On newer versions of Debian and Ubuntu, the way repos are authenticated through public keys has changed somewhat. Here’s what I’ve found.

You may recognize the command apt-key: this is a now deprecated command that was previously used to add a trusted key to the keyring at /etc/apt/trusted.gpg. This is not great, as the same keys are considered valid for any repo you add.

This can (and on newer versions, must be) resolved by using signed-by when configuring a repo. That way, only packages from that repository will be considered valid when signed by the specified key.

Configuration examples⌗ 

# OLD WAY
deb https://my.repository.com/debian distribution component

When adding a new repository the “old” way, you would typically curl and pipe the a keyfile to apt-key add, which would add it to trusted.gpg, making it a trusted key for every configured repo.

# NEW WAY
deb [signed-by=/path/to/key.gpg] https://my.repository.com/debian distribution component

In this example, keys in key.gpg are only considered valid for that specific repository.

When it might cause issues⌗

This will normally not cause problems, as both the keys and the correct configuration (hopefully) comes as part of your default installation. However, when migrating between major versions, or when adding new repositories, you may encounter warnings with the “old” configuration.

A short demonstration: if you run apt-get update with no pubkeys available at all, a situation you could provoke by for example gzipping trusted.gpg, you will get an error similar to the following:

The following signatures couldn't be verified because the public key is not available: NO_PUBKEY 9165938D90FDDD2E

It’s pretty obvious from the error that 9165938D90FDDD2E is a public key, but we don’t have it so we can’t proceed.

First of all, what is this string? The answer is that it’s an abbreviated fingerprint of a public key. You can get these from gpg. For now, let’s ignore how we know which file it’s in:

# gpg --show-keys --with-fingerprint --keyid-format long raspbian-archive-keyring.gpg | grep 9165938D90FDDD2E -A1

pub   rsa2048/9165938D90FDDD2E 2012-04-01 [SC]
      Key fingerprint = A0DA 38D0 D76E 8B5D 6388  7281 9165 938D 90FD DD2E

On the first line of the output you can see the pubkey fingerprint, with a keyid-format of long matching the error message. Notice how this is actually the four last parts of the entire fingerprint (and short would only give us the last two: 90FDDD2E).

Note: using the short format is violently insecure, as it only “takes 4 seconds to generate a colliding 32bit key id on a GPU” (2020).

Ok, so now that we know what this string represents, the next question might be how we know that this is the right key. If the repository is accessed over HTTPS at least we know it’s what the repo gave us, because a man-in-the-middle attack is pretty unlikely.

How do we know that the repo key hasn’t been compromised? We could look for the key in other places, for example by searching for it online. In this case, the repo itself has the key listed on a web page with instructions on how to add the repo, as well as a link to where you can find the key.

Finding the key isn’t usually the issue, it’s even registered at this public key server:

https://keys.openpgp.org/search?q=9165938D90FDDD2E

It’s more important to ensure that this key is legit, and for now we’ll assume that a guide that has been around for years served over HTTPS from the official repository page is proof enough.

On Debian, keys are provided through the debian-keyring package, which will put them in /usr/share/keyrings. On Raspberry Pi OS, there are two packages available: raspbian-archive-keyring and raspberrypi-archive-keyring, which will put keys in the same folder.

The first raspbian package is what provides the file we inspected previously:

# dpkg-query -L raspbian-archive-keyring | grep "\.gpg"
/usr/share/keyrings/raspbian-archive-keyring.gpg

So if we already have this file on disk, we can use that for our repo, since we now feel pretty confident that is the key that we expect packages from there to be signed with:

deb [signed-by=/usr/share/keyrings/raspbian-archive-keyring.gpg] https://archive.raspbian.org/raspbian bookworm main contrib non-free rpi

But for the sake of learning, let’s pretend we did not have this key available locally, how do we get it from the Internet and use it?

The instructions from raspbian illustrate perfectly the “old” way of doing things:

# OLD REPO SYNTAX
deb http://archive.raspbian.org/raspbian wheezy main contrib non-free

Adding the key

# DEPRECATED
wget https://archive.raspbian.org/raspbian.public.key -O - | sudo apt-key add -

What we really want is to grab that file, make it into a .gpg file and use it with the new syntax.

First, let’s just inspect it and make sure it’s the key we’re looking for:

$ curl --silent https://archive.raspbian.org/raspbian.public.key | gpg --show-keys --fingerprint --keyid-format long
pub   rsa2048/9165938D90FDDD2E 2012-04-01 [SC]
      Key fingerprint = A0DA 38D0 D76E 8B5D 6388  7281 9165 938D 90FD DD2E
(...)

Since this looks fine, we can now grab it and perform “dearmoring”, which really only means to convert it from ASCII to binary (the inverse is called “enarmoring”). The ASCII form of a key is probably familiar to you:

$ curl --silent https://archive.raspbian.org/raspbian.public.key | head -n5
-----BEGIN PGP PUBLIC KEY BLOCK-----
Version: GnuPG v1.4.12 (GNU/Linux)

mQENBE94wmkBCADPW5ga8ZyIsW0pym3c+o7l/N1ipRfs2+9HaEWeyPZS6wdTdSp3
Wo0OOv3rGQDGclbvsrMZoJFzxfsADoMfPkToWg+pY4w3xkjZt4Mh7gO/kDsaOMDz

In order to dearmor and place this key somewhere, we can run:

# curl --silent https://archive.raspbian.org/raspbian.public.key | gpg --dearmor > /usr/share/keyrings/raspbian.public.gpg

This binary representation of the key can now be used when specifying signed-by for a repo.

Note: As I later found out, de-armoring the key (converting to binary) isn’t strictly necessary, you can also use the plaintext (armored) key directly, but I’ll keep the above instructions anyway since the alternative of using an armored key is as simple as just pointing to it without conversion.

In summary:

  • Packages in repos should be signed-by specific keys, not just any key that’s ever been added.
  • If a repo does not have the signed-by attribute, you may get warnings. It’s a good idea to fix your configuration.
  • If you lack public keys completely, it breaks apt-get
  • What public keys are trusted is completely up to you, so exercise caution.

Final notes: