Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-09-08 Thread Murray S. Kucherawy
On Fri, Sep 8, 2023 at 7:17 AM Jesse Thompson  wrote:

>
> Is rfc6651 a lost cause? It looks like it defines a reporting mechanism in
> control of the signer, as opposed to the attacker.
>
>
> Has anyone (else) implemented it?
>
>
> That's what I want to understand. Or, more specifically, if no one
> implemented it, why? And have those blockers changed due to the changed
> landscape with dkim replay, etc.
>

When DKIM was young, a mechanism like the one defined in RFC 6651 was
enormously valuable to me when two implementations were trying to debug
interoperability problems.  It allowed us to see why signatures were
failing.  Once all the bugs were worked out and things like
canonicalization and common MTA mutations were well understood, the need
for this sort of thing faded away.

Thus, I never heard of any implementations besides the first one.

-MSK
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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-09-08 Thread Jesse Thompson
On Thu, Sep 7, 2023, at 11:42 PM, Murray S. Kucherawy wrote:
> On Thu, Sep 7, 2023 at 9:38 PM Jesse Thompson  wrote:
>> __
>> Is rfc6651 a lost cause? It looks like it defines a reporting mechanism in 
>> control of the signer, as opposed to the attacker.
> 
> Has anyone (else) implemented it?

That's what I want to understand. Or, more specifically, if no one implemented 
it, why? And have those blockers changed due to the changed landscape with dkim 
replay, etc.

Jesse

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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-09-07 Thread Murray S. Kucherawy
On Thu, Sep 7, 2023 at 9:38 PM Jesse Thompson  wrote:

> Is rfc6651 a lost cause? It looks like it defines a reporting mechanism in
> control of the signer, as opposed to the attacker.
>

Has anyone (else) implemented it?

-MSK
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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-09-07 Thread Jesse Thompson


On Thu, Sep 7, 2023, at 12:02 PM, Dave Crocker wrote:
> On 9/2/2023 7:29 AM, Jesse Thompson wrote:
>> On Tue, Aug 29, 2023, at 9:02 PM, Dave Crocker wrote:
>>> DKIM, SPF, et al, are all 'collaborative' mechanisms.  Originators and 
>>> receivers opt in to use them.  Both sides are necessary.  So I'm wondering 
>>> about looking for something the furthers the collaboration.
>> 
>> The lack of reporting to the originating DKIM signers about Replay and other 
>> kinds of DKIM failure modes is an example of "limitations at the sending 
>> side [...] trying to detect". Alex and I are starting to draft a proposal 
>> for receivers to report to signers using rfc5965 and rfc7489 semantics.
> Since a Replay Attack has the act of replaying being done by an attacker, it 
> would not help to have a reporting mechanism for DKIM, because the attacker 
> would not use it.
> 
> If you are thinking of reporting by the later receiving platform, how would 
> this get used?
> 

Is rfc6651 a lost cause? It looks like it defines a reporting mechanism in 
control of the signer, as opposed to the attacker.

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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-09-07 Thread Murray S. Kucherawy
On Thu, Sep 7, 2023 at 3:15 PM Evan Burke  wrote:

> To be clear, for us x= was one of the most effective defenses against
> large-scale replay attacks. Not perfect, obviously, but applied carefully
> and in conjunction with header oversigning, it created a significantly
> narrower window for attacks, and reduced the potential financial return to
> attackers from replay spam.  I would note that the effectiveness of x= for
> reducing replay risk will likely vary considerably from signer to signer,
> depending on a number of factors; we may be better positioned than many
> signers in that respect.
>

So this is interesting, in the sense that:

(1) RFC 7489 warns against using "x=" for this purpose, so if that turns
out to have been the wrong advice and there's evidence to back that up,
then this is an opportunity for us to say so; and

(2) If such a combined (e.g., with oversigning) technique isn't terribly
IPR-encumbered, you're free to put forward a description of what you did as
a mitigation strategy, which this WG was hoping to produce; even if DKIM
itself isn't modified, this could be an Applicability Statement.

-MSK, participating
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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-09-07 Thread Brian Godiksen
On Sep 7, 2023, at 6:15 PM, Evan Burke 
 wrote:
On Thu, Sep 7, 2023 at 10:17 AM Murray S. Kucherawy 
mailto:superu...@gmail.com>> wrote:
On Thu, Sep 7, 2023 at 10:03 AM Dave Crocker 
mailto:d...@dcrocker.net>> wrote:

Keys cannot be rotated fast enough to be useful within the time frame that 
attackers work in.

Key rotation works in a timeframe of days or weeks.  Attackers work in the 
timeframe of minutes.

I think we disqualified use of "x=" as a mitigation on the same basis.

To be clear, for us x= was one of the most effective defenses against 
large-scale replay attacks. Not perfect, obviously, but applied carefully and 
in conjunction with header oversigning, it created a significantly narrower 
window for attacks, and reduced the potential financial return to attackers 
from replay spam.  I would note that the effectiveness of x= for reducing 
replay risk will likely vary considerably from signer to signer, depending on a 
number of factors; we may be better positioned than many signers in that 
respect.

+1 Signature expiration seemed to be a very helpful deterrent for us too. While 
a very limited dataset, the replay attacks that I’ve seen over the last few 
months mostly seem to focus on domains that don’t expire signatures.

Brian


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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-09-07 Thread Evan Burke
On Thu, Sep 7, 2023 at 10:17 AM Murray S. Kucherawy 
wrote:

> On Thu, Sep 7, 2023 at 10:03 AM Dave Crocker  wrote:
>
>> Keys cannot be rotated fast enough to be useful within the time frame
>> that attackers work in.
>>
>> Key rotation works in a timeframe of days or weeks.  Attackers work in
>> the timeframe of minutes.
>>
>
> I think we disqualified use of "x=" as a mitigation on the same basis.
>

To be clear, for us x= was one of the most effective defenses against
large-scale replay attacks. Not perfect, obviously, but applied carefully
and in conjunction with header oversigning, it created a significantly
narrower window for attacks, and reduced the potential financial return to
attackers from replay spam.  I would note that the effectiveness of x= for
reducing replay risk will likely vary considerably from signer to signer,
depending on a number of factors; we may be better positioned than many
signers in that respect.
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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-09-07 Thread Murray S. Kucherawy
On Thu, Sep 7, 2023 at 10:03 AM Dave Crocker  wrote:

>
> The "new header field" (or similar) approach alone would not open any
> doors for revocation/invalidation of the fact that the signature was
> applied on that first single message. Relying solely on fast key
> rotation/invalidation would mean TTLs would need to be very low to have any
> effect.
>
> Keys cannot be rotated fast enough to be useful within the time frame that
> attackers work in.
>
> Key rotation works in a timeframe of days or weeks.  Attackers work in the
> timeframe of minutes.
>

I think we disqualified use of "x=" as a mitigation on the same basis.

-MSK, participating
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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-09-07 Thread Dave Crocker

On 9/2/2023 7:29 AM, Jesse Thompson wrote:

On Tue, Aug 29, 2023, at 9:02 PM, Dave Crocker wrote:
DKIM, SPF, et al, are all 'collaborative' mechanisms.  Originators 
and receivers opt in to use them.  Both sides are necessary.  So I'm 
wondering about looking for something the furthers the collaboration.


The lack of reporting to the originating DKIM signers about Replay and 
other kinds of DKIM failure modes is an example of "limitations at the 
sending side [...] trying to detect". Alex and I are starting to draft 
a proposal for receivers to report to signers using rfc5965 and 
rfc7489 semantics.


Since a Replay Attack has the act of replaying being done by an 
attacker, it would not help to have a reporting mechanism for DKIM, 
because the attacker would not use it.


If you are thinking of reporting by the later receiving platform, how 
would this get used?



And the attacker can't bypass it, if the signature covers enough (or 
all) of the message.




The "new header field" (or similar) approach alone would not open any 
doors for revocation/invalidation of the fact that the signature was 
applied on that first single message. Relying solely on fast key 
rotation/invalidation would mean TTLs would need to be very low to 
have any effect.


Keys cannot be rotated fast enough to be useful within the time frame 
that attackers work in.


Key rotation works in a timeframe of days or weeks.  Attackers work in 
the timeframe of minutes.



d/


--

Dave Crocker
Brandenburg InternetWorking
bbiw.net
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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-09-02 Thread Jesse Thompson
On Tue, Aug 29, 2023, at 9:02 PM, Dave Crocker wrote:
> DKIM, SPF, et al, are all 'collaborative' mechanisms.  Originators and 
> receivers opt in to use them.  Both sides are necessary.  So I'm wondering 
> about looking for something the furthers the collaboration.

The lack of reporting to the originating DKIM signers about Replay and other 
kinds of DKIM failure modes is an example of "limitations at the sending side 
[...] trying to detect". Alex and I are starting to draft a proposal for 
receivers to report to signers using rfc5965 and rfc7489 semantics. 

Even with the best FBLs, it is too reactionary to prevent the "single message" 
from slipping through, not to mention all of the other scenarios discussed in 
this conversation. The originator has to make a boolean decision, based on 
limited and untimely information, about whether to send the message. So, we 
need a mechanism for receivers/evaluators to look up additional information 
about the context in which the message was originally signed (i.e. Ale's "Use 
segmented signature domains")

Does it make sense to address the evaluator-->signer and signer-->evaluator 
feedback problem in a unified document, or keep them separate?

I have thoughts that an out of band lookup mechanism (i.e. via signer-hosted 
DNS policy/intent records and signer-hosted DNSxL hash tables keyed on d= 
domains) is needed for evaluators to understand the meaning of the different d= 
subdomain signatures that a signer has applied to a message. 

> And the attacker can't bypass it, if the signature covers enough (or all) of 
> the message.
> 

The "new header field" (or similar) approach alone would not open any doors for 
revocation/invalidation of the fact that the signature was applied on that 
first single message. Relying solely on fast key rotation/invalidation would 
mean TTLs would need to be very low to have any effect. 

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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-09-01 Thread Laura Atkins


> On 1 Sep 2023, at 18:31, Grant Taylor 
>  wrote:
> 
> On 9/1/23 3:32 AM, Laura Atkins wrote:
>> You don’t know that they don’t do spamfiltering on outbound messages. You 
>> don’t see what they catch and don’t send. What you do see is when that spam 
>> filtering fails.
> 
> I do know that a small number of operators don't do any outbound spam 
> filtering because it has come up in conversations comparing systems / 
> configurations.

Are those operators being targeted with replay attacks? if they’re not, I don’t 
think this discussion is really relevant to the group. 

laura (participating) 



> 
>> Many ESPs are doing that, and doing blocklist checking on URLs.
> 
> I'm glad for the ESP's efforts.
> 
> I wish more people would do so.
> 
>> But all it takes is for one message to slip through and amplified.
> 
> I'm not talking about the false positives / false negatives.
> 
> I'm talking about the lack of any outbound filtering period.  Not what slips 
> through said filtering.
> 
>> I don’t understand how this is going to address the problem.
> 
> It won't solve the problem.  No single thing will solve the problem.
> 
> But it's another simple test that can be done between the MSA and the MTA to 
> reject things early in the flow.
> 
>> As Bron said: the inbound system has a lot more information about the mail 
>> than the outbound system.
> 
> Having more or less information doesn't have anything to do with acting on 
> the information that you do have, especially if it's verifiable and reliable.
> 
>> I’ll also point out that if it’s one-to-one or one-to-few there are 
>> legitimate reasons to send spam. Say, mail to an abuse address reporting 
>> spam. I’m sure we can agree that MTAs shouldn’t be blocking abuse reports, 
>> yes? What you’re asking for means a lot of spam reports will be blocked (or 
>> incomplete).
> 
> I'm trusting that's not a "but think of the children" knee jerk response 
> along the lines of "we can't filter outbound spam because we want to not 
> block spam reports."
> 
> There's reasonable basic filtering and then there's deep filtering.
> 
> I'm sure that we all know what we need to do t in order to get spam reports 
> through our respective systems.
> 
> 1)  Try forwarding spam as a message/rfc822 attachment.
> 2)  Try forwarding spam headers as a text/rfc822-headers attachment.
> 3)  Try putting #1 in a zip file.
> 4)  Try putting #2 in a zip file.
> 5)  Try password protecting #3.
> 6)  Try password protecting #4.
> ...
> n)  Ask your postmaster how you are supposed to report spam.
> 
> I maintain that basic spam and virus filtering should be done on outbound 
> email.
> 
>> You’re asserting there are no basic checks being done. Do you have any 
>> evidence other than sometimes mail evades the outbound filters?
> 
> I have had conversations with multiple small email operators over the years 
> that have told me that they only do any spam and virus filtering on inbound 
> email and that they do not do any such filtering on outbound email.
> 
> 
> 
> -- 
> Grant. . . .
> unix || die
> 
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The Delivery Expert

Laura Atkins
Word to the Wise
la...@wordtothewise.com

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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-09-01 Thread Grant Taylor

On 9/1/23 3:32 AM, Laura Atkins wrote:
You don’t know that they don’t do spamfiltering on outbound messages. 
You don’t see what they catch and don’t send. What you do see is when 
that spam filtering fails.


I do know that a small number of operators don't do any outbound spam 
filtering because it has come up in conversations comparing systems / 
configurations.



Many ESPs are doing that, and doing blocklist checking on URLs.


I'm glad for the ESP's efforts.

I wish more people would do so.


But all it takes is for one message to slip through and amplified.


I'm not talking about the false positives / false negatives.

I'm talking about the lack of any outbound filtering period.  Not what 
slips through said filtering.



I don’t understand how this is going to address the problem.


It won't solve the problem.  No single thing will solve the problem.

But it's another simple test that can be done between the MSA and the 
MTA to reject things early in the flow.


As Bron said: the inbound system has a lot more information about the 
mail than the outbound system.


Having more or less information doesn't have anything to do with acting 
on the information that you do have, especially if it's verifiable and 
reliable.


I’ll also point out that if it’s one-to-one or one-to-few there 
are legitimate reasons to send spam. Say, mail to an abuse address 
reporting spam. I’m sure we can agree that MTAs shouldn’t be 
blocking abuse reports, yes? What you’re asking for means a lot of 
spam reports will be blocked (or incomplete).


I'm trusting that's not a "but think of the children" knee jerk response 
along the lines of "we can't filter outbound spam because we want to not 
block spam reports."


There's reasonable basic filtering and then there's deep filtering.

I'm sure that we all know what we need to do t in order to get spam 
reports through our respective systems.


1)  Try forwarding spam as a message/rfc822 attachment.
2)  Try forwarding spam headers as a text/rfc822-headers attachment.
3)  Try putting #1 in a zip file.
4)  Try putting #2 in a zip file.
5)  Try password protecting #3.
6)  Try password protecting #4.
...
n)  Ask your postmaster how you are supposed to report spam.

I maintain that basic spam and virus filtering should be done on 
outbound email.


You’re asserting there are no basic checks being done. Do you have any 
evidence other than sometimes mail evades the outbound filters?


I have had conversations with multiple small email operators over the 
years that have told me that they only do any spam and virus filtering 
on inbound email and that they do not do any such filtering on outbound 
email.




--
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unix || die

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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-09-01 Thread Laura Atkins


> On 1 Sep 2023, at 03:49, Grant Taylor 
>  wrote:
> 
> On 8/31/23 8:02 PM, Bron Gondwana wrote:
>> The classic case was that spam about V*gra was very common, but blocking 
>> that word in every anti-spam filter would create something that was really 
>> not fit for purpose for Pfizer to use for their email system.  The sender 
>> and recipient really make a difference about what is spam - and as the 
>> sender you don't know who the end recipient is, because there are plenty of 
>> recipients.
> 
> I've seen -- what I consider to be -- too many systems -- read more than zero 
> -- that apply some amount of spam filtering to inbound message and no spam 
> filtering on outbound messages.

You don’t know that they don’t do spamfiltering on outbound messages. You don’t 
see what they catch and don’t send. What you do see is when that spam filtering 
fails.

> I've also seen many of these systems wonder why they ended up black listed 
> when an account was compromised and someone was sending spam through said 
> system.
> 
> I feel like there should be basic spam filtering on outbound messages. Even 
> if it's as simple as logistical checks; making sure the from makes sense, 
> probably running the message through something like a default configuration 
> of SpamAssassin (without Bayes), and probably through something like ClamAV.  
> Just basic sanity checking on messages.

Many ESPs are doing that, and doing blocklist checking on URLs. But all it 
takes is for one message to slip through and amplified. 

> Dare I say, I'd add SPF between the MSA and MTA.

I don’t understand how this is going to address the problem.

> Things to prevent blatant spam / viruses much closer to the -- likely to be 
> authenticated -- sender.
> 
> I'll say it this way, if there's a 90% chance that your inbound system would 
> block it, then why should your outbound system send it?

As Bron said: the inbound system has a lot more information about the mail than 
the outbound system. I’ll also point out that if it’s one-to-one or one-to-few 
there are legitimate reasons to send spam. Say, mail to an abuse address 
reporting spam. I’m sure we can agree that MTAs shouldn’t be blocking abuse 
reports, yes? What you’re asking for means a lot of spam reports will be 
blocked (or incomplete). 

>> Fact: recipient spam filter has more information than sender spam filter
>> Result: recipient spam filter can be more restrictive without causing excess 
>> damage.
> 
> Yes, there is different data.
> 
> But there is still data on the sending side that can be used to perform basic 
> checks.

You’re asserting there are no basic checks being done. Do you have any evidence 
other than sometimes mail evades the outbound filters?

>> There's no hypocrisy in recognising the asymmetry, and designing with that 
>> in mind.
> 
> I still think that it's hypocritical to have zero spam filtering on outbound 
> email while having any spam filtering on inbound email.

laura (participating) 

-- 
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Laura Atkins
Word to the Wise
la...@wordtothewise.com

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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-31 Thread Bron Gondwana
On Fri, Sep 1, 2023, at 12:49, Grant Taylor wrote:
> On 8/31/23 8:02 PM, Bron Gondwana wrote:
> > The classic case was that spam about V*gra was very common, but blocking 
> > that word in every anti-spam filter would create something that was 
> > really not fit for purpose for Pfizer to use for their email system.  
> > The sender and recipient really make a difference about what is spam - 
> > and as the sender you don't know who the end recipient is, because there 
> > are plenty of recipients.
> 
> I've seen -- what I consider to be -- too many systems -- read more than 
> zero -- that apply some amount of spam filtering to inbound message and 
> no spam filtering on outbound messages.
> 
> I've also seen many of these systems wonder why they ended up black 
> listed when an account was compromised and someone was sending spam 
> through said system.
> 
> I feel like there should be basic spam filtering on outbound messages. 
> Even if it's as simple as logistical checks; making sure the from makes 
> sense, probably running the message through something like a default 
> configuration of SpamAssassin (without Bayes), and probably through 
> something like ClamAV.  Just basic sanity checking on messages.
> 
> Dare I say, I'd add SPF between the MSA and MTA.
> 
> Things to prevent blatant spam / viruses much closer to the -- likely to 
> be authenticated -- sender.
> 
> I'll say it this way, if there's a 90% chance that your inbound system 
> would block it, then why should your outbound system send it?

We do all that, we still have messages go out sometimes that are unwanted by 
the recipient, side effect of having hundreds of thousands of users, some of 
which get their accounts stolen, even before you have to deal with the other 
problem, bad actors signing up.

So replay of a single one of them and there goes the domain reputation.  I've 
already posted in this thread examples of things that could be phishing or a 
legit business email, not enough detail for us to tell.

Bron.

--
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  br...@fastmailteam.com

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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-31 Thread Dave Crocker

On 8/31/2023 7:23 PM, Bron Gondwana wrote:
Now - there is a fact known to my system that's not known to yours (my 
signed-in identity, which isn't br...@fastmailteam.com, and may not 
appear at all other than an opaque header that other systems can't 
parse).  So that's a fair call, there's asymmetric information both ways.


To the extent it can help the receiver, a hashed version of the address 
might be useful without divulging too much ( though yes, I know that 
approach can be problematic.)


d/

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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-31 Thread Grant Taylor

On 8/31/23 8:02 PM, Bron Gondwana wrote:
The classic case was that spam about V*gra was very common, but blocking 
that word in every anti-spam filter would create something that was 
really not fit for purpose for Pfizer to use for their email system.  
The sender and recipient really make a difference about what is spam - 
and as the sender you don't know who the end recipient is, because there 
are plenty of recipients.


I've seen -- what I consider to be -- too many systems -- read more than 
zero -- that apply some amount of spam filtering to inbound message and 
no spam filtering on outbound messages.


I've also seen many of these systems wonder why they ended up black 
listed when an account was compromised and someone was sending spam 
through said system.


I feel like there should be basic spam filtering on outbound messages. 
Even if it's as simple as logistical checks; making sure the from makes 
sense, probably running the message through something like a default 
configuration of SpamAssassin (without Bayes), and probably through 
something like ClamAV.  Just basic sanity checking on messages.


Dare I say, I'd add SPF between the MSA and MTA.

Things to prevent blatant spam / viruses much closer to the -- likely to 
be authenticated -- sender.


I'll say it this way, if there's a 90% chance that your inbound system 
would block it, then why should your outbound system send it?



Fact: recipient spam filter has more information than sender spam filter
Result: recipient spam filter can be more restrictive without causing 
excess damage.


Yes, there is different data.

But there is still data on the sending side that can be used to perform 
basic checks.


There's no hypocrisy in recognising the asymmetry, and designing with 
that in mind.


I still think that it's hypocritical to have zero spam filtering on 
outbound email while having any spam filtering on inbound email.




--
Grant. . . .
unix || die

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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-31 Thread Bron Gondwana
On Fri, Sep 1, 2023, at 11:33, Stephen Farrell wrote:
> 
> Hi Bron,
> 
> On 01/09/2023 02:02, Bron Gondwana wrote:
> > Fact: recipient spam filter has more information than sender spam filter
> 
> I've no axe to grind here, but wondered - is there e.g. a
> peer-reviewed publication that conclusively demonstrates
> that?

Probably not, because it's blindingly obvious - as you can see from the raw 
copy of this very message when your read it.  Fastmail's outbound spam scanner 
doesn't know that you'll receive this message, since the recipient address is 
"ietf-dkim@ietf.org", and it doesn't know for sure that you're a member of that 
list.

> Not saying that that's necessary, but I wondered. Reason
> to ask is that I'm not sure I understand how to compare the
> sender's (filter's) information vs. the receiver's in a
> partial order.

As I see Dave has already replied - there's all the extra headers showing the 
path it took, and if there were any mailing lists or alias expansions along the 
way, the receiving system knows the actual recipient mailbox where this may be 
not known at all by the sending system.

Strictly - there's a fact that's known to your system and not to mine.

Now - there is a fact known to my system that's not known to yours (my 
signed-in identity, which isn't br...@fastmailteam.com, and may not appear at 
all other than an opaque header that other systems can't parse).  So that's a 
fair call, there's asymmetric information both ways.

But - spam is in the eyes of the recipient, and for sure your system will have 
more information about whether you might want an email than my system will.

Bron.

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  br...@fastmailteam.com

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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-31 Thread Dave Crocker

On 8/31/2023 6:02 PM, Bron Gondwana wrote:

Fact: recipient spam filter has more information than sender spam filter


The key bit, I think, is that more has happened, by the time of 
receiving.  Namely more copies sent through bots, etc.


Anyhow, the limitations at the sending side is why I am now wondering 
about the sending side providing more information to the receiver, 
rather than just trying to detect and stop on their own.


d/

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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-31 Thread Stephen Farrell


Hi Bron,

On 01/09/2023 02:02, Bron Gondwana wrote:

Fact: recipient spam filter has more information than sender spam filter


I've no axe to grind here, but wondered - is there e.g. a
peer-reviewed publication that conclusively demonstrates
that?

Not saying that that's necessary, but I wondered. Reason
to ask is that I'm not sure I understand how to compare the
sender's (filter's) information vs. the receiver's in a
partial order.

Ta,
S.


OpenPGP_0xE4D8E9F997A833DD.asc
Description: OpenPGP public key


OpenPGP_signature
Description: OpenPGP digital signature
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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-31 Thread Bron Gondwana
On Wed, Aug 30, 2023, at 12:38, Grant Taylor wrote:
> On 8/29/23 3:15 PM, Steve Atkins wrote:
> > Any attempt by senders to filter outbound emails based solely on 
> > content is going to have a lot of false negatives and positives, 
> > wherever you decide to draw the line.
> 
> I find the idea of using different, probably less stringent, filtering 
> on outbound than on inbound to be hypocritical.
> 
> I find it tantamount to someone saying they only accept the most 
> pristine message while sending less pristine, and sometimes really 
> tarnished, email.
> 
> Sure, there are some differences, e.g. lack of user preferences.
> 
> Why the asymmetry?
> 
> Why not apply the same filtering for outbound messages as applied to 
> inbound messages?

The classic case was that spam about V*gra was very common, but blocking that 
word in every anti-spam filter would create something that was really not fit 
for purpose for Pfizer to use for their email system.  The sender and recipient 
really make a difference about what is spam - and as the sender you don't know 
who the end recipient is, because there are plenty of recipients.

Fact: recipient spam filter has more information than sender spam filter
Result: recipient spam filter can be more restrictive without causing excess 
damage.

There's no hypocrisy in recognising the asymmetry, and designing with that in 
mind. 

Bron.

--
  Bron Gondwana, CEO, Fastmail Pty Ltd
  br...@fastmailteam.com

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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-30 Thread Alessandro Vesely

On Wed 30/Aug/2023 14:14:41 +0200 Dave Crocker wrote:

On 8/30/2023 1:21 AM, Alessandro Vesely wrote:

On Wed 30/Aug/2023 07:35:08 +0200 Murray S. Kucherawy wrote:

On Tue, Aug 29, 2023 at 8:11 PM Dave Crocker  wrote:

On 8/29/2023 7:46 PM, Grant Taylor wrote:

On 8/29/23 9:02 PM, Dave Crocker wrote:

Why not re-use the existing DKIM solution, just with a different domain / 
set of keys?


Because it does not provide the affirmative information that I am 
postulating/guessing the originating platform can supply.


I have to agree.  It's compelling to consider that a high-trust domain might 
flag something for my extra consideration.  This could be done per-message, 
rather than per-key, which was Grant's counterproposal; the equivalent is to 
generate a selector per message, which appears at least on the surface to 
suffer problems of scale.



The affirmative information can be provided by using semantic subdomain 
names, whose purpose and meaning has been registered. See the strawman here:

https://mailarchive.ietf.org/arch/msg/ietf-dkim/ez0PYqMdCDoR4-sN2toPGObMMFI


Except that there are no semantics to the domain naming components in DKIM, 
beyond the ones already defined.



That was defined in the strawman linked above, from last Friday.  Please have a 
look at it.



Best
Ale
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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-30 Thread Wei Chuang
On Wed, Aug 30, 2023 at 1:18 AM Laura Atkins 
wrote:

>
>
> On 29 Aug 2023, at 19:07, Dave Crocker  wrote:
>
> Not that this is all that new a question, but I think it might be worthy
> of more (and maybe different focus)...
>
> When a message is used in a DKIM Replay Attack:
>
>1. It originates from a domain name having good reputation
>2. It passes quality checks from that sending domain
>3. It goes to a collaborating receiving site, which presumably means
>that site is not conducting quality assessments
>4. It is re-posted, preserving the original DKIM signature, but now
>becomes an attack
>
> Two thoughts:
>
>1. If the substance of the message should fail a quality assessment,
>why does it pass at the outbound (sending) site?
>
> Spam isn’t really about substance, though, it’s about being unwanted and
> volume. A lot of things outbound folks use to identify spam require volume
> - like ‘is this audience similar to the audience we’ve seen report high
> levels of spam in the past’ or ‘does this send to addresses we know receive
> a lot of spam’ or ‘is this account sending to a lot of bad addresses’.
> There are other checks, like ‘does this email contain a link pointing to a
> hostname on any of these DNSBLs’ - but that’s trivially solved by just
> pulling out a link that isn’t on a DNSBL. The professional spam gangs, who
> are likely behind the attacks, have a deep bench of domains that they pull
> in and out of circulation on a regular basis.
>
> This also doesn’t address the problem that Google mentioned where they saw
> Youtube alerts / welcome messages replayed, possibly as a way to create a
> good IP reputation.
>

+1 to the points above, especially about professional spam gangs that have
the resources to bypass the outbound spam protections.

>
>1. If the problem is reasonable content, but sent to many unintended
>(or, rather, undeclared) recipients, then the only characteristic of note
>is the fact of multiple transmissions.  So I'd guess it is only a real-time
>network of receivers, working in /very/ close coordination, to detect and
>deal with the attack. (it's not difficult to imagine scattered
>retransmissions, over time, to hide the coordination.  Sort of a spread
>spectrum transmission style...)
>
> My understanding is that one of the primary ways to ID a replay is using
> Google postmaster tools and seeing increases in their graphs without a
> corresponding increase in volume from their systems.
>

+1.  Also getting at Dave's point about creating meaningful signals out of
the replay spam amplification, yes, the magnitude and shape might be
helpful.  The Yahoo signature counting certainly represents using
magnitude as a signal and presumably in their distributed system they have
some framework that effectively evaluates these thresholds.  But a caveat,
at a certain threshold, large mailing-lists broadcasts are going to look
similar to spam attacks.  A different tack is the notion of getting
spammers to declare and sign their recipients (DARA).  If they do, then it
provides a forwarding identity to associate with the amplified traffic
pattern.  And if they don't, then block that traffic.

-Wei

laura
>
> --
> The Delivery Expert
>
> Laura Atkins
> Word to the Wise
> la...@wordtothewise.com
>
> Delivery hints and commentary: http://wordtothewise.com/blog
>
>
>
>
>
>
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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-30 Thread Mark Alley

On 8/30/2023 9:58 AM, Laura Atkins wrote:




On 30 Aug 2023, at 14:52, Grant Taylor 
 wrote:


On 8/30/23 12:35 AM, Murray S. Kucherawy wrote:
And I've never understood why people get enamored of the idea of 
relying on bad reputations to spot bad actors.


I think of it as the other way around; good reputation to spot good 
actors.


Much like a brand new domain is effectively neutral immediately after 
it's created.  Said domain earns a reputation either good or bad over 
time.


In reality “new” domains are actually treated more negatively than 
neutral in many circumstances.



--
The Delivery Expert

Laura Atkins
Word to the Wise
la...@wordtothewise.com


There are several F500 companies I know of that bounce mail from domains 
<30~60 days old as a spam and security precaution from newly registered 
lookalike domains.


Granted, that only affects external mail to their users specifically, 
but for these companies, they've decided the benefits outweigh the risks 
in terms of any legitimate mail blocked.


- Mark Alley
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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-30 Thread Laura Atkins


> On 30 Aug 2023, at 14:52, Grant Taylor 
>  wrote:
> 
> On 8/30/23 12:35 AM, Murray S. Kucherawy wrote:
>> And I've never understood why people get enamored of the idea of relying on 
>> bad reputations to spot bad actors.
> 
> I think of it as the other way around; good reputation to spot good actors.
> 
> Much like a brand new domain is effectively neutral immediately after it's 
> created.  Said domain earns a reputation either good or bad over time.

In reality “new” domains are actually treated more negatively than neutral in 
many circumstances. 


-- 
The Delivery Expert

Laura Atkins
Word to the Wise
la...@wordtothewise.com

Delivery hints and commentary: http://wordtothewise.com/blog






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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-30 Thread Grant Taylor

On 8/30/23 12:35 AM, Murray S. Kucherawy wrote:
And I've never understood why people get enamored of the idea of relying 
on bad reputations to spot bad actors.


I think of it as the other way around; good reputation to spot good actors.

Much like a brand new domain is effectively neutral immediately after 
it's created.  Said domain earns a reputation either good or bad over time.




--
Grant. . . .
unix || die

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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-30 Thread Dave Crocker

On 8/30/2023 1:21 AM, Alessandro Vesely wrote:

On Wed 30/Aug/2023 07:35:08 +0200 Murray S. Kucherawy wrote:

On Tue, Aug 29, 2023 at 8:11 PM Dave Crocker  wrote:

On 8/29/2023 7:46 PM, Grant Taylor wrote:

On 8/29/23 9:02 PM, Dave Crocker wrote:

Why not re-use the existing DKIM solution, just with a different 
domain / set of keys?


Because it does not provide the affirmative information that I am 
postulating/guessing the originating platform can supply.


I have to agree.  It's compelling to consider that a high-trust 
domain might flag something for my extra consideration.  This could 
be done per-message, rather than per-key, which was Grant's 
counterproposal; the equivalent is to generate a selector per 
message, which appears at least on the surface to suffer problems of 
scale.



The affirmative information can be provided by using semantic 
subdomain names, whose purpose and meaning has been registered. See 
the strawman here:
https://mailarchive.ietf.org/arch/msg/ietf-dkim/ez0PYqMdCDoR4-sN2toPGObMMFI 



Except that there are no semantics to the domain naming components in 
DKIM, beyond the ones already defined.


Whatever naming choices a signer might make, the validator has no access 
to their meaning.


It's a bit like the www convention for domain naming. Humans associate 
an intention to it, but computers don't.



d/

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Dave Crocker
Brandenburg InternetWorking
bbiw.net
mast:@dcrocker@mastodon.social

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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-30 Thread Dave Crocker

On 8/29/2023 10:35 PM, Murray S. Kucherawy wrote:

On Tue, Aug 29, 2023 at 8:11 PM Dave Crocker  wrote:

On 8/29/2023 7:46 PM, Grant Taylor wrote:
> On 8/29/23 9:02 PM, Dave Crocker wrote:
>



Rather than doing it in a header field, though, could it be done 
simply with a new tag?


In terms of semantics, that would work too.  In terms of overall design 
approach, it is essentially the difference between CISC and RISC.


The feature under discussion has nothing to do with core DKIM 
functionality.  Even better, it is likely to be used by a limited set of 
signers.  So keep it out of the core specification and make it an add-on.


In practical terms, putting something into a core specification say that 
everyone has to implement it.  Even if the text says or implies otherwise.




> Let a domain establish a bad reputation.  Especially if it's being
> used for sending messages that are considered to be questionable.

Establishing a reputation takes time.  The likely behavior of a bad
actor is within a very short time-frame.

And it is a single account, not the entire domain, that is the
problem.


Or even a single message.


Indeed.


And I've never understood why people get enamored of the idea of 
relying on bad reputations to spot bad actors.  A bad actor who thinks 
it has attracted a negative reputation need only move to a new name in 
an otherwise gigantic public namespace (domain name or IP address) to 
start over from zero.


> Just use different domains / keys to indicate different things.
>
> No new standards.  No new code.  No new config.

And no new information.  Hence, current mechanisms only, which are
not
all that successful for this problem.


This also presumes that operators currently develop reputation based 
on (d=, s=) pairs.  Is that so?  I thought it was mostly just the d= 
that matters.


For the current DKIM spec, d= was specified as /the/ domain that DKIM 
was offering as an identifier.


Further, s= does not have precise, reliable semantics.  It is, in 
essence, a cookie that might be delivered back to the signer.


d/


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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-30 Thread Steve Atkins


> On 30 Aug 2023, at 09:21, Alessandro Vesely  wrote:
> 
> On Wed 30/Aug/2023 06:20:47 +0200 Steve Atkins wrote:
>>> On 30 Aug 2023, at 03:38, Grant Taylor 
>>>  wrote:
>>> On 8/29/23 3:15 PM, Steve Atkins wrote:
 Any attempt by senders to filter outbound emails based solely on content 
 is going to have a lot of false negatives and positives, wherever you 
 decide to draw the line.
>>> I find the idea of using different, probably less stringent, filtering on 
>>> outbound than on inbound to be hypocritical.
>> You have much more data for inbound email, and access to a much wider range 
>> of reactions. That’s not “hypocritical”.
>> The only information a sender has that a receiver doesn’t is a broader view 
>> of who the recipients of messages being sent are - and that’s exactly the 
>> information that DKIM replay hides from the sender.
> 
> 
> Large sites should exchange reputation information on each other's accounts. 
> Murray already proposed a standard for doing so.

That doesn’t seem like something that would have any effect on someone sending 
a single message to themselves, which is the perspective a sender is likely to 
have of a DKIM replay.

Cheers,
  Steve

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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-30 Thread Alessandro Vesely

On Wed 30/Aug/2023 06:20:47 +0200 Steve Atkins wrote:

On 30 Aug 2023, at 03:38, Grant Taylor 
 wrote:
On 8/29/23 3:15 PM, Steve Atkins wrote:

Any attempt by senders to filter outbound emails based solely on content is 
going to have a lot of false negatives and positives, wherever you decide to 
draw the line.


I find the idea of using different, probably less stringent, filtering on 
outbound than on inbound to be hypocritical.


You have much more data for inbound email, and access to a much wider range of 
reactions. That’s not “hypocritical”.

The only information a sender has that a receiver doesn’t is a broader view of 
who the recipients of messages being sent are - and that’s exactly the 
information that DKIM replay hides from the sender.



Large sites should exchange reputation information on each other's accounts. 
Murray already proposed a standard for doing so.


Best
Ale
--





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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-30 Thread Alessandro Vesely

On Wed 30/Aug/2023 07:35:08 +0200 Murray S. Kucherawy wrote:

On Tue, Aug 29, 2023 at 8:11 PM Dave Crocker  wrote:

On 8/29/2023 7:46 PM, Grant Taylor wrote:

On 8/29/23 9:02 PM, Dave Crocker wrote:

Why not re-use the existing DKIM solution, just with a different 
domain / set of keys?


Because it does not provide the affirmative information that I am 
postulating/guessing the originating platform can supply.


I have to agree.  It's compelling to consider that a high-trust domain 
might flag something for my extra consideration.  This could be done 
per-message, rather than per-key, which was Grant's counterproposal; the 
equivalent is to generate a selector per message, which appears at least on 
the surface to suffer problems of scale.



The affirmative information can be provided by using semantic subdomain names, 
whose purpose and meaning has been registered.  See the strawman here:

https://mailarchive.ietf.org/arch/msg/ietf-dkim/ez0PYqMdCDoR4-sN2toPGObMMFI


Rather than doing it in a header field, though, could it be done simply 
with a new tag?



The advantage of a subdomain w.r.t. a tag is that many receivers can operate on 
it natively, assigning reputation as normal, like Grant said, whereas a new tag 
would be ignored.



Let a domain establish a bad reputation.  Especially if it's being 
used for sending messages that are considered to be questionable.


Establishing a reputation takes time.  The likely behavior of a bad 
actor is within a very short time-frame.


And it is a single account, not the entire domain, that is the problem.


Or even a single message.



Or the ellipsis in Dave's "deemed spammy by the originating platform, or for 
new users who do not yet have an established quality record, or..."



And I've never understood why people get enamored of the idea of relying on 
bad reputations to spot bad actors.  A bad actor who thinks it has 
attracted a negative reputation need only move to a new name in an 
otherwise gigantic public namespace (domain name or IP address) to start 
over from zero.



I reject messages from domains newer than 30 days.  What is the time frame 
everybody else uses?



Best
Ale
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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-30 Thread Laura Atkins


> On 29 Aug 2023, at 19:07, Dave Crocker  wrote:
> 
> Not that this is all that new a question, but I think it might be worthy of 
> more (and maybe different focus)...
> 
> When a message is used in a DKIM Replay Attack:
> 
> It originates from a domain name having good reputation
> It passes quality checks from that sending domain
> It goes to a collaborating receiving site, which presumably means that site 
> is not conducting quality assessments
> It is re-posted, preserving the original DKIM signature, but now becomes an 
> attack
> Two thoughts:
> 
> If the substance of the message should fail a quality assessment, why does it 
> pass at the outbound (sending) site?
Spam isn’t really about substance, though, it’s about being unwanted and 
volume. A lot of things outbound folks use to identify spam require volume - 
like ‘is this audience similar to the audience we’ve seen report high levels of 
spam in the past’ or ‘does this send to addresses we know receive a lot of 
spam’ or ‘is this account sending to a lot of bad addresses’. There are other 
checks, like ‘does this email contain a link pointing to a hostname on any of 
these DNSBLs’ - but that’s trivially solved by just pulling out a link that 
isn’t on a DNSBL. The professional spam gangs, who are likely behind the 
attacks, have a deep bench of domains that they pull in and out of circulation 
on a regular basis. 

This also doesn’t address the problem that Google mentioned where they saw 
Youtube alerts / welcome messages replayed, possibly as a way to create a good 
IP reputation.
> If the problem is reasonable content, but sent to many unintended (or, 
> rather, undeclared) recipients, then the only characteristic of note is the 
> fact of multiple transmissions.  So I'd guess it is only a real-time network 
> of receivers, working in /very/ close coordination, to detect and deal with 
> the attack. (it's not difficult to imagine scattered retransmissions, over 
> time, to hide the coordination.  Sort of a spread spectrum transmission 
> style...)
My understanding is that one of the primary ways to ID a replay is using Google 
postmaster tools and seeing increases in their graphs without a corresponding 
increase in volume from their systems.

laura 

-- 
The Delivery Expert

Laura Atkins
Word to the Wise
la...@wordtothewise.com

Delivery hints and commentary: http://wordtothewise.com/blog






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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-30 Thread Steve Atkins


> On 30 Aug 2023, at 06:35, Murray S. Kucherawy  wrote:
>> 
> 
> This also presumes that operators currently develop reputation based on (d=, 
> s=) pairs.  Is that so?  I thought it was mostly just the d= that matters.

That some major consumer mailbox providers use s= to track reputation is one of 
the reasons nobody wants to rotate their keys.

I’m not sure whether that’s still true but I wouldn’t want to do anything that 
would dissuade people from doing sensible key management still further.

Cheers,
  Steve


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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-29 Thread Murray S. Kucherawy
On Tue, Aug 29, 2023 at 8:11 PM Dave Crocker  wrote:

> On 8/29/2023 7:46 PM, Grant Taylor wrote:
> > On 8/29/23 9:02 PM, Dave Crocker wrote:
> >
> > Why not re-use the existing DKIM solution, just with a different
> > domain / set of keys?
>
> Because it does not provide the affirmative information that I am
> postulating/guessing the originating platform can supply.
>

I have to agree.  It's compelling to consider that a high-trust domain
might flag something for my extra consideration.  This could be done
per-message, rather than per-key, which was Grant's counterproposal; the
equivalent is to generate a selector per message, which appears at least on
the surface to suffer problems of scale.

Rather than doing it in a header field, though, could it be done simply
with a new tag?

> Let a domain establish a bad reputation.  Especially if it's being
> > used for sending messages that are considered to be questionable.
>
> Establishing a reputation takes time.  The likely behavior of a bad
> actor is within a very short time-frame.
>
> And it is a single account, not the entire domain, that is the problem.
>

Or even a single message.

And I've never understood why people get enamored of the idea of relying on
bad reputations to spot bad actors.  A bad actor who thinks it has
attracted a negative reputation need only move to a new name in an
otherwise gigantic public namespace (domain name or IP address) to start
over from zero.


> > Just use different domains / keys to indicate different things.
> >
> > No new standards.  No new code.  No new config.
>
> And no new information.  Hence, current mechanisms only, which are not
> all that successful for this problem.
>

This also presumes that operators currently develop reputation based on
(d=, s=) pairs.  Is that so?  I thought it was mostly just the d= that
matters.

-MSK, participating
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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-29 Thread Steve Atkins


Sent from my iPhone

> On 30 Aug 2023, at 03:38, Grant Taylor 
>  wrote:
> 
> On 8/29/23 3:15 PM, Steve Atkins wrote:
>> Any attempt by senders to filter outbound emails based solely on content is 
>> going to have a lot of false negatives and positives, wherever you decide to 
>> draw the line.
> 
> I find the idea of using different, probably less stringent, filtering on 
> outbound than on inbound to be hypocritical.

You have much more data for inbound email, and access to a much wider range of 
reactions. That’s not “hypocritical”.

The only information a sender has that a receiver doesn’t is a broader view of 
who the recipients of messages being sent are - and that’s exactly the 
information that DKIM replay hides from the sender.

> 
> I find it tantamount to someone saying they only accept the most pristine 
> message while sending less pristine, and sometimes really tarnished, email.
> 
> Sure, there are some differences, e.g. lack of user preferences.
> 
> Why the asymmetry?
> 
> Why not apply the same filtering for outbound messages as applied to inbound 
> messages?

Because they’re quite different environments. 

> 
>> Inbound content-based filtering is much easier to get right - not least 
>> because the fallback is “just deliver it to the spam folder” - and we’re not 
>> great at that.
> 
> I guess I'm coming from a different place.  I always was more worried about 
> what I send and not upsetting the rest of the Internet than I am about what I 
> accept in.

That’s not the issue. It’s much easier to filter inbound mail accurately than 
it is outbound mail. And we’re not great at filtering inbound mail.

Cheers,
  Steve
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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-29 Thread Dave Crocker

On 8/29/2023 7:46 PM, Grant Taylor wrote:

On 8/29/23 9:02 PM, Dave Crocker wrote:

Why not re-use the existing DKIM solution, just with a different 
domain / set of keys?


Because it does not provide the affirmative information that I am 
postulating/guessing the originating platform can supply.





Let a domain establish a bad reputation.  Especially if it's being 
used for sending messages that are considered to be questionable.


Establishing a reputation takes time.  The likely behavior of a bad 
actor is within a very short time-frame.


And it is a single account, not the entire domain, that is the problem.




Plumbing historically has had clean water and waste water. 


The behavior of spammers is not as discrete or as stable as your example 
requires.




    3. Receiving hosts can take this as a flag for extra caution. The
    damn thing still gets to victim platforms, but those platform have a
    bit more information to factor in.


I feel like this falls back to a priming problem of who sends the flag 
because not enough people are checking for it and not enough people 
will check for it because not enough people are sending it.  What's 
more is that this is going to be viewed as some as tantamount to 
$SO_AND_SO is sending $SPAM, see they even tag it as such.


The nature of a collaborative mechanism is that, yes, both sides have to 
adopt it.  Adoption takes time.


The upside of the model I'm suggesting is that a) it's pretty cheap, and 
b) it's likely to be useful to a relatively, small set of very, very 
valuable domains. So it does not have to gain widespread adoption on the 
origination side, to be useful.





DKIM, SPF, et al, are all 'collaborative' mechanisms. Originators and 
receivers opt in to use them.  Both sides are necessary.  So I'm 
wondering about looking for something the furthers the collaboration.


Or re-use the existing systems that are already in place and being 
used by much of the email community.


Just use different domains / keys to indicate different things.

No new standards.  No new code.  No new config. 


And no new information.  Hence, current mechanisms only, which are not 
all that successful for this problem.



Maybe I'm too salty for the end of a long day, but I feel like this is 
in some ways "nothing new to see here, move along".
That view has been constantly asserted here, by some folk.  Why anyone 
believing that continues to participate in this effort is a mystery.


d/

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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-29 Thread Grant Taylor

On 8/29/23 9:02 PM, Dave Crocker wrote:

A possible way to think about how to approach this:

1. Use the mechanism for messages deemed spammy by the originating
platform, or for new users who do not yet have an established
quality record, or...

2. Add a header field that has semantics along the lines of "Yes I
signed this and yes I sent it, but I'm not happy about it."


Why not re-use the existing DKIM solution, just with a different domain 
/ set of keys?


Let a domain establish a bad reputation.  Especially if it's being used 
for sending messages that are considered to be questionable.


Plumbing historically has had clean water and waste water.  Now -- what 
is called -- grey water is being used in some places in parallel to the 
other two.  There is no false pretense that grey water is new nor waste. 
 Grey water is it's own thing and it is treated as such.



3. Receiving hosts can take this as a flag for extra caution. The
damn thing still gets to victim platforms, but those platform have a
bit more information to factor in.


I feel like this falls back to a priming problem of who sends the flag 
because not enough people are checking for it and not enough people will 
check for it because not enough people are sending it.  What's more is 
that this is going to be viewed as some as tantamount to $SO_AND_SO is 
sending $SPAM, see they even tag it as such.


DKIM, SPF, et al, are all 'collaborative' mechanisms. Originators and 
receivers opt in to use them.  Both sides are necessary.  So I'm 
wondering about looking for something the furthers the collaboration.


Or re-use the existing systems that are already in place and being used 
by much of the email community.


Just use different domains / keys to indicate different things.

No new standards.  No new code.  No new config.  Just a new domain / set 
of keys that need to establish a reputation, whatever that is.  That's 
something that already happens day in and day out.


And the attacker can't bypass it, if the signature covers enough (or 
all) of the message.


Maybe I'm too salty for the end of a long day, but I feel like this is 
in some ways "nothing new to see here, move along".




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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-29 Thread Grant Taylor

On 8/29/23 3:15 PM, Steve Atkins wrote:
Any attempt by senders to filter outbound emails based solely on 
content is going to have a lot of false negatives and positives, 
wherever you decide to draw the line.


I find the idea of using different, probably less stringent, filtering 
on outbound than on inbound to be hypocritical.


I find it tantamount to someone saying they only accept the most 
pristine message while sending less pristine, and sometimes really 
tarnished, email.


Sure, there are some differences, e.g. lack of user preferences.

Why the asymmetry?

Why not apply the same filtering for outbound messages as applied to 
inbound messages?


Inbound content-based filtering is much easier to get right - not least 
because the fallback is “just deliver it to the spam folder” - 
and we’re not great at that.


I guess I'm coming from a different place.  I always was more worried 
about what I send and not upsetting the rest of the Internet than I am 
about what I accept in.




--
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unix || die

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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-29 Thread Dave Crocker

On 8/29/2023 1:15 PM, Steve Atkins wrote:

Many, many people sign up to receive content that is, by any objective 
content-filtering standard, as spammy as an incredibly spammy thing.

Seriously, people sign up for things you would not believe.

Any attempt by senders to filter outbound emails based solely on content is 
going to have a lot of false negatives and positives, wherever you decide to 
draw the line.


So, what you say makes complete sense, of course.

And yet, I suspect that this problem nonetheless requires active 
measures at that point in the handling sequence.


The question, then, is what might help, without causing too much problem.

My immediate thought is an overlay to DKIM.  That is, an added mechanism 
that is protected by the DKIM signature.


A possible way to think about how to approach this:

   1. Use the mechanism for messages deemed spammy by the originating
   platform, or for new users who do not yet have an established
   quality record, or...

   2. Add a header field that has semantics along the lines of "Yes I
   signed this and yes I sent it, but I'm not happy about it."

   3. Receiving hosts can take this as a flag for extra caution. The
   damn thing still gets to victim platforms, but those platform have a
   bit more information to factor in.

DKIM, SPF, et al, are all 'collaborative' mechanisms. Originators and 
receivers opt in to use them.  Both sides are necessary.  So I'm 
wondering about looking for something the furthers the collaboration.


And the attacker can't bypass it, if the signature covers enough (or 
all) of the message.



d/

d/

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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-29 Thread Steve Atkins


Sent from my iPhone

> On 29 Aug 2023, at 20:54, Dave Crocker  wrote:
> 
> On 8/29/2023 12:30 PM, Murray S. Kucherawy wrote:
>> For (1), I presume the outbound site did not make a quality assessment that 
>> identified the message as "likely to be replayed".  Does this reduce to the 
>> "don't sign spam" argument?
> 
> I have no idea what the current levels of outbound filtering are, among major 
> platforms.  If it ain't already very high, yeah, seems like it should be and 
> that this is an added incentive why.

Many, many people sign up to receive content that is, by any objective 
content-filtering standard, as spammy as an incredibly spammy thing.

Seriously, people sign up for things you would not believe.

Any attempt by senders to filter outbound emails based solely on content is 
going to have a lot of false negatives and positives, wherever you decide to 
draw the line.

Inbound content-based filtering is much easier to get right - not least because 
the fallback is “just deliver it to the spam folder” - and we’re not great at 
that.

Cheers,
  Steve
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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-29 Thread Dave Crocker

On 8/29/2023 12:30 PM, Murray S. Kucherawy wrote:
For (1), I presume the outbound site did not make a quality assessment 
that identified the message as "likely to be replayed".  Does this 
reduce to the "don't sign spam" argument?


I have no idea what the current levels of outbound filtering are, among 
major platforms.  If it ain't already very high, yeah, seems like it 
should be and that this is an added incentive why.


d/

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Re: [Ietf-dkim] What makes this posting different from the original posting?

2023-08-29 Thread Murray S. Kucherawy
On Tue, Aug 29, 2023 at 11:10 AM Dave Crocker  wrote:

> Two thoughts:
>
>1. If the substance of the message should fail a quality assessment,
>why does it pass at the outbound (sending) site?
>2. If the problem is reasonable content, but sent to many unintended
>(or, rather, undeclared) recipients, then the only characteristic of note
>is the fact of multiple transmissions.  So I'd guess it is only a real-time
>network of receivers, working in /very/ close coordination, to detect and
>deal with the attack. (it's not difficult to imagine scattered
>retransmissions, over time, to hide the coordination.  Sort of a spread
>spectrum transmission style...)
>
>
For (1), I presume the outbound site did not make a quality assessment that
identified the message as "likely to be replayed".  Does this reduce to the
"don't sign spam" argument?

 -MSK
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[Ietf-dkim] What makes this posting different from the original posting?

2023-08-29 Thread Dave Crocker
Not that this is all that new a question, but I think it might be worthy 
of more (and maybe different focus)...


When a message is used in a DKIM Replay Attack:

1. It originates from a domain name having good reputation
2. It passes quality checks from that sending domain
3. It goes to a collaborating receiving site, which presumably means
   that site is not conducting quality assessments
4. It is re-posted, preserving the original DKIM signature, but now
   becomes an attack

Two thoughts:

1. If the substance of the message should fail a quality assessment,
   why does it pass at the outbound (sending) site?
2. If the problem is reasonable content, but sent to many unintended
   (or, rather, undeclared) recipients, then the only characteristic of
   note is the fact of multiple transmissions. So I'd guess it is only
   a real-time network of receivers, working in /very/ close
   coordination, to detect and deal with the attack. (it's not
   difficult to imagine scattered retransmissions, over time, to hide
   the coordination.  Sort of a spread spectrum transmission style...)

d/

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