[c#] Gmail Error :The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.5.1 Authentication Required

I am using following code to send email. The Code works correctly in my local Machine. But on Production server i am getting the error message

var fromAddress = new MailAddress("[email protected]");
var fromPassword = "xxxxxx";
var toAddress = new MailAddress("[email protected]");

string subject = "subject";
string body = "body";

System.Net.Mail.SmtpClient smtp = new System.Net.Mail.SmtpClient
{
    Host = "smtp.gmail.com",
    Port = 587,
    EnableSsl = true,
    DeliveryMethod = System.Net.Mail.SmtpDeliveryMethod.Network,
    UseDefaultCredentials = false,
    Credentials = new NetworkCredential(fromAddress.Address, fromPassword)       
};

using (var message = new MailMessage(fromAddress, toAddress)
{
    Subject = subject,
    Body = body
})

smtp.Send(message);

And on my Gmail A/c I have received the following email after i ran the code from production server

Hi ,

Someone recently used your password to try to sign in to your Google Account [email protected]. This person was using an application such as an email, client or mobile device.

We prevented the sign-in attempt in case this was a hijacker trying to access your account. Please review the details of the sign-in attempt:

Friday, 3 January 2014 13:56:08 o'clock UTC IP Address: xxx.xx.xx.xxx (abcd.net.) Location: Philadelphia PA, Philadelphia, PA, USA

If you do not recognise this sign-in attempt, someone else might be trying to access your account. You should sign in to your account and reset your password immediately.

Reset password

If this was you and you are having trouble accessing your account, complete the troubleshooting steps listed at http://support.google.com/mail?p=client_login

Yours sincerely, The Google Accounts team

You might need to create/generate a specific APP password from gmail. you app or script will then use this new password instead of your regular password. Your regular password will still work fine for you.

That is what did it for me. I still used the same email account but had to generate a new app specific password.

https://support.google.com/accounts/answer/185833?hl=en

Basically you can do it here: https://security.google.com/settings/security/apppasswords

NOVEMBER 2018, have tried everything above with no success.

Below is the solution that worked finally. Unfortunately it's not using SSL, but it works!!!

var fromAddress = new MailAddress([email protected], "From Name");
var toAddress = new MailAddress("[email protected]", "To Name");

const string subject = "Subject";
const string body = "Body";

var smtp = new SmtpClient
{
    Host = "aspmx.l.google.com",
    Port = 25,
    EnableSsl = false
};
using (var message = new MailMessage(fromAddress, toAddress)
{
    Subject = subject,
    Body = body
})
{
    smtp.Send(message);
}

A comment from Tomasz Madeyski is what fixed my problem... he tells that exists a bug on SetDefaultCredential, him says:

"The issue is that in UseDefaultCredentials setter there is this code: this.transport.Credentials = value ? (ICredentialsByHost) CredentialCache.DefaultNetworkCredentials : (ICredentialsByHost) null; which overrides credentials set by Credentials setter. For me it looks like SmtpClient's bug"

if you put smtpClient.UseDefaultCredentials = false after set credentials... this line set to null those credentials...

You need to turn on "Allow less secure apps" from here https://myaccount.google.com/lesssecureapps

just turn on the setting of or gmail. see below given image:

Just follow the step in the google email and enable less secure apps.

I'm a google apps for business subscriber and I spend the last couple hours just dealing with this, even after having all the correct settings (smtp, port, enableSSL, etc). Here's what worked for me and the web sites that were throwing the 5.5.1 error when trying to send an email:

1. Login to your admin.google.com
2. Click SECURITY <-- if this isn't visible, then click 'MORE CONTROLS', and add it from the list
3. Click Basic Settings
4. Scroll to the bottom of the Basic Settings box, click the link: 'Go to settings for less secure apps'
5. Select the option #3 : Enforce access to less secure apps for all users (Not Recommended)
6. Press SAVE at the bottom of the window

After doing this my email forms from the website were working again. Good luck!

I have faced the same problem. It happens when you turn on 2 Step Verification (MFA). Just Turn off 2 Step Verification and your problem should be solved.

What worked for me was to activate the option for less secure apps (I am using VB.NET)

Public Shared Sub enviaDB(ByRef body As String, ByRef file_location As String)
        Dim mail As New MailMessage()
        Dim SmtpServer As New SmtpClient("smtp.gmail.com")
        mail.From = New MailAddress("[email protected]")
        mail.[To].Add("[email protected]")
        mail.Subject = "subject"
        mail.Body = body
        Dim attachment As System.Net.Mail.Attachment
        attachment = New System.Net.Mail.Attachment(file_location)
        mail.Attachments.Add(attachment)
        SmtpServer.Port = 587
        SmtpServer.Credentials = New System.Net.NetworkCredential("user", "password")
        SmtpServer.EnableSsl = True
        SmtpServer.Send(mail)
    End Sub

So log in to your account and then go to google.com/settings/security/lesssecureapps

I tried all of the suggestions found here, from enabling less secure apps, to trying port 587... nothing worked. Finally I just commented out the line UseDefaultCredentials = false. Everything worked if I didn't touch that boolean.

I have a previously-working code that throws this error now. No issue on password. No need to convert message to base64 either. Turns out, i need to do the following:

1. Turn off 2-factor authentication
2. Set "Allow less secure apps" to ON
3. Login to your gmail account from production server
4. Go here as well to approve the login activity
5. Run your app in production server

Working code

    public static void SendEmail(string emailTo, string subject, string body)
    {
        var client = new SmtpClient("smtp.gmail.com", 587)
        {
            Credentials = new NetworkCredential("[email protected]", "secretpassword"),
            EnableSsl = true
        };

        client.Send("[email protected]", emailTo, subject, body);
    }

Turning off 2-factor authentication

Set "Allow less secure apps" to ON (same page, need to scroll to bottom)

You should disallow less secure apps to access your google account.

to do:

https://myaccount.google.com/lesssecureapps

I had the same problem for an application deployed to Microsoft Azure.

SmtpException: The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.5.1 Authentication Required.

First I approved all unknown devices (some ip-addresses originating from Ireland) on the following page (signed in as the gmail user): https://security.google.com/settings/u/1/security/secureaccount

I used the following settings for the client:

var client = new SmtpClient("smtp.gmail.com");
client.Port = 587;
client.EnableSsl = true;
client.UseDefaultCredentials = false;
client.Credentials = new NetworkCredential("[email protected]", "my_password"); 

It started working only after I set the following property on the smtp-client:

client.TargetName = "STARTTLS/smtp.gmail.com";

First, I purchased the domain in GoDaddy, and when I clicked this link https://www.google.com/settings/security/lesssecureapps I didn't have the option, it show this message "The domain administrator manages these settings", so I go to the Admin Console https://admin.google.com/

There is this option

Then appears the option that I needed in

I used all of the above mentioned solutions but it finally worked only after i enabled IMAP Access from Gmail settings Link to Enable IMAP Access in gmail settings

Of course, the points in the other solutions were required too.

I have really looked at a lot of ideas, the only solution was this way (works with different email Providers):

            try
        {
            ViewProgressbar("Try to connect mail-server...", progressBar1.Value = 20);
            string host = dsProvider.Rows[y]["POP_hostOut"].ToString();
            int port = int.Parse(dsProvider.Rows[y]["POP_portOut"].ToString());  //587
            string[] email = von1.Split('@');
            string userName = (dsProvider.Rows[y]["login"].ToString() == "email[0]@email[1]")? email[0]+"@"+email[1] : email[0];
            string password = layer.getUserPassword(listSender.SelectedValue.ToString());
            SmtpClient client = new SmtpClient(host, port);
            client.DeliveryMethod = SmtpDeliveryMethod.Network;
            client.UseDefaultCredentials = false;
            //A idea from MSDN but it not works. You got "The server response was: 5.5.1 Authentication Required."
            //System.Net.NetworkCredential myCreds = new System.Net.NetworkCredential(userName, password, host);
            //System.Net.CredentialCache cache = new System.Net.CredentialCache();
            //cache.Add(host, port, "NTLM", myCreds);
            ///cache.GetCredential(host, port, "NTLM");   //NTLM
            client.Credentials = new System.Net.NetworkCredential(userName, password);
            client.Host = host;
            client.Port = port;
            client.EnableSsl = true;
            client.Send(message);
            ViewProgressbar();
        }
        catch (SmtpException ex)...

try changing the host, this is the new one, I got this configuring mozilla thunderbird

Host = "smtp.googlemail.com"

that work for me

Its a security issue, Gmail by default prevents access for your e-mail account from custom applications. You can set it up to accept the login from your application.

After Logging in to your e-mail, CLICK HERE

This will take you to the following page

When you try to send mail from code and you find the error "The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.5.1 Authentication Required", than the error might occur due to following cases.

case 1: when the password is wrong

case 2: when you try to login from some App

case 3: when you try to login from the domain other than your time zone/domain/computer (This is the case in most of scenarios when sending mail from code)

There is a solution for each

solution for case 1: Enter the correct password.

solution 1 for case 2: go to security settings at the followig link https://www.google.com/settings/security/lesssecureapps and enable less secure apps . So that you will be able to login from all apps.

solution 2 for case 2:(see https://stackoverflow.com/a/9572958/52277) enable two-factor authentication (aka two-step verification) , and then generate an application-specific password. Use that newly generated password to authenticate via SMTP.

solution 1 for case 3: (This might be helpful) you need to review the activity. but reviewing the activity will not be helpful due to latest security standards the link will not be useful. So try the below case.

solution 2 for case 3: If you have hosted your code somewhere on production server and if you have access to the production server, than take remote desktop connection to the production server and try to login once from the browser of the production server. This will add excpetioon for login to google and you will be allowed to login from code.

But what if you don't have access to the production server. try the solution 3

solution 3 for case 3: You have to enable login from other timezone / ip for your google account.

to do this follow the link https://g.co/allowaccess and allow access by clicking the continue button.

And that's it. Here you go. Now you will be able to login from any of the computer and by any means of app to your google account.

If your are using gmail.

• 1-logon to your account

  2- browse this link

  3- Allow less secure apps: ON

Enjoy....

Hi I had the same issue,

what I've done to solve it. is to turn on the less secure app. after connecting to my gmail account. I entered this link: https://www.google.com/settings/security/lesssecureapps

Then I turn on the secure app and, and the it worked. it has been said also above

Below is my code.I also had the same error but the problem was that i gave my password wrong.The below code will work perfectly..try it

            MailMessage mail = new MailMessage();
            SmtpClient SmtpServer = new SmtpClient("smtp.gmail.com");             
            mail.From = new MailAddress("[email protected]");
            mail.To.Add("[email protected]");
            mail.To.Add("[email protected]");
            mail.Subject = "Password Recovery ";
            mail.Body += " <html>";
            mail.Body += "<body>";
            mail.Body += "<table>";
            mail.Body += "<tr>";
            mail.Body += "<td>User Name : </td><td> HAi </td>";
            mail.Body += "</tr>";

            mail.Body += "<tr>";
            mail.Body += "<td>Password : </td><td>aaaaaaaaaa</td>";
            mail.Body += "</tr>";
            mail.Body += "</table>";
            mail.Body += "</body>";
            mail.Body += "</html>";
            mail.IsBodyHtml = true;
            SmtpServer.Port = 587;
            SmtpServer.Credentials = new System.Net.NetworkCredential("sendfrommailaddress.com", "password");
            SmtpServer.EnableSsl = true;
            SmtpServer.Send(mail);

You can refer it in my blog

dont put break-point before await smtp.SendMailAsync(mail);

:)

when it waits with a break point giving this error when i remove break point it has worked

After spending a couple of hours today trying every solution here, I was still unable to get past this exact error. I have used gmail many times in this way so I knew it was something dumb, but nothing I did fixed the problem. I finally stumbled across the solution in my case so thought I would share.

First, most of the answers above are also required, but in my case, it was a simple matter of ordering of the code while creating the SmtpClient class.

In this first code snippet below, notice where the Credentials = creds line is located. This implementation will generate the error referenced in this question even if you have everything else set up properly.

System.Net.Mail.SmtpClient client = new System.Net.Mail.SmtpClient
{
    Host = Emailer.Host,
    Port = Emailer.Port,
    Credentials = creds,
    EnableSsl = Emailer.RequireSSL,
    UseDefaultCredentials = false,
    DeliveryMethod = System.Net.Mail.SmtpDeliveryMethod.Network
}

However, if you move the Credentials setter call to the bottom, the email will be sent without error. I made no changes to the surrounding code...ie...the username/password, etc. Clearly, either the EnableSSL, UseDefaultCredentials, or the DeliveryMethod is dependent on the Credentials being set first... I didn't test all to figure out which one it was though.

System.Net.Mail.SmtpClient client = new System.Net.Mail.SmtpClient
{
    Host = Emailer.Host,
    Port = Emailer.Port,
    EnableSsl = Emailer.RequireSSL,
    UseDefaultCredentials = false,
    DeliveryMethod = System.Net.Mail.SmtpDeliveryMethod.Network,
    Credentials = creds
}

Hope this helps save someone else some headaches in the future.