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V4/User Certificates

Revision as of 15:21, 21 January 2016 by Adelton (talk | contribs) (https://fedorahosted.org/sssd/ticket/2742 was resolved)
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Name: V4/User Certificates
Ticket: #4238
Target version: 4.2.0
Author: Mkosek
Incomplete.png Pending review
Last updated: 2016-01-21 by Adelton


FreeIPA 4.1.0 or older and its PKI component can release certificates for hosts and services, both are using the same PKI profile. This functionality covers basic needs of servers and their services, mostly TLS encryption, rarely also TLS authentication (current profile can serve both as client and server certificate for authentication). However, it does not allow users to also leverage the benefits of the integrated PKI, making it a long standing PKI debt. With multiple certificate profiles and ability to create lightweight sub-CAs, the user certificate extension is finally realizable.

Use Cases

Smart Card Authentication

This is the primary use case for this feature. FreeIPA administrators should be able to issue Smart Cards (or X509 certificates in general) to their users and configure FreeIPA to enable matching of the certificate to the user entry itself. The feature will primarily focus on the new SSSD PKCS#11 interface (SSSD RFE ticket #546). The alternative for SSSD PKCS#11 interface is the standard pam_pkcs11 that is available also on non-Linux platforms, but does not provide tight integration with FreeIPA - certificate matching has to be configured on each client (example config).

This use case is generic and can result in different implementations, given there are several options how the Smart Card certificate is loaded to FreeIPA and if it is available before hand at all.

Client Certificate Authentication

PKI needs to be able to issue user certificates that can be used for user certificate authentication against server, for example to mod_nss or mod_ssl Apache modules.

S/MIME and User Signing Certificates

Certificates can be used not only for user authentication, but also for signing (S/MIME). Mail user agents are even able to catch them automatically from LDAP, as long as the certificate is in user entry in userCertificate;binary attribute (related MozillaZine discussion). FreeIPA should be able to to both issue the certificate for signing in its default profiles, but be able to serve as a server for MUAs to automatically download the user S/MIME certificates.


This feature consists of 4 main parts that need to be designed to met the proposed use cases:

  • Ability to issue user certificate with different profiles and key usage (client/server authentication, signing or subject). This is being solved by V4/Certificate Profiles and V4/Sub-CAs designs.
  • Requesting and storing user certificates from PKI in the tree so that they can be searched, displayed by Web UI and revoked, when needed
  • Searching certificates by clients - Smart Card, S/MIME use cases
  • Enrolling external certificates to the system - Smart Card use case

Storing User Certificates

Service and Host certificates are currently stored in the entries themselves, when the certificate is request by the cert-request command. When service/host is deleted, the stored certificate is decoded, serial number identified and certificate then revoked in the PKI. The certificate is also revoked when the service/host requests another certificate. There is thus always just one active certificate for a service/host. Web UI is able to display the service/host certificate and allow also manual revocation.

User certificates, multiple certificate profiles and sub-CAs add a twist to this design as not all certificates need to be stored directly in the user/service/host entry. For example, while S/MIME signing certificates should be in the user entry so that mail clients can search for them, TLS encryption or especially short-lived certificates (Web SSO or kx509) should not be in the user entry at all to avoid unnecessary pollution of the Directory Server replication changelog or making user entry unnecessary big (and thus adding a risk of LDAP performance problems).

This design therefore removes the assumption that all certificates are stored in user entry.

Searching Certificates by Clients

In both cases, when (user) certificate is stored in an entry or not, clients searching user authenticating with such certificate (read - Smart Card use case) have to identify the user entry. The certificate entry itself does not always identify the user entry in LDAP, the clients (SSSD or pam_pkcs11) have to search for the user by other means.

There are several options how the clients can run the search:

  • Binary match on whole certificate: this is the simplest approach to do as the user certificate can be retrieved from the Smart Card and used in an LDAP filter. This approach requires the certificate to be loaded in FreeIPA before Smart Card authentication. The performance cost for searching by the whole blob (around 1K of binary certificate) was not found to be significant enough to not allow this as an option.
  • CertificateMatch or CertificateExactMatch: support of the RFC 4523, section 3.2 in the Directory Server would allow search by a certificate field directly in the LDAP search. However, this standard is not supported in the 389 Directory Server yet, it is a complex feature to add. See for example research done based on other LDAP server variants (OpenLDAP paper, related presentation). This approach also assumes that the certificate is in the user entry.
  • Match on custom certificate attributes: in some environments it is not possible for FreeIPA to dictate what should be in the certificate as the certificate is provided by a 3rd party CA. However this CA includes information in the certificate that is known in advance and is unique per user. In this case is important to be able to pre-provision user objects with the matching attribute+value that will be found on the user's Smart Card. This also means SSSD needs to find, from a global configuration entry, what attribute it needs to extract in order to use it to search the correct user entry. This allows use of certificates without an explicit per-user provisioning step when they are given a certificate/Smart Card.
  • Match on a Kerberos principal: this is a special case of the Match on custom certificate attributes option, but it is being called out specifically as it would be the best default for FreeIPA issued certificates that already contain the Kerberos principal SAN extension and thus no modification to FreeIPA is needed.

Given the high development costs of a CertificateMatch, this design aims to cover support for Binary match on whole certificate option and also discusses the proposal for the Match on custom certificate attributes option.

Certificate Identity Mapping

Not Supported Yet
Certificate Identity Mapping feature was not implemented in FreeIPA 4.2.0 release and was postponed to later release

As noted in the Match on custom certificate attributes option, admin should be able to specify custom rules for extracting the selected certificate fields and use them in a user search filter. This leads to a new Certificate Identity Mapping concept - a server side configuration that would specify how the user should be search when specific certificates are used.

Certificate Identity Mapping parts

  • Selector: what certificates does it apply to - especially issuer. It can also select key usage or other certificate fields that the client (SSSD) will use to match the authentication Smart Card/certificate
  • LDAP filter: the actual LDAP filter with placeholders from the certificate that will be used for searching the user. The placeholder should be an ASN.1 compatible way of telling SSSD the path to the attribute itself. It should also support custom certificate extensions, i.e. custom OID

When Smart Card is authenticating to the system, SSSD would check all the Certificate Identity Mapping, see which matches the public certificate, extract the selected fields and use the resulting LDAP filter for user search.

The search itself is only one part of the problem. FreeIPA also needs to be able to store the unique per user configuration and an attribute and let admin set it.

Storing Custom User Identifier

When Certificate Identity Mapping are used, FreeIPA should be able to provide a convenient attribute that can be used for storing the custom matching field value (unless standard user attribute like employeID is used). There should be a new attribute just for this purpose, with Syntax and MatchingRule flexible enough to cover most use cases:

OID Attribute Name Syntax Description
TBD ipaUserCertMatch TBD Custom matching attribute selection.

Granularity of the Certificate Identity Mapping

Admins should be able to set the profile both for internal CA, but especially for the external CA, from which each may use different combination of the fields for the matching.

Changes to Certificate Bookkeeping

This design changes the default expectation of current cert management API for hosts and services as it always expected userCertificate to be filled and used for certificate manipulation and bookkeeping (listing, revoking). Instead, some certificates may not be stored in the user entry at all and only stored in Dogtag (especially the short lived certificates).

Revocation of the Certificates

All older version of FreeIPA always revoked the certificate when an object (host, service) was deleted or disabled. With every revocation, the certificate has to be added to the revocation list and properly distributed in the CRL object. Big CRL revocation lists may cause issues with replication (#4048) or CRL processing.

With this feature, objects are likely to have multiple certificates and the revocation list growth would increase even more. This design therefore plans to stop revoking certificates automatically as in most cases (deleting objects/certificates when not useful) the certificate does not have to be added to the revocation list and can be simply deleted and left for natural expiration. However, there are still cases when revocation is due (the key was compromised, user leaves organization and retained a copy of the private key) and FreeIPA needs to have ability to revoke these certificates.

Feature Management


When viewing an active user's entry in FreeIPA WebUI the number of certificates issued to the user will be displayed along with a button to view a list of these certificates as Base64 encoded blobs. The functionality to add and remove arbitrary certificates to the user (UI counterpart of commands discussed in the section below) will also be developed.

WebUI with also be extended to allow to request certificates for users when a suitable Certificate Profile to handle this task is configured.


Both userCertificate values for externally issued certificates and the special matching attribute (ipaUserCertMatch) can be added with the standard object-mod command. These entries can live in similar tree as the Sub-CAs.

Using Certificate Profiles feature it is possible to issue certificates to users using ipa cert-request command. If the profile has ipaCertProfileStoreIssued attribute set to TRUE, then the whole DER encoded certificate blob will be stored in the userCertificate;binary attribute of the user entry.

Moreover, ipa user-add-cert and ipa user-remove-cert commands were developed to add or remove arbitrary certificates to/from user's userCertificate;binary attribute. Both command share the following syntax:

 ipa user-{add|remove}-cert [UID] --certificate=[BASE64 BLOB] 

where UID corresponds to the user login and BASE64 BLOB is the Base64 encoded blob between -----BEGIN CERTIFICATE----- and -----END CERTIFICATE----- lines in standard PEM certificate. The --certificate can be specified more that once to add or remove multiple certificates in one call.


A per certificate profile configuration (Certificate Profile design) should be added, allowing admin select the proper userCertificate field treatment for the respective profile, mostly based whether the certificate is short-lived or long-lived:

  • Store certificate
  • Do not track issued certificate

If the Store certificate option is selected, there should be another option available:

  • Automatically revoke certificate when identity is disabled or deleted


Upgraded FreeIPA servers should default to Store issued and enrolled certificates to avoid change of behavior with service and host certificates. New installations should default to only Record issued and enrolled certificate to avoid storing unnecessary data.

How to Test

Using FreeIPA/Dogtag PKI to issue user certificates

  • create/import a new certificate profile for handling requests for user certificates. For quick testing of the feature you can just export the default FreeIPA certificate profile to a file, change the profileId and desc fields to values you like and import the modified profile back to FreeIPA:
$ ipa certprofile-show caIPAserviceCert --out=caIPAuserCert.txt
...edit the resulting file...
$ ipa certprofile-import caIPAuserCert --file=caIPAuserCert.txt --store=True

For a comprehensive guide to preparation of certificate profile tailored to a specifc use case see this blog post from Fraser Tweedale

  • add a new CA ACL which permits requesting certificates for user entries and add the custom profile to this CA ACL
$ ipa caacl-add users_caIPAuserCert --usercat=all
$ ipa caacl-add-profile users_caIPAuserCert --certprofiles=caIPAuserCert
  • generate a certificate request for the user e.g. using OpenSSL
$ openssl req -new -newkey rsa:2048 -days 365 -nodes -keyout private.key -out cert.csr -subj '/CN=tuser'
  • use ipa cert-request command to request a new certificate for the user.
$ ipa cert-request cert.csr --principal=tuser --profile-id=caIPAuserCert
  • If using WebUI go to AuthenticationCertificates and click the Issue button. Select the custom profile in the Profile ID drop-down menu, fill in the user login in Principal field and paste the Base64 encoded CSR into the text field
  • ipa user-show and the user entry in WebUI should now display the Base64 encoded certificate in addition to other attributes
$ ipa user-show tuser
  User login: tuser
  First name: Test
  Last name: User
  Home directory: /home/tuser
  Login shell: /bin/sh
  Email address: tuser@ipadom.org
  UID: 553000003
  GID: 553000003
  Certificate: MIID/zCCAuegAwIBAgIBCz...
  Account disabled: False
  Password: False
  Member of groups: ipausers
  Kerberos keys available: False
  • the newly issued certificate should be visible when viewing list of certificates in WebUI

Using CLI commands to manager user certificates

  • generate one or more self-signed certificates using e.g. OpenSSL
$ openssl req -x509 -newkey rsa:2048 -days 365 -nodes -keyout private.key -out cert.pem -subj '/CN=tuser'
  • convert the certificate do DER for easier handling through CLI
$ openssl x509 -outform der -in cert.pem -out cert.der
  • use ipa user-add-cert to add the certificate(s) to the user:
$ ipa user-add-cert tuser --certificate="$(base64 cert.der)"
  • use ipa user-show tuser or view the user in the WebUI to verify that the newly added certificate is displayed
$ ipa user-show tuser
  User login: tuser
  First name: Test
  Last name: User
  Home directory: /home/tuser
  Login shell: /bin/sh
  Email address: tuser@ipadom.org
  UID: 553000003
  GID: 553000003
  Certificate: MIIC8zCCAdugAwIBAgI...
  Account disabled: False
  Password: False
  Member of groups: ipausers
  Kerberos keys available: False
  • check that the following error is raised when you try to add the same certificate again
ipa: ERROR: 'usercertificate;binary' already contains one or more values
  • remove the certificate from the user entry using ipa user-remove-cert
$ ipa user-remove-cert tuser --certificate="$(base64 cert.der)"
  • run ipa user-show tuser or view the user in the WebUI; the certificate will be no longer present
$ ipa user-show tuser
  User login: tuser
  First name: Test
  Last name: User
  Home directory: /home/tuser
  Login shell: /bin/sh
  Email address: tuser@ipadom.org
  UID: 553000003
  GID: 553000003
  Account disabled: False
  Password: False
  Member of groups: ipausers
  Kerberos keys available: False
  • check that an attempt to remove already removed certificate will raise the error:
ipa: ERROR: usercertificate;binary does not contain 'one or more values to remove'

Using SSSD to lookup users by certificate

Starting with version 1.13.0 SSSD is now able to lookup user entries by the certificates issued to them. To test this feature sssd-dbus package must be installed.

  • enable SSSD Infopipe D-Bus interface by adding ifp to the services entry in the [sssd] section of SSSD configuration file (/etc/sssd/sssd.conf on Fedora).
  • restart sssd
  • add a certificate to the user entry with one of the methods discussed in previous sections. Make sure you have the PEM certificate file at hand
  • Query the SSSD D-Bus interface for the user entry associated with the certificate by running the following command as root:
# dbus-send --system --print-reply  --dest=org.freedesktop.sssd.infopipe /org/freedesktop/sssd/infopipe/Users \
org.freedesktop.sssd.infopipe.Users.FindByCertificate string:"$(cat cert.pem)"
  • check that the last element of the object path returned by the D-Bus interface is the same as the UID of the user possessing the certificate:
method return sender=:1.792 -> dest=:1.793 reply_serial=2 object path 

Use case: smart card authentication using SSSD and FreeIPA

Nathan Kinder put together blog series focused on practical provisioning of Smart Cards using OpenSC and testing it with FreeIPA:


Test Plan