How to Debug POP

POP (Post Office Protocol) is the most used protocol for receiving mail from a server to a MUA (Mail User Agent) for reading. It is specified in RFC1939.

But the way it works (in most cases) is quite simple and doesn’t require reading the RFC, connect to port 110 (the standard port for POP3) and a basic session transcript is as follows (data sent by the client is prefixed with C: and data sent by the server is prefixed with S:):
S:+OK POP3 Ready [HOST NAME]
C:user ABC
S:+OK USER ABC set, mate
C:pass asecret
S:+OK Mailbox locked and ready
C:list
S:+OK scan listing follows
S:1 2989
S:.
C:quit
S:+OK

When the server successfully completes an operation it will precede it’s response with “+OK“, when it fails it will precede it’s response with “-ERR“. The data after the OK or ERR statement is for humans not machines, so in most cases your MUA will discard it. Therefore connecting to the service manually is required to properly debug problems. The unfortunate thing is that often on big mail servers it takes time for the sys-admin to do such tests. If the user can do it for them and give a bug report saying “your POP server said -ERR user unknown” then things will get fixed a lot faster than if the report is “the POP server didn’t work”.

One thing that is quite important is the initial greeting string, on any system of moderate size you will have multiple back-end servers and the greeting will tell you which server you are connecting to. If POP sometimes works and sometimes fails then your ISP might have one server failing so making a note of this greeting string in a transcript of a failed session can really help in tracking down problems.

When the list of messages is displayed, the first column is message numbers (starting at one and going up sequentially) and the second column is message sizes. If you have a POP session timing out and you have an extremely large message then that might be the cause.

A commonly used program for testing POP (and other Internet services) is telnet. So start the above process you would type telnet mail.example.com 110.

There are methods of hashing POP passwords (which make things a little more complex), but they often aren’t used – and in any case don’t encrypt the data. So it’s common to run POP servers with SSL, and the standard port for this is 995. This makes testing a little more complicated (but actually no more difficult).

To make an SSL connection you can use the program stunnel, it is included in many (most?) distributions of Linux, and Windows binaries are apparently at this link (NB I’ve never tested the Windows binaries as I don’t use Windows).

The command stunnel -c -r mail.example.com:995 will connect you to your mail server via SSL and you can then type in the POP commands as normal.

If your POP server supports the STLS command (which allows negotiation of TLS/SSL on port 110) then you can use the command stunnel -n pop3 -c -r mail.example.com:110.

To use gnutls, you can use the command “gnutls-cli mail.example.com -p 995” or to work with STLS on port 110 you use the command “gnutls-cli -s mail.example.com -p 110” and press ^D after entering the STLS command.