4. Connect LDAP clients to the Secure LDAP service

Follow these steps:

1. Follow steps 1–11 in ldp.exe (Windows) to install the client certificates.
2. Go to Action > Connect to…
3. Enter the following connection settings:
   
   Name: Type a name for your connection, such as Google LDAP.
   Connection Point: “Select or type a Distinguished Name or Naming Context”
   Enter your domain name in DN format (for example, dc=example,dc=com for example.com).
   
   Computer: “Select or type a domain or server”
   ldap.google.com
   
   Use SSL-based Encryption: Checked
    
4. Click Advanced..., and enter the following details:
   
   Specify credentials: Checked
   Username: The access credential username from the Admin console
   Password: The access credential password from the Admin console
   Port Number: 636
   Protocol: LDAP
   Simple bind authentication: Checked
    
5. Click OK, and then click OK again.
6. If connectivity is successful, active directory contents in the base DN are displayed in the right pane.

To use Apache Directory Studio, connect through stunnel and use an access credential (username and password) generated in the Google Admin console. Assuming the credentials are in place, and assuming stunnel is listening on localhost port 1389, follow these steps:

1. Click File > New…
2. Select LDAP Browser > LDAP Connection.
3. Click Next.
4. Enter the connection parameters:
   
   Connection name: Choose a name, such as Google LDAP
   Hostname: localhost
   Port: 1389 (or the stunnel listen/accept port)
   Encryption method: No encryption (Note: If stunnel is running remotely, encryption between stunnel and the client is recommended.)
    
5. Click Next.
6. Enter the authentication parameters:
   
   Authentication Method: Simple Authentication
   Bind DN or user: The access credential username from the Admin console
   Bind password: The access credential password from the Admin console
    
7. Click Next.
8. Enter the base DN.
   This is your domain name in DN format (dc=example,dc=com for example.com).
9. Click Finish.

Atlassian Jira performs a user lookup to get more information about a user during user authentication. To make sure user authentication works correctly for this LDAP client, you'll need to turn on Read user information and Read group information for all organizational units where Verify user credentials is turned on. (For instructions, see Configure access permissions.)

Important: Using the following instructions potentially exposes the keystorePassword to users and log files. Take precautions to avoid unauthorized access to the local shell, logfile, and Google Admin console. As an alternative to the following instructions, use the stunnel4 method (see Optional: Use stunnel as a proxy). 

Note: The following instructions assume Jira is installed at /opt/atlassian/jira.

To connect an Atlassian Jira client to the Secure LDAP service:

1. Copy the certificate and key to your Jira server(s). (This is the certificate that’s generated in the Google Admin console while adding the LDAP client to the Secure LDAP service.)
   
   For example:
   $  scp ldap-client.key user@jira-server:
    
2. Convert the certificate and keys to Java keystore format. You will be prompted for passwords throughout this process. For simplicity, select a secure password and use the same one for all of the prompts.
   
   $  openssl pkcs12 -export -out jira-ldap.pkcs12 -in ldap-client.crt -inkey ldap-client.key

$  sudo /opt/atlassian/jira/jre/bin/keytool -v -importkeystore -srckeystore jira-ldap.pkcs12 -srcstoretype PKCS12 -destkeystore /opt/atlassian/jira/jira-ldap.jks -deststoretype JKS
    
3. Configure Jira to use the newly created keystore. Follow the directions here to add options:
   
   “-Djavax.net.ssl.keyStore=/opt/atlassian/jira/jira-ldap.jks -Djavax.net.ssl.keyStorePassword=password”
   
   On Linux:
   1. Edit /opt/atlassian/jira/bin/setenv.sh.
   2. Find the JVM_SUPPORT_RECOMMENDED_ARGS setting.
   3. Add “-Djavax.net.ssl.keyStore=/opt/atlassian/jira/jira-ldap.jks -Djavax.net.ssl.keyStorePassword=password”, replacing “password” with the password you selected above.
4. Restart Jira.
   
   $  /opt/atlassian/jira/bin/stop-jira.sh
$  /opt/atlassian/jira/bin/start-jira.sh
    
5. Sign in to the Jira web interface as an administrator.
   1. Go to Settings > User management. (For settings, go to the gear icon in the upper right.)
   2. Click User Directories.
   3. Click Add Directory.
   4. Choose LDAP as the type.
   5. Click Next.
6. Enter the following:

   Name	Google Secure LDAP
   Directory type	OpenLDAP
   Hostname	ldap.google.com
   Port	636
   Use SSL	Checked
   Username	Generate a username and password in the Google Admin console. For instructions, see Generate access credentials.
   Password	Generate a username and password in the Google Admin console. For instructions, see Generate access credentials.
   Base DN	Your domain name in DN format. (for example, dc=example,dc=com for example.com)
   Additional User DN	Optional. “ou=Users”
   Additional Group DN	Optional. “ou=Groups”
   LDAP Permissions	Read only
   Advanced Settings	Unchanged
   User Schema Settings > User Name Attribute	googleUid
   User Schema Settings > User Name RDN Attribute	uid
   Group Schema Settings > Group Object Class	groupOfNames
   Group Schema Settings > Group Object Filter	(objectClass=groupOfNames)
   Membership Schema Settings > Group Members Attribute	member
   Membership Schema Settings > Use the User Membership Attribute	Checked

    

7. Grant a role to a group.
   
   Before Atlassian Jira can allow a user to log in, that user must be a member of a group that's granted access to Jira.
   
   To grant a role to a group:
   1. Go to Settings > Applications > Application access. 
   2. In the Select group text box, enter the name of the Google group for which you want to provide access to Jira.

For instructions on connecting CloudBees Core to the Secure LDAP service, see Configure CloudBees Core with Google's Cloud Identity Secure LDAP.

Follow these steps:

1. Install and configure FreeRADIUS at /etc/freeradius/3.0/.
   
   Once FreeRADIUS is installed, you can add the LDAP configuration by installing the freeradius-ldap plugin.
   
   $  sudo apt-get install freeradius freeradius-ldap
    
2. Copy the LDAP client key and cert files to /etc/freeradius/3.0/certs/ldap-client.key and /etc/freeradius/3.0/certs/ldap-client.crt respectively.
   
   $  chown freeradius:freeradius
     /etc/freeradius/3.0/certs/ldap-client.*
$  chmod 640 /etc/freeradius/3.0/certs/ldap-client.*
    
3. Enable the LDAP module.
   
   $  cd /etc/freeradius/3.0/mods-enabled/
$  ln -s ../mods-available/ldap ldap
    
4. Edit /etc/freeradius/3.0/mods-available/ldap.
   1. ldap->server = 'ldaps://ldap.google.com:636'
   2. identity = username from the application credentials
   3. password = password from the application credentials
   4. base_dn = ‘dc=domain,dc=com’
   5. tls->start_tls = no
   6. tls->certificate_file = /etc/freeradius/3.0/certs/ldap-client.cer
   7. tls->private_key_file = /etc/freeradius/3.0/certs/ldap-client.key
   8. tls->require_cert = ‘allow’
   9. Comment out all fields in the breadcrumb representing the section 'ldap -> post-auth -> update'
5. ​Edit /etc/freeradius/3.0/sites-available/default.
   This modifies the FreeRadius client connection. If you are not using the default client, be sure to update the relevant client (inner-tunnel or any custom client) that you have configured.
    
   1. Modify the authorize section to add the following block at the bottom after the password authentication protocol (PAP) statement:
      
      if (User-Password) {
    update control {
        Auth-Type := ldap
    }
}
       
   2. In the authorize section, enable LDAP by removing the ‘-’ sign before it.
      
          #
          #  The ldap module reads passwords from the LDAP database.
          ldap
       
   3. Modify the authenticate section by editing the Auth-Type LDAP block as follows:
      
      # Auth-Type LDAP {
    ldap
# }
       
   4. Modify the authenticate section by editing the Auth-Type PAP block as follows:
      
      Auth-Type PAP {
    #  pap
    ldap
}

For instructions on connecting GitLab to the Secure LDAP service, see Configure Google Secure LDAP for GitLab.

For instructions on connecting Itopia/Ubuntu to the Secure LDAP service, see Configuring Google Cloud Identity LDAP on Ubuntu 16.04 for user logins.

Follow these steps:

1. On your Ivanti Web server, open OpenLDAPAuthenticationConfiguration.xml or OpenLDAPSSLAuthenticationConfiguration.xml in a text editor in both of the following folders:
   
   C:\ProgramData\LANDesk\ServiceDesk\servicedesk.Framework and C:\ProgramData\LANDesk\ServiceDesk\servicedesk.WebAccess (where servicedesk is the instance name)
2. Update the <Server> value to ldap.google.com.
3. Update the <Port> value to port 3268 for clear text with StartTLS enabled and to 3269 for SSL/TLS Port (the defaults are 389 for the clear text port or 636 for the SSL/TLS port). 
4. Set the <TestDN> value to your domain name in DN format. (for example, dc=example,dc=com for example.com).
5. To both ..ProgramData\LANDesk\ServiceDesk\ServiceDesk.Framework\tps.config, and ..ProgramData\LANDesk\ServiceDesk\WebAccess\tps.config, add the line:
   
   <add key="AuthenticationProvider" value="Touchpaper.Integrations.OpenLDAPLogon.OpenLDAPAuthenticationProvider" />
   
   or the line:
   
   <add key="AuthenticationProvider" value="Touchpaper.Integrations.OpenLDAPSSLLogon.OpenLDAPSSLAuthenticationProvider" />
    
6. In the Ivanti Configuration Center, open the required instance.
7. Adjacent to the Service Desk Framework application, click Edit.
   The Edit Application dialog for the Service Desk Framework appears.
8. In the Configuration parameters group, select Explicit only in the Logon policy list, then click OK.
9. Adjacent to the Web Access application, click Edit.
   The Edit Application dialog for Web Access appears.
10. In the Configuration parameters group, select Explicit only in the Logon policy list, and then click OK.

When logging in, use the associated domain user's network password.

Exception logging for LDAP server authentication

If you're having problems configuring LDAP server authentication, you can enable exception logging to help you to identify the problem. By default, this is disabled, and we recommend that you disable the exception logging again when you have finished your investigations.

To enable exception logging for LDAP Server authentication:

1. Open the appropriate authentication configuration XML file in a text editor:
   
   DirectoryServiceAuthenticationConfiguration.xml, OpenLDAPAuthenticationConfiguration.xml, or OpenLDAPSSLAuthenticationConfiguration.xml
2. Change the line:
   
   <ShowExceptions>false</ShowExceptions>
   to 
   <ShowExceptions>true</ShowExceptions>
    
3. Save the changes.

Follow these steps:

1. Convert the certificate and key files to one PKCS12 formatted file. At a command prompt, enter the following:
   
   If you are in macOS or Linux, use the following commands:​
   
   openssl pkcs12 -inkey ldap-client.key -in ldap-client.crt -export -out ldap-client.p12
   
   Enter a password to encrypt the output file.
    

   If you are in Windows, use the following commands:

   $  certutil -mergepfx ldap-client.crt ldap-client.p12
   
   Important:  The two files (<CERT_FILE>.crt and <CERT_FILE>.key) must be located in the same directory. Also, make sure both key and crt have an identical name (with a different extension). In this example, we use the names ldap-client.crt and ldap-client.key.

2. Go to the Control Panel.
3. In the search box, search for “certificate," and click Manage user certificates.
4. Go to Action > All Tasks > Import…
5. Select Current User, and click Next.
6. Click Browse…
7. In the file type dropdown in the lower-right corner of the dialog box, select Personal Information Exchange (*.pfx;*.p12).
8. Select the ldap-client.p12 file from step 2, click Open, and then click Next.
9. Enter the password from step 2 and click Next.
10. Select the Personal certificate store, click Next, and then click Finish.
11. Run Ldp.exe.
12. Go to Connection > Connect...
13. Enter the following connection details:
    
    Server: ldap.google.com
    Port: 636
    Connectionless: Unchecked
    SSL: Checked
     
14. Click OK.
15. Go to View > Tree.
16. Enter the base DN. This is your domain name in DN format. (for example, dc=example,dc=com for example.com).
17. Click OK.
18. If connectivity is successful, LDP.exe displays the Active Directory contents—such as all attributes present in the base DN—in the right pane.

For instructions on connecting Netgate/pfSense to the Secure LDAP service, see Configuring Google Cloud Identity as an Authentication Source.

To access your LDAP directory from the command line, you may use the OpenLDAP ldapsearch command.

Assuming your client certificate and key files are ldap-client.crt and ldap-client.key, your domain is example.com, and the username is jsmith:

$   LDAPTLS_CERT=ldap-client.crt LDAPTLS_KEY=ldap-client.key ldapsearch -H ldaps://ldap.google.com -b dc=example,dc=com '(uid=jsmith)'

This sets the relevant environment variables to point to the client keys. You can replace the other ldapsearch options with your desired filters, requested attributes, and so on. For other details, please see the ldapsearch man pages (“man ldapsearch”).

Follow these steps:

1. Convert the certificate and key files to one PKCS12 formatted file. At a command prompt, enter the following:
   
   openssl pkcs12 -inkey ldap-client.key -in ldap-client.crt -export -out ldap-client.p12
   
   Enter your password to encrypt the output file.
    
2. Click  in the upper-right corner of the menu bar, and type Keychain Access.
3. Open the Keychain Access application, and from the list on the left, click System.
4. Click the File option in the top-left menu bar and select Import Items.
5. Browse to the location with the generated ldap-client.p12, select ldap-client.p12, and click Open.
   If prompted, enter your password.
   A certificate with the name LDAP Client should now appear on the list of System Keychain certificates. 
6. Click the arrow next to the LDAP Client certificate. A private key appears below that. 
   1. Double-click the private key.
   2. From the dialog box, select the Access Control tab and click + in the lower-left corner.

   3. From the window that opens, type Command+Shift+G to open a new window, and then replace the existing text with /usr/bin/ldapsearch.

   4. Click Go.
      
      This opens a window with ldapsearch highlighted.

   5. Click Add.

   6. Click Save Changes, and enter your password if prompted.
      
      You are now ready to access your LDAP directory from the command line, using the OpenLDAP ldapsearch command.

7. Assuming the ldap-client.p12 file that you imported into the keychain earlier has the name LDAP Client, your domain is example.com, and the username is jsmith, enter the following:
   
   $   LDAPTLS_IDENTITY="LDAP Client" ldapsearch -H ldaps://ldap.google.com:636 -b dc=example,dc=com '(uid=jsmith)'

This sets the relevant environment variables to point to the imported client certificate. You can replace the other ldapsearch options with your desired filters, requested attributes, and so on. For more details, please see the ldapsearch man pages (man ldapsearch).

Follow these steps:

1. If needed, install and configure OpenVPN, or if you have already done so, open the settings page in OpenVPN.
   
   General VPN configuration is beyond the scope of this help article. Once a VPN is configured, you may add user authentication and authorization via LDAP. In particular, you will need to install the openvpn-auth-ldap plugin.
   
   $  sudo apt-get install openvpn openvpn-auth-ldap
    
2. Copy the LDAP client key and cert files to /etc/openvpn/ldap-client.key and /etc/openvpn/ldap-client.crt.
3. Create a file, /etc/openvpn/auth-ldap.conf, containing the following (assuming that example.com is the domain name):
   
   <LDAP>
  URL ldaps://ldap.google.com:636 #
  Timeout 15
  TLSEnable false
  TLSCACertDir /etc/ssl/certs
  TLSCertFile /etc/openvpn/ldap-client.crt
  TLSKeyFile /etc/openvpn/ldap-client.key
</LDAP>
<Authorization>
  BaseDN "dc=example,dc=com"
  SearchFilter "(uid=%u)" # (or choose your own LDAP filter for users)
  RequireGroup false
</Authorization>
    
4. Edit the OpenVPN configuration file, often named /etc/openvpn/server.conf, or similar. At the bottom of the file, add the following:
   
   plugin /usr/lib/openvpn/openvpn-auth-ldap.so /etc/openvpn/auth-ldap.conf
verify-client-cert optional
    
5. Restart the OpenVPN server.
   
   $  sudo systemctl restart openvpn@server
    
6. Configure the VPN clients to use the users’ usernames and passwords. For example, in an OpenVPN client configuration, add auth-user-pass to the end of the OpenVPN client configuration file and start the OpenVPN client:
   
   $  openvpn --config /path/to/client.conf
    
7. Follow instructions for using stunnel as a proxy.

For instructions on connecting OpenVPN Access Server to the Secure LDAP service, see Configuring Google Secure LDAP with OpenVPN Access Server.

For instructions on connecting PaperCut to the Secure LDAP service, see How to sync and authenticate Google Workspace and Google Cloud Identity users in PaperCut.

For instructions on connecting Puppet Enterprise to the Secure LDAP service, see Google Cloud Directory for PE.

Important: Before you begin, be sure you've installed Softerra LDAP Browser with version number 4.5 (4.5.19808.0) or later. See LDAP Browser 4.5.

Follow these steps:

1. Convert the certificate and key files to one PKCS12 formatted file. At a command prompt, enter the following:
   
   If you are in macOS or Linux, use the following commands:​
   
   openssl pkcs12 -inkey ldap-client.key -in ldap-client.crt -export -out ldap-client.p12
   
   Enter a password to encrypt the output file.
    

   If you are in Windows, use the following commands:

   $  certutil -mergepfx ldap-client.crt ldap-client.p12
   
   Important:  The two files (<CERT_FILE>.crt and <CERT_FILE>.key) must be located in the same directory. Also, make sure both key and crt have an identical name (with a different extension). In this example, we use the names ldap-client.crt and ldap-client.key.

2. In the Softerra LDAP Browser, install the key pair.
   1. Go to Tools > Certificate Manager.
   2. Click Import…
   3. Click Next.
   4. Click Browse…
   5. In the File type drop-down list in the lower-right corner of the dialog box, select Personal Information Exchange (*.pfx;*.p12).
   6. Select the ldap-client.p12 file from step 2 above.
   7. Click Open and then click Next.
   8. Enter the password from step 2 above, and click Next.
   9. Select the Personal certificate store.
   10. Click Next.
   11. Click Finish.
3. Add a server profile.
   1. Go to File > New > New Profile…
   2. Enter a name for the profile, such as Google LDAP.
   3. Click Next.
      
      Enter the following:
      
      Host: ldap.google.com
      Port: 636
      Base DN: Your domain name in DN format. (eg. dc=example,dc=com for example.com)
      Use secure connection (SSL): Checked
       
   4. Click Next.
   5. Select External (SSL Certificate).
   6. Click Next.
   7. Click Finish.

For instructions on connecting Sophos Mobile to the Secure LDAP service, see Connecting Sophos Mobile to Google Cloud Identity / Google Cloud Directory using Secure LDAP.

When connecting Splunk to the Secure LDAP service, be sure to use Splunk version 8.1.4 or later. When using older Splunk versions such as Splunk version 8.1.3, excessive LDAP queries might be sent to the LDAP server, which could result in your LDAP quota being exhausted quickly. For more information about Splunk version 8.1.3 issues, see Splunk known issues.

Follow these steps:

1. Copy the LDAP client key and cert files to /home/splunk/splunkadmin/etc/openldap/certs/ldap-client.key and /home/splunkadmin/splunk/etc/openldap/certs/ldap-client.crt.
   
   $  cat /home/splunkadmin/splunk/etc/openldap/certs/ldap-client.crt /home/splunkadmin/splunk/etc/openldap/certs/ldap-client.key > /home/splunkadmin/splunk/etc/openldap/certs/ldap-client.pem

$  sudo chown $(splunkuser):$(splunkuser) /home/splunkadmin/splunk/etc/openldap/certs/ldap-client.*

$  sudo chmod 644 /home/splunkadmin/splunk/etc/openldap/certs/ldap-client.*
    
2. Edit the ldap.conf file to add the following configs:

   ssl start_tls
TLS_REQCERT never
TLS_CERT /home/splunkadmin/splunk/etc/openldap/certs/ldap.pem
TLS_KEY /home/splunkadmin/splunk/etc/openldap/certs/ldap.pem

3.  Add the following configs in the user's /home/splunkadmin/.ldaprc file:
   
   TLS_CERT /home/splunkadmin/splunk/etc/openldap/certs/ldap-client.pem
TLS_KEY /home/splunkadmin/splunk/etc/openldap/certs/ldap-client.pem
    
4. Add the LDAP strategy using the Splunk web UI. Enter the following details, and then click Save:
    

Name	Google Secure LDAP
Host	ldap.google.com
Port	636
SSL enabled	Checked
Connection order	1
Bind DN	Enter the access credentials that you generated in the Google Admin console.
Bind DN password	Enter the access credentials that you generated in the Google Admin console.
Base DN	Your domain name in DN format (for example, dc=example,dc=com for the domain, example.com)
User base filter	Enter the User base filter for the object class you want to filter your users on.
User name attribute	uid
Real name attribute	displayname
Email attribute	mail
Group mapping attribute	dn
Group base DN	Your domain name in DN format (for example, ou=Groups,dc=example,dc=com for the domain, example.com)
Static group search filter	Enter the Static group search filter for the object class you want to filter your static groups on.
Group name attribute	cn
Static member attribute	member

 

SSSD performs a user lookup to get more information about a user during user authentication. To make sure user authentication works correctly for this LDAP client, you'll need to turn on Read user information and Read group information for all organizational units where Verify user credentials is turned on. (For instructions, see Configure access permissions.)

To connect an SSSD client on Red Hat 8 or CentOS 8 to the Secure LDAP service:

1. Add the SSSD client to the Secure LDAP service:
   1. From the Google Admin console, go to Apps > LDAP > ADD CLIENT.
      Be sure to sign in with your corporate account, and not with your personal Gmail account.
   2. Enter the Client details, and click CONTINUE.
   3. Configure the Access permissions:
      Verify user credentials—Entire domain
      Read user information—Entire domain
      Read group information—On
   4. Click ADD LDAP CLIENT.
   5. Download the generated certificate.
   6. Click CONTINUE TO CLIENT DETAILS.
   7. Change the Service status to ON.
2. Install dependencies:
   
   dnf install openldap-clients sssd-ldap
install -d --mode=700 --owner=sssd --group=root /etc/sssd/ldap
   
   unzip certificate .zip file and copy the .crt and .key files to /etc/sssd/ldap
    
3. (Optional) Test with ldapsearch:

   LDAPTLS_REQCERT=never \
LDAPTLS_KEY=Google.key \
LDAPTLS_CERT=Google.crt \
ldapsearch -H ldaps://ldap.google.com:636/ \
-b dc=example,dc=com \
-D [email protected] \
-W \
'([email protected])' \
mail dn
   
   Enter the user's Google password when prompted.
   
   Note: The user must have a Google Workspace Enterprise or Cloud Identity Premium license assigned to them.

4. Create the file /etc/sssd/sssd.conf with the following contents:
    

   [sssd]
services = nss, pam
domains = example.com

   [domain/example.com]
ldap_tls_cert = /etc/sssd/ldap/Google.crt
ldap_tls_key = /etc/sssd/ldap/Google.key
ldap_tls_reqcert = never
ldap_uri = ldaps://ldap.google.com
ldap_search_base = dc=example,dc=com
id_provider = ldap
auth_provider = ldap
ldap_schema = rfc2307bis
ldap_user_uuid = entryUUID

5. Update the permissions and SELinux labels:
   
   chown 0:0 /etc/sssd/sssd.conf /etc/sssd/ldap/*
chmod 600 /etc/sssd/sssd.conf /etc/sssd/ldap/*
restorecon -FRv /etc/sssd
    
6. Restart SSSD:
   
   systemctl restart sssd
    
7. Test:
   
   ssh to server:

   ssh -l [email protected] {HOSTNAME}

Troubleshooting

1. Check SSSD version (must be greater than or equal to 1.15.2):
   
   # sssd --version
2.2.3
    

2. On RHEL/CentOS (or any distro with SELinux enforcement), the SSSD config files and certificate file and key must be in a directory accessible by the sssd_conf_t role:

   # egrep "object_r:sssd_conf_t" /etc/selinux/targeted/contexts/files/file_contexts

   Check the /var/log/audit/audit.log for AVC deny messages.
    

3. Check that /etc/nsswitch.conf has "sss" for the passwd, shadow, group, and netgroup entities:
   
   passwd:  files sss
shadow:  files sss
group:   files sss
netgroup:  files sss
   
   Here, local files will override LDAP users.
    
4. Check /var/log/sssd.conf for config errors:
    

   Example:
   [sssd] [sss_ini_add_snippets] (0x0020): Config merge error: File /etc/sssd/sssd.conf did not pass access check. Skipping.

   Action: You need to chmod 600 the .conf file.

   Example:
   [sssd] [sss_ini_call_validators] (0x0020): [rule/allowed_domain_options]: Attribute 'ldap_groups_use_matching_rule_in_chain' is not allowed in section 'domain/{DOMAIN}'. Check for typos.

   [sssd] [sss_ini_call_validators] (0x0020): [rule/allowed_domain_options]: Attribute 'ldap_initgroups_use_matching_rule_in_chain' is not allowed in section 'domain/{DOMAIN}'. Check for typos.

   Action: Remove the unsupported group match LDAP extensions from sssd.conf.

5. Check /var/log/sssd_{DOMAIN}.log for LDAP/network/auth errors.
   
   Example:

   [sssd[be[example.com]]] [sss_ldap_init_sys_connect_done] (0x0020): ldap_install_tls failed: [Connect error] [error:1416F086:SSL routines:tls_process_server_certificate:certificate verify failed (self signed certificate)]

   Action: You need to add "ldap_tls_reqcert = never" to sssd.conf.

   To increase verbosity of errors, add "debug_level = 9" in sssd.conf under the domain section and restart sssd.

SSSD performs a user lookup to get more information about a user during user authentication. To make sure user authentication works correctly for this LDAP client, you'll need to turn on Read user information and Read group information for all organizational units where Verify user credentials is turned on. (For instructions, see Configure access permissions.)

To connect an SSSD client to the Secure LDAP service:

1. Install SSSD version  >= 1.15.2.
   
   $  sudo apt-get install sssd
    
2. Assuming your client cert and key files are named /var/ldap-client.crt and /var/ldap-client.key and your domain is example.com, edit /etc/sssd/sssd.conf with a configuration such as:

   
   [sssd]
   services = nss, pam
   domains = example.com

   [domain/example.com]
   ldap_tls_cert = /var/ldap-client.crt
   ldap_tls_key = /var/ldap-client.key
   ldap_uri = ldaps://ldap.google.com
   ldap_search_base = dc=example,dc=com
   id_provider = ldap
   auth_provider = ldap
   ldap_schema = rfc2307bis
   ldap_user_uuid = entryUUID
   ldap_groups_use_matching_rule_in_chain = true
   ldap_initgroups_use_matching_rule_in_chain = true
    

3. Change ownership and permission of the config file:
   
   $  sudo chown root:root /etc/sssd/sssd.conf
$  sudo chmod 600 /etc/sssd/sssd.conf

4. Restart SSSD:
   
   $  sudo service sssd restart

Tip: If you're using the SSSD module on Linux computers without external IP addresses on Google Compute Engine, you can still connect to the Secure LDAP service as long as you have internal access to Google services enabled. For details, see Configuring Private Google Access. 

Follow the steps below to connect the macOS client for user account authentication using the Secure LDAP service.

System requirements

• The macOS must be Catalina Version 10.15.4 or later.
• A Google super admin user ID is required to complete step 1 in the preparation phase.
• You need local admin permissions to perform this configuration.

Contents:

• Preparation phase
• Deployment phase
• Limitations and guidelines
• Troubleshooting

Preparation phase

The instructions in this section focus on how to manually set up and test macOS authentication using the Secure LDAP service.

Step 1: Onboard macOS as an LDAP client in the Google Admin console

For instructions, see Add LDAP clients, or watch this Secure LDAP demo. You will also download an auto-generated TLS client certificate during this process. 

Step 2: Import the certificate into the system keychain

1. Copy the certificate (the zip file downloaded in step 1) and key to the macOS machine.
   Tip: Unzip the file to find cert and key files.
2. Import the key pair into the system keychain:

   1. Convert the key and cert into a PKCS 12 (p12) file. Run the following command in the terminal:
      
      openssl pkcs12 -export -out ldap-client.p12 -in ldap-client.crt -inkey ldap-client.key
      
      Tip: Write down the name of the .p12 file.
      
      The system will ask you to enter a password. Enter a password with which to encrypt the p12 file.

   2. Open the Keychain Access application.

   3. Click on the System keychain.

   4. Click File > Import Items.

   5. Select the ldap-client.p12 file created above.

   6. If prompted, enter the admin password to allow modification of the system keychain.

   7. Enter the password you created above to decrypt the .p12 file.

      Note: Expect to see a new cert and associated private key show up in the list of keys. It may be called LDAP Client. Write down the cert’s name for the next step below.
       
   8. Follow step 6 in the ldapsearch (macOS) section in this article to set up Access Control for the private key to add apps specified below. If the private key is not showing under the All Items category, try to switch to the My Certificates category, and locate the correct private key entry by expanding the corresponding certificate.
      
      The ldapsearch app, as specified in the instructions, is relevant only if troubleshooting is needed, and not for other purposes. It’s typically removed before providing users access to macOS.
      
      The following three apps must be added to the Access Control list:
      
      /System/Library/CoreServices/Applications/Directory Utility
/usr/libexec/opendirectoryd
/usr/bin/dscl

3. ​Add a line to the /etc/openldap/ldap.conf file, ensuring that "LDAP Client" is exactly the same certificate name as shown in the macOS Keychain Access application after importing the .p12 file (the name comes from the X.509 Subject Common Name of the generated certificate):
   
   sudo bash -c 'echo -e "TLS_IDENTITY\tLDAP Client" >> /etc/openldap/ldap.conf'

Step 3: Point the device to Google directory for authentication

Open the Directory Utility application to create a new LDAP directory node:

1. Click the lock to make changes and enter your password.
2. Select LDAPv3 and click the pencil icon to edit settings.
3. Click New…
4. For the server name, enter ldap.google.com, select Encrypt using SSL, and click Manual.
5. Select the new server name and click Edit…
6. Enter a descriptive name such as Google Secure LDAP for the configuration name.
7. Select Encrypt using SSL and make sure the port is set to 636.
8. Go to the Search & Mappings tab.
   1. Choose RFC2307 from the Access this LDAPv3 server using dropdown list.
   2. When prompted, enter the domain-related information into Search Base Suffix. For example, enter dc=zomato,dc=com for a domain name of zomato.com.
   3. Click OK.
   4. Configure attributes under the Users record type:
      1. In the Record Types and Attributes section, select Users and click the “+” button.
      2. In the popup window, choose Attribute Types, select GeneratedUID, and then click OK to close the popup window.
         
         GeneratedUID should be displayed under Users after it’s expanded.
          
      3. Click on the GeneratedUID, and click the “+” icon in the box on the right.
      4. Enter apple-generateduid in the text box, and click Enter.
      5. Under the Users node, click the NFSHomeDirectory attribute.
      6. In the screen on the right, update the value for this attribute to #/Users/$uid$
      7. Click OK and enter your password to save the changes.
9. From the Directory Utility window, configure the new LDAP config:
   1. Go to Search Policy tab.
   2. Click the lock icon to make changes, and enter the password of the current user when prompted.
   3. Change the dropdown option from Search Path to Custom path.
   4. Open the Authentication tab and click the “+” icon. 
   5. Choose /LDAPv3/ldap.google.com from the Directory Domains list, and then click Add.
   6. Click the Apply button, and enter your admin password if prompted.
10. Run the following four commands to disable the DIGEST-MD5, CRAM-MD5, NTLM, and GSSAPI SASL authentication mechanisms. The macOS will use Simple Bind to authenticate using the Google Secure LDAP service:
    
    sudo /usr/libexec/PlistBuddy -c "add ':module options:ldap:Denied SASL Methods:' string DIGEST-MD5" /Library/Preferences/OpenDirectory/Configurations/LDAPv3/ldap.google.com.plist 

sudo /usr/libexec/PlistBuddy -c "add ':module options:ldap:Denied SASL Methods:' string CRAM-MD5" /Library/Preferences/OpenDirectory/Configurations/LDAPv3/ldap.google.com.plist

sudo /usr/libexec/PlistBuddy -c "add ':module options:ldap:Denied SASL Methods:' string NTLM" /Library/Preferences/OpenDirectory/Configurations/LDAPv3/ldap.google.com.plist

sudo /usr/libexec/PlistBuddy -c "add ':module options:ldap:Denied SASL Methods:' string GSSAPI" /Library/Preferences/OpenDirectory/Configurations/LDAPv3/ldap.google.com.plist
     
11. Reboot to reload the OpenDirectory configuration.

Step 4: Create a mobile account (allows offline login)

Any Google Workspace or Cloud Identity user can log in using a network account (Google account) using their username and password. This login process needs network connectivity. If a user needs to log in with or without connection to the network, a mobile account can be created. A mobile account lets you use your network account (Google account) username and password to sign in, whether or not you’re connected to the network. For more details, see Create and configure mobile accounts on Mac.

To create a mobile account for Secure LDAP users:

1. Run the following command to connect to the Secure LDAP server and set up a home path and mobile account(s):
   
   sudo /System/Library/CoreServices/ManagedClient.app/Contents/Resources/createmobileaccount -n $uid -v 
   
   Tip: Replace $uid with the username part of the email address associated with the user’s Google account. For example, jsmith is the username part for [email protected].

2. When prompted for the SecureToken admin user name, enter your admin username, and enter your password in the next prompt. This will add $uid into the FileVault. This is needed if the macOS disk is encrypted. 

Step 5: (Optional) Set the login screen preference

1. Go to System preferences > Users & Groups > Login Options at the bottom left.
2. Unlock the lock by providing admin credentials.
3. Change the Display login window as to Name and password.

Step 6: Reboot and log in to your device

1. Make sure the device is connected to the Internet. If you don’t have an internet connection, the login for the Secure LDAP user will not work.
   Note: Internet connection is needed only for the first login. Any subsequent logins can occur without Internet access. 
2. Sign in to the device with the user account that's configured to use Secure LDAP for authentication. 

Deployment phase

The instructions in this section focus on automating the device configuration for your users. Perform steps 1 and 2 below on the same macOS device where you completed your manual configuration during the preparation phase. 

Step 1: Create a Mac Profile with certificate using Apple Configurator 2

1. Install Apple Configurator 2 on the machine where you manually configured macOS authentication with Secure LDAP.
2. Open Apple Configurator 2, create a new profile and in the Certificate section, click Configure, and import the previously generated .p12 file.

   Note: Make sure this .p12 has a password. Enter this password in the Password section of the Certificate.

3. Save this Profile. 
4. (For devices using M1 or M2 processors, skip this step and continue to Step 5. ) Open this profile in any text editor and add the following lines in first <dict> tag:
   
   <key>PayloadScope</key>
<string>System</string>
   
   This is added, as Apple Configurator does not support profiles for macOS yet.
    
5. In the second <dict> tag, parallel to certificate data, add the following lines:
   
   <key>AllowAllAppsAccess</key>
<true/>
   
   This will make sure that this certificate can be accessed by all applications.

Step 2: Convert Directory config file (plist) to xml 

In this step, you are extracting all the manual configurations that you completed during step 3 of the preparation phase into a XML file. You can use this file and the Mac profile created in step 1 above to automatically configure other macOS devices. 

1. Copy /Library/Preferences/OpenDirectory/Configurations/LDAPv3/ldap.google.com.plist to your desktop or elsewhere.
2. Convert it to XML so that you can inspect it in any text editor. Run the following command in Terminal:
   
   sudo plutil -convert xml1 <path>/ldap.google.com.plist
   
   You can access the file as <path>/ldap.google.com.plist.
    
3. Change the permission of the above file so that you can open the XML file. Make sure it is not empty.

Step 3: Create a python script to automate the configuration on your end-user devices

Copy the python script below and save it as a python file (.py file).

Note: This sample script is designed to be compatible with Python version 3.10.x. This script is provided on an as-is basis. Google support will not provide support for sample scripts. 

Ldap_python_config.py

#!/usr/bin/python
from OpenDirectory import ODNode, ODSession, kODNodeTypeConfigure
from Foundation import NSMutableData, NSData

import os
import sys

# Reading plist
GOOGLELDAPCONFIGFILE = open(sys.argv[1], "r")
CONFIG = GOOGLELDAPCONFIGFILE.read()
GOOGLELDAPCONFIGFILE.close()

# Write the plist
od_session = ODSession.defaultSession()
od_conf_node, err = ODNode.nodeWithSession_type_error_(od_session, kODNodeTypeConfigure, None)
request = NSMutableData.dataWithBytes_length_(b'\x00'*32, 32)
request.appendData_(NSData.dataWithBytes_length_(str.encode(CONFIG), len(CONFIG)))
response, err = od_conf_node.customCall_sendData_error_(99991, request, None)

# Edit the default search path and append the new node to allow for login
os.system("dscl -q localhost -append /Search CSPSearchPath /LDAPv3/ldap.google.com")
os.system("bash -c 'echo -e \"TLS_IDENTITY\tLDAP Client\" >> /etc/openldap/ldap.conf' ")

Step 4: Auto configure end-user devices

Go to other macOS devices that you would like to configure and follow these steps:

1. Copy the Mac Profile file generated in step 1, XML config file generated in step 2, and the python script from step 3 to the device.
2. Run the following command:
   
   sudo python </path/to/saved_python_script> </path/to/ldap.google.com.plist generated in step 2>
    
3. To import certificates into the macOS system keychain, double-click on the Mac profile file generated in step 1, and when prompted provide your macOS local admin credentials. You will then be prompted to enter the .p12 password that you set during the preparation phase. 
4. Restart the macOS machine.
5. Create mobile accounts as instructed in step 4 of the preparation phase, and optionally set additional preferences outlined in step 5 of the preparation phase.

Limitations and guidelines

• For users signing in to macOS using their Google credentials, their Workspace account username must be different from their macOS user profile user ID, or sign-in is blocked.
• Once a user starts signing in to macOS using Google credentials, user password management (reset or recovery) must happen on the Google website (for example, at myaccount.google.com or in the Google Admin console). If you choose to do password management using a third-party solution, then make sure the latest password is synchronized with Google.
• If the admin creates a new user or resets an existing user’s password with the Ask for a password change at the next sign-in setting turned on, the user cannot sign in to Mac using the temporary password set by the admin. 
  Workaround: The user needs to sign in to Google using another device (for example, their mobile device or other desktop device), set a permanent password, and then sign in to macOS using the new password. 
• The Mac must be connected to a working internet connection so that ldap.google.com is reachable during the first sign-in after the above configuration.  Any subsequent sign-ins won't need Internet access as long as you opted to set up a mobile account.
• Google Secure LDAP integration with macOS is tested on macOS Catalina, Big Sur, and Monterey.

Troubleshooting

If you have problems connecting to the Secure LDAP service, follow the instructions below.

Step 1: Verify the connection.

Verify the connection using odutil.
Run the odutil show nodenames command in the terminal.
Verify that the /LDAPv3/ldap.google.com status is online. If it's not online, try the telnet option.

Verify the connection using nc.
Execute the following command in the terminal: nc -zv  ldap.google.com 636
If you aren't able to connect to Google using this approach, try connecting using IPv4.

Verify the connection with IPv4.
You can change your device to use IPv4 using the following steps:

1. Go to System Preferences > Network > Wi-Fi > Advanced.
2. Under the Advanced menu, go to the TCP/IP tab.
3. Change the drop-down selection from Configure IPv6 to Link-local only.
4. Click OK, and then click Apply to save the changes.
5. Check service authentication via ldapsearch connectivity and valid search.

Step 2: Check whether you are able to see directory objects.

1. Open Directory Utility, and then open the Directory Editor tab. 
2. Select the /LDAPv3/ldap.google.com node in the drop-down list.
3. Verify whether you are able to see users and groups from your Google domain.