Background
Internet email is becoming more reliant on DKIM, a scheme for having mail servers cryptographically sign emails. The Big Email providers have started silently spambinning messages that lack either DKIM signatures, or SPF. DKIM is arguably less broken than SPF, so I wanted to deploy it.
But it has a problem: if done in a naive way, it makes all your emails non-repudiable, forever. This is not really a desirable property - at least, not desirable for you, although it can be nice for someone who (for example) gets hold of leaked messages obtained by hacking mailboxes.
This problem was described at some length in Matthew Green s article
Ok Google: please publish your DKIM secret keys. Following links from that article does get you to a short script to achieve key rotation but it had a number of problems, and wasn t useable in my context.
dkim-rotate
So I have written my own software for rotating and revoking DKIM keys:
dkim-rotate.
I think it is a good solution to this problem, and it ought to be deployable in many contexts (and readily adaptable to those it doesn t already support).
Here s the feature list taken from the README:
- Leaked emails become unattestable (plausibily deniable) within a few days soon after the configured maximum email propagation time.
- Mail domain DNS configuration can be static, and separated from operational DKIM key rotation. Domain owner delegates DKIM configuration to mailserver administrator, so that dkim-rotate does not need to edit your mail domain s zone.
- When a single mail server handles multiple mail domains, only a single dkim-rotate instance is needed.
- Supports situations where multiple mail servers may originate mails for a single mail domain.
- DNS zonefile remains small; old keys are published via a webserver, rather than DNS.
- Supports runtime (post-deployment) changes to tuning parameters and configuration settings. Careful handling of errors and out-of-course situations.
- Convenient outputs: a standard DNS zonefile; easily parseable settings for the MTA; and, a directory of old keys directly publishable by a webserver.
Complications
It seems like it should be a simple problem. Keep N keys, and every day (or whatever), generate and start using a new key, and deliberately leak the oldest private key.
But, things are more complicated than that. Considerably more complicated, as it turns out.
I didn t want the DKIM key rotation software to have to edit the actual DNS zones for each relevant mail domain. That would tightly entangle the mail server administration with the DNS administration, and there are many contexts (including many of mine) where these roles are separated.
The solution is to use DNS aliases (
CNAME). But, now we need a fixed, relatively small, set of
CNAME records for each mail domain. That means a fixed, relatively small set of key identifiers ( selectors in DKIM terminology), which must be used in rotation.
We don t want the private keys to be published
via the DNS because that makes an ever-growing DNS zone, which isn t great for performance; and, because we want to place barriers in the way of processes which might
enumerate the set of keys we use (and the set of keys we have leaked) and keep records of what status each key had when. So we need a separate publication channel - for which a webserver was the obvious answer.
We want the private keys to be readily noticeable and findable by someone who is verifying an alleged leaked email dump, but to be hard to enumerate. (One part of the strategy for this is to leave a note about it, with the prospective private key url, in the email headers.)
The key rotation operations are more complicated than first appears, too. The short summary, above, neglects to consider the fact that DNS updates have a nonzero propagation time: if you change the DNS, not everyone on the Internet will experience the change immediately. So as well as a timeout for how long it might take an email to be delivered (ie, how long the DKIM signature remains valid), there is also a timeout for how long to wait after updating the DNS, before relying on everyone having got the memo. (This same timeout applies both before starting to sign emails with a new key, and before deliberately compromising a key which has been withdrawn and deadvertised.)
Updating the DNS, and the MTA configuration, are fallible operations. So we need to cope with out-of-course situations, where a previous DNS or MTA update failed. In that case, we need to retry the failed update, and not proceed with key rotation. We mustn t start the timer for the key rotation until the update has been implemented.
The rotation script will usually be run by cron, but it might be run by hand, and when it is run by hand it ought not to jump the gun and do anything too early (ie, before the relevant timeout has expired). cron jobs don t always run, and don t always run at precisely the right time. (And there s daylight saving time, to consider, too.)
So overall, it s not sufficient to drive the system via cron and have it proceed by one unit of rotation on each run.
And, hardest of all, I wanted to support post-deployment configuration changes, while continuing to keep the whole the system operational. Otherwise, you have to bake in all the timing parameters right at the beginning and can t change anything ever. So for example, I wanted to be able to change the email and DNS propagation delays, and even the number of selectors to use,
without adversely affecting the delivery of already-sent emails, and without having to shut anything down.
I think I have solved these problems.
The resulting system is one which keeps track of the timing constraints, and the next event which might occur, on a per-key basis. It calculates on each run, which key(s) can be advanced to the next stage of their lifecycle, and performs the appropriate operations. The regular key update schedule is then an emergent property of the config parameters and cron job schedule. (I provide some example config.)
Exim
Integrating dkim-rotate itself with Exim was fairly easy. The
lsearch lookup function can be used to fish information out of a suitable data file maintained by
dkim-rotate.
But a final awkwardness was getting Exim to make the right DKIM signatures, at the right time.
When making a DKIM signature, one must choose a signing authority domain name: who should we claim to be? (This is the SDID in DKIM terms.) A mailserver that handles many different mail domains will be able to make good signatures on behalf of many of them. It seems to me that domain to be the mail domain in the
From: header of the email. (The RFC doesn t seem to be clear on what is expected.) Exim doesn t seem to have anything builtin to do that.
And, you only want to DKIM-sign emails that are originated locally or from trustworthy sources. You don t want to DKIM-sign messages that you received from the global Internet, and are sending out again (eg because of an email alias or mailing list). In theory if you verify DKIM on all incoming emails, you could avoid being fooled into signing bad emails, but rejecting all non-DKIM-verified email would be a very strong policy decision. Again, Exim doesn t seem to have cooked machinery.
The resulting Exim configuration parameters run to
22 lines, and because they re parameters to an existing config item (the
smtp transport) they can t even easily be deployed as a drop-in file via Debian s split config Exim configuration scheme.
(I don t know if the file written for Exim s use by dkim-rotate would be suitable for other MTAs, but this part of dkim-rotate could easily be extended.)
Conclusion
I have today
released dkim-rotate 0.4, which is the first public release for general use.
I have it deployed and working, but it s new so there may well be bugs to work out.
If you would like to try it out, you can get it
via git from Debian Salsa. (Debian folks can also find it freshly in Debian unstable.)
comments
It s mostly a robotic existence atm. I try to distract myself via movies, web series, the web, books, etc. whatever can take my mind off. From the day she died to date, I have a lower back pain which acts as a reminder. It s been a month, I eat, drink, and am surviving but still feel empty. I do things suggested by extended family but within there is no feeling, just emptiness :(. I have no clue if things will get better and even if I do want the change. I clearly have no idea, so let me share a little about what I know.
A new release 0.1.1 of 
I spent an enormous amount of time examining the recipient s OpenPGP key. I
made sure it was not expired. I made sure it was actually in my Thunderbird key
store not just in my OpenPGP keychain. I made sure I had indicated that I trust it
enough to use. I re-downloaded it.
I eventually gave up and didn t send the email. Then I responded to another
encrypted email and it worked. What!?!?
I spent more time comparing the recipients before I realized the problem was
the sending address, not the recipient address.
I have an OpenPGP key that lists several identities. I have a Thunderbird
Account that uses the Identities feature to add several from addresses. And, it
turns out that in Thunderbird, you need to indicate which OpenPGP key to use
for your main account but also for each identity. When you drill down to
Manage Identities for your account, you are able to indicate which OpenPGP key
you want to use for each identity. Once I indicated that each identity should
use my OpenPGP key, the issue was resolved.
And here s my ![“Screen shot of error message saying: End-to-end encryption requires resolving certificate issues for [blacked out email address]”](https://current.workingdirectory.net/tags/debian/resolving-certificate-issues.png)
I spent an enormous amount of time examining the recipient s OpenPGP key. I
made sure it was not expired. I made sure it was actually in my Thunderbird key
store not just in my OpenPGP keychain. I made sure I had indicated that I trust it
enough to use. I re-downloaded it.
I eventually gave up and didn t send the email. Then I responded to another
encrypted email and it worked. What!?!?
I spent more time comparing the recipients before I realized the problem was
the sending address, not the recipient address.
I have an OpenPGP key that lists several identities. I have a Thunderbird
Account that uses the Identities feature to add several from addresses. And, it
turns out that in Thunderbird, you need to indicate which OpenPGP key to use
for your main account but also for each identity. When you drill down to
Manage Identities for your account, you are able to indicate which OpenPGP key
you want to use for each identity. Once I indicated that each identity should
use my OpenPGP key, the issue was resolved.
And here s my 
I arrived in Prizren late on Wednesday. Here s what I did during debcamp (so over 3 days). I hope this post just motivates others to contribute more to Debian.
At least 2 DDs want to upload packages that need a new version of python3-jsonschema (ie: version > 4.x). Unfortunately, version 4 broke a few packages. I therefore uploaded it to Experimental a few months/week, so I could see the result of autopkgtest reading the 
The Rcpp team is please to announce the newest release 1.0.9 of