Question:
I get the following error w/ smtp.office365.com when trying to send email:
SmtpConnect: SmtpHost: smtp.office365.com SmtpPort: 587 SmtpUsername: abc SmtpSsl: 0 StartTLS: 0 SmtpAuthMethod: LOGIN Need new SMTP connection checkForExistingConnection: Elapsed time: 0 millisec SMTP_Connect: Connecting to SMTP server smtp.office365.com:587 smtp_host: smtp.office365.com smtp_port: 587 smtp_user: abc auth-method: LOGIN ConnectTimeoutMs_1: 300000000 calling ConnectSocket2 IPV6 enabled connect with NO heartbeat. connectingTo: smtp.office365.com resolveHostname1: Resolving domain name (IPV4) via gethostbyname --resolveHostname1 GetHostByNameHB_ipv4: Elapsed time: 16 millisec connect successful (1) Turning on TCP_NODELAY. socketOptions: SO_SNDBUF: 8192 SO_RCVBUF: 8192 TCP_NODELAY: 1 --socketOptions socketConnect: Elapsed time: 78 millisec SmtpCmdResp: 220 DM2PR02CA006.outlook.office365.com Microsoft ESMTP MAIL Service ready at Tue, 11 Mar 2014 19:54:07 +0000 initialResponse: Elapsed time: 63 millisec ehloCommand: EHLO xyz SmtpCmdSent: EHLO xyz<crlf> sendEhlo: Elapsed time: 0 millisec SmtpCmdResp: 250-DM2PR02CA006.outlook.office365.com Hello [11.12.33.24] SmtpCmdResp: 250-SIZE 78643200 SmtpCmdResp: 250-PIPELINING SmtpCmdResp: 250-DSN SmtpCmdResp: 250-ENHANCEDSTATUSCODES SmtpCmdResp: 250-STARTTLS SmtpCmdResp: 250-8BITMIME SmtpCmdResp: 250-BINARYMIME SmtpCmdResp: 250 CHUNKING ehloResponse: 250-DM2PR02CA006.outlook.office365.com Hello [11.12.33.24] 250-SIZE 78643200 250-PIPELINING 250-DSN 250-ENHANCEDSTATUSCODES 250-STARTTLS 250-8BITMIME 250-BINARYMIME 250 CHUNKING smtpAuthMethod: LOGIN login_method: LOGIN auth_login_1: SmtpCmdSent: AUTH LOGIN<crlf> SmtpCmdResp: 504 5.7.4 Unrecognized authentication type 504 5.7.4 Unrecognized authentication type Failed to send AUTH LOGIN --auth_login_1 Failed to login using LOGIN method --SMTP_Connect checkOrMakeSmtpConnection: Elapsed time: 5382 millisec --SmtpConnect Failed. --SendEmail --ChilkatLog
The cause of the problem is that smtp.office365.com is not allowing the LOGIN authentication method over a non-secure connection. The LastErrorText reveals that no SSL/TLS is being used with this connection:
SmtpSsl: 0 StartTLS: 0We can also see that port 587 is being used, and this port is a typical alternative SMTP port that is customarily used w/ STARTTLS (which is explicit SSL/TLS).
The solution is to set the mailman.StartTLS property = true.