Tags: dogtag, renewal, troubleshooting, freeipa

Offline expired certificate renewal for Dogtag

The worst has happened. Somehow, certificate renewal didn’t happen when it should have, and now you have expired certificates. Worst, these are Dogtag system certificates; you can’t even start Dogtag to issue new ones! Unfortunately, this situation arises fairly often. Sometimes due to administrator error or extended downtime; sometimes due to bugs. These cases are notoriously difficult (and expensive) to analyse and resolve. It often involves time travel:

  1. Set the system clock to a time setting just before certificates started expiring.
  2. Fix whatever caused renewal not to work in the first place.
  3. Renew expiring certificates.
  4. Reset system clock.

That is the simple case! I have seen much gnarlier scenarios. Ones where multiple times must be visited. Ones where there is no time at which all relevant certs are valid.

It would be nice to avoid these scenarios, and the FreeIPA team continues to work to improve the robustness of certificate renewal. We also have a monitoring / health check solution on the roadmap, so that failure of automated renewal sets off alarms before everything else falls over. But in the meantime, customers and support are still dealing with scenarios like this. Better recovery tools are needed.

And better tools are on the way! Dinesh, one of the Dogtag developers, has built a tool to simplify renewal when your Dogtag CA is offline due to expired system certificates. This post outlines what the tool is, what it does, and my first experiences using it in a FreeIPA deployment. Along the way and especially toward the end of the post, I will discuss the caveats and potential areas for improvement, and FreeIPA-specific considerations.

pki-server cert-fix §

The tool is implemented as a subcommand of the pki-server utility–namely cert-fix (and I will use this short name throughout the post). So it is implemented in Python, but in some places it calls out to certutil or the Java parts of Dogtag via the HTTP API. The user documentation is maintained the source repository.

The insight at the core of cert-fix is that even if Dogtag is not running or cannot run, we still have access to the keys needed to issue certificates. We do need to use Dogtag to properly store issued certificates (for revocation purposes) and produce an audit trail. But if needed, we can use the CA signing key to temporarily fudge the important certificates to get Dogtag running again, then re-issue expired system certificates properly.

Assumptions §

cert-fix makes the following assumptions about your environment. If these do not hold, then cert-fix, as currently implemented, cannot do its thing.

These assumptions have been made for good reasons, but there are several certificate expiry scenarios that breach them. I will discuss in detail later in the post. For now, we must accept them.

What cert-fix does §

The cert-fix performs the following actions to renew an expired system certificate:

  1. Inspect the system and identify which system certificates need renewing. Or the certificates can be specified on the command line.
  2. If Dogtag’s HTTPS certificate is expired, use certutil commands to issue a new “temporary” certificate. The validity period is three months (from the current time). The serial number of the current (expired) HTTPS is reused (a big X.509 no-no, but operationally no big deal in this scenario). There is no audit trail and the certificate will not appear in the LDAP database.
  3. Disable the startup self-test for affected subsystems, then start Dogtag.
  4. For each target certificate, renew the certificate via API, using given credential. Validity periods and other characteristics are determined by relevant profiles. Serial numbers are chosen in the usual manner, the certificates appear in LDAP and there is an audit trail.
  5. Stop Dogtag.
  6. For each target certificate, import the new certificate into Dogtag’s NSSDB.
  7. Re-enable self-test for affected subsystems and start Dogtag.

Using cert-fix §

There are a couple of ways to try out the tool—without waiting for certificates to expire, that is. One way is to roll your system clock forward, beyond the expiry date of one or more certificates. Another possibility is to modify a certificate profile used for a system certificate so that it will be issued with a very short validity period.

I opted for the latter option. I manually edited the default profile configuration, so that Dogtag’s OCSP and HTTPS certificates would be issued with a validity period of 15 minutes. By the time I installed FreeIPA, grabbed a coffee and read a few emails, the certificates had expired. Certmonger didn’t even attempt to renew them. Dogtag was still running and working properly, but ipactl restart put Dogtag, and the whole FreeIPA deployment, out of action.

I used pki-server cert-find to have a peek at Dogtag’s system certificates:

[root@f29-0 ca]# pki-server cert-find
  Cert ID: ca_signing
  Nickname: caSigningCert cert-pki-ca
  Serial Number: 0x1
  Subject DN: CN=Certificate Authority,O=IPA.LOCAL 201902271325
  Issuer DN: CN=Certificate Authority,O=IPA.LOCAL 201902271325
  Not Valid Before: Wed Feb 27 14:30:22 2019
  Not Valid After: Mon Feb 27 14:30:22 2034

  Cert ID: ca_ocsp_signing
  Nickname: ocspSigningCert cert-pki-ca
  Serial Number: 0x2
  Subject DN: CN=OCSP Subsystem,O=IPA.LOCAL 201902271325
  Issuer DN: CN=Certificate Authority,O=IPA.LOCAL 201902271325
  Not Valid Before: Wed Feb 27 14:30:24 2019
  Not Valid After: Wed Feb 27 14:45:24 2019

  Cert ID: sslserver
  Nickname: Server-Cert cert-pki-ca
  Serial Number: 0x3
  Subject DN: CN=f29-0.ipa.local,O=IPA.LOCAL 201902271325
  Issuer DN: CN=Certificate Authority,O=IPA.LOCAL 201902271325
  Not Valid Before: Wed Feb 27 14:30:24 2019
  Not Valid After: Wed Feb 27 14:45:24 2019

  Cert ID: subsystem
  Nickname: subsystemCert cert-pki-ca
  Serial Number: 0x4
  Subject DN: CN=CA Subsystem,O=IPA.LOCAL 201902271325
  Issuer DN: CN=Certificate Authority,O=IPA.LOCAL 201902271325
  Not Valid Before: Wed Feb 27 14:30:24 2019
  Not Valid After: Tue Feb 16 14:30:24 2021

  Cert ID: ca_audit_signing
  Nickname: auditSigningCert cert-pki-ca
  Serial Number: 0x5
  Subject DN: CN=CA Audit,O=IPA.LOCAL 201902271325
  Issuer DN: CN=Certificate Authority,O=IPA.LOCAL 201902271325
  Not Valid Before: Wed Feb 27 14:30:24 2019
  Not Valid After: Tue Feb 16 14:30:24 2021

Note the Not Valid After times for the ca_ocsp_signing and sslserver certificates. These are certificates we must renew.

Preparing the agent certificate §

The cert-fix command requires an agent certificate. We will use the IPA RA certificate. The pki-server CLI tool needs an NSSDB with the agent key and certificate. So we have to set that up. First initialise the NSSDB:

[root@f29-0 ~]# mkdir ra-nssdb
[root@f29-0 ~]# cd ra-nssdb
[root@f29-0 ra-nssdb]# certutil -d . -N
Enter a password which will be used to encrypt your keys.
The password should be at least 8 characters long,
and should contain at least one non-alphabetic character.

Enter new password: XXXXXXXX
Re-enter password: XXXXXXXX

Then create a PKCS #12 file containing the required key and certificates:

[root@f29-0 ra-nssdb]# openssl pkcs12 -export \
  -inkey /var/lib/ipa/ra-agent.key \
  -in /var/lib/ipa/ra-agent.pem \
  -name "ra-agent" \
  -certfile /etc/ipa/ca.crt > ra-agent.p12
Enter Export Password:
Verifying - Enter Export Password:

Import it into the NSSDB, and fix up trust flags on the IPA CA certificate:

[root@f29-0 ra-nssdb]# pk12util -d . -i ra-agent.p12
Enter Password or Pin for "NSS Certificate DB":
Enter password for PKCS12 file:

[root@f29-0 ra-nssdb]# certutil -d . -L

Certificate Nickname                                         Trust Attributes

ra-agent                                                     u,u,u
Certificate Authority - IPA.LOCAL 201902271325               ,,

[root@f29-0 ra-nssdb]# certutil -d . -M \
    -n 'Certificate Authority - IPA.LOCAL 201902271325' \
    -t CT,C,C
Enter Password or Pin for "NSS Certificate DB":

[root@f29-0 ra-nssdb]# certutil -d . -L

Certificate Nickname                                         Trust Attributes

ra-agent                                                     u,u,u
Certificate Authority - IPA.LOCAL 201902271325               CT,C,C

Running cert-fix §

Let’s look at the cert-fix command options:

[root@f29-0 ra-nssdb]# pki-server cert-fix --help
Usage: pki-server cert-fix [OPTIONS]

      --cert <Cert ID>            Fix specified system cert (default: all certs).
  -i, --instance <instance ID>    Instance ID (default: pki-tomcat).
  -d <NSS database>               NSS database location (default: ~/.dogtag/nssdb)
  -c <NSS DB password>            NSS database password
  -C <path>                       Input file containing the password for the NSS database.
  -n <nickname>                   Client certificate nickname
  -v, --verbose                   Run in verbose mode.
      --debug                     Run in debug mode.
      --help                      Show help message.

It’s not a good idea to put passphrases on the command line in the clear, so let’s write the NSSDB passphrase to a file:

[root@f29-0 ra-nssdb]# cat > pwdfile.txt

Finally, I was ready to execute cert-fix:

[root@f29-0 ra-nssdb]# pki-server cert-fix \
    -d . -C pwdfile.txt -n ra-agent \
    --cert sslserver --cert ca_ocsp_signing \

Running with --verbose causes INFO and higher-level log messages to be printed to the terminal. Running with --debug includes DEBUG messages. If neither of these is used, nothing is output (unless there’s an error). So I recommend running with --verbose.

So, what happened? Unfortunately I ran into several issues.

389 DS not running §

The first issue was trivial, but likely to occur if you have to cert-fix a FreeIPA deployment. The ipactl [re]start command will shut down every component if any component failed to start. Dogtag didn’t start, therefore ipactl shut down 389 DS too. As a consequence, Dogtag failed to initialise after cert-fix started it, and the command failed.

So, before running cert-fix, make sure LDAP is working properly. To start it, use systemctl instead of ipactl:

# systemctl start dirsrv@YOUR-REALM

Connection refused §

One issue I encountered was that a slow startup of Dogtag caused failure of the tool. cert-fix does not wait for Dogtag to start up properly. It just ploughs ahead—only to encounter ConnectionRefusedError.

I worked around this—temporarily—by adding a sleep after cert-fix starts Dogtag. A proper fix will require a change to the code. cert-fix should perform a server status check, retrying until it succeeds or times out.

TLS handshake failure §

The next error I encountered was a TLS handshake failure:

  HTTPSConnectionPool(host='f29-0.ipa.local', port=8443): Max retries
  exceeded with url: /ca/rest/certrequests/profiles/caManualRenewal
  (Caused by SSLError(SSLError(185073780, '[X 509: KEY_VALUES_MISMATCH]
  key values mismatch (_ssl.c:3841)')))

I haven’t worked out yet what is causing this surprising error. But I wasn’t the first to encounter it. A comment in the Bugzilla ticket indicated that the workaround was to remove the IPA CA certificate from the client NSSDB. This I did:

[root@f29-0 ra-nssdb]# certutil -d . -D \
    -n "Certificate Authority - IPA.LOCAL 201902271325"

After this, my next attempt at running cert-fix succeeded.

Results §

Looking at the previously expired target certificates, observe that the certificates have been updated. They have new serial numbers, and expire in 15 months:

[root@f29-0 ra-nssdb]# certutil -d /etc/pki/pki-tomcat/alias \
    -L -n 'Server-Cert cert-pki-ca' | egrep "Serial|Not After"
      Serial Number: 12 (0xc)
          Not After : Wed May 27 12:45:25 2020

[root@f29-0 ra-nssdb]# certutil -d /etc/pki/pki-tomcat/alias \
    -L -n 'ocspSigningCert cert-pki-ca' | egrep "Serial|Not After"
      Serial Number: 13 (0xd)
          Not After : Wed May 27 12:45:28 2020

Looking at the output of getcert list for the target certificates, we see that Certmonger has not picked these up (some lines removed):

[root@f29-0 ra-nssdb]# getcert list -i 20190227033149
Number of certificates and requests being tracked: 9.
Request ID '20190227033149':
   ca-error: Internal error
   stuck: no
   CA: dogtag-ipa-ca-renew-agent
   issuer: CN=Certificate Authority,O=IPA.LOCAL 201902271325
   subject: CN=OCSP Subsystem,O=IPA.LOCAL 201902271325
   expires: 2019-02-27 14:45:24 AEDT
   eku: id-kp-OCSPSigning

[root@f29-0 ra-nssdb]# getcert list -i 20190227033152
Number of certificates and requests being tracked: 9.
Request ID '20190227033152':
   ca-error: Internal error
   stuck: no
   CA: dogtag-ipa-ca-renew-agent
   issuer: CN=Certificate Authority,O=IPA.LOCAL 201902271325
   subject: CN=f29-0.ipa.local,O=IPA.LOCAL 201902271325
   expires: 2019-02-27 14:45:24 AEDT
   dns: f29-0.ipa.local
   key usage: digitalSignature,keyEncipherment,dataEncipherment
   eku: id-kp-serverAuth

Restarting Certmonger (systemctl restart certmonger) resolved the discrepancy.

Finally, ipactl restart puts everything back online. cert-fix has saved the day!

[root@f29-0 ra-nssdb]# ipactl restart
Restarting Directory Service
Starting krb5kdc Service
Starting kadmin Service
Starting httpd Service
Starting ipa-custodia Service
Starting pki-tomcatd Service
Starting ipa-otpd Service
ipa: INFO: The ipactl command was successful

Issues and caveats §

Besides the issues already covered, there are several scenarios that cert-fix cannot handle.

Expired CA certificate §

Due to the the long validity period of a typical CA certificate, the assumption that the CA certificate is valid is the safest assumption made by cert-fix. But it is not a safe assumption.

The most common way this assumption is violated is with externally-signed CA certificates. For example, the FreeIPA CA in your organisation is signed by Active Directory CA, with a validity period of two years. Things get overlooked and suddenly, your FreeIPA CA is expired. It may take some time for the upstream CA administrators to issue a new certificate. In the meantime, you want to get your FreeIPA/Dogtag CA back up.

Right now cert-fix doesn’t handle this scenario. I think it should. As far as I can tell, this should be straightforward to support. Unlike the next few issues…

Agent certificate expiry §

This concerns the assumption that you have a valid agent certificate. Dogtag requires authentication to perform privilieged operations like certificate issuance. Also, the authenticated user must be included in audit events. cert-fix must issue certificates properly (with limiited temporary fudging tolerated for operational efficacy), therefore there must be an agent credential. And if your agent credential is a certificate, it must be valid. So if your agent certificate is expired, it’s Catch-22. That is why the tool, as currently implemented, must assume you have a valid, non-expired agent certificate.

In some deployments the agent certificate is renewed on a different cadence from subsystem certificates. In that case, this scenario is less like to occur—but still entirely possible! The assumption is bad.

In my judgement it is fairly important to find a workaround for this. One idea could be to talk directly to LDAP and set a randomly-generated password on an agent account, and use that to authenticate. After the tool exits, the passphrase is forgotten. This approach means cert-fix needs a credential and privileges to perform those operations in LDAP.

Speaking of LDAP…

389 DS certificate authentication §

In FreeIPA deployments, Dogtag is configured to use the subsystem certificate to bind (authenticate) to the LDAP server. If the subsystem certificate is expired, 389 DS will reject the certificate; the connection fails and and Dogtag cannot start.

A workaround for this may be to temporarily reconfigure Dogtag to use a password to authenticate to LDAP. Then after the new subsystem certificate was issued, it must be added to the pkidbuser entry in LDAP, and certificate authentication reinstated.

This is not a FreeIPA-specific consideration. Using TLS client authentication to bind to LDAP is a supported configuration in Dogtag / RHCS. So we should probably support it in cert-fix too, somehow, since the point of the tool is to avoid complex manual procedures in recovering from expired system certificates.

389 DS service certificate expiry §

You know the tune by now… if this certificate is expired, Dogtag can’t talk to LDAP and can’t start, therefore a new LDAP certificate can’t be issued.

Issuing a temporary certificate with the same serial number may be the best way forward here, like what we do for the Dogtag HTTPS certificate.

Re-keying §

…is not supported. But it is a possible future enhancement

Serial number reuse §

Re-using a serial number is prohibited by the X.509 standard. Although the temporary re-issued HTTPS certificate is supposed to be temporary, what if it did leak out? For example, another client that contacted Dogtag while that certificate is in use could log it to a Certificate Transparency log (not a public one, unless your Dogtag CA is chained to a publicly trusted CA). If this occurred, there would be a record that the CA had misbehaved.

What are the ramifications? If this happened in the public PKI, the offending CA would at best get a harsh and very public admonishment, and be put on notice. But trust store vendors might just straight up wash their hands of you and yank trust.

In a private PKI is it such a big deal? Given our use case—the same subject names are used—probably not. But I leave it as an open topic to ponder how this might backfire.

Conclusion §

In this post I introduced the pki-server cert-fix subcommand. The purpose of this tool is to simplify and speed up recovery when Dogtag system certificates have expired.

It does what it says on the tin, with a few rough edges and, right now, a lot of caveats. The fundamentals are very good, but I think we need to address number of these caveats for cert-fix to be generally useful, especially in a FreeIPA context. Based on my early experiences and investigation, my suggested priorities are:

  1. Workaround for when the agent certificate is expired. This can affect every kind of deployment and the reliance on a valid agent certificate is a significant limitation.
  2. Workaround for expired subsystem certificate when TLS client authentication is used to bind to LDAP. This affects all FreeIPA deployments (standalone Dogtag deployments less commonly).
  3. Support renewing the CA certificate in cert-fix. A degree of sanity checking or confirmation may be reasonable (e.g. it must be explicitly listed on the CLI as a --cert option).
  4. Investigate ways to handle expired LDAP certificate, if issued by Dogtag. In some deployments, including some FreeIPA deployments, the LDAP certificate is not issued by Dogtag, so the risk is not universal.

In writing this post I by no means wish to diminish Dinesh’s work. On the contrary, I’m impressed with what the tool already can do! And, mea culpa, I have taken far too long to test this tool and evaluate it in a FreeIPA setting. Now that I have a clearer picture, I see that I will be very busy making the tool more capable and ready for action in FreeIPA scenarios.

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