Send email from gmail using Telnet

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.

Using regular expressions is probably the best way. You can see a bunch of tests here (taken from chromium)

function validateEmail(email) {
    const re = /^(([^<>()[\]\\.,;:\s@"]+(\.[^<>()[\]\\.,;:\s@"]+)*)|(".+"))@((\[[0-9]{1,3}\.[0-9]{1,3}\.[0-9]{1,3}\.[0-9]{1,3}\])|(([a-zA-Z\-0-9]+\.)+[a-zA-Z]{2,}))$/;
    return re.test(String(email).toLowerCase());
}

Here's the example of regular expresion that accepts unicode:

const re = /^(([^<>()[\]\.,;:\s@\"]+(\.[^<>()[\]\.,;:\s@\"]+)*)|(\".+\"))@(([^<>()[\]\.,;:\s@\"]+\.)+[^<>()[\]\.,;:\s@\"]{2,})$/i;

But keep in mind that one should not rely only upon JavaScript validation. JavaScript can easily be disabled. This should be validated on the server side as well.

Here's an example of the above in action:

function validateEmail(email) {
  const re = /^(([^<>()[\]\\.,;:\s@\"]+(\.[^<>()[\]\\.,;:\s@\"]+)*)|(\".+\"))@((\[[0-9]{1,3}\.[0-9]{1,3}\.[0-9]{1,3}\.[0-9]{1,3}\])|(([a-zA-Z\-0-9]+\.)+[a-zA-Z]{2,}))$/;
  return re.test(email);
}

function validate() {
  const $result = $("#result");
  const email = $("#email").val();
  $result.text("");

  if (validateEmail(email)) {
    $result.text(email + " is valid :)");
    $result.css("color", "green");
  } else {
    $result.text(email + " is not valid :(");
    $result.css("color", "red");
  }
  return false;
}

$("#email").on("input", validate);

<script src="https://ajax.googleapis.com/ajax/libs/jquery/2.1.1/jquery.min.js"></script>

<label for=email>Enter an email address:</label>
<input id="email">
<h2 id="result"></h2>