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20 changes: 18 additions & 2 deletions docs/COMMANDS.md
Original file line number Diff line number Diff line change
Expand Up @@ -114,8 +114,13 @@ nylas email list [grant-id] # List emails
nylas email read <message-id> # Read email
nylas email read <message-id> --raw # Show raw body without HTML
nylas email read <message-id> --mime # Show raw RFC822/MIME format
nylas email read <message-id> --decrypt # Decrypt PGP/MIME encrypted email
nylas email read <message-id> --verify # Verify GPG signature
nylas email read <message-id> --decrypt --verify # Decrypt and verify signature
nylas email send --to EMAIL --subject SUBJECT --body BODY # Send email
nylas email send --to EMAIL --subject SUBJECT --body BODY --sign # Send GPG-signed email
nylas email send ... --sign # Send GPG-signed email
nylas email send ... --encrypt # Send GPG-encrypted email
nylas email send ... --sign --encrypt # Sign AND encrypt (recommended)
nylas email send --list-gpg-keys # List available GPG signing keys
nylas email search --query "QUERY" # Search emails
nylas email delete <message-id> # Delete email
Expand All @@ -129,6 +134,15 @@ nylas email metadata show <message-id> # Show message me

**Filters:** `--unread`, `--starred`, `--from`, `--to`, `--subject`, `--has-attachment`, `--metadata`

**GPG/PGP security:**
```bash
nylas email send --to EMAIL --subject S --body B --sign # Sign with your GPG key
nylas email send --to EMAIL --subject S --body B --encrypt # Encrypt with recipient's key
nylas email send --to EMAIL --subject S --body B --sign --encrypt # Both (recommended)
nylas email read <message-id> --decrypt # Decrypt encrypted email
nylas email read <message-id> --decrypt --verify # Decrypt + verify signature
```

**AI features:**
```bash
nylas email ai analyze # AI-powered inbox summary
Expand All @@ -138,7 +152,7 @@ nylas email ai analyze --provider claude # Use specific AI provider
nylas email smart-compose --prompt "..." # AI-powered email generation
```

**Details:** `docs/commands/email.md`, `docs/commands/email-signing.md`, `docs/commands/ai.md`
**Details:** `docs/commands/email.md`, `docs/commands/email-signing.md`, `docs/commands/encryption.md`, `docs/commands/ai.md`

---

Expand Down Expand Up @@ -711,6 +725,8 @@ All commands follow consistent pattern:

**For detailed documentation on any feature, see:**
- Email: `docs/commands/email.md`
- Email Signing: `docs/commands/email-signing.md`
- Email Encryption: `docs/commands/encryption.md`
- Calendar: `docs/commands/calendar.md`
- Contacts: `docs/commands/contacts.md`
- Webhooks: `docs/commands/webhooks.md`
Expand Down
15 changes: 5 additions & 10 deletions docs/commands/email-signing.md
Original file line number Diff line number Diff line change
Expand Up @@ -302,16 +302,10 @@ gpg --send-keys YOUR_KEY_ID --keyserver keys.openpgp.org

### Current Limitations

- **Signing only**: Emails are not encrypted (content is readable)
- **Signing only**: This document covers signing. For encryption, see [GPG Email Encryption](encryption.md)
- **No S/MIME**: Only PGP/MIME format is supported
- **Manual verification**: Some email clients don't auto-verify signatures

### Future Enhancements

Planned features (not yet implemented):
- Email encryption with recipient's public key
- S/MIME certificate support

---

## Technical Details
Expand Down Expand Up @@ -393,13 +387,14 @@ nylas email send \

---

## Related Commands
## Related Documentation

- [GPG Email Encryption](encryption.md) - Encrypt emails for confidentiality
- [GPG Explained](explain-gpg.md) - Understanding GPG concepts
- `nylas email send --help` - See all email sending options
- `gpg --list-keys` - List all GPG keys
- `gpg --gen-key` - Generate new GPG key
- `git config user.signingkey` - Set default signing key

---

**Last Updated:** 2026-02-01
**Last Updated:** 2026-02-04
35 changes: 35 additions & 0 deletions docs/commands/email.md
Original file line number Diff line number Diff line change
Expand Up @@ -118,6 +118,41 @@ Email preview:
Scheduled to send: Mon Dec 16, 2024 4:30 PM PST
```

### GPG Signing and Encryption

Sign and/or encrypt emails using GPG/PGP:

```bash
# Sign email with your GPG key
nylas email send --to "to@example.com" --subject "Signed" --body "..." --sign

# Encrypt email with recipient's public key
nylas email send --to "to@example.com" --subject "Encrypted" --body "..." --encrypt

# Sign AND encrypt (recommended for maximum security)
nylas email send --to "to@example.com" --subject "Secure" --body "..." --sign --encrypt

# List available GPG keys
nylas email send --list-gpg-keys
```

**Reading encrypted/signed emails:**

```bash
# Decrypt an encrypted email
nylas email read <message-id> --decrypt

# Verify a signed email
nylas email read <message-id> --verify

# Decrypt and verify (for sign+encrypt emails)
nylas email read <message-id> --decrypt --verify
```

**See also:**
- [GPG Email Signing](email-signing.md) - Detailed signing documentation
- [GPG Email Encryption](encryption.md) - Detailed encryption documentation

### Search Emails

```bash
Expand Down
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