Configuration

Email Setup

Send recovery emails from your own address. Configure Gmail, Yahoo, Outlook, or any custom SMTP provider.

Why Your Own Email Matters

StayPaid sends recovery emails from your email address, not a generic no-reply address. This is the core of the founder-in-the-loop approach.

When your customer sees an email from sarah@herstartup.com in their inbox, they know it's real. They can reply directly to you. The email lands in their primary inbox, not promotions or spam.

To make this work, you need to configure your SMTP settings. This tells StayPaid how to send emails through your email provider.

Supported Providers

StayPaid supports all major email providers:

  • •Gmail / Google Workspace — Most popular. Uses app passwords for security.
  • •Yahoo Mail — Standard SMTP with app password.
  • •Outlook / Hotmail — Microsoft accounts with app password.
  • •Custom SMTP — Any provider that supports SMTP (Zoho, Fastmail, ProtonMail Bridge, etc.).

Gmail Setup

Gmail is the most common setup. You'll need to create an app password because Gmail doesn't allow "less secure apps" anymore.

Step 1: Enable 2-Step Verification

  1. Go to your Google Account.
  2. Navigate to Security.
  3. Under "Signing in to Google," click 2-Step Verification.
  4. Follow the prompts to enable it.

Step 2: Generate an App Password

  1. In Google Account → Security, go to App passwords.
  2. Select Mail as the app and Other as the device.
  3. Type "StayPaid" and click Generate.
  4. Copy the 16-character password (it looks like abcd efgh ijkl mnop).

Step 3: Enter in StayPaid

During onboarding, select Gmail as your provider and enter:

  • Sender email: your Gmail address
  • SMTP host: smtp.gmail.com (pre-filled)
  • SMTP port: 587 (pre-filled)
  • SMTP password: the app password you generated

Yahoo Mail Setup

Yahoo uses a similar app password system:

  1. Go to your Yahoo Account → Account Security.
  2. Click Generate app password.
  3. Select Other App and name it "StayPaid".
  4. Copy the generated password.
  5. In StayPaid, select Yahoo as your provider. The host smtp.mail.yahoo.com and port 587 are pre-filled.

Outlook / Hotmail Setup

Microsoft accounts also use app passwords:

  1. Go to your Microsoft Account → Security.
  2. Click Advanced security options.
  3. Under "App passwords," click Create a new app password.
  4. Copy the generated password.
  5. In StayPaid, select Outlook as your provider. The host smtp-mail.outlook.com and port 587 are pre-filled.

Custom SMTP Setup

If you use a different provider (Zoho, Fastmail, ProtonMail Bridge, etc.), select "Custom" and enter your provider's SMTP settings:

  • SMTP host: Your provider's SMTP server address.
  • SMTP port: Usually 587 (TLS) or 465 (SSL).
  • SMTP user: Your email address.
  • SMTP password: Your app password or account password.

Check your provider's documentation for the exact settings. Most support pages have an "SMTP settings" section.

Security

Your SMTP password is encrypted at rest using AES-256. It is never exposed in the UI, never logged, and never sent to the client-side. StayPaid only uses it to send recovery emails on your behalf.

We recommend using app passwords instead of your main account password. App passwords are limited in scope and can be revoked independently.

Troubleshooting

"Authentication failed"

Double-check that you're using an app password, not your main account password. Also verify that 2-step verification is enabled (required for app passwords on most providers).

"Connection timed out"

Check that the SMTP host and port are correct. Some providers block port 587 and require 465 instead. Also check your firewall settings.

Emails going to spam

Make sure your SPF and DKIM records are configured for your domain. Also, send a test email to yourself first to verify it lands in the inbox.

Ready to set up your email?

Start Free — First 3 recoveries