(Sorry, "frontage" was a Swype typo. I meant "deliberate")

The intent of this proposal itself is to resist downgrades and *deliberate*
mis-routing of messages

/m

---
Mark Risher | Google | 650-253-3123
On Apr 4, 2016 11:03 AM, "Mark Risher" <[email protected]> wrote:

> >> Do you really think an end-user can understand what it means if the MTA
> will transport encrypt the next hop of mail relay but can say nothing about
> relay hops after that or how the mail is handled by either service
> provider? Perhaps I’m missing the motivation for doing this, can you
> explain why this is useful?
>
> The intent of this proposal itself is to resist downgrades and frontage
> mis-routing of messages. I agree users will not understand this, and any
> effort for communicating encryption status covering the entirety of the
> journey from user to user would require additional work beyond STS (such as
> DEEP, REQUIRETLS, and other proposals).
>
> >> I’ve seen few DNS additions deploy effectively, and I’ve seen a bunch
> of SMTP extensions deploy effectively.
>
> Can you share examples of each? We chose DNS over the new verb for ease of
> deployment; one example is the rates of adoption of SPF (which only
> requires DNS updates) versus DKIM.
>
> Thanks for the feedback. Looking forward to the face to face in a few
> hours,
> /m
>
> ---
> Mark Risher | Google | 650-253-3123
> On Apr 4, 2016 10:44 AM, "Chris Newman" <[email protected]> wrote:
>
>> On April 4, 2016 at 2:42:15 , Daniel Margolis ([email protected])
>> wrote:
>>
>> Thanks for the clarification.
>>
>> Sounds like a feature to me. Having MUAs do insecure DNS lookups (which
>>> is what they’d probably do) and make misleading assertions about relay
>>> security (which couldn’t be made even if DNSSEC/HTTPS was employed to trust
>>> the STS information, given that forwarding is in the infrastructure and all
>>> that). If you want to have MUAs make assertions, you’re moving in the
>>> direction of the SMTP extension draft, and as Victor pointed out, the
>>> infrastructure is going to ignore even those assertions under some
>>> circumstances if that were to deploy.
>>
>> I am (perhaps parochially) thinking mostly about webmail systems where
>> the MUA and the sending MTA are mostly the same piece of infrastructure. So
>> my real goal is for the MTA to be able to tell the MUA at compose time that
>> it has a policy for the recipient domain and can guarantee certain
>> behavior.
>>
>> Do you really think an end-user can understand what it means if the MTA
>> will transport encrypt the next hop of mail relay but can say nothing about
>> relay hops after that or how the mail is handled by either service
>> provider? Perhaps I’m missing the motivation for doing this, can you
>> explain why this is useful?
>>
>> In this context, I think having policies be per-domain is important, but
>> as you note, you could have a policy semantic which allows a single MX to
>> communicate a domain-wide policy even with an in-band channel.
>>
>> > Your suggestion, in that light, should be interpreted to say that
>>> > the STS URI should be used to only secure the routing information
>>> > (security for MX records via HTTPS rather than DNSSEC), and that
>>> > once the routing information is secured, security policy for the
>>> > given relay be in-band via SMTP and modeled on DEEP.
>>>
>>> Mostly yes. I’d also want to consider an optimization to skip the HTTPS
>>> step for self-hosted domains just to reduce overall new traffic.
>>
>>
>> To clarify a bit the individual steps needed, then, it seems like you're
>> proposing that given the following stages:
>>
>> 1. Routing information: What MX hostnames are expected
>> 2. Authenticating the MX: Determining that the server TLS cert matches
>> 3. Policy: Ensuring the minimum level of transport-layer encryption
>>
>> You propose to put #1 in either DNSSEC or HTTPS (with an optimization to
>> use in-channel in place of HTTPS if the MX domain matches the email domain)
>> and #2 and #3 in the SMTP exchange?
>>
>> Basically right.
>>
>> But this doesn't necessarily eliminate the extra DNS or HTTPS lookup (at
>> least in the case where the MX domain does not match the email domain),
>> right? You still need to get the routing information somehow, and we're
>> still trying to make this viable for domains that can't yet deploy DNSSEC.
>> So in that light, you're proposing that all domains would need at least the
>> SMTP in-band exchange and that some domains would also need step #1 to be
>> done over HTTPS--meaning that sending domains would have to still support
>> both options, right?
>>
>> Presuming there is WG rough consensus that use of HTTPS meets the
>> cost/benefit cutoff when compared to DNSSEC, then yes that is correct.
>>
>> I can see the appeal of doing much of this in-band given that it's
>> consistent with what DEEP proposes, but I'm still concerned that if we need
>> *also* support out-of-band, we're just increasing complexity. What do
>> you think?
>>
>> As long as the only out-of-band is verification of routing information
>> and not policy, then I don’t see it as increasing complexity. Indeed it’s a
>> somewhat more conservative approach to architectural cost (trying to
>> minimize use of extra packets and protocols when performing the core SMTP
>> relay operation).
>>
>> But I’ll admit I have some experiential bias in that I’ve seen few DNS
>> additions deploy effectively, and I’ve seen a bunch of SMTP extensions
>> deploy effectively.
>> - Chris
>>
>> On Mon, Apr 4, 2016 at 6:27 AM, Chris Newman <[email protected]>
>>  wrote:
>>
>>> On April 1, 2016 at 19:18:31 , Viktor Dukhovni ([email protected])
>>> wrote:
>>>
>>> On Fri, Apr 01, 2016 at 06:48:00PM -0300, Chris Newman wrote:
>>>
>>> > I feel very strongly that policy for SMTP relay should be advertised
>>> by
>>> > SMTP and protected by SMTP TLS. Doing anything else creates a much
>>> larger
>>> > attack surface on the policy information and is both more complex and
>>> less
>>> > secure. The preferred mechanism to sign SMTP relay routing (DNS MX) is
>>> > DNSSEC. I'm open to proposals for alternate mechanisms to sign MX
>>> record
>>> > information due to the difficulty of deploying DNSSEC, but such
>>> mechanisms
>>> > should not be confused with security policy.
>>>
>>> Unfortunately, in MTA-to-MTA SMTP, the receiving SMTP server has
>>> no idea what domain the sending SMTP client wants to deliver mail
>>> to at the time that it advertises its ESMTP extensions in the EHLO
>>> response.
>>>
>>> This correctly identifies a key difference between SMTP relay and SMTP
>>> submission. I had missed this, thank you for raising it!
>>>
>>> For SMTP submission, there’s an early-indication of domain ownership
>>> from the mandatory user authentication (multi-domain hosting services tend
>>> to use email address as user name to get this benefit). For SMTP relay we
>>> have no mechanism to indicate the intended domain so to handle the case of
>>> a multi-domain hosting service that offers different policies for different
>>> domains we’d need to add a way to communicate intended domain early. This
>>> can be done with an SMTP verb (adding a round trip) or by using TLS ALPN or
>>> something similar (no new round trip).
>>>
>>> For this (and other related) reasons, in-band SMTP security policy
>>> can only be communicated for the given SMTP server, and not the
>>> recipient domain.
>>>
>>> I’m not convinced this is true. I’d like to hear those other reasons.
>>>
>>> A relay MTA MUST NOT make any conclusions about recipient domain
>>> security based on security policy advertised by a particular MX
>>> host. An individual MX host cannot advertise security policy
>>> (implicitly) for every single domain it happens to receive mail
>>> for, except for future relaying via that *same* MX host.
>>>
>>> If the MX-from-DNS isn’t trusted, then no policy can be trusted. But
>>> STS-from-DNS has the same issue.
>>>
>>> To secure SMTP relay traffic to a recipient domain, the routing
>>> needs to be secured by some means. STS (with sensible modifications)
>>> proposes doing so via an HTTPS well-known URI associated with the
>>> recipient domain. This is achieved via DNS-based signalling of
>>> the existence of the STS well-known URI, and likely DNS-based
>>> signalling that a cached policy is stale and should be refreshed.
>>>
>>> Your suggestion, in that light, should be interpreted to say that
>>> the STS URI should be used to only secure the routing information
>>> (security for MX records via HTTPS rather than DNSSEC), and that
>>> once the routing information is secured, security policy for the
>>> given relay be in-band via SMTP and modeled on DEEP.
>>>
>>> Mostly yes. I’d also want to consider an optimization to skip the HTTPS
>>> step for self-hosted domains just to reduce overall new traffic.
>>>
>>> Note that consequently, a domain would be able to downgrade to a
>>> non-TLS provider, by serving a routing-only policy that references
>>> new MX hosts that don't support a new relay-MTA flavour of DEEP.
>>>
>>> We decide in the specification whether the policy attaches to the domain
>>> or the SMTP hostname. This is a design choice.
>>>
>>> Also, when a sending relay sees new MX RRs incompatible with a
>>> cached routing policy, it would be able to refresh that policy,
>>> (provided the well-known STS URI is still up and running) and
>>> deliver via the subset of MX hosts that match the refreshed policy.
>>>
>>> This all follows from a conclusion I don’t agree with.
>>>
>>> [ MX hosts that don't match the policy MUST NOT be ignored when
>>> doing relay loop elimination. They would have to be treated
>>> as though connections to them are failing, not as though they
>>> weren't part of the MX RRset. ]
>>>
>>> Once policy is latched for a domain, any SMTP relay not complying with
>>> the policy is a failure. We’ll want to make sure we get the 4xx vs. 5xx
>>> rules right in the spec for this.
>>>
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