C# – Send smtp gmail email ”Failure sending mail”

Be sure to use System.Net.Mail, not the deprecated System.Web.Mail. Doing SSL with System.Web.Mail is a gross mess of hacky extensions.

using System.Net;
using System.Net.Mail;

var fromAddress = new MailAddress("from@gmail.com", "From Name");
var toAddress = new MailAddress("to@example.com", "To Name");
const string fromPassword = "fromPassword";
const string subject = "Subject";
const string body = "Body";

var smtp = new SmtpClient
{
    Host = "smtp.gmail.com",
    Port = 587,
    EnableSsl = true,
    DeliveryMethod = SmtpDeliveryMethod.Network,
    UseDefaultCredentials = false,
    Credentials = new NetworkCredential(fromAddress.Address, fromPassword)
};
using (var message = new MailMessage(fromAddress, toAddress)
{
    Subject = subject,
    Body = body
})
{
    smtp.Send(message);
}

Additionally go to the Google Account > Security page and look at the Signing in to Google > 2-Step Verification setting.

• If it is enabled, then you have to generate a password allowing .NET to bypass the 2-Step Verification. To do this, click on Signing in to Google > App passwords, select app = Mail, and device = Windows Computer, and finally generate the password. Use the generated password in the fromPassword constant instead of your standard Gmail password.
• If it is disabled, then you have to turn on Less secure app access, which is not recommended! So better enable the 2-Step verification.

CVertex, make sure to review your code, and, if that doesn't reveal anything, post it. I was just enabling this on a test ASP.NET site I was working on, and it works.

Actually, at some point I had an issue on my code. I didn't spot it until I had a simpler version on a console program and saw it was working (no change on the Gmail side as you were worried about). The below code works just like the samples you referred to:

using System;
using System.Collections.Generic;
using System.Linq;
using System.Text;
using System.Net.Mail;
using System.Net;

namespace ConsoleApplication2
{
    class Program
    {
        static void Main(string[] args)
        {
            var client = new SmtpClient("smtp.gmail.com", 587)
            {
                Credentials = new NetworkCredential("myusername@gmail.com", "mypwd"),
                EnableSsl = true
            };
            client.Send("myusername@gmail.com", "myusername@gmail.com", "test", "testbody");
            Console.WriteLine("Sent");
            Console.ReadLine();
        }
    }
}

I also got it working using a combination of web.config, http://msdn.microsoft.com/en-us/library/w355a94k.aspx and code (because there is no matching EnableSsl in the configuration file :( ).

2021 Update

By default you will also need to enable access for "less secure apps" in your gmail settings page: google.com/settings/security/lesssecureapps. This is necessary if you are getting the exception "`The server response was: 5.5.1 Authentication Required. – thanks to @Ravendarksky