# AutoMailSender Support

**Version:** 1.0.0
**Last Updated:** October 27, 2025

## Get Help

If you need assistance with AutoMailSender, please use one of the following methods:

### 📧 Email Support

**Email:** nick@example.com
**Response Time:** Typically within 48 hours

### 📚 Built-in Help

AutoMailSender includes comprehensive help documentation:
1. Open AutoMailSender
2. Click Settings (⚙️ icon)
3. Click the Help button (? icon)

The built-in help includes:
- SMTP setup guides for Gmail, Outlook, Yahoo, and iCloud
- Troubleshooting common issues
- Privacy and security information

---

## Quick Start Guide

### 1️⃣ Initial Setup

1. **Open Settings** - Click the ⚙️ icon in the main window
2. **Choose Email Provider** - Select from:
   - Gmail
   - Outlook
   - Yahoo Mail
   - iCloud Mail
   - Custom SMTP server
3. **Enter Credentials**:
   - Email address
   - App-specific password (recommended)
4. **Add Recipients** - Go to Recipients tab and add email addresses

### 2️⃣ Sending Files

1. **Drag & Drop** - Drag any file onto the main window
2. **Confirm** - Review the file and click "Send Email"
3. **Done!** - You'll see a success message

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## Common Issues

### 🔐 Authentication Failed

**Problem:** "Authentication failed" error when sending emails

**Solutions:**
1. **Use App-Specific Password** instead of your regular password:
   - **Gmail:** https://myaccount.google.com/apppasswords (requires 2FA)
   - **Outlook:** https://account.microsoft.com/security (App passwords)
   - **Yahoo:** https://login.yahoo.com/account/security (Generate app password)
   - **iCloud:** https://appleid.apple.com (App-specific passwords)

2. **Check SMTP Settings**:
   - Gmail: smtp.gmail.com, port 587, TLS
   - Outlook: smtp-mail.outlook.com, port 587, STARTTLS
   - Yahoo: smtp.mail.yahoo.com, port 587, TLS
   - iCloud: smtp.mail.me.com, port 587, TLS

3. **Enable "Less Secure Apps"** (Gmail only, not recommended):
   - Only if you can't use app-specific passwords
   - Not available if 2FA is enabled

### 📁 File Too Large

**Problem:** "File size exceeds limit" error

**Solutions:**
1. **Check provider limits**:
   - Gmail: 25 MB
   - Outlook: 20 MB
   - Yahoo: 25 MB
   - iCloud: 20 MB

2. **Compress the file** using macOS Finder (Right-click → Compress)
3. **Use cloud storage** and send a link instead

### ❌ Connection Failed

**Problem:** "Connection to SMTP server failed"

**Solutions:**
1. **Check your internet connection**
2. **Verify SMTP server address and port**
3. **Check firewall settings** - Ensure outgoing connections on port 587/465 are allowed
4. **Try different security settings**:
   - TLS (port 587)
   - SSL (port 465)
   - STARTTLS (port 587)

### 🔒 Keychain Access Denied

**Problem:** "Cannot access macOS Keychain"

**Solutions:**
1. **Allow Keychain Access**:
   - Open Keychain Access app
   - Find "AutoMailSender" entries
      - Right-click → Get Info → Access Control
   - Add AutoMailSender to "Always allow access"

2. **Reset Keychain** (last resort):
   - Settings → Email tab → Clear credentials
   - Re-enter your email and password

---

## SMTP Setup Guides

### Gmail Setup

1. **Enable 2-Factor Authentication**:
   - Go to https://myaccount.google.com/security
   - Enable 2-Step Verification

2. **Generate App Password**:
   - Visit https://myaccount.google.com/apppasswords
   - Select "Mail" and "Mac" as device
   - Copy the 16-character password

3. **Configure AutoMailSender**:
   - Provider: Gmail
   - Email: your-email@gmail.com
   - Password: [16-character app password]

### Outlook/Hotmail Setup

1. **Enable 2-Step Verification**:
   - Go to https://account.microsoft.com/security
   - Enable two-step verification

2. **Generate App Password**:
   - Visit https://account.microsoft.com/security
   - Select "App passwords"
   - Create new password for "Mail on Mac"

3. **Configure AutoMailSender**:
   - Provider: Outlook
   - Email: your-email@outlook.com (or @hotmail.com)
   - Password: [app password]

### Yahoo Mail Setup

1. **Generate App Password**:
   - Visit https://login.yahoo.com/account/security
   - Click "Generate app password"
   - Select "Other App" → name it "AutoMailSender"

2. **Configure AutoMailSender**:
   - Provider: Yahoo
   - Email: your-email@yahoo.com
   - Password: [app password]

### iCloud Mail Setup

1. **Generate App-Specific Password**:
   - Visit https://appleid.apple.com
   - Sign in → Security section
   - Generate Password → name it "AutoMailSender"

2. **Configure AutoMailSender**:
   - Provider: iCloud
   - Email: your-email@icloud.com (or @me.com)
   - Password: [app-specific password]

---

## Frequently Asked Questions (FAQ)

### Is AutoMailSender free?

**Yes!** AutoMailSender is completely free with no in-app purchases, subscriptions, or hidden costs.

### Does AutoMailSender collect my data?

**No!** AutoMailSender:
- Does NOT collect analytics or telemetry
- Does NOT use tracking or advertising
- Does NOT upload your data to any servers (except your SMTP server)
- Stores all data locally on your Mac
- Uses macOS Keychain for secure credential storage

See [PRIVACY_POLICY.md](./PRIVACY_POLICY.md) for full details.

### Can I send to multiple recipients?

**Yes!** Add multiple recipients in Settings → Recipients tab. All recipients will receive the same file.

### What file types are supported?

AutoMailSender supports all common file types **except** blocked executable formats (.exe, .bat, .cmd, .com, .msi, .scr, .vbs, .js, .jar) for security reasons.

### What's the maximum file size?

File size limits depend on your email provider:
- **Gmail:** 25 MB
- **Outlook:** 20 MB
- **Yahoo:** 25 MB
- **iCloud:** 20 MB
- **Custom SMTP:** Depends on your server

### Can I customize the email subject and message?

**Yes!** Go to Settings → Email tab → scroll down to "Email Content" section. You can customize:
- Subject line
- Email body message
- Both support placeholders like {filename}

### Does AutoMailSender work offline?

**No.** AutoMailSender requires an internet connection to send emails via SMTP.

### Can I use AutoMailSender for bulk email marketing?

**No.** AutoMailSender is designed for personal/business file sharing, not mass marketing. Email providers enforce daily sending limits:
- Gmail: 500 emails/day
- Outlook: 300 emails/day
- Yahoo: 500 emails/day

Bulk email marketing violates most email providers' Terms of Service.

### Is my password stored securely?

**Yes!** AutoMailSender uses macOS Keychain to store credentials with system-level encryption. Passwords are never stored in plain text.

### Can I use AutoMailSender on multiple Macs?

**Yes!** However, settings do NOT sync between devices. You'll need to configure each Mac separately.

### Does AutoMailSender support Windows or Linux?

**No.** AutoMailSender is designed exclusively for macOS.

---

## System Requirements

- **macOS:** 12.0 (Monterey) or later
- **RAM:** 4 GB minimum
- **Disk Space:** 50 MB
- **Internet:** Required for sending emails
- **Email Account:** SMTP-enabled email account

---

## Privacy & Security

AutoMailSender is built with privacy and security as top priorities:

### 🔐 Security Features

- **macOS Keychain Integration** - Credentials encrypted at system level
- **App Sandbox** - Runs in restricted environment
- **TLS/SSL Encryption** - Secure SMTP connections
- **Input Validation** - Protects against injection attacks
- **No Plain-Text Passwords** - Passwords never stored in readable format

### 🛡️ Privacy Features

- **No Analytics** - Zero telemetry or tracking
- **No Advertising** - No ad networks or trackers
- **No Cloud Storage** - All data stays on your Mac
- **No Third Parties** - No data sharing with anyone
- **Open Source Ready** - Code available for inspection

Read the full [Privacy Policy](./PRIVACY_POLICY.md).

---

## Feature Requests

Have an idea for AutoMailSender? Send your suggestions to:

**📧 Email:** nick@example.com
**Subject:** Feature Request - [Your Idea]

Please include:
- What feature you'd like to see
- Why it would be useful
- How you envision it working

We review all feature requests but cannot guarantee implementation.

---

## Bug Reports

Found a bug? Please report it with the following information:

**📧 Email:** nick@example.com
**Subject:** Bug Report - [Brief Description]

**Include:**
1. macOS version (System Settings → About)
2. AutoMailSender version (Settings → About)
3. Steps to reproduce the bug
4. Expected behavior vs. actual behavior
5. Screenshots (if applicable)
6. Error messages (if any)

**Privacy Note:** Never include your email password in bug reports!

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## Contributing

Interested in contributing to AutoMailSender?

- **Code Contributions:** Coming soon (open source plans)
- **Translations:** Email nick@example.com to help translate
- **Documentation:** Improvements to help docs welcome
- **Testing:** Beta testing opportunities available

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## Legal

- **Privacy Policy:** [PRIVACY_POLICY.md](./PRIVACY_POLICY.md)
- **License:** MIT License
- **Copyright:** © 2025 Nick Roodenrijs. All rights reserved.

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## Version History

### Version 1.0.0 (Current)
- Initial release
- Drag & drop file sending
- Multi-provider SMTP support (Gmail, Outlook, Yahoo, iCloud, Custom)
- Multiple recipients
- 26 language translations
- Dark mode support
- macOS Keychain integration
- Built-in help system

---

## Useful Links

- **Privacy Policy:** https://git.plet.i234.me/Nick/automailsender-public/src/branch/main/PRIVACY_POLICY.md
- **Support:** mailto:nick@example.com
- **Mac App Store:** [App Store Link - Coming Soon]

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**Thank you for using AutoMailSender! 🚀**

*Last updated: October 27, 2025*