On 2013/03/15 20:39, Todd And Margo Chester wrote:
On 03/15/2013 08:05 PM, Paul Robert Marino wrote:
Well that depends.
If its clear text and you have the right flags set it will show you all
of the raw data.
Wireshark can in many cases decode it further.
However if it ssl/tls encrypted there is a tool much to most infosec
peoples dismay (and joy when its useful ) called ssldump that can take a
tcpdump that captures the full conversation and decode it.
But that answered is no not out of the box.



-- Sent from my HP Pre3

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On Mar 15, 2013 10:27 PM, jdow <j...@earthlink.net> wrote:

On 2013/03/15 19:14, Todd And Margo Chester wrote:
 >> On 03/15/2013 02:17 PM, Todd And Margo Chester wrote:
 >>> Hi All,
 >>>
 >>> The connection just times out. Does anyone know what I am
 >>> doing wrong here? This is Linux and the nail program.
 >>> (The account does work from Thunderbird.)
 >>>
 >>> #!/bin/bash
 >>> echo "nail test" | \
 >>> nail -v \
 >>> -S smtp-use-starttls \
 >>> -S from=taperepo...@xxxx.com \
 >>> -S smtp-auth=login \
 >>> -S ssl-verify=ignore \
 >>> -S smtp-auth-user=taperepo...@xxxx.com \
 >>> -S smtp-auth-password=zzzzzz \
 >>> -S smtp=smtp.zoho.com:465 \
 >>> -s `dnsdomainname`" zoho smtp test subject" y...@zoho.com
 >>>
 >>>
 >>> Many thanks,
 >>> -T
 >>
 >>
 >> Okay, I've have gotten a little further along. I am able to test
 >> with gmail but not yet with zoho:
 >>
 >> #!/bin/bash
 >> echo "nail test" | nail -v -s `dnsdomainname`" zoho smtp test
subject" \
 >> -S smtp-use-starttls \
 >> -S smtp-auth=plain \
 >> -S ssl-verify=ignore \
 >> -S smtp=smtps://smtp.zoho.com:465 \
 >> -S from=x...@zoho.com \
 >> -S smtp-auth-user=xxxx \
 >> -S smtp-auth-password="hahahahaha" \
 >> -S nss-config-dir=/home/linuxutil/mailcerts/ \
 >> yy...@zoho.com
 >>
 >>
 >> Gives me:
 >>
 >> 250 AUTH LOGIN PLAIN
 >>>>> STARTTLS
 >> 220 Ready to start TLS
 >> SSL/TLS handshake failed: Unknown error -5938.
 >>
 >> Anyone know what causes this?
 >>
 >> Many thanks,
 >> -T
 >
 >
 > Okay. I figured it out. I commented out "-S smtp-use-starttls".
 > Go figure.
 >
 > [editorial comment] AAAAAAAAAAAAAAHHHHHH!!!!!![/editorial comment]
 >
 > -T

Out of curiosity does tcpdump show the plain text login and message
transfer or is it encrypted?

{O.O}


Don't know.  Does this help?

# ./MailxTest.rla
Resolving host smtp.zoho.com . . . done.
Connecting to 74.201.154.90 . . . connected.
220 mx.zohomail.com SMTP Server ready March 15, 2013 8:34:27 PM PDT
 >>> EHLO server.aaaaaa.local
250-mx.zohomail.com Hello server.aaaaaaa.local
(static-50-124-80-106.drr01.grdv.nv.nv.frontiernet.net (50.124.80.106))
250-SIZE 25000000
250 AUTH LOGIN PLAIN
 >>> AUTH LOGIN
334 VXNlcm5hbWU6
 >>> YWNjb3VudGluZ0BhbHBpbmVmYXN0ZW5lci5jb20=
334 UGFzc3dvcmQ6
 >>> ZmNhOTMyRGNtYQ==
235 Authentication Successful
 >>> MAIL FROM:<account...@xxxx.com>
250 Sender <account...@xxxx.com> OK
 >>> RCPT TO:<a...@bbbb.com>
250 Recipient <a...@bbbb.com> OK
 >>> RCPT TO:<cc...@bbbb.net>
250 Recipient <cc...@bbbb.net> OK
 >>> DATA
354 Ok Send data ending with <CRLF>.<CRLF>
 >>> .
250 Message received
 >>> QUIT
221 mx.zohomail.com closing connection


tcpdump would show whether the transaction was in clear text or not. It
does appear there might be some encryption on the login, though.

{^_^}

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