Mail service testing notes

Mail service testing notes

Last updated Wed Feb 9 15:06:54 EST 2005, to fix html formatting, not content

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Computer types
User types
What to check for that computer types

SMTP answers port 25, and offers STARTTLS and AUTH LOGIN and PLAIN

SMTP incoming mail is accepted

bb@pike> telnet eelpout 25
Trying 128.227.141.35...
Connected to eelpout.stat.ufl.edu.
Escape character is '^]'.
220 eelpout.stat.ufl.edu ESMTP Postfix
EHLO example.com
250-eelpout.stat.ufl.edu
250-PIPELINING
250-SIZE 10240000
250-VRFY
250-ETRN
250-STARTTLS
250-AUTH LOGIN PLAIN
250-AUTH=LOGIN PLAIN
250-XVERP
250 8BITMIME
MAIL FROM:<bb@stat.ufl.edu>
250 Ok
RCPT TO:<bb@stat.ufl.edu>
250 Ok
DATA
354 End data with <CR><LF>.<CR><LF>
From: bb@stat.ufl.edu
To: bb@stat.ufl.edu
Subject: Test

This is a test
.
250 Ok: queued as E27693F9A7
QUIT
221 Bye
Connection closed by foreign host.
bb@pike>

SMTP STARTTLS works

bb@herring$ openssl s_client -starttls smtp -connect eelpout:25
CONNECTED(00000003)
depth=0 /C=US/ST=Florida/L=Gainesville/O=University of Florida/OU=Department of Statistics/CN=eelpout.stat.ufl.edu/emailAddress=system@stat.ufl.edu
verify error:num=20:unable to get local issuer certificate
verify return:1
depth=0 /C=US/ST=Florida/L=Gainesville/O=University of Florida/OU=Department of Statistics/CN=eelpout.stat.ufl.edu/emailAddress=system@stat.ufl.edu
verify error:num=21:unable to verify the first certificate
verify return:1
---
Certificate chain
0 s:/C=US/ST=Florida/L=Gainesville/O=University of Florida/OU=Department of Statistics/CN=eelpout.stat.ufl.edu/emailAddress=system@stat.ufl.edu
i:/C=US/ST=Florida/L=Gainesville/O=University of Florida/OU=Department of Statistics/CN=eelpout.stat.ufl.edu/emailAddress=system@stat.ufl.edu
---
Server certificate
-----BEGIN CERTIFICATE-----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-----END CERTIFICATE-----
subject=/C=US/ST=Florida/L=Gainesville/O=University of Florida/OU=Department of Statistics/CN=eelpout.stat.ufl.edu/emailAddress=system@stat.ufl.edu
issuer=/C=US/ST=Florida/L=Gainesville/O=University of Florida/OU=Department of Statistics/CN=eelpout.stat.ufl.edu/emailAddress=system@stat.ufl.edu
---
No client certificate CA names sent
---
SSL handshake has read 1711 bytes and written 356 bytes
---
New, TLSv1/SSLv3, Cipher is DHE-RSA-AES256-SHA
Server public key is 1024 bit
SSL-Session:
Protocol : TLSv1
Cipher : DHE-RSA-AES256-SHA
Session-ID: 9B6A9E9447E10FA7C994AF6CB50407F51AC3936100263CDCE85A23B29D9E2176
Session-ID-ctx:
Master-Key: FDF1491A39D627EA8907F2D731ABFDD4A1D6FD70785A5D7F8BEE9BCF8228F3B27EB0852FFD1265F82D7F74BD950CCB9F
Key-Arg : None
Start Time: 1106240734
Timeout : 300 (sec)
Verify return code: 21 (unable to verify the first certificate)
---
220 eelpout.stat.ufl.edu ESMTP Postfix
EHLO example.com
250-eelpout.stat.ufl.edu
250-PIPELINING
250-SIZE 10240000
250-VRFY
250-ETRN
250-AUTH LOGIN PLAIN
250-AUTH=LOGIN PLAIN
250-XVERP
250 8BITMIME
QUIT
DONE
bb@herring$

SMTP answers on secure port, and offers AUTH LOGIN and PLAIN

bb@herring$ openssl s_client -connect eelpout:465
CONNECTED(00000003)
depth=0 /C=US/ST=Florida/L=Gainesville/O=University of Florida/OU=Department of Statistics/CN=eelpout.stat.ufl.edu/emailAddress=system@stat.ufl.edu
verify error:num=20:unable to get local issuer certificate
verify return:1
depth=0 /C=US/ST=Florida/L=Gainesville/O=University of Florida/OU=Department of Statistics/CN=eelpout.stat.ufl.edu/emailAddress=system@stat.ufl.edu
verify error:num=21:unable to verify the first certificate
verify return:1
---
Certificate chain
0 s:/C=US/ST=Florida/L=Gainesville/O=University of Florida/OU=Department of Statistics/CN=eelpout.stat.ufl.edu/emailAddress=system@stat.ufl.edu
i:/C=US/ST=Florida/L=Gainesville/O=University of Florida/OU=Department of Statistics/CN=eelpout.stat.ufl.edu/emailAddress=system@stat.ufl.edu
---
Server certificate
-----BEGIN CERTIFICATE-----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-----END CERTIFICATE-----
subject=/C=US/ST=Florida/L=Gainesville/O=University of Florida/OU=Department of Statistics/CN=eelpout.stat.ufl.edu/emailAddress=system@stat.ufl.edu
issuer=/C=US/ST=Florida/L=Gainesville/O=University of Florida/OU=Department of Statistics/CN=eelpout.stat.ufl.edu/emailAddress=system@stat.ufl.edu
---
No client certificate CA names sent
---
SSL handshake has read 1647 bytes and written 346 bytes
---
New, TLSv1/SSLv3, Cipher is DHE-RSA-AES256-SHA
Server public key is 1024 bit
SSL-Session:
Protocol : TLSv1
Cipher : DHE-RSA-AES256-SHA
Session-ID: 8F1C5FCAE2576E1B8FE9098469F67756894C421C06AEBDAF2F20254A488F45B9
Session-ID-ctx:
Master-Key: D3CDA575AB39ABC76A22A00B631F62F76CD56BD7EF28176CA09D60676476E289D9B00733A9AC15D92CDD390E30518F0B
Key-Arg : None
Start Time: 1106239212
Timeout : 300 (sec)
Verify return code: 21 (unable to verify the first certificate)
---
220 eelpout.stat.ufl.edu ESMTP Postfix
EHLO example.com
250-eelpout.stat.ufl.edu
250-PIPELINING
250-SIZE 10240000
250-VRFY
250-ETRN
250-AUTH LOGIN PLAIN
250-AUTH=LOGIN PLAIN
250-XVERP
250 8BITMIME
QUIT
DONE
bb@herring$

SMTP AUTH works

bb@herring$ printf 'bb\0bb\0mypassword' | mimencode
YmIAYmJcbXlwYXNzd29yZA==

bb@herring$ openssl s_client -connect eelpout:465
[...]
220 eelpout.stat.ufl.edu ESMTP Postfix
EHLO example.com
250-eelpout.stat.ufl.edu
250-PIPELINING
250-SIZE 10240000
250-VRFY
250-ETRN
250-AUTH LOGIN PLAIN
250-AUTH=LOGIN PLAIN
250-XVERP
250 8BITMIME
AUTH PLAIN YmIAYmJcbXlwYXNzd29yZA==
235 Authentication successful
QUIT
DONE
bb@herring$

POP does not answer

bb@pike> telnet eelpout 110
Trying 128.227.141.35...
telnet: Unable to connect to remote host: Connection refused
bb@pike>

IMAP does not answer on ordinary port

bb@pike> telnet eelpout 143
Trying 128.227.141.35...
telnet: Unable to connect to remote host: Connection refused
bb@pike>

IMAP answers on secure port, and allows login

bb@herring$ openssl s_client -connect eelpout:993
[...]
* OK dovecot ready.
1 login bb mypassword
1 OK Logged in.
1 logout
* BYE Logging out
1 OK Logout completed.
read:errno=0
bb@herring$