CODEWITHSUNDEEP
phpsmtpphpmailertelnetsmtp-auth
chiliNUT
chiliNUT

Reputation: 19573

cannot connect to an smtp server over telnet error 504

I am getting a 504 error when trying to log in to my email server over telnet. I have tried ports 25 as well as 587. (Masking domains and ips with *s and xs).

>EHLO domain.com 
250-************.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-8BITMIME
250-BINARYMIME
250 CHUNKING
> HELP
214-This server supports the following commands:
214 HELO EHLO STARTTLS RCPT DATA RSET MAIL QUIT HELP AUTH BDAT
> AUTH
504 5.7.4 Unrecognized authentication type 
[*************.********.****.outlook.com]
> auth
504 5.7.4 Unrecognized authentication type 
[*************.********.****.outlook.com]
> AUTH LOGIN
504 5.7.4 Unrecognized authentication type 
[*************.********.****.outlook.com]
> auth login
504 5.7.4 Unrecognized authentication type 
[*************.********.****.outlook.com]

I can do it just fine using phpmailer though!:

        <?php
        $mail = new PHPMailer(true);
        $mail->IsSMTP();
        $mail->Host = $host;
        $mail->Port = 587;
        $mail->SMTPDebug = 2;
        $mail->SMTPSecure = "tls";
        $mail->SMTPAuth = true;
        $mail->Username = $user;
        $mail->Password = $password;
        $mail->SetFrom($user, "chiliNUT");
        $mail->Subject = $subject;
        $mail->MsgHTML($content);
        $mail->send();

And under the hood for auth it is doing:

public function Authenticate($username, $password) {
    // Start authentication
    fputs($this->smtp_conn,"AUTH LOGIN" . $this->CRLF);
    //...

How can I get this working on the command line?

Upvotes: 1

Views: 7194

Answers (1)

Synchro
Synchro

Reputation: 37810

It's because most sensible mail servers do not permit unencrypted AUTH - note that the capability list you receive from the server does not include AUTH - you need to call STARTTLS first, which PHPMailer does automatically. You can't easily do this manually with telnet - use openssl's s_client command to do it better. There's an example in the PHPMailer troubleshooting guide, something like:

openssl s_client -starttls smtp -connect smtp.outlook.office365.com:587

Upvotes: 2

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