Hi Brandon,

Thank you for the responses.  I’ll send you some examples off list of successes 
and failures from the exact same sender and final recipient, both Gmail users.  
I’d very much like to understand why we are seeing what appears to be an 
increase in DKIM validation failures in order to determine what can be done to 
improve the situation.  We are aware of DKIM signatures using the strict 
canonicalization option failing validation after forwarding, but in these 
examples the relaxed canonicalization was used.

We do not rewrite the envelope sender as we forward. I’m not convinced the 
non-trivial effort needed to shift to rewriting the sender would yield a 
durable solution to this problem, as it would not help with a DMARC check since 
the resulting SPF pass will be out of alignment with the sender in the From: 
header.  It would seem we’re dependent on the initial DKIM signature passing 
validation.  I’d welcome any other perspectives on the topic.

Best,
Jason


From: Brandon Long <bl...@google.com>
Date: Tuesday, September 12, 2023 at 8:29 PM
To: Jason R Cowart <jcow...@stanford.edu>
Cc: mailop@mailop.org <mailop@mailop.org>
Subject: Re: [mailop] Authentication Bounces by Gmail
Looking at the messages from that IP getting that rejection message, I'm seeing 
a lot of DKIM body hash did not verify, I'd also verify that your system isn't 
modifying the messages that it is forwarding.

Brandon

On Tue, Sep 12, 2023 at 8:20 PM Brandon Long 
<bl...@google.com<mailto:bl...@google.com>> wrote:
That message did not have a DKIM header ... or was so garbled that we didn't 
extract it.

Due to DKIM replay, we may spam reject forwarded messages that DKIM verify but 
not SPF, but those would not have that rejection message.

And yes, we are continuing to ramp no auth, no entry.

I'm sure I've had a long explanation on here in the past year, but the short 
answer is if the message is not DKIM valid and you're forwarding, you should 
rewrite
the MAIL FROM to a domain you own that will SPF authn the message... and try 
not to forward spam.

Brandon

On Tue, Sep 12, 2023 at 6:00 PM Jason R Cowart via mailop 
<mailop@mailop.org<mailto:mailop@mailop.org>> wrote:
We are seeing an increasing number of bounces by Gmail related to failed 
authentication checks.  The bounces include language like:
<<< 550-5.7.26 This mail is unauthenticated, which poses a security risk to
the
<<< 550-5.7.26 sender and Gmail users, and has been blocked. The sender must
<<< 550-5.7.26 authenticate with at least one of SPF or DKIM. For this
message,
<<< 550-5.7.26 DKIM checks did not pass and SPF check for 
[mcn.org<https://urldefense.com/v3/__http:/mcn.org__;!!G92We9drHetJ8EofZw!bcfdgTyulTUmQKo1vrF--AjiXti3tNVYB_Md2jNzKH5HdHgzwQrWe10SlqFuXZpImNccCVLZ-KAaRcSj$>]
 did not
pass
<<< 550-5.7.26 with ip: [67.231.157.125]. The sender should visit
<<< 550-5.7.26 
https://support.google.com/mail/answer/81126#authentication<https://urldefense.com/v3/__https:/support.google.com/mail/answer/81126*authentication__;Iw!!G92We9drHetJ8EofZw!bcfdgTyulTUmQKo1vrF--AjiXti3tNVYB_Md2jNzKH5HdHgzwQrWe10SlqFuXZpImNccCVLZ-FftiJ0V$>
for
<<< 550 5.7.26 instructions on setting up authentication.
z6-20020a05622a028600b00403a8e58423si1377805qtw.448 - gsmtp
554 5.0.0 Service unavailable

This is occurring in situations where our users forward their mail to a 
personal Gmail account.  SPF checks will of course fail in the scenario, but 
DKIM checks should pass.  In fact, they most often do pass—users impacted by 
this are only seeing a small subset of their mail from a given sender bounced 
(which often times will be a Gmail sender).  In cases where the user retains a 
copy locally we’ve been able to verify that the DKIM signature was present and 
was successfully validated by our system.

Is anyone else experiencing this?
Is anyone from Google could reach out to me off-list to discuss that would be 
much appreciated.

Best,
Jason Cowart
Stanford University IT
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