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
>
> ------------------------------------------------------------------------
> On Mar 15, 2013 10:27 PM, jdow <[log in to unmask]> 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 [log in to unmask] \
>  >>> -S smtp-auth=login \
>  >>> -S ssl-verify=ignore \
>  >>> -S [log in to unmask] \
>  >>> -S smtp-auth-password=zzzzzz \
>  >>> -S smtp=smtp.zoho.com:465 \
>  >>> -s `dnsdomainname`" zoho smtp test subject" [log in to unmask]
>  >>>
>  >>>
>  >>> 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 [log in to unmask] \
>  >> -S smtp-auth-user=xxxx \
>  >> -S smtp-auth-password="hahahahaha" \
>  >> -S nss-config-dir=/home/linuxutil/mailcerts/ \
>  >> [log in to unmask]
>  >>
>  >>
>  >> 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:<[log in to unmask]>
250 Sender <[log in to unmask]> OK
 >>> RCPT TO:<[log in to unmask]>
250 Recipient <[log in to unmask]> OK
 >>> RCPT TO:<[log in to unmask]>
250 Recipient <[log in to unmask]> OK
 >>> DATA
354 Ok Send data ending with <CRLF>.<CRLF>
 >>> .
250 Message received
 >>> QUIT
221 mx.zohomail.com closing connection