Send SMTP email using System.Net.Mail via Exchange Online (Office 365)

Question

We are testing the new Office 365 beta, and i have a mail account on the Exchange Online service. Now I'm trying to connect a LOB application that can send smtp emails from my test account.

However the Exchange 365 platform requires TLS encryption on port 587, and there is a 'feature' of System.Net.Mail that does not permit Implicit SSL encryption.

Has anyone managed to get C# sending mails via this platform?

I have the following basic code that should send the mail - any advice would be appreciated.

SmtpClient server = new SmtpClient("ServerAddress");
server.Port = 587;
server.EnableSsl = true;
server.Credentials = new System.Net.NetworkCredential("[email protected]", "password");
server.Timeout = 5000;
server.UseDefaultCredentials = false;

MailMessage mail = new MailMessage();
mail.From = new MailAddress("recipent@anyaddress");
mail.To.Add("[email protected]");
mail.Subject = "test out message sending";
mail.Body = "this is my message body";
mail.IsBodyHtml = true;

server.Send(mail);

Solution 1

Fixed a few typos in the working code above:

MailMessage msg = new MailMessage();
msg.To.Add(new MailAddress("[email protected]", "SomeOne"));
msg.From = new MailAddress("[email protected]", "You");
msg.Subject = "This is a Test Mail";
msg.Body = "This is a test message using Exchange OnLine";
msg.IsBodyHtml = true;

SmtpClient client = new SmtpClient();
client.UseDefaultCredentials = false;
client.Credentials = new System.Net.NetworkCredential("your user name", "your password");
client.Port = 587; // You can use Port 25 if 587 is blocked (mine is!)
client.Host = "smtp.office365.com";
client.DeliveryMethod = SmtpDeliveryMethod.Network;
client.EnableSsl = true;
try
{
    client.Send(msg);
    lblText.Text = "Message Sent Succesfully";
}
catch (Exception ex)
{
    lblText.Text = ex.ToString();
}

I have two web applications using the above code and both work fine without any trouble.

Solution 2

In year of 2020, these code seems to return exception as

System.Net.Mail.SmtpStatusCode.MustIssueStartTlsFirst or The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM

This code is working for me.

            using (SmtpClient client = new SmtpClient()
            {
                Host = "smtp.office365.com",
                Port = 587,
                UseDefaultCredentials = false, // This require to be before setting Credentials property
                DeliveryMethod = SmtpDeliveryMethod.Network,
                Credentials = new NetworkCredential("[email protected]", "password"), // you must give a full email address for authentication 
                TargetName = "STARTTLS/smtp.office365.com", // Set to avoid MustIssueStartTlsFirst exception
                EnableSsl = true // Set to avoid secure connection exception
            })
            {

                MailMessage message = new MailMessage()
                {
                    From = new MailAddress("[email protected]"), // sender must be a full email address
                    Subject = subject,
                    IsBodyHtml = true,
                    Body = "<h1>Hello World</h1>",
                    BodyEncoding = System.Text.Encoding.UTF8,
                    SubjectEncoding = System.Text.Encoding.UTF8,

                };
                var toAddresses = recipients.Split(',');
                foreach (var to in toAddresses)
                {
                    message.To.Add(to.Trim());
                }

                try
                {
                    client.Send(message);
                }
                catch (Exception ex)
                {
                    Debug.WriteLine(ex.Message);
                }
            }

Solution 3

Quick answer: the FROM address must exactly match the account you are sending from, or you will get a error 5.7.1 Client does not have permissions to send as this sender.

My guess is that prevents email spoofing with your Office 365 account, otherwise you might be able to send as [email protected].

Another thing to try is in the authentication, fill in the third field with the domain, like

Dim smtpAuth = New System.Net.NetworkCredential(
    "TheDude", "hunter2password", "MicrosoftOffice365Domain.com")

If that doesn't work, double check that you can log into the account at: https://portal.microsoftonline.com

Yet another thing to note is your Antivirus solution may be blocking programmatic access to ports 25 and 587 as a anti-spamming solution. Norton and McAfee may silently block access to these ports. Only enabling Mail and Socket debugging will allow you to notice it (see below).

One last thing to note, the Send method is Asynchronous. If you call

Dispose

---

Detailed Answer: With Visual Studio (VB.NET or C# doesn't matter), I made a simple form with a button that created the Mail Message, similar to that above. Then I added this to the application.exe.config (in the bin/debug directory of my project). This enables the Output tab to have detailed debug info.

<?xml version="1.0" encoding="utf-8" ?>
<configuration>
    <system.diagnostics>
        <sources>
            <source name="System.Net">
                <listeners>
                    <add name="System.Net" />
                </listeners>
            </source>
            <source name="System.Net.Sockets">
                <listeners>
                    <add name="System.Net" />
                </listeners>
            </source>
        </sources>
        <switches>
            <add name="System.Net" value="Verbose" />
            <add name="System.Net.Sockets" value="Verbose" />
        </switches>
        <sharedListeners>
            <add name="System.Net"
              type="System.Diagnostics.TextWriterTraceListener"
              initializeData="System.Net.log"
            />
        </sharedListeners>
        <trace autoflush="true" />
    </system.diagnostics>
</configuration>

Solution 4

Office 365 use two servers, smtp server and protect extended sever.

First server is smtp.office365.com (property Host of smtp client) and second server is STARTTLS/smtp.office365.com (property TargetName of smtp client). Another thing is must put Usedefaultcredential =false before set networkcredentials.

    client.UseDefaultCredentials = False
    client.Credentials = New NetworkCredential("[email protected]", "Password")
    client.Host = "smtp.office365.com"
    client.EnableSsl = true
    client.TargetName = "STARTTLS/smtp.office365.com"
    client.Port = 587

    client.Send(mail)

Solution 5

Have you seen this? Sending email using Smtp.mail.microsoftonline.com

Setting the UseDefaultCredentials after setting the Credentials would be resetting your Credentials property.

View more solutions