SMIME Toolkit vs PassPony

SMIME Toolkit: S/MIME Setup - Secure Email Certificates SMIME Toolkit guides you through S/MIME setup on iPhone and iPad in clear steps. Generate keys on-device, request certificates from your organization or SMIME Toolkit's backend, and export identities for manual installation in iOS Settings. Sign and encrypt email in Apple Mail while keeping your private keys under your control. WHAT THIS APP DOES SMIME Toolkit guides you through the full S/MIME enrollment process: - Generates cryptographic keys securely on your device (RSA-2048 default, optional ECC P-384) - Builds standards-compliant certificate signing requests (CSRs) - Requests signed certificates from your organization's secure backend - Exports PKCS#12 (.p12) identities for manual installation in iOS Settings - Optionally generates both RSA and ECC identities for compatibility targets The app never configures Mail automatically and never accesses your email content. KEY FEATURES - On-device key generation (Keychain-backed) - Standards-compliant CSR with email address (subjectAltName) - Secure HTTPS requests to your organization's issuer - PKCS#12 (.p12) export with a password you choose - Face ID / Touch ID for sensitive actions - Manual install flow (required by iOS) - CA certificate export and optional trust profile for easier setup - Optional ECC P-384 support and dual-identity export flow HOW IT WORKS - Enter your email address - Generate a key pair and CSR on your device - Request a certificate from your signing service - Export your identity (.p12) or trust profile - Install manually in Settings > Mail > Accounts > Advanced Once installed, enable S/MIME signing and encryption in Apple Mail. PRIVACY & SECURITY - Your private key never leaves your device - Only your CSR and email address are sent for certificate issuance - No access to Mail, messages, or accounts - No ads or tracking IMPORTANT NOTES - This app cannot configure Apple Mail automatically - Manual installation is required by iOS - Certificate issuance depends on your organization's backend - Private CAs must be trusted in Certificate Trust Settings FOR TEAMS & ENTERPRISES SMIME Toolkit is designed for organizations that want a simple, user-driven S/MIME enrollment flow: - Works with internal CAs and private trust roots - Predictable, auditable issuance workflows - Pluggable backend interface for partner CA integrations - Enterprise bulk generation supports RSA default, ECC opt-in, or both TROUBLESHOOTING - Ensure your network can reach the signing service - Certificate chain errors usually indicate issuer misconfiguration - If Mail doesn't show encryption, confirm CA trust and recipient certificates COMPATIBILITY - Works with Apple Mail on iOS after manual installation - Compatible with clients that support PKCS#12 identities once installed SMIME Toolkit is a certificate utility. It does not provide email hosting, account management, or message delivery. Apple Mail remains controlled by iOS settings and your email provider.

PassPony is a password manager for people who want to own their passwords. Every entry is one encrypted file in a store you control, in the same format as the pass and passage command line tools. Your Mac, your server, and your phone can all work on the same store. WHY A FILE-BASED STORE One entry, one file: the password on the first line, anything else after it. Encrypted with your keys: age identities for passage stores, OpenPGP keys for pass stores. Synced with git over HTTPS or SSH: clone your existing store, publish a new one, and resolve conflicts per entry, never with a silent merge. Interoperable: commits match the pass CLI format, so the store stays fully usable from the desktop tools. EVERYDAY USE AutoFill: your passwords appear above the keyboard when you sign in. Only entry names are indexed; nothing decrypts until you fill. Passkeys: save a passkey for a site and sign in with it. It lives in that site's entry, encrypted with your keys, and syncs like everything else. One-time codes: TOTP with a countdown ring, HOTP counters, and import from an authenticator app's export QR codes. Face ID or Touch ID unlock, with a five-minute grace window shared with AutoFill. Ephemeral clipboard: copies are local only and clear after 45 seconds. Field-level editing that preserves the exact bytes of lines it does not touch. YOUR KEYS STAY YOURS Back up every key on your phone to one file locked with a recovery code, and restore it on a new phone. SSH sync uses a key made on your phone or imported; hosts are trusted on first use and a changed host key is refused. Phones that share a store each add their own public key to it when they sync, and you approve every new key before your entries are re-encrypted for it. Secret keys never leave a device. PRIVATE BY ARCHITECTURE No account, no signup, no PassPony server. The only network connection is the git remote you configure. No analytics, no ads, no tracking. Open source, Apache-2.0. The full app and its Rust core are published in a public git repository for anyone to audit. FORMATS passage stores encrypt with modern age identities. pass stores encrypt with OpenPGP keys (Cv25519 and X25519/Ed25519 in software). RSA-keyed stores need a smartcard, which is not supported yet. Each format keeps its own store; switching never touches the other. Localized in English, Spanish, French, German, Simplified Chinese, Brazilian Portuguese, and Russian. If you already run pass or passage, PassPony is the missing phone half of your setup. If you have never used them, the first-run tour will have you adding your first pass in about a minute.