automailsender-public/SUPPORT.md

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

---

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 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.

---

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!

---

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

---

Legal

• Privacy Policy: PRIVACY_POLICY.md
• License: MIT License
• Copyright: © 2025 Nick Roodenrijs. All rights reserved.

---

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]

---

Thank you for using AutoMailSender! 🚀

Last updated: October 27, 2025