How to Send Secure Email Attachments in Gmail

June. 26, 2020

1:00-2:00AM PST

With more than 1.5 billion active users worldwide, Google's Gmail currently dominates the email provider market and has grown leaps and bounds since its inception in 2004. And professionally, Google's G Suite service is utilized by more than 5 million companies, empowering businesses across countless industries to communicate, collaborate, and share important files, documents, etc. every day. In 2020, the platform is both frequented and beloved for the convenience and efficiency that it offers users.

Unfortunately, Gmail does not provide adequate data protective measures. By performing regular scans of user emails and gathering data to inform advertisers, Google ultimately puts users' utmost sensitive and valuable information in jeopardy. Although many users have come to brush this fact off, in some cases, deeming it a harmless, unavoidable part of technological life, emails in transit can become intercepted by third parties with the potential to become leveraged for malicious purposes. Although seamless and built-in, Gmail's S/MIME (Secure/Multipurpose Internet Mail Extensions) and TLS encryption options are lacking, only working correctly if both the sender and recipient are equipped with it. Without proper email encryption enabled, confidential attachments pertaining to business, financial, and even personal information might fall into the wrong hands. Thankfully, third-party encryption software is available to ensure the security of all attachments and messages transmitted via Gmail.

Confidential Mode in Gmail

To boost email security offerings, Gmail rolled out its confidential mode option in 2018, allowing "users to send emails that recipients can't forward, copy, print, or download." Although the name of this security method evokes a sense of heightened data safety and confidentiality, in actuality, it effectively provides neither. With confidential mode enabled, users are also empowered to generate passcodes, activate message expiration dates, and rescind recipient access to specific emails. Thus, Gmail's confidential mode thwarts any sharing -- whether accidental or otherwise -- on the part of the email's recipient. And a recipient that intends to share an email's messages or attachments with unintended viewers is not prevented from doing so with ease via a simple screenshot. Furthermore, this security mode does not offer end-to-end encryption, permitting Gmail and additional providers to scan and collect email contents.

How to Encrypt Your Emails and Attachments

The attachments shared via email are often just as sensitive, or potentially more so than their corresponding messages. End-to-end encryption masterfully encrypts an email's contents while in flight and at rest, ridding emails of most security vulnerabilities. Undoubtedly, this makes end-to-end encryption the most secure method of email encryption, as it protects the user's valuable messages, files, documents, etc. Although Google has often entertained the conversation around implementing end-to-end encryption on Gmail, it has failed to do so as of yet. Gmail offers users a few added security options at a price. Still, to fill the void left behind by Google, several third-party encryption services have stepped up to offer their own applications and extensions.

Upgrade Your Account

In order to upgrade the data security which operates within your email account, one might consider upgrading their Gmail account from the free model to one of the platform's paid offerings. Both the G Suite Enterprise and G Suite Education plans provide S/MIME encryption. A step up from the standard TLS encryption provided by Google, which performs automatic encryption on all outgoing emails, S/MIME encryption enables users to encrypt emails with keys unique to the user and are required to be shared with the intended recipient. Users of either of Gmail's paid models can discern the level of encryption being employed by any given email.

With this being said, S/MIME encryption can only be successful if exercised by both the sender and the recipient. In other words, an email, even if sent utilizing S/MIME encryption, will remain unencrypted if the intended recipient uses an email provider free of encryption. And to top it off, S/MIME does not prevent Google's scanning of emails for advertising data collection. 

Find Another Email Provider

For those transmitting highly sensitive, confidential, or classified data via email, Gmail might not be a suitable fit. Although creating and transitioning to a new email account can be burdensome, it may help to achieve the level of security that is necessitated by your business, personal affairs, etc. It is critical to be incredibly diligent when researching a new email provider to ensure that this switch will be permanent and provide the desired privacy and data protection. Along with end-to-end encryption, the most secure email provider should offer guaranteed encryption, no matter the recipient's provider, as well as a zero-knowledge policy.

Use Encryption Software from Trustifi

In order to securely use Gmail, email attachments must be encrypted before being sent. By doing so, in the event that an email is intercepted and/or forwarded by a malicious actor, the attachments will remain encrypted, rendering them useless to cybercriminals, hackers, and other third-party entities. However, discovering the most streamlined, user-friendly, and efficient method of email encryption does not have to be a daunting task. While the encryption solutions provided by Google seem to miss the mark and most third-party plug-ins are challenging to use, users who intend to stick with Gmail can seek the assistance of an encryption software provider. 

Trustifi is a comprehensive email security platform that offers cost-effective and versatile encryption options to a variety of clients, spanning virtually all industries, including highly regulated ones like: Pharmaceutical, Healthcare, Financial, Legal, and Real Estate. As an add-on extension, Trustifi integrates seamlessly with Gmail. And with NSA-grade end-to-end email encryption and secure mobile relay, Trustifi delivers user-friendly, complete protection for both incoming and outgoing messages to all clients. Moreover, Trustifi's customizable encryption solutions enable clients to recall, block, modify, and set expirations on previously sent and received emails. Trustifi also allows clients to prevent the printing and removal of metadata from email attachments. Overall, Trustifi's encryption solutions provide Gmail users with unmatched visibility and security measures, enabling increased oversight and peace of mind.


Email messages and attachments landing in the wrong hands is not an uncommon occurrence. And "this is especially frightening because email remains the most popular business communication method, which puts millions of companies at risk of both reputational and financial loss." Highly sensitive data in the form of business presentations, contracts, agreements, mock-ups, and the like are sent and received via email every day. And typically, once such emails are sent out, users lose control over these attachments entirely.

Fortunately, email encryption software and solutions like those provided by Trustifi are here to help, serving as the user's first line of defense against email data breaches and malicious interceptions. With Trustifi's NSA grade end-to-end email encryption services, clients can rest assured that any attachments sent and received via Gmail will be secured, protected, and only accessed by intended viewers.


“How to Easily Encrypt and Track Your Gmail Attachments.” Digify, 26 May 2020,

Simpson, Eva. “How to Send Secure Email Attachments in Gmail.” NordLocker, NordLocker, 15

Nov. 2019,

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