C# – Sending email in .NET through Gmail

Use email authentication methods, such as SPF, and DKIM to prove that your emails and your domain name belong together, and to prevent spoofing of your domain name. The SPF website includes a wizard to generate the DNS information for your site.

Check your reverse DNS to make sure the IP address of your mail server points to the domain name that you use for sending mail.

Make sure that the IP-address that you're using is not on a blacklist

Make sure that the reply-to address is a valid, existing address.

Use the full, real name of the addressee in the To field, not just the email-address (e.g. "John Smith" <john@blacksmiths-international.com> ).

Monitor your abuse accounts, such as abuse@yourdomain.com and postmaster@yourdomain.com. That means - make sure that these accounts exist, read what's sent to them, and act on complaints.

Finally, make it really easy to unsubscribe. Otherwise, your users will unsubscribe by pressing the spam button, and that will affect your reputation.

That said, getting Hotmail to accept your emails remains a black art.

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>