Greetings Mr. Chappa and the rest of the alpine-info mailing list!!,

This is simply a follow up to a portion of a post I made quite some time ago. 
See further below for the full contents of that post, but I wanted to expand on 
this request with some new information:

> Another possible privacy related information leak can be found in the way 
> that Alpine can send your host in the SMTP EHLO or HELO greeting.
> Can another option you can use to change it be added to handle this problem?
> Or maybe Alpine can send a more generic host such as [192.168.1.1] with an 
> opt out option instead?

I would still love to see this become configurable in Alpine, but I wanted to 
point out another interesting approach Alpine could possibly take by default: 
to use a host it controls, like maybe setting up a new ehlo.alpineapp.email or 
similar subdomain?
This is an approach already used by Thunderbird, which sends 
ehlo.thunderbird.net, and FairEmail, which sends dummy.faircode.eu. Each of 
those hosts can actually be visited in a web browser to get more information on 
the privacy concerns behind their use.
***---> Perhaps Alpine can add a new option that offers three choices for what 
to send in the SMTP EHLO/HELO command: 1) choose the new default? behavior of 
sending an Alpine specific host, 2) choose the old default behavior of sending 
your real host, or 3) choose to enter a custom value?

In addition, I had not considered this item in my original SMTP privacy leak 
assessment:
> * Timezone: The sent date is usually encoded in the timezone of the sender. 
> By looking at the offset from the Greenwich Mean Time (GMT), the recipient 
> learns from which longitude a message was sent. In my opinion, mail clients 
> should always encode the Date field in Greenwich Mean Time.
Found here: 
https://explained-from-first-principles.com/email/#sender-towards-recipients - 
Email explained from first principles
Alpine does seem to have a "Suppress Timezone Comment When Sending" "[ Advanced 
User Preferences ]" option, but it only causes Alpine to strip out the 
parenthesized symbolic timezone comment from the mail it sends, in other words:
  Thu, 01 Jan 1970 12:00:00 +0000 (UTC) 
becomes:
  Thu, 01 Jan 1970 12:00:00 +0000
***---> Extra feature request: add a new option to Alpine to force it to use 
UTC time in all relevant headers to mitigate this privacy leak.


On 6/13/24 12:12, via Alpine-info wrote:

> Greetings alpine-info mailing list!!
> 
> Some time ago when Mr Chappa was adding oauth2 support for Alpine and had 
> been working on a privacy policy for it he made an interesting comment:
> > Date: Thu, 11 Jun 2020 14:05:59 -0600 (MDT)
> > From: Eduardo Chappa <[email protected]>
> > To: Andrew C Aitchison <[email protected]>
> > In-Reply-To: 
> > <[email protected]>
> > Message-ID: <alpine.LNX.2.22.439.2006111239040.9525@linux-aknz>
> > References: <[email protected]>
> > Cc: [email protected]
> > Subject: Re: [Alpine-info] Microsoft Outlook "Modern Authentication"
> >
> > - SNIPPED -
> > In addition, Alpine discloses its name and version to IMAP servers that 
> > support the ID extension. I put this in a separate category of privacy 
> > disclosure. I think this information is valuable for the server 
> > maintainers, because it establishes our presence (in other words, it tells 
> > the ownser of the server that there are users using Alpine, and so they 
> > need to support us.)
> > - SNIPPED -
> 
> Does Mr Chappa still maintain this position or would he reconsider and maybe 
> make this feature something that you can change or opt out of even disclosing 
> at all as there are practical benefits too.
> It can help work around buggy IMAP servers as seen here:
> https://support.mozilla.org/si/questions/1275339 - How do I fix "Unrecognized 
> command: ID" | Thunderbird Support Forum | Mozilla Support
> 
> Another possible privacy related information leak can be found in the way 
> that Alpine can send your host in the SMTP EHLO or HELO greeting.
> Can another option you can use to change it be added to handle this problem?
> Or maybe Alpine can send a more generic host such as [192.168.1.1] with an 
> opt out option instead?
> 
> These changes would help mitigate the last low hanging fruit privacy leaks in 
> Alpine that I am aware of?:
> - IMAP
> > Current mitigations:
> > 
> > ?
> > 
> > Todo: add Suppress IMAP ID When Connecting option ?
> 
> - NNTP
> > Current mitigations:
> > 
> > v2.26 added:
> >  *  To protect the privacy of a user, the message-id of a message will be 
> > generated using the domain in the From field of the message.
> > 
> > v2.24 added:
> >  *  Modifications to protect the privacy of users:
> >      +  Alpine uses the domain in the From: header of a message to generate 
> > a message-id and suppresses all information about Alpine, version, 
> > revision, and time of generation of the
> >         message-id from this header. This information is replaced by a 
> > random string.
> > 
> >   [ News Preferences ]
> >       [X]  Hide NNTP Path (NNTP)
> > 
> >   [ Advanced User Preferences ]
> >       [X]  Scramble the Message-ID When Sending (SMTP)
> >       [X]  Suppress User Agent When Sending (SMTP)
> > 
> > Todo: None ?
> 
> - POP3
> > Current mitigations:
> > 
> > ?
> > 
> > Todo: None ?
> 
> - SMTP
> > Current mitigations:
> > 
> > v2.26 added:
> >  *  To protect the privacy of a user, the message-id of a message will be 
> > generated using the domain in the From field of the message.
> > 
> > v2.24 added:
> >  *  Modifications to protect the privacy of users:
> >      +  Alpine uses the domain in the From: header of a message to generate 
> > a message-id and suppresses all information about Alpine, version, 
> > revision, and time of generation of the
> >         message-id from this header. This information is replaced by a 
> > random string.
> > 
> >   [ Sending Preferences ]
> >       [X]  Do Not Generate Sender Header (SMTP)
> > 
> >   [ Advanced User Preferences ]
> >       [X]  Scramble the Message-ID When Sending (SMTP)
> >       [X]  Suppress User Agent When Sending (SMTP)
> > 
> > Todo: add Change SMTP EHLO or HELO Greeting and or Use Generic SMTP EHLO or 
> > HELO Greeting option ?
> 
> 
> I became interested in seeing these issues fixed after reading this article 
> which also notes other possible issues:
> https://explained-from-first-principles.com/email/#sender-towards-recipients 
> - Email explained from first principles
> _______________________________________________
> Alpine-info mailing list
> [email protected]
> http://mailman12.u.washington.edu/mailman/listinfo/alpine-info
> 
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