I had a hell of a time getting my v1 iPod touch to send mail through my Linux Postfix SMTP server with authentication…  for starters the iPod seems to be sending odd, invalid SMTP commands at first.

Dec 26 22:52:23 postfix/smtpd[20714]: match_list_match: $IP: no match
Dec 26 22:52:23 postfix/smtpd[20714]: auto_clnt_open: connected to private/anvil
Dec 26 22:52:23 postfix/smtpd[20714]: send attr request = connect
Dec 26 22:52:23 postfix/smtpd[20714]: send attr ident = smtp:$IP
Dec 26 22:52:23 postfix/smtpd[20714]: private/anvil: wanted attribute: status
Dec 26 22:52:23 postfix/smtpd[20714]: input attribute name: status
Dec 26 22:52:23 postfix/smtpd[20714]: input attribute value: 0
Dec 26 22:52:23 postfix/smtpd[20714]: private/anvil: wanted attribute: count
Dec 26 22:52:23 postfix/smtpd[20714]: input attribute name: count
Dec 26 22:52:23 postfix/smtpd[20714]: input attribute value: 2
Dec 26 22:52:23 postfix/smtpd[20714]: private/anvil: wanted attribute: rate
Dec 26 22:52:23 postfix/smtpd[20714]: input attribute name: rate
Dec 26 22:52:23 postfix/smtpd[20714]: input attribute value: 1
Dec 26 22:52:23 postfix/smtpd[20714]: private/anvil: wanted attribute: (list terminator)
Dec 26 22:52:23 postfix/smtpd[20714]: input attribute name: (end)
Dec 26 22:52:23 postfix/smtpd[20714]: > $HOSTNAME[$IP]: 220 $MYSERVER ESMTP Postfix
Dec 26 22:52:23 postfix/smtpd[20714]: watchdog_pat: 0x7f336bbae5c0
Dec 26 22:52:23 postfix/smtpd[20714]: < $HOSTNAME[$IP]: ???
Dec 26 22:52:23 postfix/smtpd[20714]: match_string: ??? ~? CONNECT
Dec 26 22:52:23 postfix/smtpd[20714]: match_string: ??? ~? GET
Dec 26 22:52:23 postfix/smtpd[20714]: match_string: ??? ~? POST
Dec 26 22:52:23 postfix/smtpd[20714]: match_list_match: ???: no match
Dec 26 22:52:23 postfix/smtpd[20714]: > $HOSTNAME[$IP]: 502 5.5.2 Error: command not recognized
Dec 26 22:52:23 postfix/smtpd[20714]: watchdog_pat: 0x7f336bbae5c0
Dec 26 22:52:23 postfix/smtpd[20714]: < $HOSTNAME[$IP]: ??A?Q??????~??x??  ?A??J%???^kd?????ha4?????'b^9?I[
Dec 26 22:52:23 postfix/smtpd[20714]: match_string: ??A?Q??????~??x?? ~? CONNECT
Dec 26 22:52:23 postfix/smtpd[20714]: match_string: ??A?Q??????~??x?? ~? GET
Dec 26 22:52:23 postfix/smtpd[20714]: match_string: ??A?Q??????~??x?? ~? POST
Dec 26 22:52:23 postfix/smtpd[20714]: match_list_match: ??A?Q??????~??x??: no match
Dec 26 22:52:23 postfix/smtpd[20714]: > $HOSTNAME[$IP]: 502 5.5.2 Error: command not recognized
Dec 26 22:52:23 postfix/smtpd[20714]: watchdog_pat: 0x7f336bbae5c0

What is this junk?  The only way I finally got the thing to work was to turn on

debug_peer_list

in my postfix config so I could see what was happening, remove & re-add my email account, then it went into it’s spinny “I’m doing something mode” and I watched the server debug messages (as above).  IMAP logged in fine, iPod tells me the cert isn’t signed by a known authority, many many more seconds of spinny-something, then the above crap gets sent to the server, eventually it connects properly and does STARTTLS, iPod complains about this certificate too, I say Continue again, and wait, and wait…

Eventually it did the right thing, and mail sends ok after that.

In a nutshell, then the trick seemed to be to keep the iPod awake while it was doing it’s spinny-doing-something-thing, and eventually it got hooked up.  No way that I know to look under the covers, though, to see what it’s doing.

Interestingly my wife’s v2 touch worked right off the bat.