Send It Secure

Send It Secure encrypts email messages sent through existing business workflows, with recipient verification and controls over access after delivery. It best suits organizations that handle confidential communications and rely on Outlook, SMTP, or connected business applications. Its strength is controlled delivery to recipients without requiring them to register; its limits are restrictive file allowances on lower plans and a lifetime send cap on the free account.

Overview

Senders can revoke messages, receive read receipts, set expiry and retention, apply message policies, and choose how recipients authenticate. Recipients can open messages without an account, using a shared secret or phone verification. That pairing helps reduce friction for outside recipients while preserving useful control for teams sending sensitive information.

The maker says messages are encrypted in transit with TLS and at rest with AES 256-bit encryption, and that its SOC 2 Type 2 attestations are available to clients. It enters into a HIPAA Business Associate Agreement with every client and supports HIPAA and GLBA compliance needs. These features make it relevant to regulated communications, though organizations should assess whether they meet their own requirements.

Key features

• Recipient verification: A shared secret or phone verification adds a check before a recipient opens a message, without requiring registration. That is useful for external communications where a sender needs more assurance than a plain email provides.
• Post-send controls: Revocation, expiry, retention settings, read receipts, and message policies help teams manage access and follow-up. These controls matter most when confidentiality or a recordkeeping schedule applies.
• Business workflow connections: Outlook support spans New Outlook, Classic Outlook, Outlook for Mac, and Outlook on the web. The service also integrates with practice management software, EHR applications, and Windows apps that send email, including dental systems such as Eaglesoft, Dentrix, Open Dental, and Carestream Dental. That breadth can suit teams that need secure messaging within their existing tools.
• SMTP and API: SMTP can send secure messages from applications that support it. Fewer than 300 sends per month are included with a business account; 301 or more require contacting the company. Teams with higher or variable volume should account for that before choosing this route.
• File capacity: The security page says messages can include files up to 2 GB, with limits up to 5 GB on some plans. The named plan allowances are lower: 25 MB on Guest, 50 MB on Essentials, and 1 GB on Professional. Buyers should match the plan allowance to their routine attachments.

Pricing

Send It Secure uses per-user pricing on its first two paid plans, while Professional includes two users. The free Guest tier can help evaluate the service, but its lifetime cap makes it unsuitable for ongoing use with non-paid recipients.

The trade-off between the paid plans is clear: Essentials keeps the monthly per-user price lower but limits files to 50 MB and retention to one year. Professional raises file capacity to 1 GB and retention to seven years, and its $29 monthly price covers two users before additional seats cost $10 per month each. Guest offers only 25 MB files and 30-day retention, alongside its lifetime cap of 10 sends to non-paid users.

Platforms

Send It Secure supports API, extension, iOS, web, and Windows. Outlook support covers desktop and web versions, including Mac. Gmail integration is not available, so organizations that require a Gmail connection should choose another service.

Who it's for

The maker describes Send It Secure for dental, medical, financial, legal, and other organizations that send confidential communications. Healthcare teams may value the HIPAA Business Associate Agreement and EHR connections; legal and financial teams may find recipient checks, message revocation, and retention controls useful. The product is a stronger fit when secure email needs to slot into Outlook or existing Windows and SMTP workflows than when Gmail integration is essential.

Pros and cons

• Pro: Recipients can open protected messages without registering, with shared-secret and phone verification options to add a check on access.
• Pro: Senders can revoke messages and set expiry, retention, policies, and read receipts, giving teams control after delivery.
• Pro: Outlook coverage and connections to practice management software and EHR applications support established business workflows.
• Con: Guest allows only 10 sends to non-paid users over the account's lifetime, so it is not a continuing free option for regular external correspondence.
• Con: Essentials allows 50 MB files and Professional 1 GB, which may constrain teams that routinely send larger attachments.
• Con: Gmail integration is absent, ruling it out for organizations that require that connection.

Alternatives

Lockbin is worth considering if Linux or macOS support matters, or if its free plan's one user, 25 MB attachment allowance, and six months of inbox storage suit the workload.

SecureMyEmail may fit users looking for support across Android, iOS, macOS, and Windows, with a free plan covering one email address.

gpg4o is an option for Windows users seeking OpenPGP functions within Classic Outlook; its listed gpg4o plan is €99.95 a month.

Secure Message may suit organizations seeking a Linux, web, or self-hosted option, with a Community plan for one domain and one administrator.

c.Email is a free extension option that supports existing email addresses and unlimited email addresses.

FlowCrypt may suit extension users with fewer than 100 users who can work within its 5 MB attachment threshold.

Mimecast Secure Messaging is another paid secure messaging option, with plans for secure messages and large files.

DataMotion Secure Email Exchange is an enterprise offering to consider if its Android, iOS, API, and web platform coverage fits.

For more options, browse Email Encryption Software or File encryption tools.

Verdict

Send It Secure is a strong choice for organizations that need verified, controlled email delivery through Outlook or established business applications. Recipient access without registration, post-send controls, and regulated-workflow support give it a clear purpose. Choose a paid tier based on file size and retention needs; look elsewhere if Gmail integration is required or the lower plan file allowances are too small.