> On 17 May 2025, at 02:37, Matthew Tse <[email protected]> wrote:
> 
> Hey everyone,
> 
> Thanks for the quick responses! This is super helpful.
> 
> It seems there is some debate over whether forwarders should sign DKIM or not 
> for forwarded email. Kind of a question on if we want to take "ownership" of 
> this email. 

Exactly. Another thing to consider is what you’re forwarding. If the mail 
you’re signing is spam (and reported a spam by the final recipient) that’s 
going to be a hit to your domain reputation and will affect deliverability for 
all your customers. If your filters are good you shouldn’t be forwarding spam. 
But no filters are 100% accurate. Depending on volumes of legit vs. spam you 
might be acquiring yourself a poor reputation by forwarding spam. 

> But regardless, there definitely exists a problem with INKY mail filter 
> software, where they rewrite the contents in a way that breaks DKIM, and 
> causes gmail to mark these messages as spam. So we're not really at fault for 
> that. I'll work with our customer to try to work with INKY.

So you’re forwarding to INKY who is breaking the signature and then forwarding 
to Gmail? 

laura 

> 
> Best,
> Matthew Tse
> CEO @ ImprovMX <http://improvmx.com/>
> 
> On Thu, May 15, 2025 at 7:09 AM Laura Atkins <[email protected] 
> <mailto:[email protected]>> wrote:
>> 
>> 
>>> On 15 May 2025, at 06:36, Matthew Tse via mailop <[email protected] 
>>> <mailto:[email protected]>> wrote:
>>> 
>>> Hey Mailops!
>>> 
>>> I'm new to the email forwarding community, having taken over ImprovMX 
>>> <https://improvmx.com/> a few months ago. This is my first message to the 
>>> mailing group (I've been very curiously lurking for months)!
>>> 
>>> I'm looking for advice regarding DKIM signing. So it turns out ImprovMX 
>>> re-signs all forwarded emails with our own DKIM signature, which from my 
>>> research might not be standard (documentation suggests that mail forwarders 
>>> add ARC headers, but NOT re-sign using DKIM).
>> 
>> Resigning is a statement that you are taking responsibility for the mail. 
>> I’m not sure that’s what you mean to do. It also means you break DMARC 
>> alignment using DKIM and that will cause your final recipients to lose mail 
>> when the senders designate p=reject (or possibly quarantine). 
>> 
>>> This is not a problem for most of our users, but some have been complaining 
>>> that when ImprovMX forwards emails to a destination guarded by email 
>>> phishing protection software like Inky <https://www.inky.com/products>, 
>>> they rewrite the body, and that breaks DKIM and the emails often end up in 
>>> spam. 
>> 
>> This is actually a separate issue. If the destination is rewriting the 
>> messages before they check DKIM, it doesn’t matter if you resign or not - 
>> the mail will still fail DKIM. Is it possible that the problem is actually 
>> that resigning the mail is breaking DMARC and therefore the messages are 
>> going to spam? 
>> 
>>> Is my thinking correct--that we should stop DKIM signing forwarded emails, 
>>> and rely on ARC? Also let me know if this is not the right place or type of 
>>> question to ask here!
>> 
>> Part of the original DKIM intention was to be able to authenticate mail in a 
>> way that would survive forwarding. I’m not sure what made the ImprovMX folks 
>> decide resigning was the right decision, but I don’t think it was 
>> necessarily the right one. While ARC isn’t in widespread deployment, it’s 
>> probably worth leaving the original DKIM signature intact and resigning with 
>> ARC. If nothing else, it will distinguish between what your users are 
>> telling you (Inky is rewriting and causing mail to go to spam) and what 
>> might be the case (Inky is respecting DMARC p=reject and rejecting messages 
>> that fail due to you resigning DKIM with your own domain. 
>> 
>> laura 
>> 
>> -- 
>> The Delivery Expert
>> 
>> Laura Atkins
>> Word to the Wise
>> [email protected] <mailto:[email protected]>
>> 
>> Delivery hints and commentary: http://wordtothewise.com/blog 
>> 
>> 
>> 
>> 
>> 
>> 

-- 
The Delivery Expert

Laura Atkins
Word to the Wise
[email protected]

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






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