Smart Card resources, services, workflows and guidance

Apple Macintosh macOS Smart Card resources

Smart Card usage: Apple Platform Development

Apple Smart Card Configuration Profile Settings: Link

Matt Woodruff github SmartCard-Scripts: Link

PIV Authentication on macOS
As federal IT networks and systems expand, especially in light of recent Bring-Your-Own-Device (BYOD) models gaining popularity, it has become necessary to extend mandatory security controls to previously unsupported devices. This guide provides implementation resources to enable smart card authentication on Mac operating system (macOS) workstations and laptops for macOS-local and windows-domain accounts.

https://playbooks.idmanagement.gov/piv/network/mac/

synthetic-intelligence github: Link

a) Local account pairing

Configuring a Mac for smart card–only enforces authentication

Link

Enabling screen saver on token removal

The screen saver can be configured to start automatically when a user removes their token. This option appears only after a smart card has been paired. There are two main ways to accomplish this:

In Security & Privacy preferences on the Mac, use the Advanced button and select “Turn on screen saver when login token is removed”. Make sure the screen saver settings are configured, then select “Require a password immediately after sleep or screen saver begins”.

In a mobile device management (MDM) solution, use the tokenRemovalAction key.

Apple Source Browser – SmartCardServices.xcode

SmartCardServices(7) Miscellaneous Information Manual SmartCardServices(7)

NAME
SmartCardServices – overview of SmartCard support

DESCRIPTION
SmartCardServices is a set of components for macOS SmartCard support.

SmartCards which adhere to the PIV standard are supported natively by
macOS. Additional smartcard support is provided through the installation
of third party drivers. Access to SmartCard content is possible using
the keychain interface.

SmartCard certificates are automatically added to a user’s keychain when
a SmartCard is inserted and authenticated. SmartCard certificates can be
listed with the security command using the list-smartcards or
export-smartcard options. Keychain Access GUI cannot be used to
manipulate or list these certificates.

Card Provisioning
In order to use smartcards with macOS, identities must be
populated into Slot 9a (PIV Authentication) and 9d (Key
Managment), and optionally 9c, if signing functions such as e-
mail signing are to be used.

Supported Services
Authentication Login, Screen Saver, ssh, sudo, Safari, PAM
Authorization, su, Finder

Authentication is performed using the PIV Authentication
Identity (9a). For login, the Key Management key (9d) is used
to unlock the encrypted harddrive (Apple Silicon devices) and to
unlock Keychain.

Encryption and Signing Mail and code signing

Requires signing certificate.

Mail in macOS will use Digital Signing and Encryption Identities
on an attached smartcard. Signing and Encryption buttons will
appear in the toolbar when a case-sensitive email address
matches the subject or subject alternative name on a smartcard’s
signing or encryption certificate.

SETUP
macOS smart card support can be configured for either fixed key mapping
or attribute based mapping. To configure fixed keymapping, use sc_auth(8)
or use the pairing notification dialog which automatically appears when
an unassociated SmartCard is inserted into a reader. This dialog can be
globally suppressed by:

sudo defaults write /Library/Preferences/com.apple.security.smartcard UserPairing -bool NO

To configure attribute mapping, use the appropriate AttributeMapping
section in the configuration file as described below. A configuration
file is not provided by default. If no AttributeMapping section exists or
the configuration file is missing, attribute matching is not used. If
both fixed key mapping and attribute mapping are able to associate the
inserted SmartCard with a user, attribute mapping takes precedence.

By default, certificates do not need to be trusted to allow pairing.
Certificate trust can be globally modified using the
checkCertificateTrust setting:

sudo defaults write /Library/Preferences/com.apple.security.smartcard checkCertificateTrust -int

Possible trust level values are:

0 certificate trust check is turned off

1 certificate trust check is turned on

2 certificate trust check is turned on and revocation check is set to
the soft level (If the OCSP/CRL server is unreachable, authentication
succeeds)

3 certificate trust check is turned on and revocation check is set to
the hard level (A verified positive response from the OCSP/CRL server
is needed to succeed)

CONFIGURATION FILE
A configuration file for SmartCardServices may be set up using
/etc/SmartcardLogin.plist and should use a standard plist format. The
file permissions must be world readable (644) and recommended ownership
is root or a system administrator.

It may contain the following optional sections:

UserSelectorPath
This string value points to the custom UserSelector process
which is used for associating users with SmartCards. If this
section is not found or the component at that path does not
exist, the system UserSelector is used.

TrustedAuthorities
It is possible to specify the Certificate Authorities to be used
for the trust evaluation of SmartCard certificates. This trust
works in conjunction with Certificate Trust settings (1, 2, or 3
required) and is also referred to as Certificate Pinning. Place
SHA-256 fingerprints of Certificate Authorities (as string
values, comma delimited, and without spaces) in an array named
TrustedAuthorities. When Certificate Pinning is used, only
SmartCard certificates issued by a Certificate Authorities in
this list will be evaluated as trusted. Please note that
TrustedAuthorities will be ignored when the
checkCertificateTrust setting is set to 0 (off).

AttributeMapping
This section is used to set up an optional attribute mapping for the system UserSelector. For each available user record in OpenDirectory, certificate field values are combined into a format string which is then compared to a predefined attribute string. Specifying multiple OpenDirectory attribute strings or using conditional formatting in the format string is not supported. All items in this section are mandatory.

Built into Sierra 10.12 and High Sierra 10.13 is the ability for organizations to build out Active Directory attribute mapping for SmartCards. If the mapping is done correctly could allow any individual with the correct certificate on their SmartCard to log into the Mac without the need of creating a local user account beforehand.

LOCAL ACCOUNTS

Download and change the name of Local-SmartcardLogin.plist to “SmartcardLogin.plist”
Customize the SmartCardLogin.plist to build the correct field mappings to AD for your environment.
Use Composer to build a package that installs this plist into the /etc folder
Use Jamf Pro to distribute to your Macs

MOBILE ACCOUNTS

Download and change the name of Mobile-SmartcardLogin.plist to “SmartcardLogin.plist”
Customize the SmartCardLogin.plist to build the correct field mappings to AD for your environment.
Use Composer to build a package that installs this plist into the /etc folder

2) Use Jamf Pro to distribute to your Macs

—– eof Jamf

fields contains an array of string values. This is the list of
certificate field names that will be used to compare against the
attribute string. The following field names are supported:

– Common Name

– RFC 822 Name

– NT Principal Name

– Organization

– OrganizationalUnit:1

– OrganizationalUnit:2

– OrganizationalUnit:3

– Country

formatString contains a string value which specifies how
certificate fields will be concatenated. Dollar sign plus number
(starting with 1) is replaced with the field value at the
appropriate index.

dsAttributeString contains a string value. This defines the
target attributes for the desired OpenDirectory user record. It
will be compared against the generated format strings.

NotEnforcedGroup
NotEnforcedGroup contains a string value. This defines the name
of an Open Directory group that will not be included in
mandatory smartcard enforcement, when enabled. This is
sometimes referred to as User Based Enforcement, and provides
per-user granularity to SmartcardServices.

Please see section SMARTCARD ENFORCEMENT for more details.

In addition, the system must be configured to allow users who
are not paired with SmartCard to login with password:

sudo defaults write /Library/Preferences/com.apple.security.smartcard allowUnmappedUsers -int 1

Remember to update the FileVault Login settings using the
diskutil apfs updatePreboot command.

ATTRIBUTE MAPPING CONFIG EXAMPLE
Sample configuration (Please note that if copying and pasting the
provided example, the second line starting with should be a single line. This example presents it as
two lines due to formatting and will need a line break removed to be a
properly formatted plist):

AttributeMapping

fields

Common Name
RFC 822 Name

formatString
$2-$1
dsAttributeString
dsAttrTypeNative:longName

In this example, assume that a certificate has a Common Name with value
“John Appleseed” and an RFC 822 Name with value “jappleseed@apple.com”.
The formatString “$1-$2” will join both values and the result will be
jappleseed@apple.com-John Appleseed. This result will be compared to a
directory attribute – in this case, the dsAttrTypeNative:email field.
When a match is found, the corresponding user is considered associated
with the SmartCard.

OFFLINE SMARTCARD LOGIN VIA KERBEROS CACHING
In environments where macOS clients may not always be able to reach
Directory Servers, cached SmartCard login support is possible via
Kerberos caching. This configuration allows users with network accounts
to authenticate via SmartCard when operating outside the enterprise
environment. Note: Initial account setup requires machine binding and
access to the directory server.

KERBEROS ATTRIBUTE MAPPING CONFIG EXAMPLE
Sample configuration (Please note that if copying and pasting the
provided example, the second line starting with should be a single line. This example presents it as
two lines due to formatting and will need a line break removed to be a
properly formatted plist).

The following example SmartcardLogin.plist file matches the Subject
Alternative Name type, NT Principal Name, in the identity on the
SmartCard against the Directory Server’s altSecurityIdentities field
(Kerberos), allowing for offline login and authentication:

AttributeMapping

fields

NT Principal Name

formatString
Kerberos:$1
dsAttributeString
dsAttrTypeStandard:AltSecurityIdentities

Additional considerations
Certificate Checking: checkCertificateTrust should not be set to 3 (hard
revocation check) if certificate revocation or OCSP servers are not
always available to the client machines.
User accounts should be created setting the “Create Mobile User on Login”
flag in the Directory Utility application, when binding client machines
via the command line, or with a Configuration Profile. When used in
conjunction with Kerberos Caching, a mobile user account will allow users
to authenticate either online and offline.

SMARTCARD ENFORCEMENT
There may be a requirement to use a SmartCard for user authentication in
your environment. Enforcing the use of the SmartCard for the entire
system can be done using MDM or a command:

sudo defaults write /Library/Preferences/com.apple.security.smartcard enforceSmartCard -bool true

In addition, the system might be configured to allow users who are not
paired with SmartCard to login with password using MDM or the command:

sudo defaults write /Library/Preferences/com.apple.security.smartcard allowUnmappedUsers -int 1

Remember to update the FileVault Login settings using the diskutil apfs
updatePreboot command.

It is also possible to specify an entire group whose members will be
exempted from using the card. See the NotEnforcedGroup section above for
usage. Please note that this option is not compatible with FileVault
Unlock.

In addition, it is possible to use the attribute
kDSNativeAttrTypePrefix:SmartCardEnforcement in the OpenDirectory user
record. It always refers to that specific user and can take the following
values:

0 the system default is respected

1 card use is always enforced

2 card enforcement is always disabled, the user can use a password

If ActiveDirectory is used in your environment, the value of the
userAccountControl attribute is respected.

Temporarily disabling card enforcement
In case the system is configured for SmartCard enforced login and this
cannot be used, the following command can be used to enable password
login once:

security filevault skip-sc-enforcement

For more details please see the man page of the security command.

Evaluation order
The exceptions for enforcement are processed in the following order:

– OD kDSNativeAttrTypePrefix:SmartCardEnforcement

– AD userAccountControl

– NotEnforced group (not available in FileVault Unlock)

– AllowUnmappedUsers setting

– System-wide setting using defaults or MDM

EXTENSIONS
Extensions can be created using the Xcode SmartCard Token Extension
template. Refer to the developer documentation for further details.
To enable the app extension and make the token available to the system
for authentication, launch the sc_auth command line tool with value of
‘‘com.apple.ctk.class-id’ from Info.plist:

sudo sc_auth enable_for_login -t com.example.HostApp.TokenExtension

SYSTEM REPORT
It is possible to show the current status of SmartCardServices by
command:

system_profiler SPSmartCardsDataType

Information presented includes reader, reader driver, card, card driver,
available smartcards and provisioned certificates.

USB SMART CARD READER DRIVERS
OS X has built-in support for USB CCID class-compliant SmartCard readers.
For other readers, install the reader driver in
/usr/local/libexec/SmartCardServices/drivers. Each driver is a bundle.
The bundle contains an XML file Info.plist which contains the device’s
USB vendor ID and product ID. For detailed description of the plist
format and how to write a reader driver, see
http://pcsclite.alioth.debian.org/api/group__IFDHandler.html

SMART CARD APDU LOGGING
It is possible to turn on logging for SmartCards by setting the global
preference:

sudo defaults write /Library/Preferences/com.apple.security.smartcard Logging -bool yes

After a SmartCard reader is connected (or after reboot) all operations
including contents of sent and received APDU messages are logged into the
system log. Logging uses the subsystem com.apple.CryptoTokenKit and
category APDULog so it is possible to set up logging with a predicate
(see log(1) ). Example:

log show –predicate ‘(subsystem == “com.apple.CryptoTokenKit”) && (category == “APDULog”)’

To avoid security and privacy risks that could occur if logging is turned
on indefinitely, the logging setting is one-shot – it must be turned on
by the command above to start logging again with a new reader. This
includes unplugging and replugging the same reader. If a USB token is
used, it is treated as both a card and a reader. Use ssh from a remote
system to log back in and re-enable logging as needed

DISABLING SMART CARD DRIVERS
It is possible to turn off token drivers by setting the global
preference:

sudo defaults write /Library/Preferences/com.apple.security.smartcard DisabledTokens -array com.apple.CryptoTokenKit.pivtoken

This statement disables built-in PIV SmartCard driver, but it can be used
to disable any token driver or set of token drivers just by replacing
token driver extension identifier.

ENTITLEMENT
Sandboxed PCSC clients require ‘com.apple.security.smartcard=YES’
entitlement. Non-sandboxed PCSC clients do not require such entitlement
(in order to keep backward compatibility with macOS < 10.10). Users of
TKSmartCard* API from CryptoTokenKit.framework always require that
entitlement no matter whether they are sandboxed or not.

SEE ALSO
defaults(1), log(1), security(1), UserSelector(7), pam_smartcard(8),
sc_auth(8), ssh-keychain(8)

macOS Security Link:
https://github.com/usnistgov/macos_security/blob/main/rules/supplemental/supplemental_smartcard.yaml

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