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Groups > comp.mail.misc > #384 > unrolled thread

What linux clients do gmail:smtp TLS/SSL

Started byAvoid9Pdf@gmail.com
First post2013-02-07 18:31 +0000
Last post2013-02-09 15:14 +0000
Articles 13 — 7 participants

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Contents

  What linux clients do gmail:smtp TLS/SSL Avoid9Pdf@gmail.com - 2013-02-07 18:31 +0000
    Re: What linux clients do gmail:smtp TLS/SSL "David W. Hodgins" <dwhodgins@nomail.afraid.org> - 2013-02-07 14:59 -0500
      Re: What linux clients do gmail:smtp TLS/SSL Ivan Shmakov <oneingray@gmail.com> - 2013-02-08 09:48 +0000
        Re: What linux clients do gmail:smtp TLS/SSL Avoid9Pdf@gmail.com - 2013-02-08 13:42 +0000
          Re: What linux clients do gmail:smtp TLS/SSL Ivan Shmakov <oneingray@gmail.com> - 2013-02-08 21:32 +0000
          Re: What linux clients do gmail:smtp TLS/SSL Whiskers <catwheezel@operamail.com> - 2013-02-08 22:13 +0000
            Re: What linux clients do gmail:smtp TLS/SSL Ivan Shmakov <oneingray@gmail.com> - 2013-02-09 06:51 +0000
      Re: What linux clients do gmail:smtp TLS/SSL David Brown <david@westcontrol.removethisbit.com> - 2013-02-08 11:25 +0100
    Re: What linux clients do gmail:smtp TLS/SSL David Brown <david@westcontrol.removethisbit.com> - 2013-02-08 11:20 +0100
    Re: What linux clients do gmail:smtp TLS/SSL Whiskers <catwheezel@operamail.com> - 2013-02-08 21:54 +0000
      Re: What linux clients do gmail:smtp TLS/SSL Unknown <dog@gmail.com> - 2013-02-09 07:55 +0000
        TLS/SSL Ivan Shmakov <oneingray@gmail.com> - 2013-02-09 09:22 +0000
        Re: What linux clients do gmail:smtp TLS/SSL J G Miller <miller@yoyo.ORG> - 2013-02-09 15:14 +0000

#384 — What linux clients do gmail:smtp TLS/SSL

FromAvoid9Pdf@gmail.com
Date2013-02-07 18:31 +0000
SubjectWhat linux clients do gmail:smtp TLS/SSL
Message-ID<kf0rur$rij$1@dont-email.me>
smtp is rather simple, but what's all this TLS/SSL about ?

I really don't want to know about `sendmail` if it makes
such a drama about plain smtp.

It would be nice if the smtp-client was integrated with
a pop/imap client too.

http: gmail is becoming unbearable, even with `links`.

== TIA.

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#385

From"David W. Hodgins" <dwhodgins@nomail.afraid.org>
Date2013-02-07 14:59 -0500
Message-ID<op.wr5i5tbta3w0dxdave@hodgins.homeip.net>
In reply to#384
On Thu, 07 Feb 2013 13:31:57 -0500, <Avoid9Pdf@gmail.com> wrote:

> smtp is rather simple, but what's all this TLS/SSL about ?

smtps is an smtp session encrypted with an ssl key, similar
to https. Similar for pop3s

> http: gmail is becoming unbearable, even with `links`.

Gmail's implementation of imap is rather broken.  I use
a pop3 connection, to get/send email with my gmail account.

Login to the web interface, then go to the account settings,
and enable pop3/smtp.

I'm currently using opera for web browsing, usenet, and email.
Most email clients support pop3s and smtps.

For my gmail account ...
Incoming Servername=pop.gmail.com, port 995 (tls on)
Outgoing Servername=smtp.gmail.com, port 465 (tls on)

Regards, Dave Hodgins

-- 
Change nomail.afraid.org to ody.ca to reply by email.
(nomail.afraid.org has been set up specifically for
use in usenet. Feel free to use it yourself.)

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#386

FromIvan Shmakov <oneingray@gmail.com>
Date2013-02-08 09:48 +0000
Message-ID<877gmjcf05.fsf@violet.siamics.net>
In reply to#385
>>>>> David W Hodgins <dwhodgins@nomail.afraid.org> writes:
>>>>> On Thu, 07 Feb 2013 13:31:57 -0500, <Avoid9Pdf@gmail.com> wrote:

	[Cross-posting to news:comp.internet.services.google.]

	FWIW, I use Gnus/Emacs on my GNU/Linux system for both Usenet
	and email, including sending via Google Mail's :587 (RFC 6409.)
	My guess is that both Alpine and Mutt are capable of securely
	interfacing Google Mail, too.

 >> smtp is rather simple, but what's all this TLS/SSL about ?

 > smtps is an smtp session encrypted with an ssl key, similar to
 > https.  Similar for pop3s

	Not quite.  ESMTPS, as used by Google Mail's :587, begins just
	like a plain SMTP session, which then proceeds to EHLO (thus
	becoming ESMTP), and STARTTLS, which finally enables TLS/SSL.

	Consider, for instance, the following example session:

$ gnutls-cli --starttls --port=submission -- smtp.gmail.com 
|<1>| Note that the security level of the Diffie-Hellman key exchange has been lowered to 512 bits and this may allow decryption of the session data
Processed 152 CA certificate(s).
Resolving 'smtp.gmail.com'...
Connecting to '2a00:1450:4010:c04::6d:587'...

- Simple Client Mode:

220 mx.google.com ESMTP pz15sm16403877lab.3 - gsmtp
EHLO MX.EXAMPLE.NET 
250-mx.google.com at your service, [2XXX:XXXX:XXXX:XXXX:XXXX:XXXX:XXXX:XXXX]
250-SIZE 35882577
250-8BITMIME
250-STARTTLS
250 ENHANCEDSTATUSCODES
STARTTLS 
220 2.0.0 Ready to start TLS

	[There, one sends EOF (C-d) for gnutls-cli(1) to start TLS.]

*** Starting TLS handshake
- Peer's certificate is trusted
- The hostname in the certificate matches 'smtp.gmail.com'.
- Session ID: 28:0B:94:74:7F:4A:5D:B7:72:DA:C6:EA:50:63:B8:6B:B9:C7:F7:02:61:60:8B:0E:81:63:45:CE:24:31:9C:30
...

 >> http: gmail is becoming unbearable, even with `links`.

 > Gmail's implementation of imap is rather broken.

	Could you please elaborate on that?  I never had an issue with
	it (though I wasn't pushing IMAP to the extremes.)

 > I use a pop3 connection, to get/send email with my gmail account.

	Last time I've checked (which was probably c. 2002) POP3 had
	multiple issues, including that should the connection be lost
	during the session, there was no easy way /not/ to download the
	messages already received for a second time.  (Which was a major
	inconvenience for dial-up Internet users back in the day.)

	Ultimately, however, IMAP allows for rather comprehensive set of
	mailbox operations, to the point that one may even think of IMAP
	as of a generic "file transfer protocol."  Which, in particular,
	makes two-way synchronization possible.

[...]

-- 
FSF associate member #7257

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#389

FromAvoid9Pdf@gmail.com
Date2013-02-08 13:42 +0000
Message-ID<kf2vc6$jt8$1@dont-email.me>
In reply to#386
In article <877gmjcf05.fsf@violet.siamics.net>, Ivan Shmakov <oneingray@gmail.com> wrote: 

> >>>>> David W Hodgins <dwhodgins@nomail.afraid.org> writes:
> >>>>> On Thu, 07 Feb 2013 13:31:57 -0500, <Avoid9Pdf@gmail.com> wrote:
> 
> 	[Cross-posting to news:comp.internet.services.google.]
> 
Jees, I try to design a 'Subject' so that people can know what I'm
asking, but I forgot that many consider their monster-browser as
a smtp-client; which I supose it is.
OTOH I *did* write:
>  >> http: gmail is becoming unbearable, even with `links`.
...
> 	FWIW, I use Gnus/Emacs on my GNU/Linux system for both Usenet
> 	and email, including sending via Google Mail's :587 (RFC 6409.)
> 	My guess is that both Alpine and Mutt are capable of securely
> 	interfacing Google Mail, too.
> 
===snip from here, but file for reference: TLS-explanation & trace ===

> Resolving 'smtp.gmail.com'...
> Connecting to '2a00:1450:4010:c04::6d:587'...
> 
> - Simple Client Mode:
> 
> 220 mx.google.com ESMTP pz15sm16403877lab.3 - gsmtp
> EHLO MX.EXAMPLE.NET 
> 250-mx.google.com at your service, [2XXX:XXXX:XXXX:XXXX:XXXX:XXXX:XXXX:XXXX]
> 250-SIZE 35882577
> 250-8BITMIME
> 250-STARTTLS
> 250 ENHANCEDSTATUSCODES
> STARTTLS 
> 220 2.0.0 Ready to start TLS
> 
> 	[There, one sends EOF (C-d) for gnutls-cli(1) to start TLS.]  <--* ! OK !
> 
> *** Starting TLS handshake
> - Peer's certificate is trusted
> - The hostname in the certificate matches 'smtp.gmail.com'.
> - Session ID: 28:0B:94:74:7F:4A:5D:B7:72:DA:C6:EA:50:63:B8:6B:B9:C7:F7:02:61:60:8B:0E:81:63:45:CE:24:31:9C:30
> ....
> 
OK, that looks interesting.  Perhaps I'll try it. Previously I'd used gnus
for news. But probably gnus, passes the MTA job to sendmail,
and I don't want to SEE sendmail.

Every thing seems to have degenerated since the 90s.
My proper system: ETHOberon did:
1 klik to fetch the pop-dir [of articles at the ISP]
1 klik to select any dir-article & 1 klik to fetch it
1 klik to select a dir-article & 1 klik to delete it @ ISP
1 klik to select a dir-article & 1 klik to deleteALL following
1 klik to select a TextFrame-written-email & 1 klik to Send it

Later they introduced TxAuthenticate, so I extended it.
Yet later the ISP became unreliable and I switched gmail.
---------
Now I started up `mutt` again, which I had previously setup
for gmail.  But after I go off-line, I can't scroll through the dir.
I vaguely remember that it assumes you're on line all the time.
I.e. the amerikan dream of infinite-frontier and unlimited resources.
IIRC mutt needs sendmail setup, to reply. And `pine` would too.

How can you people tolerate this crap?
If I use [eg. links], to http:fetch the article-dir, I can only fetch 
ONE article from the article-dir, next time I go on-line.
Or do you open <a new page/screen> for each fetch and
keep the article-dir in its own page/screen?

Have you even noticed that the ratio of envelope to contents
of emails, has changed from 40:60  to 95:5 since the 90s?
All packaging and no contents.

How would I find if/where I've got TLS facilities ?
`man s_client` is good
`which s_client` is empty

== TIA.

 


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#390

FromIvan Shmakov <oneingray@gmail.com>
Date2013-02-08 21:32 +0000
Message-ID<87txpmbifo.fsf@violet.siamics.net>
In reply to#389
>>>>> Avoid9Pdf  <Avoid9Pdf@gmail.com> writes:

[...]

 > Previously I'd used gnus for news.  But probably gnus, passes the MTA
 > job to sendmail, and I don't want to SEE sendmail.

	Gnus (or, rather, its message.el part) is capable of passing
	outgoing mail to smtpmail.el, which is a stand-alone and
	ESMTP-capable Message Submission Agent (MSA.)

	Using either gnutls-cli(1) or openssl(1) as a helper, it's
	capable of ESMTPS, too.

	An example set up would be as follows:

--cut: ~/.emacs --
(setq smtpmail-auth-credentials "~/.smtpauthinfo"
      smtpmail-starttls-credentials '(("smtp.gmail.com" "587" nil nil))
      smtpmail-smtp-server  "smtp.gmail.com"
      smtpmail-smtp-service "25")
--cut: ~/.emacs --

--cut: ~/.smtpauthinfo --
machine smtp.gmail.com login YOUR-LOGIN-HERE
--cut: ~/.smtpauthinfo --

	I'd assume that by now, both Alpine and Mutt have gained an
	ability to interface ESMTPS message submission servers, too.

[...]

 > Have you even noticed that the ratio of envelope to contents of
 > emails, has changed from 40:60 to 95:5 since the 90s?  All packaging
 > and no contents.

	YMMV.

[...]

 > `man s_client` is good

 > `which s_client` is empty

	Try also $ man openssl and $ which openssl.

-- 
FSF associate member #7257

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#392

FromWhiskers <catwheezel@operamail.com>
Date2013-02-08 22:13 +0000
Message-ID<slrnkhau40.8mm.catwheezel@ID-107770.user.individual.net>
In reply to#389
On 2013-02-08, Avoid9Pdf@gmail.com <Avoid9Pdf@gmail.com> wrote:
> In article <877gmjcf05.fsf@violet.siamics.net>, Ivan Shmakov <oneingray@gmail.com> wrote: 
>
>> >>>>> David W Hodgins <dwhodgins@nomail.afraid.org> writes:
>> >>>>> On Thu, 07 Feb 2013 13:31:57 -0500, <Avoid9Pdf@gmail.com> wrote:
>> 
>> 	[Cross-posting to news:comp.internet.services.google.]

[...]

> ---------
> Now I started up `mutt` again, which I had previously setup
> for gmail.  But after I go off-line, I can't scroll through the dir.
> I vaguely remember that it assumes you're on line all the time.
> I.e. the amerikan dream of infinite-frontier and unlimited resources.
> IIRC mutt needs sendmail setup, to reply. And `pine` would too.

There are simpler smaller alternatives to "Sendmail"; "msmtp" seems to work
OK.  "Alpine" (the current version of Pine) is said to be simpler than
Mutt.

"OfflineIMAP" provides off-line facilities for IMAP.

> How can you people tolerate this crap?

I suspect very few of "us people" do; we use current Linux distros and
their package repositories to get sensible software to do what we want to
do.

> If I use [eg. links], to http:fetch the article-dir, I can only fetch 
> ONE article from the article-dir, next time I go on-line.
> Or do you open <a new page/screen> for each fetch and
> keep the article-dir in its own page/screen?

Using a text-only web browser to access the Google webmail pages?  I'm
surprised anything works at all!

> Have you even noticed that the ratio of envelope to contents
> of emails, has changed from 40:60  to 95:5 since the 90s?
> All packaging and no contents.

I think you must be looking at Google's webmail HTML etc, which is nothing
to do with POP IMAP or SMTP.

> How would I find if/where I've got TLS facilities ?
> `man s_client` is good
> `which s_client` is empty
>
> == TIA.

You don't know what software is available to you?  Ask your system
administrator!  (s_client seems to be rather old and cranky; "stunnel" is
pretty easy to use if your Mail User Agent or Mail Transfer Agent can't
handle TLS/SSL for itself).

-- 
-- ^^^^^^^^^^
--  Whiskers 
-- ~~~~~~~~~~

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#393

FromIvan Shmakov <oneingray@gmail.com>
Date2013-02-09 06:51 +0000
Message-ID<87pq0aaskk.fsf@violet.siamics.net>
In reply to#392
>>>>> Whiskers  <catwheezel@operamail.com> writes:
>>>>> On 2013-02-08, Avoid9Pdf@gmail.com <Avoid9Pdf@gmail.com> wrote:

[...]

 >> If I use [eg. links], to http:fetch the article-dir, I can only
 >> fetch ONE article from the article-dir, next time I go on-line.  Or
 >> do you open <a new page/screen> for each fetch and keep the
 >> article-dir in its own page/screen?

 > Using a text-only web browser to access the Google webmail pages?
 > I'm surprised anything works at all!

	FWIW, I use Lynx for the Google Mail's Web interface for years.

	As it seems, contrary to their plans for Google Groups, they
	aren't planning to drop support for the "minor" browsers there.

[...]

-- 
FSF associate member #7257

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#388

FromDavid Brown <david@westcontrol.removethisbit.com>
Date2013-02-08 11:25 +0100
Message-ID<v9OdnQvJ9_YBT4nMnZ2dnUVZ8oidnZ2d@lyse.net>
In reply to#385
On 07/02/13 20:59, David W. Hodgins wrote:
> On Thu, 07 Feb 2013 13:31:57 -0500, <Avoid9Pdf@gmail.com> wrote:
> 
>> smtp is rather simple, but what's all this TLS/SSL about ?
> 
> smtps is an smtp session encrypted with an ssl key, similar
> to https. Similar for pop3s
> 
>> http: gmail is becoming unbearable, even with `links`.
> 
> Gmail's implementation of imap is rather broken.  I use
> a pop3 connection, to get/send email with my gmail account.
> 

Most imap servers are "broken" - there are very few that actually
implement imap 4 without flaws.  And even if the server follows the
standard correctly, the clients often have issues.  So both servers and
clients usually have work-arounds in place.  To my knowledge, gmail is
less broken than Exchange server - I have no problem using it with
Thunderbird.

Pop3 is a terrible choice for most email accounts.  It can make sense
for some specialised uses, but for a normal account you should /always/
prefer imap - especially if you consider your emails at all valuable to
keep.

> Login to the web interface, then go to the account settings,
> and enable pop3/smtp.
> 
> I'm currently using opera for web browsing, usenet, and email.
> Most email clients support pop3s and smtps.
> 
> For my gmail account ...
> Incoming Servername=pop.gmail.com, port 995 (tls on)
> Outgoing Servername=smtp.gmail.com, port 465 (tls on)
> 
> Regards, Dave Hodgins
> 

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#387

FromDavid Brown <david@westcontrol.removethisbit.com>
Date2013-02-08 11:20 +0100
Message-ID<RaydnYCB_u3ITInMnZ2dnUVZ7oqdnZ2d@lyse.net>
In reply to#384
On 07/02/13 19:31, Avoid9Pdf@gmail.com wrote:
> smtp is rather simple, but what's all this TLS/SSL about ?
> 
> I really don't want to know about `sendmail` if it makes
> such a drama about plain smtp.
> 
> It would be nice if the smtp-client was integrated with
> a pop/imap client too.
> 
> http: gmail is becoming unbearable, even with `links`.
> 
> == TIA.
> 

I use imap and smtp over TSL/SSL to access my gmail account.  It works
fine with Thunderbird.

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#391

FromWhiskers <catwheezel@operamail.com>
Date2013-02-08 21:54 +0000
Message-ID<slrnkhat1d.8mm.catwheezel@ID-107770.user.individual.net>
In reply to#384
On 2013-02-07, Avoid9Pdf@gmail.com <Avoid9Pdf@gmail.com> wrote:
> smtp is rather simple, but what's all this TLS/SSL about ?

Encryption of all packets between the computers concerned, so that no-one
else can read your login details or messages.

> I really don't want to know about `sendmail` if it makes
> such a drama about plain smtp.
>
> It would be nice if the smtp-client was integrated with
> a pop/imap client too.
>
> http: gmail is becoming unbearable, even with `links`.
>
> == TIA.

I don't know of any graphical email user agents for Unix/Linux that can't
handle TLS/SSL and integrate IMAP POP SMTP and local "folders".  I use
Claws-Mail, but I don't use a gmail account so I can't comment on that.

Use "stunnel" if your preferred user agent can't handle TLS/SSL for itself.

"msmtp" is a small easily configured SMTP server, as an alternative to
"sendmail" for basic functions.

"Alpine" and "Mutt" are popular text-interface mail user agents. 

-- 
-- ^^^^^^^^^^
--  Whiskers 
-- ~~~~~~~~~~

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#394

FromUnknown <dog@gmail.com>
Date2013-02-09 07:55 +0000
Message-ID<kf4vd2$61r$1@dont-email.me>
In reply to#391
On Fri, 08 Feb 2013 21:54:53 +0000, Whiskers wrote:

> On 2013-02-07, Avoid9Pdf@gmail.com <Avoid9Pdf@gmail.com> wrote:
>> smtp is rather simple, but what's all this TLS/SSL about ?
> 
> Encryption of all packets between the computers concerned, so that
> no-one else can read your login details or messages.
> 
>> I really don't want to know about `sendmail` if it makes such a drama
>> about plain smtp.
>>
>> It would be nice if the smtp-client was integrated with a pop/imap
>> client too.
>>
>> http: gmail is becoming unbearable, even with `links`.
>>

> 
> Use "stunnel" if your preferred user agent can't handle TLS/SSL for
> itself.

--> stunnel -help == ....
OMG it's got a zillion options !!  
Why couldn't they just LEAVE the system as it was WORKING in the 90s ?!

> "msmtp" is a small easily configured SMTP server, as an alternative to
> "sendmail" for basic functions.
> 
-->  which msmtp == which: no msmtp in PATH

> "Alpine" and "Mutt" are popular text-interface mail user agents.
As previously stated `mutt` seems to need permanent-on-line to scroll
in the directory-of-headers. Plus that doesn't solve the TLS problem.


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#395 — TLS/SSL

FromIvan Shmakov <oneingray@gmail.com>
Date2013-02-09 09:22 +0000
SubjectTLS/SSL
Message-ID<87liaxc053.fsf_-_@violet.siamics.net>
In reply to#394
>>>>> Unknown  <dog@gmail.com> writes:

	[Cross-posting to news:comp.security.misc.]

[...]

 > --> stunnel -help == ....  OMG it's got a zillion options !!  Why
 > couldn't they just LEAVE the system as it was WORKING in the 90s ?!

	Because no one anymore believes that all the corporate network
	operators, all the ISP's, and all the transit network operators,
	would under no circumstances monitor and record one's network
	traffic, just in the case it would later be requested by the
	authorities (or by the company's own management)?

	And it wasn't the 90'ies, actually.  I saw a few students at a
	local university getting the passwords send unencrypted over the
	network as recently as in 2005.  (Quite an easy task, I'd say,
	given the availability of tcpdump(8), and the similar
	unfamiliarity with TLS/SSL of the university's staff.)

[...]

-- 
FSF associate member #7257

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#396

FromJ G Miller <miller@yoyo.ORG>
Date2013-02-09 15:14 +0000
Message-ID<kf5p4s$mf0$2@dont-email.me>
In reply to#394
On Saturday, February 9th, 2013, at 07:55:15h +0000,
the nym shifting Chris Glurr demanded:
 
> Why couldn't they just LEAVE the system as it was WORKING in the 90s ?!

Because that was so last millenium.  ;+)

And also so insecure.  The Internet is no longer the preserve
of the academic elite but is the hunting ground of highly
organised criminal gangs.

And get ready to patch your openSSL libraries.

<http://arstechnica.COM/security/2013/02/lucky-thirteen-attack-snarfs-cookies-protected-by-ssl-encryption/>

<http://www.isg.rhul.ac.UK/tls/>

<http://www.theregister.co.UK/2013/02/04/unlucky_13_crypto_attack/>

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