a cryptographic hash function that generates a fixed-size output based on the input data. It is used to ensure the integrity of the data being transmitted, and it provides a mechanism for detecting any unauthorized modifications to the data.

Overall, the OpenPGP protocol and its encryption algorithms provide a high level of security for email and file transmission. The use of public-key cryptography ensures that messages are only read by the intended recipient, while the encryption algorithms ensure that the data being transmitted is protected from unauthorized access.

For a useful implementation of OpenPGP for Windows desktop encryption and add-in for Outlook email encryption, look into Encryptomatic OpenPGP. It's free for personal and non-profit use, and affordable and supported for business use.  Learn more at the Encryptomatic OpenPGP website.

Related: How to create an OpenPGP key pair?

Why Encryptomatic OpenPGP is Arguably Best OpenPGP Tool for Businesses on the Windows Platform

As a business, it is important to keep your confidential information and data secure from prying eyes. This is where the OpenPGP protocol comes into play, as it provides a secure way of encrypting and decrypting emails and files. There are several OpenPGP tools available in the market, but Encryptomatic OpenPGP is arguably the best OpenPGP tool for Windows because of their longevity, support, ease of use, and accessibility. 

User-Friendly Interface

Encryptomatic OpenPGP is designed with a user-friendly interface, making it easy for even the most novice users to encrypt and decrypt their files and emails. The software is easy to navigate, and the encryption process is simple and straightforward. The user interface is intuitive and makes the process of encrypting and decrypting files and emails a breeze.

Compatibility with Multiple Email Clients

Encryptomatic OpenPGP email encryption add-in for Outlook is compatible with other OpenPGP implementations on major email clients, including Microsoft Outlook, Thunderbird, and others. This means that you can use Encryptomatic OpenPGP to encrypt and decrypt your emails across various email clients. This is a huge plus for businesses that use multiple email clients to communicate with their clients and customers. 

Encryptomatic OpenPGP is also a desktop encryption application, allowing easy "right click" encryption of Windows files and folders.

Advanced Encryption Capabilities

Encryptomatic OpenPGP offers advanced encryption capabilities, including the use of RSA and AES encryption algorithms. RSA encryption is the most widely used public-key encryption algorithm, while AES encryption is a symmetric-key encryption algorithm that is used to protect sensitive data. The combination of these two encryption algorithms ensures that your confidential information is protected from unauthorized access.

Secure Key Management

Encryptomatic OpenPGP has a secure key management system that allows you to manage your keys with ease. The software allows you to generate your own keys, import existing keys, and revoke keys if necessary. This ensures that your keys are secure and that only authorized personnel have access to them.

Excellent Customer Support

Encryptomatic OpenPGP offers excellent customer support to its users. The company has a dedicated team of professionals who are available to assist you with any issues that you may encounter while using the software. The customer support team is knowledgeable and responsive, ensuring that you receive prompt assistance whenever you need it.

Affordable Pricing

Encryptomatic OpenPGP is free for individuals and non-profit organizations. For commercial use, it's very affordable at $29.99 annually, making it accessible to businesses of all sizes. Businesses can make use of a free trial, which allows them to test the software before committing to a paid plan. 

Conclusion

Considering the above, Encryptomatic OpenPGP could be the best OpenPGP tool for Windows, offering a user-friendly interface, compatibility with multiple email clients, advanced encryption capabilities, secure key management, excellent customer support, and affordable pricing. If you want to keep your confidential information and data secure, then Encryptomatic OpenPGP is the tool for you.

Download Encryptomatic OpenPGP free.

How to Send an OpenPGP Encrypted Email from Microsoft Outlook

Encryptomatic OpenPGP add-in brings strong public key encryption to the Microsoft Outlook menu system. If you have need to send OpenPGP messages from Outlook, give us a try.  You can download the latest version from our website.

Encryptomatic OpenPGP works with Outlook 365/2021/2019/2016/2013/2010.

After installing Encryptomatic OpenPGP, start Outlook.  You will be prompted to create a key pair.  If you're unsure exactly which settings to use, use our defaults.   A private key and a public key will be created.

You can share your public key with the world. Others will use your public key to encrypt their messages to you.  Through the magic of math and prime numbers, only your private key will be able to decipher a message that has been encrypted with your public key. That's why it is so important to keep your private key private! Do not share your private key with anyone, or they will able to open all messages sent to you and can fake your identity to others.

Public key = share with the world

Private key = keep it secret!

To send an encrypted message, you will need to have the recipient's public key.  And they will need to have your public key to send to you.  An easy way to get started is to just send your public key to anyone you want to communicate with through OpenPGP. 

If someone sends you their public key, you can copy it and import it into the Encryptomatic OpenPGP keyring from your clipboard. Go to Key Management > Key Import > ...From Clipboard.

When you have a recipient's private key in your keyring, create a new email message.  

Click the "Encrypt" button in the Outlook toolbar, and then send the message.

Encrypt button in MS Outlook

Your email will be encrypted using the recipient's public key.  Only the recipient will be able to decipher the message.  

Encryptomatic OpenPGP is free for personal use, and for those who are working at a non-profit organization to do good work for the world.  Its affordable for everyone else!  Give it a try, and let us know how we can improve it.

Setting Domain and Address Rules for OpenPGP Email Signing and Encryption.

Encryptomatic OpenPGP add-in works with Microsoft Outlook to encrypt and/or sign your email messages.  Encrypting Outlook emails protects them from being read by anyone but the recipient.  Signing an email protects your message from being tampered with.

Buttons in Outlook message to Encrypt or Sign an email message.

When you open a new email messages, Encryptomatic OpenPGP will be part of the Outlook menu.  To sign an email message, click the "Sign" button before sending the message.   To encrypt the email message entirely, click the "Encrypt" button.

Yes, it is possible to both encrypt and sign an Outlook email message. As you would expect, just select both buttons, and then send your email.

Automatically Encrypting or Signing Outlook Emails

You can establish default rules for Encryptomatic OpenPGP for encrypting and signing emails. The rules can be based either on a domain, or a specific email.  Setting up a rule takes just a moment.

First, click the Encryptomatic OpenPGP  "Options" button, and go to the "Rules" tab.

Set rules for encrypting or signing Outlook emails

To add a default rule to encrypt and sign all emails we send to bob@encryptomatic.com, type the email address in the Rules Setting, check the boxes for Encrypt and Sign, then click "Add New Rule".

The rule has now been added to the list of rules.  Save and Close to exit.

Now when ever you send to bob@encryptomatic.com,  the message will be signed and encrypted.

Please note that Encryptomatic OpenPGP's rules are a backup, helping if should forget to select the Encrypt and Sign buttons.  Its best to develop the habit of remembering to encrypt and sign messages.

If you have any questions, please post them below!

Managing Public Keys in Encryptomatic OpenPGP for Outlook

Before any OpenPgp software can encrypt an email message, it needs to have access the recipient's public key.  

A public key allows anyone to encrypt a message to the recipient, but only the recipient can decrypt the message. A public key can be shared a number of different ways.

Sometimes the public key is attached as a file to an email message. 
Other times, the key may be uploaded to a public server that you can search.
If Encryptomatic OpenPGP can't find the recipient's public key in its local key store, it will ask your permission to search public key servers. 

Public key servers have worked fairly well for decades, but lately there has been problems with people spamming or "poisoning" the key server network to make it hard to discern the correct public key for certain people.  

Because anyone can upload a public key for any email address, and because some keys never expire (unexpired keys persist forever in the SKS key servers), this has started to become a problem.  Nevertheless, searching key servers is a good way to discover keys for many people, even while some high profile people are struggling with this spam.

How we help you manage public OpenPgp keys.

Given the present realities and limitations of the public key server network, we at Encryptomatic LLC advocate setting your keys to expire after a year or two. The expiration date can always be extended later, but try to avoid the problem of key accumulation that might confuse others as to which public key is the correct one.

Encryptomatic OpenPGP provides various capabilities around key management to help you.  From Settings > Key Management, you can import public keys several ways: from a text file,  from your Windows clipboard, or from the public key servers.

Key Management Button in Microsoft Oulook

You can also share your public key by exporting it to a file, your clipboard, by attaching it directly to an email, or by uploading it to a public key server. You can work to keep your keys up to date by refreshing them from the public key server network.

Protecting your Private Key

While you can share your public key with anyone, make sure that protect your private key with a strong password.  Anyone who has your private key will be able to access any emails sent to you that were encrypted with your public key.  Keep the private key secure.

Creating an OpenPGP Key Pair for Outlook Email Encryption

Before sending or receiving an OpenPGP encrypted email in Microsoft Outlook, you must create a key pair consisting of a private key and a public key.

Your private key must be kept private. Anyone who can access your private key will be able to view encrypted email messages that have been sent to you.

Your public key can be shared with anyone.  Post it on your website, if you like. Only your private key will be able to open a message that has been encrypted with your public key.  It sounds like magic, but its just math.

If you lose your private key, you will lose your ability to open a message that was obscured with your public key. Likewise, anyone who obtains your private key can send you an encrypted email message. 

Encryptomatic OpenPGP can import most existing key pairs. If you don't have a key pair or you want to make a new pair,  it can help you with that, too.

Make an OpenPGP Key Pair

When you first run Outlook after installing Encryptomatic OpenPGP,  you will be prompted to import or create your OpenPGP keys.  You can also initiate key pair generation by going to:  Key Options > Key Import >New

Creating a new OpenPGP key pair

Select "New" to proceed to the "Generate New Key" screen.  Here is where you can choose to create a key pair for email encryption. You can one or more email addresses to include in your key by checking the box next to the email address.  The email address must be setup in Microsoft Outlook to appear in the list.

Generate a key OpenPGP key pair in Encryptomatic OpenPGP

Your Passphrase protects your private key.  Before Encryptomatic OpenPGP or any other software app can access your private key to decrypt a message or file, you must enter this password.   Encryptomatic OpenPGP lets you determine the amount of time that it will have access to this password.

You may only want it to have access for a moment, preferring to enter the password each time you are sending an email.  Or, perhaps you are sending a lot of emails over a short period of time and want Encryptomatic OpenPgp to retain access to your private key for an hour or so.  Its up to you. Just make sure that your passphrase is very strong, and known only to you.

Setting Key Expiration Date and Key Strength

Your key can automatically expire after a specific date.  We urge you to consider setting an expiration date, especially if you plan to share your pubic key with the public key server network. If there is no expiration date, your key may persist forever.  You can always extend the expiration date later.

You can also select the encryption algorithm that will protect your private key. The stronger the algorithm, the longer it will take to generate your key pair.  If you are unsure about this, just use the default settings in Encryptomatic OpenPGP.

Click the "Generate" button to start the process of making your new key pair.

When you see the "Generating Keys" message, feel free to step away for a few minutes to get yourself a cup of coffee. When you return, you should see this message:

Your key will now appear in the Key Management window. To share your key, click on the "Key Share" menu.

This is where you can perform many functions for managing your key.  There are options to export your public and or private key to a file. You can also share your pubilc key with a key server so others may find your key more easily.  You can change your expiration date or passphrase,  and even revoke your key.  Revoking a key tells key servers to indicate that the key is no longer valid and should not be used.

We hope this has been helpful to you. If you have any questions or comments, please post them below, or contact us directly.