I'm configuring a Drobo on a Mac OS X 10.5 Leopard Server file server and am trying to configure email notifications. Unfortunately, when doing so, both our primary mail server and the local Mail service on the server throw a "502 5.5.2 Error: command not recognized" error when attempting to send the test message.
Both our primary mail server and the local Mail service on the file server are Mac OS X 10.5 Leopard Server and so are postfix-based. The primary mail server is set to allow relaying from the local network and the local Mail service is set to only allow relaying from 127.0.0.0/8 and it's IP address and to relay through our primary mail server. This has all worked well for years until now.
Drobo Dashboard's Email Settings cannot send through either the primary mail server or localhost without authentication without getting the aforementioned error, although all our other scripts on the server continue to send email normally.
I've set debug_peer_level = 3 & debug_peer_list = 127.0.0.1 in /etc/postfix/main.cf on the file server. When attempting to send the test message from Drobo Dashboard, I get the following debug info in /var/log/mail.log:
May 10 13:32:58 eeg postfix/smtpd[7320]: connect from localhost[127.0.0.1]
May 10 13:32:58 eeg postfix/smtpd[7320]: match_hostname: localhost ~? 127.0.0.0/8
May 10 13:32:58 eeg postfix/smtpd[7320]: match_hostaddr: 127.0.0.1 ~? 127.0.0.0/8
May 10 13:32:58 eeg postfix/smtpd[7320]: > localhost[127.0.0.1]: 220 host.domain.tld ESMTP Postfix
May 10 13:32:58 eeg postfix/smtpd[7320]: watchdog_pat: 0x109998
May 10 13:32:58 eeg postfix/smtpd[7320]: vstream_fflush_some: fd 9 flush 36
May 10 13:32:58 eeg postfix/smtpd[7320]: vstream_buf_get_ready: fd 9 got 23
May 10 13:32:58 eeg postfix/smtpd[7320]: < localhost[127.0.0.1]: EHLO host.domain.tld
May 10 13:32:58 eeg postfix/smtpd[7320]: > localhost[127.0.0.1]: 250-host.domain.tld
May 10 13:32:58 eeg postfix/smtpd[7320]: > localhost[127.0.0.1]: 250-PIPELINING
May 10 13:32:58 eeg postfix/smtpd[7320]: > localhost[127.0.0.1]: 250-SIZE
May 10 13:32:58 eeg postfix/smtpd[7320]: > localhost[127.0.0.1]: 250-VRFY
May 10 13:32:58 eeg postfix/smtpd[7320]: match_list_match: localhost: no match
May 10 13:32:58 eeg postfix/smtpd[7320]: match_list_match: 127.0.0.1: no match
May 10 13:32:58 eeg postfix/smtpd[7320]: > localhost[127.0.0.1]: 250-ETRN
May 10 13:32:58 eeg postfix/smtpd[7320]: > localhost[127.0.0.1]: 250-ENHANCEDSTATUSCODES
May 10 13:32:58 eeg postfix/smtpd[7320]: > localhost[127.0.0.1]: 250-8BITMIME
May 10 13:32:58 eeg postfix/smtpd[7320]: > localhost[127.0.0.1]: 250 DSN
May 10 13:32:58 eeg postfix/smtpd[7320]: watchdog_pat: 0x109998
May 10 13:32:58 eeg postfix/smtpd[7320]: vstream_fflush_some: fd 9 flush 116
May 10 13:32:58 eeg postfix/smtpd[7320]: vstream_buf_get_ready: fd 9 got 10
May 10 13:32:58 eeg postfix/smtpd[7320]: < localhost[127.0.0.1]: STARTTLS
May 10 13:32:58 eeg postfix/smtpd[7320]: > localhost[127.0.0.1]: 502 5.5.1 Error: command not implemented
May 10 13:32:58 eeg postfix/smtpd[7320]: watchdog_pat: 0x109998
May 10 13:32:58 eeg postfix/smtpd[7320]: vstream_fflush_some: fd 9 flush 42
Is it the 'STARTTLS' command that's not implemented? Any thoughts on why this fails on both our mail servers while other software doesn't have issues?
Yes, it's STARTTLS that the SMTP server is objecting to. The fact that it doesn't advertise STARTTLS in its response to the EHLO is a good indication that it doesn't support it.
This suggests that you need to tell the Drobo not to try using a SSL secured SMTP connection (but if you're not using authentication I wouldn't have thought you would be). If there's a "use ssl" tick box try unticking it.
Does sound like a broken SMTP client implementation (especially given the response from Drobo support).