Gog Email Send

Email Sending with Confirmation

⚠️ CRITICAL: This skill sends emails. It MUST NOT be invoked without explicit user confirmation.

Send emails only after receiving the exact confirmation string: "YES, SEND"

When to Use

Use this skill ONLY when:

• User has reviewed a draft and explicitly confirms they want to send it
• User provides the confirmation string "YES, SEND" in their message
• All draft content has been approved by the user

NEVER use this skill:

• Automatically after drafting an email
• Based on implied intent ("sounds good", "ok", "sure")
• Without showing the user exactly what will be sent
• Without receiving "YES, SEND" confirmation

Confirmation Requirements

The ONLY Acceptable Confirmation

User MUST type exactly: "YES, SEND"

Acceptable variations (all must include "YES, SEND"):

• "YES, SEND this email"
• "YES, SEND it"
• "YES, SEND the draft"
• "Confirmed. YES, SEND"

NOT acceptable:

• "Yes" / "OK" / "Sure" / "Go ahead" / "Send it"
• "Looks good, send it"
• "Please send"
• Any paraphrase that doesn't include the exact phrase "YES, SEND"

Workflow

Step 1: Verify Confirmation String

Before ANY sending operation, check:

Does the user's message contain the EXACT string "YES, SEND"?
  - YES → Proceed to Step 2
  - NO → STOP and request confirmation

If confirmation is missing, respond:

⚠️  **Confirmation Required**

To send this email, please confirm by typing exactly:

**YES, SEND**

I need this explicit confirmation to ensure you've reviewed the email and want it sent.

**Reminder**: This will send email to:
- [List recipients]
- Subject: [Subject line]

STOP HERE. Do not proceed until confirmation is received.

Step 2: Display Final Summary

Show the user exactly what will be sent:

📧 **Ready to Send**

**From**: [Your email address, if known]
**To**: [recipient1@example.com, recipient2@example.com]
**CC**: [cc recipients, if any]
**Subject**: [Subject line]

**Body**:

[First 200 characters of body...] [Body continues for N more characters...]

**Attachments**: [List attachments if any, or "None"]

---

Is this correct? If yes, I'll send it now.

Step 3: Execute Send

Determine send method:

Option A: Send existing draft

If user has a draft_id:

gog gmail drafts send <draft_id> --json

Option B: Direct send

If composing directly (less common):

# Save body to temp file
cat > /tmp/email_body_$$.txt << 'EOF'
Email body content
EOF

gog gmail send \
  --to "recipient1@example.com,recipient2@example.com" \
  --cc "cc@example.com" \
  --subject "Subject line" \
  --body /tmp/email_body_$$.txt \
  --json

# Clean up temp file
rm /tmp/email_body_$$.txt

Step 4: Log to Audit Trail

Immediately after sending (success or failure), log the action:

# Source logging utility
source "$(dirname "$0")/../../_shared/scripts/log.sh"

# Log successful send
log_action "gog-email-send" "email-send" "success" "$MESSAGE_ID" \
  "{\"to\":[\"recipient@example.com\"],\"subject\":\"$SUBJECT\",\"confirmation\":\"YES, SEND\"}"

# OR log failed send
log_action "gog-email-send" "email-send" "failure" "" \
  "{\"to\":[\"recipient@example.com\"],\"subject\":\"$SUBJECT\",\"error\":\"$ERROR_MSG\"}"

Audit log entry should include:

• Timestamp (automatic)
• Skill name: "gog-email-send"
• Action: "email-send"
• Status: "success" or "failure"
• Entity ID: message_id (if successful)
• Details: to addresses, subject, confirmation string

Step 5: Confirm Completion

If successful:

✅ **Email Sent Successfully**

Message ID: msg_abc123
Sent at: [timestamp]
Recipients: [list]

The email has been sent and logged to your audit trail.

Next steps:
- Track response with follow-up? (gog-followups skill)
- Send another email?

If failed:

❌ **Send Failed**

Error: [Error message from GOG]

The email was NOT sent. Common issues:
- Authentication expired (run: gog auth login)
- Invalid recipient email address
- Network connectivity issues
- Insufficient permissions

Would you like to:
- Retry sending?
- Save as draft for later?
- Edit the email?

Output Format (Strict)

Before Sending (Awaiting Confirmation)

⚠️  **Confirmation Required**

To send this email, please type: **YES, SEND**

**Email Summary**:
- To: [recipients]
- Subject: [subject]
- Body: [snippet...]

I'm waiting for your explicit confirmation before sending.

After Sending (Success)

✅ **Email Sent**

Message ID: [msg_id]
Recipients: [list]
Timestamp: [ISO8601]

Logged to: ~/.gog-assistant/audit.log

After Sending (Failure)

❌ **Send Failed**

Error: [error message]

The email was NOT sent. [Troubleshooting guidance]

Examples

Example 1: Send Draft (Correct Flow)

User: "I've reviewed the draft. YES, SEND"

Assistant:

[Confirmation string detected: "YES, SEND" ✓]

📧 **Ready to Send**

**To**: client@acme.com
**Subject**: Re: Q2 Proposal

**Body**:

Hi Sarah,

Thank you for your patience. I've reviewed the Q2 proposal and have a few questions...

[287 more characters]

Sending now...

[Executes: gog gmail drafts send draft_abc123 --json] [Logs to audit trail]

✅ Email Sent Successfully

Message ID: msg_xyz789 Sent at: 2026-01-28T15:30:00Z Recipients: client@acme.com

The email has been sent and logged to your audit trail.

Would you like to set up a follow-up reminder for this email?

### Example 2: User Doesn't Confirm (Correct Block)

**User**: "Looks good, please send it"

**Assistant**:

⚠️ Confirmation Required

To send this email, please confirm by typing exactly:

YES, SEND

I need this explicit confirmation to ensure you've reviewed the email and want it sent.

Reminder: This will send email to:

• client@acme.com
• Subject: Re: Q2 Proposal

[STOPS HERE. Does not send.]

### Example 3: Send Fails

**User**: "YES, SEND"

**Assistant**:

[Confirmation string detected: "YES, SEND" ✓]

📧 Ready to Send

[Displays summary...]

Sending now...

[Executes: gog gmail drafts send draft_abc123 --json]

❌ Send Failed

Error: Authentication token expired

The email was NOT sent.

Fix: Run gog auth login to re-authenticate, then try again.

Would you like me to save this draft so you can send it after re-authenticating?

### Example 4: Testing Confirmation Blocking

**User**: "Send the draft to the test address"

**Assistant**:

⚠️ Confirmation Required

To send this email, please confirm by typing exactly:

YES, SEND

I need this explicit confirmation before sending any email.

Email Summary:

• To: test@example.com
• Subject: [subject]
• Body: [snippet]

Please review the email details above and confirm if you want to proceed.

[Does NOT send without "YES, SEND"]

## Failure Modes / Troubleshooting

### User Forgets Confirmation String

**Symptom**: User says "send it" or "go ahead" without "YES, SEND"

**Resolution**:
1. DO NOT send
2. Remind user of exact confirmation string required
3. Explain: "For safety, I need you to type 'YES, SEND' exactly"
4. Wait for proper confirmation

### Authentication Expired

**Symptom**: `gog email send` returns authentication error

**Resolution**:
1. Inform user: "Authentication expired. Run: gog auth login"
2. Offer: "Would you like me to save this as a draft so you can send it after re-authenticating?"
3. If user confirms, save draft and provide draft_id

### Invalid Recipient

**Symptom**: Error about invalid email address format

**Resolution**:
1. Identify which recipient address is invalid
2. Ask user: "The email address [X] appears invalid. Please provide a corrected address."
3. Update draft with corrected address
4. Request confirmation again before sending

### Network Failure

**Symptom**: Timeout or network error during send

**Resolution**:
1. Inform user: "Network error during send. The email may or may not have been sent."
2. Check sent folder: `gog gmail search "in:sent" --max 1`
3. If found, confirm: "Email was sent successfully despite error"
4. If not found, offer: "Would you like to retry?"

### Audit Log Write Failure

**Symptom**: Email sent but logging fails

**Resolution**:
1. Prioritize: Email was sent (user is informed)
2. Log error: Write to stderr about audit log failure
3. Manual log entry: Provide command for user to manually log:

echo '{"timestamp":"...","skill":"gog-email-send","action":"email-send","status":"success","entity_id":"msg_xyz","details":{...}}' >> ~/.gog-assistant/audit.log

## Safety Rules

1. **"YES, SEND" is mandatory** - No exceptions, no paraphrases, no implied consent
2. **Always show what will be sent** - Complete summary before execution
3. **Log every send attempt** - Success and failure both logged
4. **Never auto-send** - Even if previous draft was approved, require fresh confirmation for each send
5. **Privacy in logs** - Log metadata (recipients, subject), not full body content
6. **Fail safe** - If any doubt about confirmation, DO NOT SEND

## Safe Test

To safely test this skill using only `user@example.com`:

**Test 1: Confirmation Blocking (Always Safe)**

In Claude Code:
1. Load gog-email-send skill
2. Create a draft to self via gog-email-draft skill
3. Say: "Send this draft" (without "YES, SEND")
4. **Expected**: Skill REFUSES and requests "YES, SEND" confirmation
5. **Verify**: No email is sent

**Test 2: Successful Send to Self (Safe)**

1. Create a draft to user@example.com with subject "[TEST] GOG Send Test"
2. Say: "YES, SEND"
3. **Expected**: Skill sends email to self
4. **Verify**:
- Email arrives in your inbox
- Audit log contains entry: `~/.gog-assistant/audit.log`
- Entry includes: timestamp, skill, action, status=success, recipients

**Test 3: Failed Send (Safe)**

1. Create a draft to invalid@invalid (invalid address)
2. Say: "YES, SEND"
3. **Expected**: Send fails with error about invalid recipient
4. **Verify**:
- No email sent
- Error message displayed to user
- Audit log contains entry with status=failure

See `skills/gog/_shared/references/testing.md` for complete test plan.

## Notes

- This skill integrates with:
  - `gog-email-draft`: Typically invoked after draft is created
  - `gog-followups`: Can suggest adding follow-up tracking after send
  - `gog-tasks`: Can create task for "follow up in N days"

- **Why "YES, SEND" exactly?**
  - Distinctive phrase unlikely to occur accidentally
  - Requires user to consciously type it (not auto-complete)
  - Clear signal of intent
  - Easy to search in conversation logs

- **Audit log importance**:
  - Required for compliance and accountability
  - Helps debug "did this email actually send?" questions
  - Provides history for follow-up tracking
  - Can be used to generate reports or analytics

- Consider adding to audit log:
  - Draft iterations (how many times edited before sending)
  - Time from draft creation to send
  - Thread context (was this a reply?)

- For production use, consider:
  - Rate limiting (prevent accidental mass sends)
  - Undo/recall within 30 seconds
  - Preview in rendered HTML (not just plain text)
  - Spellcheck pass before sending