SmtpException: Unable to read data from the transport connection: net_io_connectionclosed

Question

EDIT: Super Redux Version

Try port 587 instead of 465. Port 465 is technically deprecated.

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After a bunch of packet sniffing I figured it out. First, here's the short answer:

The .NET SmtpClient only supports encryption via STARTTLS. If the EnableSsl flag is set, the server must respond to EHLO with a STARTTLS, otherwise it will throw an exception. See the MSDN documentation for more details.

Second, a quick SMTP history lesson for those who stumble upon this problem in the future:

Back in the day, when services wanted to also offer encryption they were assigned a different port number, and on that port number they immediately initiated an SSL connection. As time went on they realized it was silly to waste two port numbers for one service and they devised a way for services to allow plaintext and encryption on the same port using STARTTLS. Communication would start using plaintext, then use the STARTTLS command to upgrade to an encrypted connection. STARTTLS became the standard for SMTP encryption. Unfortunately, as it always happens when a new standard is implemented, there is a hodgepodge of compatibility with all the clients and servers out there.

In my case, my user was trying to connect the software to a server that was forcing an immediate SSL connection, which is the legacy method that is not supported by Microsoft in .NET.

For anyone who stumbles across this post looking for a solution and you've set up SMTP sendgrid via Azure.

The username is not the username you set up when you've created the sendgrid object in azure. To find your username;

• Click on your sendgrid object in azure and click manage. You will be redirected to the SendGrid site.
• Confirm your email and then copy down the username displayed there.. it's an automatically generated username.
• Add the username from SendGrid into your SMTP settings in the web.config file.

Hope this helps!

Change port from 465 to 587 and it will work.

I've tried all the answers above but still get this error with Office 365 account. The code seems to work fine with Google account and smtp.gmail.com when allowing less secure apps.

Any other suggestions that I could try?

Here is the code that I'm using

int port = 587;
string host = "smtp.office365.com";
string username = "[email protected]";
string password = "password";
string mailFrom = "[email protected]";
string mailTo = "[email protected]";
string mailTitle = "Testtitle";
string mailMessage = "Testmessage";

using (SmtpClient client = new SmtpClient())
{
    MailAddress from = new MailAddress(mailFrom);
    MailMessage message = new MailMessage
    {
        From = from
    };
    message.To.Add(mailTo);
    message.Subject = mailTitle;
    message.Body = mailMessage;
    message.IsBodyHtml = true;
    client.DeliveryMethod = SmtpDeliveryMethod.Network;
    client.UseDefaultCredentials = false;
    client.Host = host;
    client.Port = port;
    client.EnableSsl = true;
    client.Credentials = new NetworkCredential
    {
        UserName = username,
        Password = password
    }; 
    client.Send(message);
}

UPDATE AND HOW I SOLVED IT:

Solved problem by changing Smtp Client to Mailkit. The System.Net.Mail Smtp Client is now not recommended to use by Microsoft because of security issues and you should instead be using MailKit. Using Mailkit gave me clearer error messages that I could understand finding the root cause of the problem (license issue). You can get Mailkit by downloading it as a Nuget Package.

Read documentation about Smtp Client for more information: https://docs.microsoft.com/es-es/dotnet/api/system.net.mail.smtpclient?redirectedfrom=MSDN&view=netframework-4.7.2

Here is how I implemented SmtpClient with MailKit

        int port = 587;
        string host = "smtp.office365.com";
        string username = "[email protected]";
        string password = "password";
        string mailFrom = "[email protected]";
        string mailTo = "[email protected]";
        string mailTitle = "Testtitle";
        string mailMessage = "Testmessage";

        var message = new MimeMessage();
        message.From.Add(new MailboxAddress(mailFrom));
        message.To.Add(new MailboxAddress(mailTo));
        message.Subject = mailTitle;
        message.Body = new TextPart("plain") { Text = mailMessage };

        using (var client = new SmtpClient())
        {
            client.Connect(host , port, SecureSocketOptions.StartTls);
            client.Authenticate(username, password);

            client.Send(message);
            client.Disconnect(true);
        }

You may also have to change the "less secure apps" setting on your Gmail account. EnableSsl, use port 587 and enable "less secure apps". If you google the less secure apps part there are google help pages that will link you right to the page for your account. That was my problem but everything is working now thanks to all the answers above.