Discussion:
New Bitcoin Core macOS signing key
(too old to reply)
Cory Fields via bitcoin-dev
2018-01-12 05:04:44 UTC
Permalink
Hi all

As discussed in a few of the last weekly meetings, Bitcoin Core's
macOS code signing certificate expired today.

We are (Greg is ;) in the process of establishing a new threshold
signing scheme that will allow us to handle code signing without any
single point of failure. But until then, releases will be signed as
before, just with a new certificate.

As a matter of record, I used the old code-signing key/certificate to
sign a message containing the pubkey that matches the new
key/certificate. It's attached at the end of this message.

The pkcs7 format is rather clunky, but I wanted to include the current
signing certificate to make verification easier. I'll leave it to the
reader to extract the certificate from a previous release in order to
make sure that they match. It was also in the Core git repo until it
was removed recently.

To verify, you can use something like:
openssl smime -verify -in sig.pkcs7 -inform pem -ignore_critical -purpose any

- "ignore_critical" setting tells openssl to ignore the Apple-specific
critical extensions that it doesn't understand.
- "-purpose any" allows the "purpose == smimesign" check to be
skipped. This would otherwise fail because this certificate is only
authorized to sign code, not arbitrary messages.

By now, the signature will probably fail to validate because the
certificate has expired.

The signed message below is timestamped on the Bitcoin blockchain
using OpenTimestamps. See the attached ots file containing the
timestamp proof. If the attachment gets scrubbed and doesn't make it
to the list, don't be afraid to nag Peter Todd about a mail-friendly
format for these proofs :)

Regards,
Cory

expire.txt.sig:
-----BEGIN PKCS7-----
MIILTwYJKoZIhvcNAQcCoIILQDCCCzwCAQExCzAJBgUrDgMCGgUAMIIDNAYJKoZI
hvcNAQcBoIIDJQSCAyFUaGUgY3VycmVudCBCaXRjb2luIENvcmUgbWFjT1MgY29k
ZSBzaWduaW5nIGNlcnRpZmljYXRlIGV4cGlyZXMNCmxhdGVyIHRvZGF5LCBKYW51
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EmHUHDdl2R+TWDf0ADXMqV3qjMuG5osFRUJbeWm5CUne1/w2BdcIkmkvfmzU+Bmh
jixGT1Xg83O4e3LL4Bww0rRY6w==
-----END PKCS7-----
Peter Todd via bitcoin-dev
2018-01-12 08:54:12 UTC
Permalink
Post by Cory Fields via bitcoin-dev
openssl smime -verify -in sig.pkcs7 -inform pem -ignore_critical -purpose any
- "ignore_critical" setting tells openssl to ignore the Apple-specific
critical extensions that it doesn't understand.
- "-purpose any" allows the "purpose == smimesign" check to be
skipped. This would otherwise fail because this certificate is only
authorized to sign code, not arbitrary messages.
By now, the signature will probably fail to validate because the
certificate has expired.
Note that you may need to add -noverify as well if your openssl doesn't have
the Apple Certificate Authority in the CA list.

While a clunky way to do it, you can use the `-signer` option to tell OpenSSL
to write the signer's certificate to a file. That certificate can then be
compared to the one from the repo, which was still in the repo as of the
(signed!) v0.15.1 tag.


Fun fact: OpenTimestamps has git integration, which means you can extract a OTS
proof from 2016 for that certificate from the repo:

$ git checkout v0.15.1
$ ots git-extract share/certs/BitcoinFoundation_Apple_Cert.pem share/certs/BitcoinFoundation_Apple_Cert.pem.ots 36f60a5d5b1bc9a12b87d6475e3245b8236775e4
$ ots verify share/certs/BitcoinFoundation_Apple_Cert.pem.ots
Assuming target filename is 'share/certs/BitcoinFoundation_Apple_Cert.pem'
Success! Bitcoin attests data existed as of Thu Oct 13 14:08:59 2016 EDT

Homework problem: write a paragraph explaining how the proof generated by the
above three commands are crypto snakeoil that proved little. :)
Post by Cory Fields via bitcoin-dev
The signed message below is timestamped on the Bitcoin blockchain
using OpenTimestamps. See the attached ots file containing the
timestamp proof. If the attachment gets scrubbed and doesn't make it
to the list, don't be afraid to nag Peter Todd about a mail-friendly
format for these proofs :)
Ha! Fortunately even the mailing list archives at lists.linuxfoundation.org
seem to contain the attachment just fine.

But anyway, I'd suggest using base64:

AE9wZW5UaW1lc3RhbXBzAABQcm9vZgC/ieLohOiSlAEITeD8FWBXd613LkHPt3JyrZBKamczrmmf
NLwSJohkYfDwEB35DezwYGb4KePty9TSWRcI//AQjTiBNRdo5I7oIeLjkGhQuAjxBFpXqSbwCN+N
8xIdwxQG/wCD3+MNLvkMji4taHR0cHM6Ly9hbGljZS5idGMuY2FsZW5kYXIub3BlbnRpbWVzdGFt
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oO6Q/6SoX7ksCKOjkt284KYyI/ELaVgI8VkBAAAAAc1gOrgz+6mCizItuiE8bQ4foKYwCz0sB9lG
7gj/kK9fAAAAAAD9////Ag9aLAAAAAAAFgAU4gDd5F6wUprr6G4WBg+5sQkAi1YAAAAAAAAAACJq
IPAEuq8HAAgI8SAQbNEWckYQhxlLHC1aYxnyzHgxatOXQCOkQGgXe7CV7wgI8SDvEAaFSJ6unpLU
CvJzUpe2ISKMquT7kvQlvOam3SbgdggI8SBKKOTuNlh0TqP0wxy+BvCN8HgXFj/CQvJm/r9061dC
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p4HsOQBoiDB3HwgI8SBpOitFwKhqpvNNL2SzSAxmCDIRpIpq+Kp5x774ovXexggI8SAtBMNMgP/r
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UF+5+QgIAAWIlg1z1xkBA7vfHvAQ5vjVlfmkli0Jsy9r6Zl5EAjxBFpXqSXwCGWEIRA/ovvQ/wCD
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gnzr8J36EGTnlaF/N3bvWi0cmhlkt1b/TVIBZuCHCPEgKqjwAWBXRj1MC6oVZK6P7MBuaB5VnC+S
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AC6uWB3K28jnM7chsxQiPXQvOmE/CPEgWmgM4iyrpd8Ip/Vs0bPeC1mdH/fgEOO+fLCR0Ae8OH0I
8CAebOJrI00jNjqWLJNxFLZaO4tY69kEKHx6AvrjoQqNzgjxWQEAAAABqY/4nDzgexnxwERsA6RG
QKS4pzagJAciBvkAbejv8mwAAAAAAP3///8CGrg4AAAAAAAWABQNuE08uA4/5oWDRYPWIW0HNrwS
ZgAAAAAAAAAAImog8AS2rwcACAjwIGQuGBXXZjCZPN527NmlDPNE7DY5jznNp8UauCoSRe3UCAjx
IPnKxEUG7HPVIm2RehYqhROpmLrZuPtr4MuMKoX+xTT1CAjwID9qxx7kHhzJrzDeZPXsvaCdQCX3
mVqkyBzlIG/Rz0TPCAjxIFHQruGgLpotZScpYu9Ou9EUmeqmizOmW77hqP04oN5/CAjwIKqKpmbK
V3weRNXWLDAWVcr0bXZndaq6th6b8dy5mjoeCAjwIA2RHHGChLN8t1f7rJJRowlLp1F3XLGD2kqK
k5M3K4c3CAjxIBwP3futX+WjxgkAS0d2TGxiyUoKMFT6bmG2o4zwmz/4CAjwIJmhwnqv64SuTiSQ
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CAjxIPjnINA1faJ/WYxuV0KSUceoHWd4EltavqltfDjTjQhcCAjwIOJixScSNRwwkg68C4HSMeRM
K5YKNh1phfaY3Du/0i68CAgABYiWDXPXGQEDt98e

On Linux, the `base64 -d` command will decode the above just fine.

The _real_ issue is that asking the user to cut-n-paste that PKCS7-encoded
message is problematic, as differences in whitespace and line endings will make
the verification fail. Works fine on Linux, but would probably have failed on
Windows.

What's nice about OpenPGP's "clearsigned" format is how it ignores whitespace;
a replica of that might be a nice thing for OTS to be able to do too. Though
that's on low priority, as there's some tricky design choices(1) to be made about
how to nicely nest clearsigned PGP within OTS.


1) For example, I recently found a security hole related to clearsigned PGP
recently. Basically the issue was that gpg --verify will return true on a file
that looks like the following:

1d7a363ce12430881ec56c9cf1409c49c491043618e598c356e2959040872f5a foo-v2.0.tar.gz
-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA256

e3b0c44298fc1c149afbf4c8996fb92427ae41e4649b934ca495991b7852b855 foo-v1.0.tar.gz
-----BEGIN PGP SIGNATURE-----

<snip pgp stuff>
-----END PGP SIGNATURE-----

The system I was auditing then did something like this to verify that the file
was signed:

set -e # exit immediately on error
gpg --verify SHA256SUMS.asc
cat SHA256SUMS.asc | grep foo-v2.0.tar.gz
<do installation>

While it makes it a bit less user friendly, the fact that PKCS7's encoding made
it impossible to see the message you signed until it's been properly verified
is a good thing re: security.

And yes, I checked: Bitcoin Core's contrib/verifybinaries/verify.sh isn't
vulnerable to this mistake. :)
--
https://petertodd.org 'peter'[:-1]@petertodd.org
nullius via bitcoin-dev
2018-01-12 10:14:11 UTC
Permalink
Post by Peter Todd via bitcoin-dev
While a clunky way to do it, you can use the `-signer` option to tell
OpenSSL to write the signer's certificate to a file. That certificate
can then be compared to the one from the repo, which was still in the
repo as of the (signed!) v0.15.1 tag.
Fun fact: OpenTimestamps has git integration, which means you can
$ git checkout v0.15.1
$ ots git-extract share/certs/BitcoinFoundation_Apple_Cert.pem share/certs/BitcoinFoundation_Apple_Cert.pem.ots 36f60a5d5b1bc9a12b87d6475e3245b8236775e4
$ ots verify share/certs/BitcoinFoundation_Apple_Cert.pem.ots
Assuming target filename is 'share/certs/BitcoinFoundation_Apple_Cert.pem'
Success! Bitcoin attests data existed as of Thu Oct 13 14:08:59 2016 EDT
Homework problem: write a paragraph explaining how the proof generated
by the above three commands are crypto snakeoil that proved little. :)
It says, “Bitcoin attests data existed”. Within the scope of those
three commands, I don’t see any proof of who put it there. Does OTS
check the PGP signatures on *commits* when it does that `git-extract`?
The signature on the v0.15.1 tag is irrelevant to that question; and
FWIW, I don’t see *that* signature being verified here, either.

Second paragraph: Moreover, with the breaking of SHA-1, it *may* be
feasible for some scenario to play out involving two different PEMs with
the same hash, but different public keys (and thus different
corresponding private keys). I don’t know off the top of my head if
somewhere could be found to stash the magic bits; and the overall
scenario would need to be a bit convoluted. I think a malicious
committer who lacked access to the signing key *may* be able to create a
collision between the real certificate, and a certificate as for which
he has the private key—then switch them, later. Maybe. I would not
discount the possibility off-hand. OTS would prove nothing, if he had
the foresight to obtain timestamps proving that both certificates
existed at the appropriate time (which they would need to anyway; it is
not a post facto preimage attack).
Post by Peter Todd via bitcoin-dev
[...]
What's nice about OpenPGP's "clearsigned" format is how it ignores
whitespace; a replica of that might be a nice thing for OTS to be able
to do too. Though that's on low priority, as there's some tricky design
choices(1) to be made about how to nicely nest clearsigned PGP within
OTS.
1) For example, I recently found a security hole related to clearsigned
PGP recently. Basically the issue was that gpg --verify will return
1d7a363ce12430881ec56c9cf1409c49c491043618e598c356e2959040872f5a foo-v2.0.tar.gz
-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA256
e3b0c44298fc1c149afbf4c8996fb92427ae41e4649b934ca495991b7852b855 foo-v1.0.tar.gz
-----BEGIN PGP SIGNATURE-----
<snip pgp stuff>
-----END PGP SIGNATURE-----
The system I was auditing then did something like this to verify that
set -e # exit immediately on error
gpg --verify SHA256SUMS.asc
cat SHA256SUMS.asc | grep foo-v2.0.tar.gz
<do installation>
While it makes it a bit less user friendly, the fact that PKCS7's
encoding made it impossible to see the message you signed until it's
been properly verified is a good thing re: security.
Potential solutions using PGP:

0. Don’t use clearsigning.

1. Use a detached signature.

2. Use `gpg --verify -o -` and pipe that to `grep`, rather than
illogically separating verification from use of data. (By the way,
where is the *hash* verified? Was `grep` piped to `sha256sum -c`?)

3. Have shell scripts written by somebody who knows how to think about
Post by Peter Todd via bitcoin-dev
Note: When verifying a cleartext signature, gpg verifies only what
makes up the cleartext signed data and not any extra data outside of
the cleartext signature or the header lines directly following the dash
marker line. The option --output may be used to write out the actual
signed data, but there are other pitfalls with this format as well. It
is suggested to avoid cleartext signatures in favor of detached
signatures.
4. Obtain an audit from Peter Todd.
Post by Peter Todd via bitcoin-dev
And yes, I checked: Bitcoin Core's contrib/verifybinaries/verify.sh
isn't vulnerable to this mistake. :)
P.S., oh my! *Unsigned data:*
Post by Peter Todd via bitcoin-dev
_______________________________________________
bitcoin-dev mailing list
https://lists.linuxfoundation.org/mailman/listinfo/bitcoin-dev
--
***@nym.zone | PGP ECC: 0xC2E91CD74A4C57A105F6C21B5A00591B2F307E0C
Bitcoin: bc1qcash96s5jqppzsp8hy8swkggf7f6agex98an7h | (Segwit nested:
3NULL3ZCUXr7RDLxXeLPDMZDZYxuaYkCnG) (PGP RSA: 0x36EBB4AB699A10EE)
“‘If you’re not doing anything wrong, you have nothing to hide.’
No! Because I do nothing wrong, I have nothing to show.” — nullius
Cory Fields via bitcoin-dev
2018-02-01 01:14:45 UTC
Permalink
A public key was published recently for future macOS releases. Sadly,
that key was created the wrong way (iPhone OS instead of macOS), so
another had to be generated.

The new, working pubkey for Bitcoin Core releases starting with
0.16.0rc1 is included in the message below. That message is signed
with the key mentioned in the previous mail.
It can be verified with: openssl smime -verify -noverify -in msg.pem

Sorry for the noise.

-----BEGIN PKCS7-----
MIIPbQYJKoZIhvcNAQcCoIIPXjCCD1oCAQExCzAJBgUrDgMCGgUAMIIC5gYJKoZI
hvcNAQcBoIIC1wSCAtNBIHB1YmxpYyBrZXkgd2FzIHB1Ymxpc2hlZCByZWNlbnRs
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-----END PKCS7-----

Regards,
Cory

On Fri, Jan 12, 2018 at 5:14 AM, nullius via bitcoin-dev
Post by Peter Todd via bitcoin-dev
While a clunky way to do it, you can use the `-signer` option to tell
OpenSSL to write the signer's certificate to a file. That certificate can
then be compared to the one from the repo, which was still in the repo as of
the (signed!) v0.15.1 tag.
Fun fact: OpenTimestamps has git integration, which means you can extract
$ git checkout v0.15.1
$ ots git-extract share/certs/BitcoinFoundation_Apple_Cert.pem
share/certs/BitcoinFoundation_Apple_Cert.pem.ots
36f60a5d5b1bc9a12b87d6475e3245b8236775e4
$ ots verify share/certs/BitcoinFoundation_Apple_Cert.pem.ots
Assuming target filename is
'share/certs/BitcoinFoundation_Apple_Cert.pem'
Success! Bitcoin attests data existed as of Thu Oct 13 14:08:59 2016 EDT
Homework problem: write a paragraph explaining how the proof generated by
the above three commands are crypto snakeoil that proved little. :)
It says, “Bitcoin attests data existed”. Within the scope of those three
commands, I don’t see any proof of who put it there. Does OTS check the PGP
signatures on *commits* when it does that `git-extract`? The signature on
the v0.15.1 tag is irrelevant to that question; and FWIW, I don’t see *that*
signature being verified here, either.
Second paragraph: Moreover, with the breaking of SHA-1, it *may* be
feasible for some scenario to play out involving two different PEMs with the
same hash, but different public keys (and thus different corresponding
private keys). I don’t know off the top of my head if somewhere could be
found to stash the magic bits; and the overall scenario would need to be a
bit convoluted. I think a malicious committer who lacked access to the
signing key *may* be able to create a collision between the real
certificate, and a certificate as for which he has the private key—then
switch them, later. Maybe. I would not discount the possibility off-hand.
OTS would prove nothing, if he had the foresight to obtain timestamps
proving that both certificates existed at the appropriate time (which they
would need to anyway; it is not a post facto preimage attack).
Post by Peter Todd via bitcoin-dev
[...]
What's nice about OpenPGP's "clearsigned" format is how it ignores
whitespace; a replica of that might be a nice thing for OTS to be able to do
too. Though that's on low priority, as there's some tricky design choices(1)
to be made about how to nicely nest clearsigned PGP within OTS.
1) For example, I recently found a security hole related to clearsigned
PGP recently. Basically the issue was that gpg --verify will return true on
1d7a363ce12430881ec56c9cf1409c49c491043618e598c356e2959040872f5a
foo-v2.0.tar.gz
-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA256
e3b0c44298fc1c149afbf4c8996fb92427ae41e4649b934ca495991b7852b855
foo-v1.0.tar.gz
-----BEGIN PGP SIGNATURE-----
<snip pgp stuff>
-----END PGP SIGNATURE-----
The system I was auditing then did something like this to verify that the
set -e # exit immediately on error
gpg --verify SHA256SUMS.asc
cat SHA256SUMS.asc | grep foo-v2.0.tar.gz
<do installation>
While it makes it a bit less user friendly, the fact that PKCS7's encoding
made it impossible to see the message you signed until it's been properly
verified is a good thing re: security.
0. Don’t use clearsigning.
1. Use a detached signature.
2. Use `gpg --verify -o -` and pipe that to `grep`, rather than illogically
separating verification from use of data. (By the way, where is the *hash*
verified? Was `grep` piped to `sha256sum -c`?)
3. Have shell scripts written by somebody who knows how to think about
Post by Peter Todd via bitcoin-dev
Note: When verifying a cleartext signature, gpg verifies only what makes
up the cleartext signed data and not any extra data outside of the cleartext
signature or the header lines directly following the dash marker line. The
option --output may be used to write out the actual signed data, but there
are other pitfalls with this format as well. It is suggested to avoid
cleartext signatures in favor of detached signatures.
4. Obtain an audit from Peter Todd.
Post by Peter Todd via bitcoin-dev
And yes, I checked: Bitcoin Core's contrib/verifybinaries/verify.sh isn't
vulnerable to this mistake. :)
P.S., oh my! *Unsigned data:*
Post by Peter Todd via bitcoin-dev
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--
3NULL3ZCUXr7RDLxXeLPDMZDZYxuaYkCnG) (PGP RSA: 0x36EBB4AB699A10EE)
“‘If you’re not doing anything wrong, you have nothing to hide.’
No! Because I do nothing wrong, I have nothing to show.” — nullius
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