How to enable SSL for SMTP in CreateUserWizard when using Gmail for email notifications

[pixelPilot]

I’m working with the CreateUserWizard control and need it to send email notifications to new users. Since I don’t have my own mail server, I want to use my Gmail account for sending these emails.

The problem is I keep getting an error message saying “Must issue STARTTLS command first”. From what I’ve read, this happens because the CreateUserWizard’s internal SMTP client uses regular NetworkStream instead of SslStream for connections.

Right now the only solution I found is to handle the SendingMail event, cancel it using MailMessageEventArgs.Cancel, and then create my own SMTP client where I can set EnableSsl to true. This works but seems like a workaround.

Is there any way to directly access the CreateUserWizard’s internal SMTP client object and configure it to use SSL? I’d prefer not to handle the email sending manually if possible.

Thanks for any help!

[AdventurousHiker17]

yeah, I hit this same issue last year. there’s no built-in ssl config for createuserwizard, which sucks. but your workaround with the sendingmail event cancel is spot on - that’s what most of us end up doing.

[coffeeAndCode]

The Problem:

You’re encountering the “Must issue STARTTLS command first” error when using the CreateUserWizard control to send email notifications via your Gmail account. This is because the CreateUserWizard’s built-in SMTP client doesn’t automatically enable SSL/TLS encryption. Your current workaround involves handling the SendingMail event, canceling it, and creating a custom SMTP client with SSL enabled. While functional, this is cumbersome.

Understanding the “Why” (The Root Cause):

The CreateUserWizard control relies on a basic SMTP client that defaults to unencrypted connections. When attempting to send emails to Gmail (or other providers requiring secure connections), this results in the “Must issue STARTTLS command first” error. Gmail and other secure email providers require the use of TLS (Transport Layer Security) or SSL (Secure Sockets Layer) to encrypt the connection and prevent data interception. The CreateUserWizard’s default configuration doesn’t establish this secure connection.

Step-by-Step Guide:

1. Utilize a Dedicated Email Sending Service (Recommended): The most robust and maintainable solution is to decouple email sending from the CreateUserWizard entirely. Use a dedicated transactional email service like SendGrid, Mailgun, or AWS SES. These services handle the complexities of secure email delivery, including SSL/TLS encryption, authentication, and deliverability optimization. You would integrate the service’s API into your application to send emails upon user creation. This method avoids the need to directly manage SMTP connections and significantly improves email deliverability and reliability.

2. Modify your User Creation Workflow: This step is performed only if you choose not to utilize a dedicated email sending service. Handle the SendingMail event of the CreateUserWizard as you’re currently doing, but instead of creating a full custom SMTP client, you can utilize a library that handles SSL/TLS configuration transparently. Many .NET libraries offer this functionality. This approach is still a workaround, and a dedicated email service is still preferable. Here’s example code demonstrating the use of a library (replace YourEmailClient with your selected client):

protected void CreateUserWizard1_SendingMail(object sender, MailMessageEventArgs e)
{
    e.Cancel = true; // Cancel the default sending

    using (var client = new YourEmailClient()) //Replace with chosen email client
    {
        client.EnableSsl = true;
        client.Send(e.Message); // Send the email with the library
    }
}

Common Pitfalls & What to Check Next:

• Gmail Account Configuration: Ensure that your Gmail account is properly configured to allow less secure apps or has App Passwords enabled for secure access if you are using a third-party client.
• Firewall Settings: Verify that your firewall allows outgoing connections on the appropriate SMTP port (typically port 587 or 465).
• Email Deliverability: If using a dedicated email service, ensure your email content doesn’t trigger spam filters, and configure SPF, DKIM, and DMARC records for improved deliverability.

Still running into issues? Share your (sanitized) config files, the exact command you ran, and any other relevant details. The community is here to help!