On Wed, 2014-01-08 at 09:44 -0800, Bobby Brewster wrote:
> --------------------------------------------
> On Tue, 1/7/14, dhanlin <mlgac...@yandex.com> wrote:
> 
>  Subject: Re: [tor-talk] Thunderbird and Tor - question/s.
>  To: tor-talk@lists.torproject.org
>  Date: Tuesday, January 7, 2014, 3:02 PM
>  
>  Bobby Brewster:
>  > I was experimenting using Tor and Thunderbird by
>  entering 127.0.0.1: 9150 in the TB Preferences.
>  > 
>  > I used my Gmail account and hence Gmail's SMTP server.
>  > 
>  > I checked the headers of the message I sent to Gmail
>  and the IP was a Tor exit node.
>  > 
>  > However, I am wondering whether using Tor and an e-mail
>  client is as safe as using webmail when using the TBB.
>  > 
>  > My point is that I don't know to what extent the
>  message is entirely encrypted.
>  > 
>  > For example, in a message send by Thunderbird there
>  exists in addition to the message body:
>  > to
>  > from
>  > date/time
>  > subject
>  > cc/bcc (perhaps)
>  > 
>  > To what extent is this so-called metadata also
>  encrypted?  This may be a stupid question for which the
>  answer is 'obvious' but I would like to know.
>  
>  >>Are you aware of TorBirdy?
>  
> Yes. I had looked at it before.  I was interested in knowing the answers to 
> the above question if one 'manually' configures TB and Tor as I mentioned 
> above.
> 
> Also, if one wants to send HTML enabled e-mail then you cannot do that with 
> TorBirdy.
> 
> So, hence, I would still like to know the answers to my original questions.  
> Thanks.

If you really want that you need to take advice more seriously. Mail
headers remain unencrypted after mail is sent regardless of client mail
software / webmail interface. Those things are completely unrelated and
also a little outside Tor's scope.

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