Techniques for checking your domain & email reputation

To manage these reputations, various tools are at your disposal. Email reputation checkers evaluate your email-sending practices, while domain reputation checks analyze the credibility of your website. IP address reputation checks are crucial for identifying any red flags associated with your web infrastructure.

Additionally, spam score checkers help you understand the likelihood of your emails being marked as spam. Utilizing these tools not only provides insights into your current standing but also guides improvements. A poor reputation can be detrimental, leading to reduced visibility and trust. Regular checks are not just a precaution; they’re a necessity.

3. MacAfee site lookup

Provides real-time information on domain reputation. They monitor databases to identify domains that are blocked or considered risky, helping you understand if your domain is flagged by these security services​​.

4. Public block lists

Tools such as MxToolBox provide information on who is allegedly sending emails from your domain, the sender’s reputation, and details like the IP address and location. These tools also offer insights into domain blocking and alert you to changes in your email reputation​​.

Outlook (Statistics)

With its impressive capabilities, Outlook has rapidly emerged as a leading email client, enjoying a surge of growth in recent years. It has succeeded in building an awe-inspiring user base of over 400 million active users from around the globe. Even in the US, it holds a significant market share, being the choice of 16% of email users.

About Outlook

Microsoft Outlook is a desktop application with a feature-rich email client and personal information manager. It is part of the Microsoft Office suite and provides advanced functionalities for managing emails, calendars, contacts, tasks, and more.

Microsoft Outlook offers offline access, extensive customization options, and integration with other Office applications. It also offers support for additional features like Outlook signatures, mail merge, and advanced rules. Outlook is a paid product, available with Microsoft 365 subscriptions. It is primarily used by individuals and businesses that prefer a robust, locally installed application. 

Outlook.com

In 2013, Microsoft rebranded its free Hotmail service as Outlook.com. Over the years Hotmail had developed a bad reputation for security issues and spam. The rebranding enabled Microsoft to leave that behind, and instead capitalize on the positive reputation and recognition of their Outlook desktop application.

Outlook.com offers a modern interface, seamless integration with other Microsoft services (like OneDrive and Skype), and features such as conversation threading, spam filtering and powerful search capabilities. Outlook.com is accessible from any web browser and provides flexibility and convenience, allowing users to access their emails and manage their personal information from anywhere. It is used by individuals or small organizations looking for a free email provider and occupies the same market segment as Gmail, AOL, and ZohoMail.

Outlook Live

Outlook Live is the email and personal information management service provided to educational institutions, typically through Microsoft Office 365 for Education. It offers similar functionalities to the desktop application and Outlook.com but is tailored specifically for educational purposes. 

Outlook Live allows students, faculty, and staff to have personalized email accounts, calendars, contacts, and more, with enhanced security and administrative controls provided by the educational institution

Office 365 (Statistics)

About Microsoft Office 365

Microsoft Office 365 is a cloud-based suite of productivity applications that includes popular tools like Word, Excel, PowerPoint, and Outlook plus the ability to add an Office 365 signature to your emails using an email signature manager. It provides access to these applications across devices, along with collaboration features, email services, and cloud storage.

Email services are an important part of Office 365 beyond the direct email application; for example, emails can be populated by an Excel spreadsheet and set up and sent from Word. While Office 365 allows you to integrate external email providers and accounts, there are distinct advantages to using one of the built-in Microsoft mail services, like Outlook or Exchange, as your Office 365 email:

The tight integration of Microsoft email services provides a seamless experience within the Office 365 ecosystem, ensuring smooth collaboration and data sharing between email, calendars, contacts, and other Office 365 applications. This integration enhances productivity and simplifies workflows.

Exchange server (Statistics)

Every Exchange Online server, of which there are 300,000, is a physical Windows server tasked with supporting a staggering 7.3 billion mailboxes. That’s not a misprint. As of April 2022, Office 365 boasted 345 million monthly active users, a number that could now be approaching 375 million. The astonishing number of mailboxes can be attributed to the variety of mailbox types deployed within Exchange Online, extending beyond the simple user count.

About Exchange

Microsoft Exchange is a messaging and collaboration platform. It provides email, calendaring, contacts, and tasks management services primarily for business and enterprise environments. Exchange serves as a centralized system that allows users to send, receive, and organize email messages, schedule appointments, manage contacts and coordinate tasks, and of course the ability to set up Email signatures for exchange.

One of Exchange’s key strengths is its server-client architecture, where Microsoft Exchange Server is installed on the server side, and clients (such as Microsoft Outlook or Outlook on the web) interact with the server to access and manage email and other data.

Features:

Exchange offers a range of features that are important at the enterprise level, including robust security measures, advanced spam filtering, and data loss prevention capabilities to safeguard sensitive information. It supports integration with other Microsoft services like SharePoint and Skype for Business, enabling seamless collaboration and communication.

Outlook VS Office 365 VS Exchange

Outlook is primarily an email client but it also includes additional features such as a calendar, task manager, and contact manager. Office 365, on the other hand, is a subscription-based service that provides access to a range of Microsoft tools. This includes Outlook as well as other applications such as Word, Excel, PowerPoint, and OneDrive for cloud storage. Lastly, Exchange Server is a mail and calendaring server developed by Microsoft. It is primarily designed to be used by businesses as an on-premises solution and is intended to be used in conjunction with Outlook.

The table below provides a more detailed comparison between these three tools, highlighting their key features and differences.

Microsoft Dynamics

Microsoft Dynamics is a suite of integrated business applications developed by Microsoft to help organizations manage and streamline various aspects of their operations. It offers a range of solutions designed to address specific business needs, including customer relationship management (CRM), enterprise resource planning (ERP), human capital management (HCM), and more.

Dynamics and business management

Business management almost always intersects with email, whether it is customer support over email, email communication with prospects and leads or emails to other team members. Accordingly, Dynamics integrates with many external email providers – but using it with Microsoft email services offers special benefits in productivity and efficiency. Read more about business management software solutions.

Microsoft Dynamics CRM, part of the Dynamics 365 suite, offers native integration with email systems such as Microsoft Outlook and Exchange. This integration allows users to access and manage their email communications directly within the CRM platform. Users can track emails, associate them with specific contacts or accounts and view email history as part of the customer’s record.

Using the Dynamics 365 App for Outlook, users can link email messages, meetings and appointments to a row in their Dynamics app, view CRM information in the context of an email message, meeting or appointment, and easily add email templates, knowledge articles and sales literature when creating an email message or setting up a meeting.

Microsoft Teams

Microsoft Teams is part of the Microsoft 365 suite of email products for organizations and is a collaboration platform that brings together chat, video meetings, file sharing, and app integration in one place. It enables teams to communicate, collaborate and work together efficiently.

Microsoft Teams and Email Functionality

One might notice that Teams itself doesn’t feature a specific email tool. That aspect of communication is catered to by Microsoft 365’s Outlook tool. As such, there is no direct integration within Teams to manage your Outlook emails. While some might see this as a disadvantage, Microsoft has made it clear that integrating an email management tool into Teams is not on their roadmap.

Integrating Teams Chat with Microsoft Outlook

On a positive note, Microsoft is working on a new feature that will integrate Teams chat into Microsoft Outlook. This addition aims to facilitate discussions about meeting times and other collaborative efforts directly within Outlook. As a result, users can seamlessly plan and coordinate their activities within the same platform where they handle their emails.

Maximizing Productivity with Microsoft Teams

Teams is more than a simple communication tool. It’s a platform that combines a multitude of functions to maximize productivity within an organization. It’s especially useful for remote teams, allowing individuals spread out across different locations to collaborate as if they were in the same room. Real-time chat, document sharing, and video conferencing – these are all readily available in Teams.

Customizing Teams for a Personalized Experience

Teams also offer robust customization options, allowing users to tailor the platform to their specific needs. These include custom backgrounds for video calls, the ability to pin important messages, and a range of plugins and integrations to further enhance productivity.

Future Developments of Microsoft Teams

The forthcoming integration of Teams chat with Microsoft Outlook underlines Microsoft’s commitment to continuously improving its platform. Users can look forward to an even more integrated experience between Teams and other Microsoft 365 applications in the future. With Microsoft Teams, the goal is not only to streamline workflows but also to facilitate more efficient communication and collaboration in a digitized working environment.

Yammer

Microsoft Yammer is an enterprise social networking platform that allows organizations to create private communication channels for employees. It promotes collaboration, knowledge sharing, and engagement across teams, departments, and the entire organization. Yammer facilitates discussions, sharing updates and fostering a sense of community within the workplace.

While Yammer is effectively an alternative to email, Microsoft does offer a native integration between Yammer and Outlook. The integration enables the user to work with Yammer in their Outlook Inbox, so they do not have to move back and forth. This provides users with a seamless communication experience, increasing comfort and productivity.

Microsoft email security

Microsoft puts a strong emphasis on security, and its email services offer advanced security features such as multi-factor authentication, encryption, and robust spam and malware protection. Microsoft also ensures compliance with various industry regulations, such as GDPR and HIPAA. Using Microsoft email services within Office 365 helps protect sensitive data and maintain regulatory compliance.

Microsoft email services offer rich collaboration features, allowing users to easily share calendars, schedule meetings and collaborate on documents directly from within their email interface. These features promote teamwork, increase efficiency, and streamline communication within your organization.

When should you use Gmail encryption?

Here are a few examples of email content or situations where the hassle of encrypting your Gmail might be worthwhile:

Sensitive Personal Information

If you send emails that contain personal and sensitive information, such as financial details, social security numbers, medical records, or legal documents, encryption ensures that only the intended recipient has access to this sensitive data.

Trade Secrets and Intellectual Property

If you exchange emails containing trade secrets, proprietary information, or intellectual property, encryption minimizes the risk of unauthorized access or potential data breaches that could lead to the theft or misuse of valuable information.

Confidential Business Communication

If you send emails discussing strategic plans, negotiations, mergers, or acquisitions, encryption can mitigate the risk of sensitive business information falling into the wrong hands or being intercepted by competitors or unauthorized parties.

Whistleblowing and Investigative Journalism 

If you handle sensitive information, you may want to communicate securely to protect your sources and maintain the confidentiality of your investigations. End-to-end encryption ensures that your email content remains secret, even from the email server, reducing the risk of potential surveillance or compromising the identity of sources.

Political Dissent and Activism

If you are engaged in political dissent and activism, encryption can protect your privacy, prevent potential surveillance or targeting, and allow for free and open dialogue without fear of repercussions.

It’s important to note that while end-to-end encryption can help protect the content of your Gmail emails from Google’s email servers, metadata such as sender, recipient, and timestamps may still be accessible to Google. For complete anonymity and privacy, additional measures like using anonymous, encrypted email services – Proton Mail is a well-regarded one – or encryption tools that don’t rely on email servers may be necessary.

Why doesn’t Google use end-to-end encryption for Gmail?

Gmail, as a widely used email service, does not provide native end-to-end encryption for a few reasons:

User Experience and Convenience 

End-to-end encryption adds complexity to the email experience. It requires users to manage encryption keys, exchange keys securely with recipients, and handle the encryption and decryption process. While this level of security is valuable to some users, it can be challenging for the average email user to set up and use effectively.

Interoperability and Compatibility

End-to-end encryption requires both the sender and the recipient to use compatible encryption methods and have the necessary encryption software or tools. While WhatsApp sends messages only to WhatsApp, Google has to send its email messages to Hotmail, Yahoo Mail, AOL Mail, and hundreds of other providers. Achieving widespread adoption and interoperability across different email providers can be challenging, as it would require a standardized encryption protocol that all email services would need to support.

Spam and Security Measures

Gmail employs various spam filters and security measures to protect users from malicious emails and phishing attempts. These measures involve scanning email content to detect potential threats and filtering out spam. Implementing end-to-end encryption could hinder these security measures, as the content would be encrypted and not easily scannable.

How to encrypt your Gmail emails:

Now that you have the full picture and all info relating to Gmail encryption, let’s get practical.

To send a truly secure, private email in Gmail, you have two different options:

1. Use a browser extension
2. Use manual PGP/GPG encryption

Let’s go through these in more detail. 

Use browser extensions to encrypt your Gmail emails

Several browser extensions and add-ons offer end-to-end encryption for Gmail. These extensions work by encrypting the email content locally on your device before it is sent. The recipient also needs to have the same extension installed.

Some of the best secure mail extensions for Gmail:

Mailvelope

Mailvelope is a browser extension available for various browsers, including Chrome and Firefox. It integrates with popular webmail services like Gmail, Yahoo Mail, and Outlook.com. Mailvelope utilizes the OpenPGP standard for encryption and digital signatures. It allows users to generate encryption keys, import existing keys, and exchange public keys with their contacts. Mailvelope provides a user-friendly interface for encrypting and decrypting emails, along with key management features.

FlowCrypt

FlowCrypt is another browser extension designed to add end-to-end encryption to webmail services. It works with Gmail and supports both Chrome and Firefox browsers. FlowCrypt uses the OpenPGP standard and provides a user-friendly interface for generating and managing encryption keys. It also offers additional features like key backup, searching encrypted emails, and integrating with third-party PGP tools.

The upside of browser extensions is that they make the encryption process much easier for the average businessperson or other non-technical individuals. 

There are a few downsides, however: 

• you are giving a third party access to your Gmail and relying on them for your security
• anything you do in a browser (clicks, keystrokes, etc.) can technically be monitored by the owner of the website you’re on
• not all browser extensions enable you to encrypt and send secure Gmail attachments

So if you don’t mind getting a little more technical for more flexibility and peace of mind, then you can move up to:

Use manual PGP/GPG encryption for Gmail

PGP (Pretty Good Privacy) is a proprietary encryption software around which an OpenPGP standard was developed, and GPG (GNU Privacy Guard) is an open-source implementation of that standard. 

In order to manually do Gmail PGP encryption for your emails, you’ll need to download a PGP or GPG software program to your local device. If you have Windows as your operating system, a good option is GPG4Win. If you have a different operating system, here is GPG’s list of software. 

Once you download and install GPG4Win (for example), you will have a local software program where you can do all your encryption, and only then paste the encrypted message into Gmail. 

Here’s what the process looks like:

You don’t necessarily need the GpgOL (for Outlook) or GpgEX, but you will need Kleopatra.

After installation, Kleopatra should open automatically. 

Create a New Key Pair if this is your first time using encryption for your email address. 

Key pair: A little bit of technical background:

This key pair consists of two distinct cryptographic keys: a public key and a private key. The public key is intended to be shared with others and is used to encrypt messages that are sent to you. The private key, on the other hand, must be kept confidential and is used to decrypt messages that are encrypted with your public key. The key pair is generated together and mathematically linked, ensuring that only the private key can decrypt messages encrypted with the corresponding public key.)

Once you’ve created your Key Pair, Kleopatra will prompt you to put in the name and email address to associate with this Key Pair. This will create an OpenPGP Certificate, which has details such as the user’s name, email address, and the public key itself. It serves as a way to verify the association between a person’s identity and their public key. 

Your recipient’s public key

One big caveat for relying on PGP/GPG and encryption keys for security, whether you’re doing it manually or through a browser extension: You do need to be 100% sure that the Key Pair and/or OpenPGP Certificate with its public key was created by the person you want to be communicating with. Your recipient should have told you their public key in person, through a different secure channel, or in any other way that leaves no doubt in your mind that this public key was not created by an impersonator claiming to be them.) 

Kleopatra gives you the option to encrypt text content for an email and also encrypt files, so you can send secure Gmail attachments.

Here’s what you get:

Copy your encrypted message (total gibberish, right?) and paste it into Gmail. 

When your intended recipient opens your email, they will see that it is encrypted. They will copy and paste the encrypted text into Kleopatra or a similar program to decrypt it and verify that it did, in fact, come from you. 

And that’s how you send an encrypted email in Gmail!

Why Gmail’s confidential mode is not encryption

Gmail’s Confidential Mode sounds like it should make your emails secure, but it’s really only an extra layer of security that makes it a bit harder for your email contents to get passed along. 

When you enable Confidential Mode, you can set an expiration date for the email, prevent recipients from forwarding, copying, or printing the message, and even require a passcode for access. 

But the email is still stored as cleartext on Google’s email servers, and it’s still saved in your Gmail Sent emails, and all one needs to do to pass your email contents along is to take a screenshot of the email. 

So while Confidential Mode is certainly helpful to prevent accidental distribution of sensitive information, it’s not encryption and it’s not wise to rely on it for any information you really want to stay private.

Gmail encryption: Your email is your own business

Gmail is one of the most popular email providers globally – and for good reason. It’s user-friendly, well-supported, and integrates with all the other Google services. But it’s not end-to-end encrypted, and therefore sending a secure email in Gmail requires special effort.

Ultimately, the decision to adopt encryption measures should be based on individual needs and the sensitivity of the information being shared. By leveraging encryption options and following best practices for online security, you can enhance the privacy, confidentiality, and integrity of your Gmail communication, ensuring that your emails remain secure and your sensitive information stays protected in an increasingly interconnected world.

What is Gmail’s confidential mode?

Gmail confidential mode is a Gmail account feature that allows you to send emails with a secure, self-expiring time limit. This means that you can send an email and set it to expire after a certain amount of time. It also allows you to revoke access to the email at any time.

Unlike regular emails, Gmail’s confidential mode does not transmit the message through regular email protocols but instead stores it on Google’s server. This prevents emails from being shared without the sender’s permission.

This great Gmail feature was introduced by Google in 2018, and it has quickly gained popularity among Gmail’s solo and business users looking to secure their emails.

The benefits of using Gmail confidential mode

Gmail’s confidential mode has many benefits that make it a great choice for sending sensitive information.

Here are some of the key benefits:

1. Increased Security: Gmail confidential mode provides a secure way to send emails, as the email is encrypted and can only be opened by the recipient. It also allows you to send attachments securely and even set up a passcode for the recipient to access the email.
2. Easy to Use: Setting up and using the feature is very easy. All you need to do is click the “Confidential Mode” button in the compose window. From there, you can set an expiry date and passcode for the email.
3. Self-Destructing: The self-destructing feature of Gmail confidential mode means that your emails will automatically be deleted after a certain amount of time.
4. Revoke Access: The feature allows you to revoke access to the email at any time. This means that you can revoke access to the email if it has been compromised or if the recipient has not opened it after a certain amount of time.
5. Attachment Support: Gmail confidential mode also allows you to send attachments securely. This makes it perfect for sending documents, photos, videos, and other files.

How to send an email in a confidential mode

Once you’ve activated confidential mode, sending an email with it is rather easy.

Here’s how to do it in 6 simple steps:

1. Log into your Gmail account and click on the “Compose” button in the top-left corner of the window

2. Click on the “Confidential Mode” button

3. Enter the recipient’s email address

4. Enter the subject and body of the email

5. Set a passcode. Here you can also ask for an SMS verification from the recipient

6. Set an expiration date

And that’s it. Just click send! Note that if you enabled the SMS option you would also have to input a phone number.

Receiving emails

When you receive an email in Gmail confidential mode, you will be asked to enter a passcode before you can access it. This passcode will be sent to your mobile device via SMS or to a separate email address that you specify.

Once you have entered the passcode, you will be able to view the email. The passcode is valid only for a certain amount of time, after which it expires and the email will be inaccessible.

Note:

When non-Gmail users receive a Gmail Confidential Mode email it might be a bit complicated since it looks like a link for viewing a massage on their browser.

Confidential mode settings

Gmail confidential mode also allows you to manage your settings for it.

1. Log into your Gmail account.
2. Click on the “Settings” icon in the top-right corner of the window.
3. Click on “Confidential Mode” in the left sidebar.
4. Here you can manage all of your confidential mode settings such as the expiry date and passcode.

Best practices for using Gmail confidential mode

Gmail confidential mode is a powerful feature. Here are the best practices to keep in mind when using it.

Best practices:

• Set a Secure Passcode: When you send an email with Gmail confidential mode, make sure to set a secure passcode for it. This will ensure that only the intended recipient can open the email.
• Set a Reasonable Expiry Date: When you send an email, make sure to set a reasonable expiry date for it. This will ensure that the email is only accessible for a certain amount of time.
• Use Attachments Securely: When you send an attachment, make sure to use a secure file-sharing service such as Dropbox or Google Drive. This will ensure that the attachment is secure and cannot be accessed by anyone other than the intended recipient.
• Revoke Access: If you think that the email has been compromised or the recipient has not opened it after a certain amount of time, then you can revoke access to the email.

Introduction to secure email providers

Secure email providers and services are designed to protect your emails from hackers, cybercriminals, and other malicious attacks. They provide a secure, encrypted connection between your email server and the recipient of your emails, which means your emails are safe from prying eyes.

They also offer additional features, such as two-factor authentication and end-to-end encryption, to ensure that your emails remain private.

In the past, these services were expensive and complicated to set up. But now, there are many FREE and affordable, user-friendly options available. So, if you’re looking for a secure email provider, you’ve got plenty of choices.

The benefits of using secure email providers & services

Secure email providers offer a number of benefits:

1. Increased Security: With a secure email provider, you can rest assured that your emails are protected from hackers and other malicious actors. All communication between your server and the recipient of your emails is encrypted, so your emails remain private and secure.
2. Reduced Spam: reduce the amount of spam you receive. Most secure email providers have advanced spam filters that block unwanted emails and help keep your inbox free of clutter.
3. Improved Privacy: additional features, such as two-factor authentication and end-to-end encryption, that help keep your emails private and secure.
4. Easy to Use: Secure email providers are also easy to use. Most providers offer a user-friendly interface and helpful tutorials that make it easy to get started.

How to choose the right secure email service for your company

Now that you know the top 8 most secure email providers and services, it’s time to choose the right one for you. When choosing a secure email provider, you should consider the following factors:

1. Security: The most important factor to consider is security. Make sure the provider offers end-to-end encryption and two-factor authentication.
2. Price: Price is also an important factor. Most secure email providers offer plans that range from free to paid. Choose a plan that fits your budget.
3. Features: Consider the features offered by the provider. Does it offer email aliases, contact lists, or other features that might be useful to you?
4. User Interface: The user interface is also important. Make sure the provider offers a user-friendly interface that’s easy to navigate.

Extra tips for keeping your email secure

Once you’ve chosen a secure email provider, there are a few steps you can take to ensure your emails remain secure. Here are some tips to keep in mind:

1. Use Strong Passwords: Make sure to use strong passwords for your email accounts. This will help protect your accounts from hackers and other malicious actors.
2. Enable Two-Factor Authentication: Most secure email providers offer two-factor authentication, which adds an extra layer of security. Make sure to enable this feature for added protection.
3. Update Software & Apps: Make sure to keep your email software and apps up to date. This will help protect your emails from security vulnerabilities.
4. Beware of Links & Attachments: Be wary of links and attachments in emails, as they may contain malicious software.
5. Monitor Your Account Activity: Keep an eye on your account activity to make sure no unauthorized activity is taking place.

For more info check out our: Email security guide

How to recognize phishing emails

Phishing emails are emails that appear to be from a legitimate source but are actually from a malicious actor. To protect yourself from phishing emails, here are a few tips to keep in mind:

1. Verify the Sender’s Email Address: Make sure to verify the sender’s email address. Make sure it matches the email address of the legitimate sender.
2. Check for Suspicious Links: Look for suspicious links or URLs in the email. Hover over the link to see where it takes you.
3. Avoid Opening Attachments: Don’t open any attachments in emails, as they may contain malicious software.
4. Don’t Reply to Suspicious Emails: If you receive a suspicious email, don’t reply to it. Delete it immediately.
5. Report Suspicious Emails: If you receive a suspicious email, make sure to report it to your email provider.

For more info check out: How to prevent phishing attacks

WiseStamp: Secure email signature

After discussing email security providers, it’s time to speak a bit about email signatures.

A secure email signature is a must for businesses, and Wisestamp makes it easy to create one. This powerful tool can help you create a professional email signature that looks great and is secure from hackers or malicious attacks.

With Wisestamp, you can also easily add HTML elements and images to your signature, making it look professional and unique.

You can also include links to your social media profiles and other important information. And best of all, Wisestamp is completely secure, so you know your emails are safe from prying eyes. It’s easy to use, and you can set it up in minutes.

Conclusion

It’s important to use a secure email provider to protect your emails from hackers and other malicious actors. There are many secure email providers and services available, so make sure to choose the right one for you.

Be sure to use strong passwords, enable two-factor authentication, and keep your software and apps up to date. And remember to be wary of email scams and spoofs, and report any suspicious emails to your email provider. With the right secure email provider and a few simple steps, you can keep your emails safe and secure.

A lack of email security leaves your business wide open to cybercriminals. Fraudsters take advantage of the fact that more companies are using increased amounts of digital tools and resources, and now 94% of malware is delivered directly to email inboxes. S/MIME is an email protocol that helps organizations maintain the integrity of their messages and reduce data breaches.

What is S/MIME?

S/MIME stands for Secure Multipurpose Internet Mail Extension. S/MIME is an email signing protocol aimed to increase email security using cryptographic functions. S/MIME certificates enable users to verify email senders with time-stamped digital signatures to help avoid phishing, breaches of data, and imposters.

S/MIME comes with built-in security services such as authentication, non-repudiation of origin, message integrity, and privacy. S/MIME lets you encrypt and decrypt emails for extra security, and there are also additional security features that you can use, including signed receipts, security labels, and secure mailing lists.

S/MIME email security protocol ensures that documents can be shared across networks while maintaining file integrity. They can even double as document signing certificates by signing and encrypting files before they leave the network.

One of the critical features of S/MIME is the different classes of certificates that it offers. Since there isn’t a single certificate authority standard, these validation levels allow organizations to tailor their level of email security according to their unique needs.

Validation levels offered by S/MIME:

• Email validation — requires a valid email address and verifies the domain.
• Individual validation — verifies the identity of employees and issues an email signing certificate for individuals.
• Organization validation — certifies the validity of an organization in a process that requires speaking to a representative from the organization and domain verification before a company certificate is issued.

Users around the world send more than 319 billion emails each day. Some may come from trusted senders, others from imposters.

Many emails include deals and discounts, while others contain malicious attachments and code. Although S/MIME has not been widely implemented, it’s still supported by numerous email clients and provides automated tools to implement and manage certificates.

How does S/MIME encryption work?

S/MIME works for a great many businesses worldwide. It’s widely accepted as a robust email encryption protocol. Its two-fold functioning as an encryption protocol and a digital signature provides end-to-end protection, so you know that the messages you send and receive are secure.

Digital Signatures

Digital signatures provide crucial security capabilities:

• Authentication — a digital signature validates the sender’s identity so that you can be sure they are who they claim to be.
• Nonrepudiation — a digital signature ensures that neither party can deny their actions under that signature. This includes sending and receiving messages, approving information, or simply using the digital signature.
• Data integrity — a digital signature assures that emails aren’t altered in transit, or else S/MIME would invalidate the signature.

While digital signatures alone provide integrity, they can’t guarantee confidentiality without encryption. That’s why S/MIME uses a combined approach to email security that includes digital signatures and encryption.

Encryption

S/MIME encryption allows the translation of information sent via email into an unreadable format. The encrypted email can only be decrypted or changed back into its original form by its intended recipient with a private decryption key.

Email encryption refers to the following security services:

• Confidentiality — encryption protects the content of your emails from unauthorized interception. It ensures the information in your messages remains private while it is in transit and when it’s sitting in your inbox.
• Data integrity — similarly to a digital signature, encryption assures that emails have not been altered in transit since no one except the intended recipient can decrypt the message.

S/MIME email security

But without a comprehensive email security protocol such as S/MIME, you can’t be sure that your emails are indeed secure.

S/MIME combines digital signatures and email encryption to create a layered approach to email security. When you receive a message, you can ensure that the sender is valid and that no one else has accessed your documents to change or view the information.

Who should use S/MIME?

S/MIME may not be practical for everyday email applications, but it can be a crucial tool to manage business email. Whether or not you should use S/MIME digital signatures and email encryption depends on how much privacy you need for business operations and the size of your organization. Of course, there are exceptions, and even some individuals, especially those with home offices, can benefit from using S/MIME.

Who needs S/MIME?

• Businesses that adhere to PCI compliance guidelines.
• Organizations that are required to keep information private according to the Healthcare Insurance Portability and Accountability Act, or HIPAA.
• Companies that do business in countries that are protected by the General Data Protection Regulation, or GDPR.
• Government agencies.
• Organizations that deploy enterprise-level security.
• Businesses and individuals that have shifted to remote and hybrid work models.
• Companies that manage email lists and collect personal information via email.
  

In general, if your company uses business email for internal and customer-facing communications, then implementing S/MIME can add a crucial layer of security.

Cybersecurity experts agree that ransomware poses the greatest threat to businesses in 2022. Since malware and ransomware are most often deployed due to phishing and other email scams, companies should prioritize email security and install S/MIME.

Pros and Cons of using S/MIME

A multi-faceted approach to email security lends itself to innovation as well as complications. Weighing the pros and cons can help you decide if S/MIME is right for your organization.

Pros

1. S/MIME is a very secure email encryption protocol. It offers digital integrity and privacy that prevent phishing attacks and enable secure communication. 
2. S/MIME integrates with several different email solutions. However, some email solutions do not provide native S/MIME certificate support.

Cons

1. S/MIME users can only send secure emails to other S/MIME users.
2. Setting up your digital signature with S/MIME requires intimate knowledge of the platform you are working on.
3. There are also a few cons that are associated with implementing S/MIME certificates. For example, its end-to-end encryption can disrupt email search since the contents must be decrypted to be understood.
4. S/MIME can interfere with other security protocols such as anti-virus scanners, archiving tools, and other data loss prevention mechanisms. For example, emails are scanned for viruses on the way out of the network. But because the email is encrypted, S/MIME will hide the contents from the receiving gateway scanner.

How do I get a S/MIME certificate?

A S/MIME certificate is prescribed by a certificate authority. There are public and private authorities of this kind. You must first find a certificate authority you trust, then you can purchase a S/MIME certificate. You can expect to pay anywhere from $25 to hundreds of dollars per year, depending on the certificate authority that you choose.

What is a S/MIME certificate authority?

A certificate authority is responsible for issuing digital certificates such as S/MIME, SSL, and TLS. The certificate authority determines the security procedures, certificate requirements, and the parameters of the certificates they issue. CAs must document these policies and make them public so that individuals can decide whether or not to trust a specific authority.

2 main types of certificate authorities:

1. Public — a third party that issues certificates to other organizations. Backed by the regulatory standards set out by the CA/Browser Forum, public certificate authorities are generally accepted as trustworthy.
2. Private — an internal certificate authority that only issues certificates for a specific organization. Since they create certificates with specs according to business needs, they are not typically trusted outside the organization.

How to enable S/MIME encrypted emails?

After you get your S/MIME certificate, you will need to enable it in your email client.

Outlook Desktop

1. Select File > Options.
2. Choose Trust Center at the bottom of the menu in the options window, and open Trust Center Settings > Email Security.
3. Now, click Import/Export under Digital IDs, then hit Browse.
4. Open the PKCS#12 file and enter your password.
5. Navigate to Encrypted Email and click Settings to enter a name for your security settings.
6. Navigate to Signing Certificate and click Choose to select your certificate, then confirm your selection.
7. Navigate to the Encryption Certificate and confirm your certificate.
8. Close the Change Security Settings Window.
9. Set your S/MIME defaults in email options.

Outlook 365 Web App (OWA)

1. Go to Settings > Mail > S/MIME.
2. When prompted, select Run or Open.
3. Verify your selection.
4. Next, you need to allow Outlook to use S/MIME.
   1. For Internet Explorer, you will be asked: “Do you want to allow the domain to use the S/MIME control to encrypt and decrypt messages in your inbox?” Select Yes.
   2. For Edge or Chrome, you will receive a message: “S/MIME isn’t configured to work with the current domain. You can add it in the S/MIME Extension options page in the settings for your browser.” Follow the link to settings and allow the domain to use S/MIME.

Gmail

1. After installing the certificate to your device, sign in to your Google console using an administrator account.
2. Go to Apps > Google Workspace > Gmail > User Settings.
3. Under Organizations on the left side of the screen, select the domain you want to enable.
4. Scroll down until you see the S/MIME setting and check the box next to Enable S/MIME Encryption.
5. It may take up to 24 hours for your S/MIME settings to update across the network.

Mac

1. Double click your downloaded certificate file to open Keychain Access. Then, enter your password to install the certificate.
2. Once installed, your certificate will appear in Keychain Access > My Certificates.
3. Close and re-open Mail and compose a new secured message.

iPhone

1. Import your .p12 file and select Open. Enter your password to open the file.
2. Select Install. You may be prompted to enter your password again.
3. To enable the certificate for iOS, go to Settings > Mail.
4. Select the email account associated with your S/MIME certificate under Accounts.
5. Tap your email address on the next screen and then again on the following screen.
6. Go to Advanced > Mail, scroll down, and toggle the slider to ON next to S/MIME.
7. To turn on digital signing and encryption, toggle their corresponding sliders to ON.
8. Close and re-open your mail app to start sending secure emails.

Exchange

1. First, install your certificate on your machine.
2. Open your Windows Start Menu and choose All Programs > EA Disclaimer and S/MIME for IIS and Exchange Server.
3. Follow the steps on the screen to set up S/MIME encryption and digital signatures.
4. When finished, make sure that the Microsoft Exchange Transport Service and the Microsoft Exchange Mail Submission Service are running. If not, then start them.

PGP vs. S/MIME: which is better?

PGP and S/MIME are both email security protocols that similarly use encryption. However, some key differences show how S/MIME has evolved from PGP.

While PGP only covers security issues related to plain text emails, S/MIME meets the needs of today’s businesses by extending this protection to other email data and attachments. Also, S/MIME is already integrated into numerous email clients, so you don’t need to download additional software to experience its benefits.

The table below details the main differences between PGP and S/MIME:

Wrapping up

S/MIME is a powerful email encryption protocol that offers digital signatures to keep your email data secure. In today’s world of rising ransomware losses and increased vulnerabilities caused by fragmented security ecosystems, email encryption is your best defense against fraud.

Implementing S/MIME increases your organization’s ability to protect consumer information, internal business data, and login credentials. The email security protocol is the strongest of its kind and is backed by Public Key Infrastructure, or PKI, to secure your email and let your recipients know that your domain can be trusted.

Use S/MIME to protect against phishing, spoofing, man-in-the-middle attacks, with the ability to encrypt and digitally sign your emails. Whether you are just beginning to grow your email list or have legacy security protocols in place, there is a S/MIME solution for every major email client.

The number of data breaches has already exceeded the number of incidents that occurred in all of 2020 by 17% so far in 2021. Today’s business environment is becoming increasingly reliant on digital technologies like email for communication within an organization, and with outside vendors and suppliers.

What is email security?

Email security refers to the practices and protocols that can be put in place in order to secure sensitive emails as well as protect against social engineering and malware attacks. Certificates and encryption are often used to protect email servers as well as technologies such as SMIME or Secure Multipurpose Internet Mail Extensions that incorporate asymmetric cryptography to keep email files safe.

Email security also involves elements such as education, fraud protection, and gateway security. You can expect to pay at least $40 an hour for a quality developer who understands email security, but many businesses rely on their email host and firewalls alone. Fortunately, there are many options available today for those that require a more secure email environment.

Is your business email protected? Let’s find out.

Does my business need email security?

Email is one of the most popular ways that organizations communicate with customers, prospects, partners, vendors, and other businesses. With so many emails going in and out every day, businesses often overlook the security implications that this can have on businesses of all sizes and industries. 

In short, all businesses that use email need some form of email security in place. Here’s why:

• Phishing emails are responsible for over 90% of successful cyber attacks
• The average web developer possesses less than 5 years of experience according to recent surveys
• According to the Verizon 2021 Data Breach Investigations Report, 43% of all data breaches involve small and medium-sized businesses

Most common email security threats:

Malware delivery. Fraudsters send spam emails impersonating trusted senders and trick their victims into downloading files that contain malicious content. The malware, going unnoticed, can then infect entire networks and cause serious data breaches.

Credential theft. Phishing emails are designed to deceive employees into giving up sensitive information including names, email addresses, bank account information, and login credentials from both customers and employees. 

Business email compromise. A more sophisticated type of spear phishing targeting high-ranking employees, BEC fraud is where attackers invest much of their time and effort into studying these individuals so that they can build trust and retrieve sensitive information that other employees may not have access to such as trade secrets.

Malicious bots and DDoS attacks. Hijacked botnets send out a large number of emails to a business, crashing the server and shutting down B2C operations. On the other hand, DDoS attacks on email servers mainly target B2B emails in order to cause the most damage possible. 

Authentication attacks. These attacks include brute force, credential stuffing, and other techniques to gain access to a company’s email server. At this point the attackers have access to all emails and attachments that are stored on the server, leading to catastrophic data leaks. 

Zero-day vulnerabilities. When vulnerabilities are discovered and disclosed but have not yet been patched, cybercriminals can take advantage of this security vulnerability and exploit businesses until a patch is finally issued. 

As you can see, the list of ways that malicious attackers can gain access and exploit email vulnerabilities is long, and these are only a few of the main security concerns regarding email security. 

Types of email security

In an effort to combat attacks created by cybercriminals, there are a number of email security techniques and tools that can be used to protect email servers and individuals within an organization from falling prey to an attacker:

1. Email phishing protection

To prevent phishing attacks, organizations typically need to take a layered approach that includes educating employees in spotting social engineering scams and multifactor authentication protocols. 

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2. Email spam protection

Protecting from unwanted spam messages that could potentially lead to a data breach or more serious cyber attack can be as simple as not giving out your personal or business email address and only using an outside email address to fill out web forms and create accounts. However, with spammers growing more sophisticated, it can be helpful to use spam filtering tools in addition to antivirus software to thwart potential attacks. 

3. Email fraud protection

In addition to regular cybersecurity education where employees learn how criminals use impersonation and other fraudulent techniques to extract information or execute malware attacks, using email scanning software can be crucial for inboxes with heavy traffic. Email scanners comb through all incoming emails in order to spot clues that identify fraudulent emails and separate them from genuine messages. 

4. Email gateway protection

Using a secure email gateway is one of the most proactive methods for preventing email cybersecurity threats. Office 365 encrypted email and other encrypted email solutions provide protection before emails are even delivered to the server to protect businesses from all kinds of email spam, viruses, malware, and DDoS attacks. A secure email gateway scans all communications, attachments, and URLs going in and out of an email server to spot malicious content before it reaches employee inboxes. 

Email security protocols

The SMTP (Simple Mail Transfer Protocol) sends and receives emails, but offers no authentication value. That’s why many email servers need an extra boost from other authentication protocols. While each protocol works slightly differently from the next, email authentication relies on a standard process.

Email authentication standard process:

• Verify the domain and sender address
• Domain server adds encryption keys
• Receiving server authenticates the encryption key
• Receiving server decides what to do with the email (i.e. send, reject, or quarantine)

Here we differentiate between three of the main email security protocols, DMARC (domain-based message authentication, reporting & conformance), SPF (sender policy framework), and DKIM (domainkeys identified mail), that are meant to be layered in order to protect against email spoofing and other malicious attacks. 

SPF

Sender Policy Framework is an email authentication protocol that helps servers decide whether or not an IP address is authorized to send an email. If the IP address is listed and there is a valid SPF record, then the email passes. If the IP address is not found in the DNS records, then the email is either rejected or moved to spam. 

Pros:

• Helps stop most domain spoofing attempts
• Prevents phishing attacks
• Builds your domain reputation

Cons:

• Emails that are forwarded may fail authentication
• Records must be updated each time there’s a change in IP address or email vendor
• Limited number of DNS lookups before the server automatically fails authentication

DKIM

Domainkeys identified mail builds on the protocols that are put in place by SPF to make email even safer. DKIM acts as an email passport that can verify your identification using cryptographic authentication keys. When you send an email, DKIM is attached so that the receiving server is able to properly identify where the email came from. 

Pros:

• Increased email deliverability 
• Increased phishing protection
• Build your domain reputation

Cons:

• Forwarded emails may not be verified in addition to the original sender
• Whitelisted domains bypass analytics
• Only authenticates the sender; not the email contents (such as malicious links)

DMARC

Domain-based message authentication, reporting, and conformance is a three-in-one tool for email security that builds on the authentication protocols of SPF and DKIM. It is an email authentication, policy, and reporting protocol all in one, helping domains prevent unauthorized use. 

Certain policies can be created by the domain owner to tell DMARC how to treat messages. During the DMARC setup process, the policy can be set to none, where the message is delivered normally; quarantine, which places the message in a quarantine folder like junk or spam; or reject, and the message is bounced. 

Additionally, DMARC also offers unique reporting features that can help further prevent phishing and spoofing attacks. In fact, domain owners using DMARC are able to see where each email using their domain is being sent from. That means that potential spoofing attacks can be stopped in their tracks.

Pros:

• The domain owner can specify how to treat unauthenticated messages
• The domain owner can see where email using their domain is being sent from
• Fills in the gaps where SPF and DKIM fail

Cons:

• Legitimate emails might fail authentication
• Doesn’t check the email contents

As you can see, a layered approach to email security protocols is the best way to ensure that your business email is safe from cybercriminals. 

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Email security best practices

Protecting your business from email security threats is no simple task. Protecting your organization from malicious content and potential threats requires an approach that includes the use of email security tools, email security services, and email security education for all employees. 

Follow these four email security best practices in order to keep your business safe from potential cyber threats:

1) Email security awareness employee training

Using email is practically a requirement for doing business today across all industries and sectors. If your company uses email for communicating internally between departments or externally with vendors and suppliers, then your organization should mandate email security awareness employee training. 

Ensure that all members of the organization, including management and C-level executives, are trained in identifying social engineering tactics and know basic cyber hygiene skills such as leaving unknown links alone and not opening messages from unknown senders. 

2) Use multi-factor authentication

In addition to stringent employee education regarding cybersecurity and online privacy practices, it is critical that all employees use multi-factor authentication in order to access all business applications. Using multi-factor authentication to access email applications is essential especially as more companies deploy IoT devices and allow workers to work remotely. Identifying users that are accessing your network at any given time is essential for email security. 

3) Email encryption

Ensure that your business is using email encryption for all users to ensure the protection of individuals, company assets, and network security. Using encryption protocols for emails can provide an extra defense against bad actors that are able to access your email servers. Without the proper encryption credentials, it is almost impossible to decrypt encrypted emails. 

4) Keep your software up to date

Finally, to make sure that your network vulnerabilities are protected, it’s of utmost importance that businesses of all types and sizes keep their software up to date and regularly scan for vulnerabilities. Even the smallest hole can lead to major disruptions if hackers with ill intent want to exploit an organization. 

For example, one of the largest ransomware attacks took advantage of companies that had not yet updated their operating systems when a simple security patch could have eliminated the vulnerability. As a result, the WannaCry attack affected nearly 230,000 systems and companies incurred $4 billion in losses across the world. 

Email protection services

Many businesses struggle to manage email threats on their own and find that turning to email protection services streamlines email security efforts. There are countless email security services and offerings, but here we will just provide a brief overview of the basic email protection services that are commonly used for business applications. 

1) Cloud email security

Cloud or cloud app email security scans and filters emails that have been received by your domain server through direct integration with APIs. This means that ransomware and other malicious content that is stored on your server in connection with your API (think Exchange, OneDrive, Dropbox, etc.) is sandboxed and won’t infect your network. Another key feature of cloud email security is that it also prevents unauthorized sharing of sensitive files like account numbers and other personal information. 

2) Secure gateway for email servers

Using a secure gateway for all email servers within an organization’s network is crucial for stopping malicious content before it can even be introduced into your communication ecosystem. With a secure email gateway, each email passes through the gateway server before it goes to your domain server. Both incoming and outgoing emails can be analyzed to keep fraudsters out and sensitive information in. 

3) Hosted email security

Hosted email security is a cloud-based email scanning and filtering service that many established online security companies make available to their customers. The advanced features of hosted email security software help organizations increase spam detection rates as well as limit the number of phishing emails that are able to enter the network, which could contain harmful malware. These services include standard anti-spam detection, the ability to block suspicious attachments, and even advanced message inspection. 

Email security tools

A mix of capable technology and continual re-education is crucial to fully protect your company from email fraud and other malicious attacks. There are many different types of security tools available that protect your network from the outside, from the inside, and even by scanning emails and suspicious links. Here are eight of the most valuable email security tools:

1. Email spam blocker – Email spam blockers detect malicious, unauthorized, and unwanted emails and prevent them from making it to your inbox. 

2. Email security scan – Email security scanners use your email address and other information to see if your email has been hacked or compromised. 

3. Network sandboxing – A network sandbox isolates emails from the rest of your network so that they don’t pose any threat while they are analyzed for suspicious activity. 

4. Content disarms and reconstruction – Content disarmament and reconstruction or content sanitization is a process that eliminates elements of an attachment that are suspicious while leaving the rest intact. 

5. URL rewriting – URL rewriting tools identify suspicious URLs within an email and rewrite them so that they either are not clickable, are removed from the message, or are redirected for a time-of-click analysis. 

6. Remote browser isolation – RBI ensures that security risks are isolated by sending users to an external browser when they click on a suspicious link where they can only interact with clean content since all malicious content is not rendered. 

7. Lookalike domain detection – Many fraudsters try to trick email recipients by using a domain that is nearly identical to a legitimate and familiar domain, but modern email security solutions allow domain owners to list suspicious lookalike domains that are not to be trusted. 

8. Anomaly detection – Using telemetry and data intelligence, email anomalies and deviations from normal behavior on email servers can be detected to prevent even the most sophisticated attacks.

Putting it all together

The best privacy email solutions often require a layered approach that includes different aspects of email security and protection since there are so many different types of attacks that can be executed using email as a tool. Hackers and cybercriminals often use email as a way of penetrating a network, either by social engineering, spam, or malicious software downloads. 

Fortunately, following these email security best practices, utilizing the right email protection tools, and understanding the ways that cybercriminals are able to use email to cause data breaches can help prevent future cyberattacks.