Encryptomatic OpenPGP vs Secure Message

Encryptomatic OpenPGP is a Windows application for encrypting and signing messages and files, with Outlook integration. Encryption happens locally on the PC, and messages remain protected end-to-end from sender to recipient; recipients need OpenPGP software to decrypt them. Files can also be encrypted or signed from the Windows right-click context menu. The software supports Windows 10 and 11, plus listed Classic Outlook versions from 2013 through Microsoft 365 in 32-bit or 64-bit editions. PGP key-server support covers key sharing, discovery, and revocation, including MIT.EDU. Administrators can customize the interface and deploy through MSI silent installation and registration; some shared environments can use activation-free enterprise versions. Personal users, nonprofits, activists, and individual journalists can use it free, while for-profit business domains require a license. Business and free editions have identical encryption capabilities. Business pricing starts at $29.99 a year for one license; Mac is not supported.

Secure Message is a self-hosted inbound email gateway that filters mail before it reaches an existing mail server. Its Community features include Postfix content filtering, spam scoring, DNSBL, SPF, DKIM and DMARC checks, quarantine, mail logs and administrator MFA. Professional adds a recipient web portal: recipients open protected messages with a one-time code, without an account or app. Its rules can encrypt, redirect or block sensitive outbound messages, and recipient checks can use SMTP callout, LDAP or directory lookups. Stored messages, attachments and quarantine use Fernet encryption with AES-128-CBC and HMAC-SHA256; the key remains on the customer host. Access controls include TOTP administrator MFA, role-based access and audit logging, with logs exportable to CSV. Enterprise adds AI Autopilot tuning, eDiscovery and archive search, DLP and disclaimers; Autopilot and the classifier are off by default. The gateway can sit in front of Microsoft 365 or an existing mail server without mailbox migration. The single-node appliance runs on Debian 13, with 2 vCPU and 4 GB RAM recommended as a starting point.