In short, yes, it is possible to send secure emails in Outlook and Gmail, but there are a number of factors that make it inconvenient to the point of impracticality. This is why many enterprises send encrypted emails using a secure email service. It's easier to activate, easier to track, and ultimately gives your organization the ability to proactively defend itself against cyberattacks.
How to send secure emails in Outlook or Gmail
Gmail and Outlook offer S/MIME certificates. S/MIME (Secure/Multipurpose Internet Mail Extension) allows the sender to send encrypted emails that can only be decoded by the recipient. Enabling (and troubleshooting) S/MIME on Gmail or Outlook can be a complicated and time-consuming process for many users, especially those without a strong technical background.
Sending secure emails with Gmail
Gmail has S/MIME embedded within it; however, both senders and recipients must activate it in order to use it.
Sending secure emails with Outlook
To send encrypted emails with outlook, users need a Digital ID or certificate that has been obtained from the administrator.
Why many businesses invest in secure email services
A secure email service can simplify enabling S/MIME for your entire organization and give your organization more control over your cybersecurity. This, along with many other benefits, make a full suite of secure email services the gold standard for enterprises.
Many secure email services are directly compatible with Gmail and Outlook, so organizations would not necessarily need to adopt a new communication system. Instead, transitioning into a secure email service is more about simplifying and improving the systems your organization already uses.
Simply create and send encrypted emails
Instead of requiring users to obtain keys or for recipients outside your organization to enable and activate their own S/MIME certificates, a secure email service can allow your users to simply send encrypted emails with a click of the button.
The secure email service can also automatically detect potential threats based on the nature of the content. Settings can be customized so that certain keywords can be flagged for further inspection or be blocked entirely — all from the email service's own secure email server.
Give your IT department the ability to monitor correspondence
It's important to be able to inspect emails for malware, which can be encrypted along with the message. This makes it possible for cyberattackers to bypass the company's gateway detectors and successfully deliver the malware.
This is one of the main reasons why the default cybersecurity features of Outlook or Gmail are often not enough for enterprises. They need secure email services that can scan for malware on end user stations after decryption.
In other words, a secure email service is constantly monitoring email correspondence for potential threats, and they enable your IT department to be readily aware of its findings. This gives your organization the power to customize your cybersecurity to your needs. Your IT department can set up automated protective measures that detect and isolate perceived threats. You can also fix any flagging issues where emails are misidentified as threats.
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Original Source: Can You Send an Encrypted Email in Outlook or Gmail?
