Mailing List Archive

SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request]
Hello NANOG, Belated new year wishes.

I would like to gather some feedback from you all.

I'm trying to propose two things to the Internet Standard and it's related
to SMTP.

(1) STARTTLS downgrade protection in a dead simple way

(2) SMTPS (Implicit TLS) on a new port (26). This is totally optional.

I posted my proposal in IETF mailing list. I got very good feedback there.
Some support my proposal. Many are against it.

I would love to know where you stand on this proposal. Let me give you the
abstract first.

-----

SMTP is still suffering from downgrade attacks like STRIPTLS. While we have
"Opportunistic TLS", we still don't have "Implicit TLS" in the SMTP.

Don't take this in the wrong way. We do have "Implicit TLS" for "SMTP
Submission" on port 465. But we don't have a secure port 25 alternative.
i.e. The real SMTPS

Both MTA-STS and MTA-DANE tries to fix the STARTTLS downgrade issue.
However the implementation is not simple. The former requires a HTTPS
server and the latter requires DNSSEC to even get started.

This proposal fixes STARTTLS downgrade issue and propose a new port 26, an
"Implicit TLS" alternative for port 25 and recommends the MX server to
signal the port via a prefix.

This proposal offers two ways.

(1) STARTTLS Prefix

Use this prefix only to deal with STARTTLS downgrade issue.

e.g. mx1.example.com should be prefixed like starttls-mx1.example.com.

Where "starttls-" says "Our port 25 supports Opportunistic TLS. So if
STARTTLS command not found in the EHLO response or certificate is invalid,
then drop the connection".

(2) SMTPS Prefix

Use this prefix if you wanna support Implicit TLS on port 26 and
Opportunistic TLS on port 25.

e.g. mx1.example.com should be prefixed like smtps-mx1.example.com.

Where "smtps-" says "We prefer if you connect to our SMTPS in port 26. But
we also accept mails in port 25. And our port 25 supports Opportunistic
TLS. So if STARTTLS command not found in the EHLO response or certificate
is invalid, then drop the connection".

In "starttls-" prefix port 25 *MUST* support encryption with *valid SSL*
certificates.

In "smtps-" prefix, *BOTH* port 26 and port 25 *MUST* support encryption
with *valid SSL* certificates.

Note: You need to enable DNSSEC to prevent MX record spoofing. My proposal
highly recommends DNSSEC. Not mandates that.

-------

What IETF Mailing list thinks? - "Implicit TLS doesn't offer any additional
security than a downgrade protected STARTTLS. Let's not waste a port."

What I think? - Implicit TLS still fall under the "best practices". So it
will send out the positive vibe that IETF still cares about email security.

What the world thinks? -
https://gist.github.com/mistergiri/138fc46ae401b7492662a32409edb07f

What do you all think? -
https://medium.com/@dombox/smtp-over-tls-on-port-26-efc67e8a99ce

--
Best Regards,

Viruthagiri Thirumavalavan
Dombox, Inc.
Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request] [ In reply to ]
Having been through this many times, I'd say that probably the best way
to advocate for something is to advocate for what the *problem* is much
more than what the *solution* is. Invariably, things are more complex
than we imagine in the solution space and the people who inhabit that
space are more than happy to inform you of it.

Writing an I-D on what the problem is can be a very useful exercise to
rally support without putting on a bullseye on your back about a
solution. I will say that downgrade attacks are taken seriously by the
security geeks I know. But everything is messy, especially with
something as ancient as email so listening is a virtue too.

Which isn't so say that running code is bad -- it's one of the best
things about ietf -- but people have to understand why it's running at
all :)

Mike, one of the authors of rfc 4871

On 1/11/19 9:38 AM, Viruthagiri Thirumavalavan wrote:
> Hello NANOG, Belated new year wishes.
>
> I would like to gather some feedback from you all.
>
> I'm trying to propose two things to the Internet Standard and it's
> related to SMTP.
>
> (1) STARTTLS downgrade protection in a dead simple way
>
> (2) SMTPS (Implicit TLS) on a new port (26). This is totally optional.
>
> I posted my proposal in IETF mailing list. I got very good feedback
> there. Some support my proposal. Many are against it.
>
> I would love to know where you stand on this proposal. Let me give you
> the abstract first.
>
> -----
>
> SMTP is still suffering from downgrade attacks like STRIPTLS. While we
> have "Opportunistic TLS", we still don't have "Implicit TLS" in the SMTP.
>
> Don't take this in the wrong way. We do have "Implicit TLS" for "SMTP
> Submission" on port 465. But we don't have a secure port 25
> alternative. i.e. The real SMTPS
>
> Both MTA-STS and MTA-DANE tries to fix the STARTTLS downgrade issue.
> However the implementation is not simple. The former requires a HTTPS
> server and the latter requires DNSSEC to even get started.
>
> This proposal fixes STARTTLS downgrade issue and propose a new port
> 26, an "Implicit TLS" alternative for port 25 and recommends the MX
> server to signal the port via a prefix.
>
> This proposal offers two ways.
>
> (1) STARTTLS Prefix
>
> Use this prefix only to deal with STARTTLS downgrade issue.
>
> e.g. mx1.example.com <http://mx1.example.com> should be prefixed like
> starttls-mx1.example.com <http://starttls-mx1.example.com>.
>
> Where "starttls-" says "Our port 25 supports Opportunistic TLS. So if
> STARTTLS command not found in the EHLO response or certificate is
> invalid, then drop the connection".
>
> (2) SMTPS Prefix
>
> Use this prefix if you wanna support Implicit TLS on port 26 and
> Opportunistic TLS on port 25.
>
> e.g. mx1.example.com <http://mx1.example.com> should be prefixed like
> smtps-mx1.example.com <http://smtps-mx1.example.com>.
>
> Where "smtps-" says "We prefer if you connect to our SMTPS in port 26.
> But we also accept mails in port 25. And our port 25 supports
> Opportunistic TLS. So if STARTTLS command not found in the EHLO
> response or certificate is invalid, then drop the connection".
>
> In "starttls-" prefix port 25 *MUST* support encryption with *valid
> SSL* certificates.
>
> In "smtps-" prefix, *BOTH* port 26 and port 25 *MUST* support
> encryption with *valid SSL* certificates.
>
> Note: You need to enable DNSSEC to prevent MX record spoofing. My
> proposal highly recommends DNSSEC. Not mandates that.
>
> -------
>
> What IETF Mailing list thinks? - "Implicit TLS doesn't offer any
> additional security than a downgrade protected STARTTLS. Let's not
> waste a port."
>
> What I think? - Implicit TLS still fall under the "best practices". So
> it will send out the positive vibe that IETF still cares about email
> security.
>
> What the world thinks? -
> https://gist.github.com/mistergiri/138fc46ae401b7492662a32409edb07f
>
> What do you all think? -
> https://medium.com/@dombox/smtp-over-tls-on-port-26-efc67e8a99ce
>
> --
> Best Regards,
>
> Viruthagiri Thirumavalavan
> Dombox, Inc.
Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request] [ In reply to ]
On 1/11/19 10:38 AM, Viruthagiri Thirumavalavan wrote:
> Hello NANOG, Belated new year wishes.
>
> I would like to gather some feedback from you all.
>
> I'm trying to propose two things to the Internet Standard and it's
> related to SMTP.
>
> (1) STARTTLS downgrade protection in a dead simple way
>
> (2) SMTPS (Implicit TLS) on a new port (26). This is totally optional.
>
> I posted my proposal in IETF mailing list. I got very good feedback
> there. Some support my proposal. Many are against it.
>

What is the IETF draft name?
Which IETF mailing list did this discussion happen on?

--

Doug Royer - (http://DougRoyer.US http://goo.gl/yrxJTu )
DouglasRoyer@gmail.com
714-989-6135
Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request] [ In reply to ]
Hello Doug, it's happening in ietf-smtp. This is my first proposal. So
haven't created the I-D yet.

I'm not sure how to create one.

That's why I published my proposal in the medium. Please see the medium
link I posted earlier.

Thanks.

On Sat, Jan 12, 2019, 6:46 AM Doug Royer <douglasroyer@gmail.com wrote:

> On 1/11/19 10:38 AM, Viruthagiri Thirumavalavan wrote:
> > Hello NANOG, Belated new year wishes.
> >
> > I would like to gather some feedback from you all.
> >
> > I'm trying to propose two things to the Internet Standard and it's
> > related to SMTP.
> >
> > (1) STARTTLS downgrade protection in a dead simple way
> >
> > (2) SMTPS (Implicit TLS) on a new port (26). This is totally optional.
> >
> > I posted my proposal in IETF mailing list. I got very good feedback
> > there. Some support my proposal. Many are against it.
> >
>
> What is the IETF draft name?
> Which IETF mailing list did this discussion happen on?
>
> --
>
> Doug Royer - (http://DougRoyer.US http://goo.gl/yrxJTu )
> DouglasRoyer@gmail.com
> 714-989-6135
>
>
Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request] [ In reply to ]
On Fri, Jan 11, 2019 at 4:22 PM Viruthagiri Thirumavalavan
<giri@dombox.org> wrote:
> What IETF Mailing list thinks? - "Implicit TLS doesn't offer any additional security than a downgrade protected STARTTLS. Let's not waste a port."

In addition, it bypasses all the security folks have built around the
idea of blocking port 25 traffic from sources which should not be
operating as mail servers. Let's not make the network less secure in
the name of making it more so.

> e.g. mx1.example.com should be prefixed like smtps-mx1.example.com.

I'm not a fan over overloading semantic information in part of a
protocol where it doesn't belong, That's dug us in to a lot of deep
holes over the years. If you want to do this, seek a new DNS record
type or do like everybody else and create a TXT record to inform
internet peers of the availability of your new semantics for port 25.

Regards,
Bill Herrin

--
William Herrin ................ herrin@dirtside.com bill@herrin.us
Dirtside Systems ......... Web: <http://www.dirtside.com/>
Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request] [ In reply to ]
>
> In addition, it bypasses all the security folks have built around the
> idea of blocking port 25 traffic from sources which should not be
> operating as mail servers. Let's not make the network less secure in
> the name of making it more so.


I already addressed this issue in the "security considerations" section.

"Port 26 will be a secure alternative for Port 25. So Internet Service
Providers are adviced to take precautions to prevent email spam abuse. They
are advised to block port 26, if necessary."

I'm not a fan over overloading semantic information in part of a
> protocol where it doesn't belong, That's dug us in to a lot of deep
> holes over the years. If you want to do this, seek a new DNS record
> type or do like everybody else and create a TXT record to inform
> internet peers of the availability of your new semantics for port 25.


Yes, This suggestion came up on our discussions.

On Sat, Jan 12, 2019 at 7:11 AM William Herrin <bill@herrin.us> wrote:

> On Fri, Jan 11, 2019 at 4:22 PM Viruthagiri Thirumavalavan
> <giri@dombox.org> wrote:
> > What IETF Mailing list thinks? - "Implicit TLS doesn't offer any
> additional security than a downgrade protected STARTTLS. Let's not waste a
> port."
>
> In addition, it bypasses all the security folks have built around the
> idea of blocking port 25 traffic from sources which should not be
> operating as mail servers. Let's not make the network less secure in
> the name of making it more so.
>
> > e.g. mx1.example.com should be prefixed like smtps-mx1.example.com.
>
> I'm not a fan over overloading semantic information in part of a
> protocol where it doesn't belong, That's dug us in to a lot of deep
> holes over the years. If you want to do this, seek a new DNS record
> type or do like everybody else and create a TXT record to inform
> internet peers of the availability of your new semantics for port 25.
>
> Regards,
> Bill Herrin
>
> --
> William Herrin ................ herrin@dirtside.com bill@herrin.us
> Dirtside Systems ......... Web: <http://www.dirtside.com/>
>


--
Best Regards,

Viruthagiri Thirumavalavan
Dombox, Inc.
Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request] [ In reply to ]
On Fri, Jan 11, 2019 at 5:52 PM Viruthagiri Thirumavalavan
<giri@dombox.org> wrote:
>> In addition, it bypasses all the security folks have built around the
>> idea of blocking port 25 traffic from sources which should not be
>> operating as mail servers. Let's not make the network less secure in
>> the name of making it more so.
>
> I already addressed this issue in the "security considerations" section.
>
> "Port 26 will be a secure alternative for Port 25. So Internet Service Providers are adviced to take precautions to prevent email spam abuse. They are advised to block port 26, if necessary."

While we're at it, let's deprecate IPv4 now that IPv6 is fully deployed.

-Bill



--
William Herrin ................ herrin@dirtside.com bill@herrin.us
Dirtside Systems ......... Web: <http://www.dirtside.com/>
Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request] [ In reply to ]
>
> While we're at it, let's deprecate IPv4 now that IPv6 is fully deployed


Come on Mr. Herrin.

Blocking a port is much easier than deprecating a heavily used protocol.
Google stats show ~75% use IPv4.

On Sat, Jan 12, 2019 at 7:30 AM William Herrin <bill@herrin.us> wrote:

> On Fri, Jan 11, 2019 at 5:52 PM Viruthagiri Thirumavalavan
> <giri@dombox.org> wrote:
> >> In addition, it bypasses all the security folks have built around the
> >> idea of blocking port 25 traffic from sources which should not be
> >> operating as mail servers. Let's not make the network less secure in
> >> the name of making it more so.
> >
> > I already addressed this issue in the "security considerations" section.
> >
> > "Port 26 will be a secure alternative for Port 25. So Internet Service
> Providers are adviced to take precautions to prevent email spam abuse. They
> are advised to block port 26, if necessary."
>
> While we're at it, let's deprecate IPv4 now that IPv6 is fully deployed.
>
> -Bill
>
>
>
> --
> William Herrin ................ herrin@dirtside.com bill@herrin.us
> Dirtside Systems ......... Web: <http://www.dirtside.com/>
>


--
Best Regards,

Viruthagiri Thirumavalavan
Dombox, Inc.
Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request] [ In reply to ]
But why do you think creating an out of band verification channel and separate port is going to work for this?

There is plenty of local policy available as well to mandate that tls be negotiated with a set of allowed ciphers and prohibit others

?srs

________________________________
From: NANOG <nanog-bounces@nanog.org> on behalf of Viruthagiri Thirumavalavan <giri@dombox.org>
Sent: Saturday, January 12, 2019 7:43 AM
To: Doug Royer
Cc: nanog@nanog.org
Subject: Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request]

Hello Doug, it's happening in ietf-smtp. This is my first proposal. So haven't created the I-D yet.

I'm not sure how to create one.

That's why I published my proposal in the medium. Please see the medium link I posted earlier.

Thanks.

On Sat, Jan 12, 2019, 6:46 AM Doug Royer <douglasroyer@gmail.com<mailto:douglasroyer@gmail.com> wrote:
On 1/11/19 10:38 AM, Viruthagiri Thirumavalavan wrote:
> Hello NANOG, Belated new year wishes.
>
> I would like to gather some feedback from you all.
>
> I'm trying to propose two things to the Internet Standard and it's
> related to SMTP.
>
> (1) STARTTLS downgrade protection in a dead simple way
>
> (2) SMTPS (Implicit TLS) on a new port (26). This is totally optional.
>
> I posted my proposal in IETF mailing list. I got very good feedback
> there. Some support my proposal. Many are against it.
>

What is the IETF draft name?
Which IETF mailing list did this discussion happen on?

--

Doug Royer - (http://DougRoyer.US http://goo.gl/yrxJTu )
DouglasRoyer@gmail.com<mailto:DouglasRoyer@gmail.com>
714-989-6135
Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request] [ In reply to ]
On 1/11/19 10:38 AM, Viruthagiri Thirumavalavan wrote:
> Hello NANOG, Belated new year wishes.
>
> I would like to gather some feedback from you all.
>
> I'm trying to propose two things to the Internet Standard and it's
> related to SMTP.

Your post to this list was (according to the headers):
11 Jan 2019 23:08:21 +0530

Yet on the IETF-smtp mailing list at:
Wed, 9 Jan 2019 12:29:43 +0530

*You* wrote (in part):
I'm the guy who proposed SMTP Over TLS on Port 26. Looks like that was
dead end. So, now coming with another proposal.

Question: Why did you post something on NANOG that you already declared
to the IETF yourself as a "dead end" 2 days earlier? I read all of the
IETF emails on this idea. They explained why it is currently a
no-starter as proposed.

--

Doug Royer - (http://DougRoyer.US http://goo.gl/yrxJTu )
DouglasRoyer@gmail.com
714-989-6135
Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request] [ In reply to ]
On Fri, 11 Jan 2019 at 20:01, William Herrin <bill@herrin.us> wrote:
>
> On Fri, Jan 11, 2019 at 5:52 PM Viruthagiri Thirumavalavan
> <giri@dombox.org> wrote:
> >> In addition, it bypasses all the security folks have built around the
> >> idea of blocking port 25 traffic from sources which should not be
> >> operating as mail servers. Let's not make the network less secure in
> >> the name of making it more so.
> >
> > I already addressed this issue in the "security considerations" section.
> >
> > "Port 26 will be a secure alternative for Port 25. So Internet Service Providers are adviced to take precautions to prevent email spam abuse. They are advised to block port 26, if necessary."
>
> While we're at it, let's deprecate IPv4 now that IPv6 is fully deployed.

100% agree.

If mx1.example.com is prefixed like ip6-smtps-mx1.example.com, then
mail should only be deliverable to the domain if all of ports 25, 26
and 27 support TLS with <blink>valid SSL</blink> certificates over
<blink><blink><big><big><big>IPv6</big></big></big></blink></blink>.

Why? Because I think there's too much confusion between the same ports
working on both IPv4 and IPv6, and with Happy-Eyeballs, no certainty
which protocol would be used; resulting in downgrade-to-IPv4 attacks
in certain situations. For this reason, we should use port 27 in
order to guarantee that the connection will happen iff
(if-and-only-if) it can be established over IPv6, so that there's no
confusion. We can then use port 26 to send out reports of mail being
undeliverable over IPv6 with TLS, and port 25 to send out bounces of
bounces, which still has to support opportunistic StartTLS, in case we
still get TLS errors on port 26 trying to deliver the bounces over
IPv4 over TLS. Does this cover every possible scenario, or does
anyone think we gotta use a few more ports?

Hopefully, this'll teach folks like CogentCo to get their IPv6 peering
act together; especially if we get Google with Gmail and G Suite on
board, and Cogent will suddenly stop getting their mails from pretty
much all of their customers due to all the peering disputes with
pretty much the rest of the IPv6 internet.

I posted my proposal to the IPv6 zealots Slack channel. I got very
good feedback there. Many support my proposal. Some are against it.

C.
Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request] [ In reply to ]
On Fri, Jan 11, 2019 at 6:14 PM Viruthagiri Thirumavalavan
<giri@dombox.org> wrote:
>> While we're at it, let's deprecate IPv4 now that IPv6 is fully deployed
>
> Come on Mr. Herrin.

Hi Viruthagiri,

If you don't want to face the hyperbole then don't stick your head in
the sand. Unless you grossly underestimate the cost of operations
change, you propose to make the spam problem worse for some nontrivial
period of time. In exchange, you offer an explanation for how a new
port will succeed where starttls fails that frankly doesn't hold
water. Any scenario where starttls is disrupted is at least as
vulnerable to a new tcp port being blocked.

Your other idea of signaling via DNS that a man in the middle is
present if the target SMTP server fails to support encryption could
have merit. I think the specific mechanism (overloading the host name)
is unwise but I'd be interested to see the concept developed further.

Regards,
Bill Herrin

--
William Herrin ................ herrin@dirtside.com bill@herrin.us
Dirtside Systems ......... Web: <http://www.dirtside.com/>
Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request] [ In reply to ]
On 1/11/19 9:52 PM, William Herrin wrote:
> Your other idea of signaling via DNS that a man in the middle is
> present if the target SMTP server fails to support encryption could
> have merit. I think the specific mechanism (overloading the host name)
> is unwise but I'd be interested to see the concept developed further.

If there's one takeaway I have from this thread to date, it's this.

An advisory mechanism in DNS, such as via a TXT record, that says
something along the lines of "We always support STARTTLS - if you can't
negotiate that, then you are probably experiencing a MITM" could have
merit. DANE appears to already offer this (and more), but as has been
pointed out, can be complex to deploy.

The downside I potentially see to this is that, if someone can MITM DNS
(even if not the SMTP TCP session itself) and DNSSEC is not mandatory
for this mechanism, that attacker could potentially cause a DoS against
anyone they choose who does NOT support STARTTLS by falsely signaling
that it is to be expected. I'm not sure how real-world of a threat that
is given increasing adoption of STARTTLS, but it's definitely something
to consider.
--
Brandon Martin
Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request] [ In reply to ]
If you all think my prefix proposal have some merits, it still paves the
way for future smtps proposals. So I have no issues with killing smtps part
of my proposal.

As for signalling, I'm not sure whether moving the signalling part to
another record type is a good idea.

Because my signalling proposal is flawed without DNSSEC as Brandon Martin
pointed out.

So if we move the signalling part to another record type, then we may have
to deal with multiple record set signatures. Also there is one more
configuration for the end user. But i'm open for suggestions.

To the person who trolled me. I'm here to have some intellectual
conversation. So please stop trolling me. You are an engineer. So don't
behave like a teen in youtube comments section. I'm proposing these
stuffs, so the world can benefit something. By trolling me, you are just
killing that.

To everyone else, please go easy on me. If I'm little off on something,
please forgive my ignorance. The reason I'm here is because you all know
these stuffs better than me. I'm here to get some feedback.

If you all think opening a new port is waste of time, I'm ok with that. But
if you see some benefits on Implicit TLS over Opportunistic TLS, please
point that out too.

Thank you for your time.
Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request] [ In reply to ]
Most new MTA implementations over the past several years default to TLS with strong ciphers. So how much of a problem is low or no TLS right now?

How much more of a problem will it be over the next year or two as older hardware is retired and new servers + software deployed, or as is more likely, people move their mail to cloud services that already do support strong ciphers for TLS?

How worth solving is rhe problem - what is the return for all this effort?

--srs

________________________________
From: NANOG <nanog-bounces+ops.lists=gmail.com@nanog.org> on behalf of Viruthagiri Thirumavalavan <giri@dombox.org>
Sent: Saturday, January 12, 2019 9:21 AM
To: nanog@nanog.org
Subject: Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request]

If you all think my prefix proposal have some merits, it still paves the way for future smtps proposals. So I have no issues with killing smtps part of my proposal.

As for signalling, I'm not sure whether moving the signalling part to another record type is a good idea.

Because my signalling proposal is flawed without DNSSEC as Brandon Martin pointed out.

So if we move the signalling part to another record type, then we may have to deal with multiple record set signatures. Also there is one more configuration for the end user. But i'm open for suggestions.

To the person who trolled me. I'm here to have some intellectual conversation. So please stop trolling me. You are an engineer. So don't behave like a teen in youtube comments section. I'm proposing these stuffs, so the world can benefit something. By trolling me, you are just killing that.

To everyone else, please go easy on me. If I'm little off on something, please forgive my ignorance. The reason I'm here is because you all know these stuffs better than me. I'm here to get some feedback.

If you all think opening a new port is waste of time, I'm ok with that. But if you see some benefits on Implicit TLS over Opportunistic TLS, please point that out too.

Thank you for your time.
Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request] [ In reply to ]
Hello Mr. Ramasubramanian,

When I originally drafted the SMTPS proposal, I thought those plaint text
part before the STARTTLS command leaks some sensitive info.

e.g. 220 mail.ashleymadison.com AshleyMadison ESMTP Service Ready

Those text will always be transferred in plain text. So I thought Implicit
TLS would prevent leaking that info.

But guys in the IETF mailing list actually showed me a way to get that
info. You just get the IP address from 3 way handshake and do reverse
lookup / Connect to port 26 to fill the rest of the info. So a new port
doesn't offer much security. And I totally I agree with them on that from
my understanding of it.

But I still want the future of email to adopt Implicit TLS. So someday we
can kill Opportunistic TLS. I already lost the case for security. So my
smtps part of the proposal not gonna fly. I'm just here to learn whether
Implicit TLS can offer anything better than Opportunistic TLS that's worth
wasting a port.

Thanks

On Sat, Jan 12, 2019 at 9:28 AM Suresh Ramasubramanian <ops.lists@gmail.com>
wrote:

> Most new MTA implementations over the past several years default to TLS
> with strong ciphers. So how much of a problem is low or no TLS right now?
>
> How much more of a problem will it be over the next year or two as older
> hardware is retired and new servers + software deployed, or as is more
> likely, people move their mail to cloud services that already do support
> strong ciphers for TLS?
>
> How worth solving is rhe problem - what is the return for all this effort?
>
> --srs
>
> ------------------------------
> *From:* NANOG <nanog-bounces+ops.lists=gmail.com@nanog.org> on behalf of
> Viruthagiri Thirumavalavan <giri@dombox.org>
> *Sent:* Saturday, January 12, 2019 9:21 AM
> *To:* nanog@nanog.org
> *Subject:* Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback
> Request]
>
> If you all think my prefix proposal have some merits, it still paves the
> way for future smtps proposals. So I have no issues with killing smtps part
> of my proposal.
>
> As for signalling, I'm not sure whether moving the signalling part to
> another record type is a good idea.
>
> Because my signalling proposal is flawed without DNSSEC as Brandon Martin
> pointed out.
>
> So if we move the signalling part to another record type, then we may have
> to deal with multiple record set signatures. Also there is one more
> configuration for the end user. But i'm open for suggestions.
>
> To the person who trolled me. I'm here to have some intellectual
> conversation. So please stop trolling me. You are an engineer. So don't
> behave like a teen in youtube comments section. I'm proposing these
> stuffs, so the world can benefit something. By trolling me, you are just
> killing that.
>
> To everyone else, please go easy on me. If I'm little off on something,
> please forgive my ignorance. The reason I'm here is because you all know
> these stuffs better than me. I'm here to get some feedback.
>
> If you all think opening a new port is waste of time, I'm ok with that.
> But if you see some benefits on Implicit TLS over Opportunistic TLS, please
> point that out too.
>
> Thank you for your time.
>


--
Best Regards,

Viruthagiri Thirumavalavan
Dombox, Inc.
Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request] [ In reply to ]
On Fri, 11 Jan 2019 at 22:00, Suresh Ramasubramanian
<ops.lists@gmail.com> wrote:
> Most new MTA implementations over the past several years default to TLS with strong ciphers. So how much of a problem is low or no TLS right now?

The real problem is that opportunistic StartTLS stops being
opportunistic the minute you encounter a `STARTTLS` extension on
`EHLO`.

At that point and henceforth, TLS is pretty much 100% mandatory.

What happens if there are SSL negotiation failures? I'll tell you
what happens — the sender will receive a few bounces, X hours and Y
days after sending the mail; recipient doesn't receive anything at
all. (Unless, of course, one of the administrators would magically
decide to change the SSL options in the meantime to be compatible, or
to disable the "opportunistic" StartTLS to start with, before the
final bounce gets generated by the MTA of the sender.)

These problems are real. They're already happening today. StartTLS
being "opportunistic" is a pretty big scam.

C.
Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request] [ In reply to ]
Any place that has a TLS misconfig will pretty much notice it very quickly indeed

Opportunistic just means use TLS if it is advertised as available else continue encrypted. Not sure why encountering a starttls negates it.

To the OP - what's the point of hiding the hostname in the smtp banner? You already know from the dns. Concerned about the MTA version? You can configure postfix to claim it is exchange or avian carrier for that matter

--srs

________________________________
From: Constantine A. Murenin <mureninc@gmail.com>
Sent: Saturday, January 12, 2019 10:08 AM
To: Suresh Ramasubramanian
Cc: nanog@nanog.org
Subject: Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request]

On Fri, 11 Jan 2019 at 22:00, Suresh Ramasubramanian
<ops.lists@gmail.com> wrote:
> Most new MTA implementations over the past several years default to TLS with strong ciphers. So how much of a problem is low or no TLS right now?

The real problem is that opportunistic StartTLS stops being
opportunistic the minute you encounter a `STARTTLS` extension on
`EHLO`.

At that point and henceforth, TLS is pretty much 100% mandatory.

What happens if there are SSL negotiation failures? I'll tell you
what happens ? the sender will receive a few bounces, X hours and Y
days after sending the mail; recipient doesn't receive anything at
all. (Unless, of course, one of the administrators would magically
decide to change the SSL options in the meantime to be compatible, or
to disable the "opportunistic" StartTLS to start with, before the
final bounce gets generated by the MTA of the sender.)

These problems are real. They're already happening today. StartTLS
being "opportunistic" is a pretty big scam.

C.
Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request] [ In reply to ]
On Sat, 12 Jan 2019 09:45:12 +0530, Viruthagiri Thirumavalavan said:

> When I originally drafted the SMTPS proposal, I thought those plaint text
> part before the STARTTLS command leaks some sensitive info.

So - given that multiple people have explained to you on the ietf-smtp list
that there's no really sensitive info before STARTTLS, what *exactly* does
your proposal buy us? What *real* problem is port 26 fixing?

And is this something that *you* think is a problem, or that somebody who
runs an actual production mail system thinks is a problem?
Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request] [ In reply to ]
On Sat, 12 Jan 2019 09:45:12 +0530, Viruthagiri Thirumavalavan said:

> But I still want the future of email to adopt Implicit TLS. So someday we
> can kill Opportunistic TLS. I already lost the case for security. So my
> smtps part of the proposal not gonna fly. I'm just here to learn whether
> Implicit TLS can offer anything better than Opportunistic TLS that's worth
> wasting a port.

Well, the summary on the ietf-smtp list was that the new port doesn't actually
buy you anything unless you have DANE, and once you have DANE, the new port
doesn't add anything.

The conclusion is that we should be deploying DANE more rather than burning a
port.

Not sure why you expect to hear much differently from NANOG.
Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request] [ In reply to ]
> To the OP - what's the point of hiding the hostname in the smtp banner?
> You already know from the dns. Concerned about the MTA version? You can
> configure postfix to claim it is exchange or avian carrier for that matter


I was concerned about the Brand name right next to the 220 hostname example
I posted earlier. I thought it would offer little more privacy. I was wrong.

So - given that multiple people have explained to you on the ietf-smtp list
> that there's no really sensitive info before STARTTLS, what *exactly* does
> your proposal buy us? What *real* problem is port 26 fixing?
> And is this something that *you* think is a problem, or that somebody who
> runs an actual production mail system thinks is a problem?


Thanks Mr. Kletnieks,

Nice to meet you again. [.To everyone else - he is one of the nicest person
who provided suggestions in ietf-smtp]

When I proposed I thought this was an issue. But seem like it's not. What
I'm looking for here is will there be any additional pros if we introduce
Implicit TLS?

Pros of introducing Implicit TLS:
+ Falls under Best Practices
+ Sets an early date to deprecate Opportunistic TLS in the future. (e.g. 20
years from now)
+ Seems like it's what the world wants.

Cons of introducing Implicit TLS:
- Wastes a port
- ISP needs to add little code to block port 26

Well, the summary on the ietf-smtp list was that the new port doesn't
> actually
> buy you anything unless you have DANE, and once you have DANE, the new port
> doesn't add anything.
> The conclusion is that we should be deploying DANE more rather than
> burning a
> port.
> Not sure why you expect to hear much differently from NANOG.


I improved my proposal a lot based on feedback I received from people like
you. My proposal doesn't rely on DANE. Only DNSSEC. Even for that part, it
doesn't mandates that.

When example.com mails are third party hosted, example.com needs DNSSEC and
third party mail servers (e.g. Google) needs DNSSEC+DANE. But google seem
like it's not interested in DNSSEC. Thus Google provides a DANE alternative
called MTA-STS.

Let's say my domain supports DNSSEC. If my domain mails are hosted in
Google, then I have no other way other than going for MTA-STS.

MTA-STS needs another https server just for the sake of mail security.

My proposal just changes that. Google gonna name their MX servers with
starttls- prefix. And now example.com can protect MX record spoofing via
DNSSEC.

My point is, the signalling mechanism is handed over to third party mail
providers like Google in DANE. My solution embeds the signalling mechanism
in the hostname. Thus google don't have to evangelise MTA-STS to their
millions of customers.

Please correct me if I'm wrong with those statements

On Sat, Jan 12, 2019 at 10:36 AM <valdis.kletnieks@vt.edu> wrote:

> On Sat, 12 Jan 2019 09:45:12 +0530, Viruthagiri Thirumavalavan said:
>
> > But I still want the future of email to adopt Implicit TLS. So someday we
> > can kill Opportunistic TLS. I already lost the case for security. So my
> > smtps part of the proposal not gonna fly. I'm just here to learn whether
> > Implicit TLS can offer anything better than Opportunistic TLS that's
> worth
> > wasting a port.
>
> Well, the summary on the ietf-smtp list was that the new port doesn't
> actually
> buy you anything unless you have DANE, and once you have DANE, the new port
> doesn't add anything.
>
> The conclusion is that we should be deploying DANE more rather than
> burning a
> port.
>
> Not sure why you expect to hear much differently from NANOG.
>


--
Best Regards,

Viruthagiri Thirumavalavan
Dombox, Inc.
Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request] [ In reply to ]
On Fri, 11 Jan 2019 at 22:51, Suresh Ramasubramanian
<ops.lists@gmail.com> wrote:
> Any place that has a TLS misconfig will pretty much notice it very quickly indeed

I disagree.

Plenty of evidence that Microsoft/Hotmail doesn't notice / doesn't
care. Many people don't notice / don't care about Hotmail, either.

Gmail doesn't care either, because it'll be the small parties that'll
notice and would probably care.

> Opportunistic just means use TLS if it is advertised as available else continue encrypted. Not sure why encountering a starttls negates it.

I'm pretty certain it's only in the TLS world where "opportunistic"
means to use it even if it doesn't actually work, just because it's
advertised as (potentially) available.

C.

[…]
> --srs
>
> ________________________________
> From: Constantine A. Murenin <mureninc@gmail.com>
> Sent: Saturday, January 12, 2019 10:08 AM
> To: Suresh Ramasubramanian
> Cc: nanog@nanog.org
> Subject: Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request]
>
> On Fri, 11 Jan 2019 at 22:00, Suresh Ramasubramanian
> <ops.lists@gmail.com> wrote:
> > Most new MTA implementations over the past several years default to TLS with strong ciphers. So how much of a problem is low or no TLS right now?
>
> The real problem is that opportunistic StartTLS stops being
> opportunistic the minute you encounter a `STARTTLS` extension on
> `EHLO`.
>
> At that point and henceforth, TLS is pretty much 100% mandatory.
>
> What happens if there are SSL negotiation failures? I'll tell you
> what happens — the sender will receive a few bounces, X hours and Y
> days after sending the mail; recipient doesn't receive anything at
> all. (Unless, of course, one of the administrators would magically
> decide to change the SSL options in the meantime to be compatible, or
> to disable the "opportunistic" StartTLS to start with, before the
> final bounce gets generated by the MTA of the sender.)
>
> These problems are real. They're already happening today. StartTLS
> being "opportunistic" is a pretty big scam.
>
> C.
Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request] [ In reply to ]
12 Jan. 2019 ?., 8:44 Viruthagiri Thirumavalavan <giri@dombox.org>:
> Pros of introducing Implicit TLS:
> + Falls under Best Practices
> + Seems like it's what the world wants.

None of the above is really a technical argument within standards process.

The world wants emojis in domain names, so what?

> + Sets an early date to deprecate Opportunistic TLS in the future.

There's nothing bad in opportunistic TLS per se, and no reason to deprecate
it. The real problem is the (absent) downgrade resistance: SMTP in
cleartext is historically the default, and there's no tool to reliably
advertise to *everyone* on the Internet that your particular SMTP server is
not obsolete. Also, TOFU is similarly unreliable for that matter and too
opaque for troubleshooting.

None of the issues above are solved by adding yet another port to the
already overblown e-mail port bundle.

In fact, implicit TLS still has some advantages over the explicit version
(e.g. 0-RTT) that you've missed, but they are of questionable profit for
e-mail.

--
Töma
Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request] [ In reply to ]
Hi Töma,

Those are valid points.

Thanks for the input.

On Sat, Jan 12, 2019 at 4:02 PM Töma Gavrichenkov <ximaera@gmail.com> wrote:

> 12 Jan. 2019 ?., 8:44 Viruthagiri Thirumavalavan <giri@dombox.org>:
> > Pros of introducing Implicit TLS:
> > + Falls under Best Practices
> > + Seems like it's what the world wants.
>
> None of the above is really a technical argument within standards process.
>
> The world wants emojis in domain names, so what?
>
> > + Sets an early date to deprecate Opportunistic TLS in the future.
>
> There's nothing bad in opportunistic TLS per se, and no reason to
> deprecate it. The real problem is the (absent) downgrade resistance: SMTP
> in cleartext is historically the default, and there's no tool to reliably
> advertise to *everyone* on the Internet that your particular SMTP server is
> not obsolete. Also, TOFU is similarly unreliable for that matter and too
> opaque for troubleshooting.
>
> None of the issues above are solved by adding yet another port to the
> already overblown e-mail port bundle.
>
> In fact, implicit TLS still has some advantages over the explicit version
> (e.g. 0-RTT) that you've missed, but they are of questionable profit for
> e-mail.
>
> --
> Töma
>


--
Best Regards,

Viruthagiri Thirumavalavan
Dombox, Inc.
Re: SMTP Over TLS on Port 26 - Implicit TLS Proposal [Feedback Request] [ In reply to ]
On 1/11/19 9:38 AM, Viruthagiri Thirumavalavan wrote:
> Hello NANOG, Belated new year wishes.
>
> I would like to gather some feedback from you all.
>
> I'm trying to propose two things to the Internet Standard and it's
> related to SMTP.
>
> (1) STARTTLS downgrade protection in a dead simple way
>
> (2) SMTPS (Implicit TLS) on a new port (26). This is totally optional.


Why would anyone need this when you can just set an option in most (all
modern?) SMTP servers to refuse clear connections if you want to force
TLS at all times?

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