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
>>
>> ------------------------------------------------------------------------
>> 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
>

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

{^_^}