To help you configure your SMTP server for Gmail properly, I'll provide some guidance based on the information available. The error you're encountering suggests there's an issue with the username and password authentication. Here are some steps to troubleshoot and configure it correctly: 1. Ensure you're using the correct username and password: - Your username should be your full Gmail address. - If you're using your regular Gmail password, make sure it's correct. 2. If you're using your regular Gmail password and still encountering issues, you should set up an "App Password" instead: - This is especially important if you have 2-Step Verification enabled on your Google account. - Go to your Google Account settings, navigate to the Security section, and create an App Password specifically for this SMTP connection. 3. Use the correct SMTP settings for Gmail: - Server: smtp.gmail.com - Port: 587 - Security: STARTTLS (TLS) 4. When configuring the SMTP URL in Ory, use this format:

<smtp://username:password@smtp.gmail.com:587/>

Make sure to URL encode your username and password. For example:

<smtp://your.email%40gmail.com:your_app_password@smtp.gmail.com:587/>

5. If you're still experiencing issues, double-check that you've allowed less secure apps to access your Google account, or preferably, use the App Password method mentioned above. [Use a custom server to send Ory Identity messages to users](https://www.ory.sh/docs/kratos/emails-sms/sending-emails-smtp) provides more detailed information on configuring SMTP settings in Ory. If you continue to face problems after trying these steps, you might want to check the [Email Delivery dashboard in the Ory Console](https://www.ory.sh/docs/kratos/emails-sms/sending-emails-smtp#troubleshooting) to see if there are any specific error messages that could provide more insight into the issue. Remember, for security reasons, it's always better to use App Passwords for SMTP authentication with Gmail, especially when setting up third-party integrations like this.

To set the SMTP URL in the Ory Console, you can follow these steps: 1. Log in to the [Ory Console](https://console.ory.sh/). 2. Navigate to Authentication → Email configuration in the Ory Console. 3. Toggle the Advanced Settings switch to access the SMTP configuration options. 4. Add the configuration for your SMTP server, including the SMTP URL. This information is based on the [Use a custom server to send Ory Identity messages to users](https://www.ory.sh/docs/kratos/emails-sms/sending-emails-smtp#send-emails-using-your-smtp-server) documentation. Remember to use the correct format for your SMTP URL, which should look something like this:

<smtp://username:password@smtp.example.com:587/>

Make sure to URL encode your username and password if they contain special characters, as mentioned in the [Invalid SMTP courier URL format troubleshooting guide](https://www.ory.sh/docs/troubleshooting/smtp-courier-OTA-112022-01). If you encounter any issues or need to verify your configuration, you can use the Ory CLI to check the SMTP settings as described in a [GitHub issue comment](https://github.com/ory/network/issues/212#issuecomment-1416150443):

shell ory get identity-config {project-id} --format jsonpath="courier.smtp"

This command will show you the current SMTP configuration for your project.