Google Apps Directory Sync: Administration Guide

Google Apps Directory Sync
Administration Guide
Release 1.3.25, January 2009

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Contents
About This Guide 7

What This Guide Contains 7
Related Documentation 7
How to Send Comments About This Guide 8
Chapter 2: Introduction 9
About Google Apps Directory Sync 9
Features and Benefits 9
Comparison with Directory Sync Hosted Edition 10
Architecture 11
Utility Overview 13
Chapter 3: Preparation 15
About Preparation 15
Overview 15
Checklist: Before You Begin 16
Useful LDAP Tools 18
Softerra LDAP Administrator 18
JXplorer 18
LDAP Queries 18
Syntax 19
Common LDAP Queries 19
Planning for Large or Complex Deployments 21
Chapter 4: Installation 23
About Installation 23
System Requirements 24
Install Google Apps Directory Sync 24
Upgrade Google Apps Directory Sync 25
Uninstall Google Apps Directory Sync 26
Chapter 5: Configuration 27
About Configuration 27
Configuration Files 28
Message Security Service Settings 29
Message Security Service Authentication 30
Contents 5
Message Security Service Orgs 32
Exclusion Filters for Service Settings 33
Sample Message Security Exclusion Rules 35
LDAP Settings 37
LDAP Connection 38
LDAP Users 40
LDAP User Attributes 41
LDAP User Sync 43
LDAP User Exclusion Rules 47
Sample LDAP User Exclusion Rules 50
LDAP Mailing List Overview 51
LDAP Mailing List Sync 53
LDAP Mailing List Exclusion Rules 55
Sample LDAP User Exclusion Rules 57
Notifications 58
Delete Limits 60
Log Files 62
Simulate Sync 63
Simulate Sync 63
Chapter 6: Synchronization 67
About Synchronization 67
Command Line Synchronization 67
Synchronization options 68
Scheduling Synchronization 69
Microsoft Windows: Scheduled Tasks 69
Linux and Solaris: cron 70
Chapter 7: Troubleshooting 71
About Troubleshooting 71
Common Issues 71
System Tests 73
Escalating Problems 74

About This Guide
What This Guide Contains

The Google Apps Directory Sync Administration Guide provides information
about:
• Google Apps Directory Sync features.
• Basic steps for installing the directory sync utility on your mail server.
• Configuration for the directory sync utility.
• Synchronizing users.
• Troubleshooting the directory sync utility.
This guide is intended for mail server administrators who are already familiar with
mail server configuration and the message security service.
This guide is a supplement to the Message Security Administration Guide. For

details about using the features and components of the message security service,
see the Message Security Administration Guide.
Related Documentation
For additional information about the message security service and related
products, refer to the following documents.
Document Description
Message Security Administration Guide for the message security

Administration Guide service. This includes information on users
and organizations, message filtering, and
other features. The Directory Sync chapter in
this guide covers only Directory Sync Hosted
Edition.
7
Document Description
Directory Sync Configuration Instructions for setting up your network

Guide environment and directory server for Directory
Sync Hosted Edition. Directory Sync Hosted
Edition is a different feature, that runs on the
message security service and requires special
configuration on your network to use.
How to Send Comments About This Guide

Google values your feedback. If you have comments about this guide, please
send an email message to:
postini-doc_comments@google.com
Please specify in your email message the section to which your comment applies.
If you want to receive a response to your comments, ensure that you include your
name and contact information.

Chapter 2
Introduction Chapter 2
About Google Apps Directory Sync

Google Apps Directory Sync is a utility that adds, deletes, and moves your users
in the message security service to match the user directory on your LDAP server.
When you synchronize, any changes on your LDAP server are reflected in the
message security service.
The directory sync utility runs on a server machine in your network environment.
You can use any machine that is able to connect to your LDAP server and the
Features and Benefits

Google Apps Directory Sync offers the following features and benefits:
• Updates registered users in the message security service to match your

LDAP user list.
• A local on-site utility that runs in your server environment. No machine outside
your perimeter will access your LDAP server.
• Can be configured to track user primary address changes, keeping

quarantines and settings intact even with user address changes.
• Runs on any Windows (XP or Vista), Linux or Solaris server.
• All needed components included in installation.
• Allows sophisticated rules to handle mailing lists, aliases, and exceptions.
• Allows complex mapping for your org hierarchy.
• Extensive tests and simulations to ensure correct synchronization.
Introduction 9
Comparison with Directory Sync Hosted Edition
Google Apps Directory Sync is a separate utility run on your server, and is
different from the Directory Sync Hosted Edition feature found in the
Administration Console.
Because of the functional advantages and ease of use, Google Apps Directory
Sync is recommended over Directory Sync Hosted Edition for most
administrators.
Both Google Apps Directory Sync and Directory Sync Hosted Edition synchronize
your LDAP server with your user list in the message security service, but they
work in very different ways.
This table compares the two methods:
Google Apps Directory Sync Directory Sync Hosted Edition
Runs on a server in your network. Runs within the message security

Location service.
Configure on your server with the Configure in the Administration

Configuration Manager utility Console.
Configuration provided.
Pushes changes to the message Pulls changes from your DSML server.
Direction of Data Flow security service.
Installation includes all needed Requires complex installation of third

Installation Needed components. party DSML server on your network.
Your firewall must allow outgoing Your firewall must allow incoming
HTTPS connections to the message HTTPS connections to your DSML
Firewall Settings security service. server.
Connects directly to your LDAP server Connects to your DSML server by

using port 389, or a port you specify. HTTPS port 443, which then connects
Connection to your LDAP server.
Requires administration access on the Requires administration access on the

message security service, and read message security service, and read
and execute permissions on your and execute permissions on your
LDAP server. Uses basic LDAP server. Uses basic
Authorization authentication. authentication or anonymous access.
Allows advanced LDAP queries, Allows advanced LDAP queries,

sophisticated organization mapping, simple organization mapping, and
Complexity and exception handling. some exception handling.
WARNING: Google Apps Directory Sync and Directory Sync Hosted Edition are
two distinct ways to synchronize. They are not designed to work together. Using
both at the same time could cause unexpected or contradictory results.
This guide describes Google Apps Directory Sync. For more information about
Directory Sync Hosted Edition, see About Directory Sync in the Message Security
Administration Guide and the Configuration Guide for Postini Directory Sync.

Architecture
Google Apps Directory Sync runs on your server and updates the message
security service to match your LDAP server. The directory sync utility never
updates or changes your LDAP server.
The following steps describe how the data flow of directory sync works.
1. The directory sync utility connects to your LDAP server (via port 389 or
another port you specify) and generates a list of users on your directory. You
can set up rules to specify how this user list is generated.
2. The directory sync utility connects to the message security service (via port
8080 if you are using a proxy server, or otherwise port 443) and generates a
list of registered users in the message security service. You can set up rules
to specify how this user list is generated.
Introduction 11
3. The directory sync utility compares the two lists, and generates a list of
changes.
4. The directory sync utility then updates the message security service to match
your LDAP server settings.

Utility Overview
The directory sync utility includes several components, designed to work together.
These components are:
• Configuration Manager - Use this graphical UI to configure how the directory

sync utility will connect to the message security service and to your LDAP
server. You can also create rules for user lists, search queries, organization
mapping, aliases, distribution lists and exceptions. For more information, see
“Configuration” on page 27.
• XML Configuration File - Save configuration information from Configuration

Manager in an XML file. Use this file during synchronization.
• Synchronization Command Line - Use the command-line utility sync-cmd to

perform actual synchronization. This utility uses settings in your XML
configuration file to connect to the message security service and your LDAP
server, and updates your users and aliases in the message security service.
For more information, see “Synchronization” on page 67.
• Scheduling - Once you have used sync-cmd successfully, use your operating
system’s scheduling functionality to schedule future synchronization.
Depending on the server you use, this might be a cron job, a Windows
Scheduled Service utility, or any other scheduling tool. For more information,
see “Synchronization” on page 67.
Introduction 13
Chapter 3
Preparation Chapter 3
About Preparation
Successful deployment of Google Apps Directory Sync requires planning.
Many steps in the configuration and synchronization process assume you already
have key information about your LDAP directory server, mail server, and message
security service organization structure.
This chapter includes a checklist of things you’ll need before you begin, LDAP
browser information, some sample LDAP queries, and a discussion of special
considerations for large deployments.
For information on system requirements, see “System Requirements” on page 24.
Overview
A typical setup for Google Apps Directory Sync involves the following steps:
1. Collect required information about your LDAP server and the message
security service.
2. Install the directory sync utility.
3. Step through Configuration Manager to configure synchronization.
4. In Configuration Manager, simulate a synchronization.
5. Revise your configuration in Configuration Manager based on the simulation.

This could take several revisions for complex environments.
6. When the simulation is successful, save your final copy of the configuration
file and exit Configuration Manager.
7. In the command line, run a manual synchronization with the configuration file
you created to update the message security service.
8. Using your server’s scheduling tools, set up automatic scheduled

synchronization.
Preparation 15
Checklist: Before You Begin
Before you configure synchronization, gather the information you need from the
message security service, as well as your own LDAP server and mail server.
Use this checklist to be sure you have the information you need:
• Message Security Org Structure
• Message Security Administrator
• LDAP Structure Information
• LDAP Base DN
• LDAP Administrator
• LDAP Queries
• Org Mapping
• Mail Server
Each item on the checklist is detailed below.
Message Security Org Structure: Before you configure synchronization, set up

your org hierarchy in the message security service. You should create
organizations for all users you want to add. For more information about your org
hierarchy, see About the Organization Hierarchy and About Organization
Management in the Email Security Administration Guide.
Note: The directory sync utility does not create these organizations, so you will
need to add them beforehand.
Collect the structure and exact org names from the Administration Console:
Message Security Administrator: Note the administrator username and

password (or Xauth string, if you are using Cross-Authentication) for an
administrator on the message security service. The administrator needs read
authority for All Standard Privileges, and write authority for all Help Desk and User
Settings.

LDAP Structure Information: Gather information about your LDAP directory
server. You will need to know what OUs contain users you want to sync and which
LDAP attributes contain important information. To collect this information, use an
LDAP browser. For more information, see “Useful LDAP Tools” on page 18.
LDAP Base DN: The directory sync utility will use this Base DN as the top level
for all LDAP queries. You can use an LDAP browser to collect this information. If
your LDAP directory server includes OUs that you do not want to sync, consider a
base DN that doesn’t include these OUs. A typical Base DN might be
ou=test,ou=sales,ou=melbourne,dc=ad,dc=mixateria,dc=com for a domain
called ad.mixteria.com.
Note: Each configuration file can only use one base DN. If you need to use
multiple base DNs, run separate synchronizations with separate XML
configuration files.
LDAP Administrator: Collect the username and password of an administrator on

your LDAP directory server. Enter the user to use when connecting to the server.
This user should have read and execute permissions for the whole LDAP subtree
you want to synchronize. You can restrict the permissions of the administrator to
match only the OUs you want to synchronize.
LDAP Queries: Decide which users to synchronization from your LDAP directory
server, and create one or more LDAP queries that will find those users. For more
information, see “LDAP Queries” on page 18.
Org Mapping: Plan which users will go into which organizations in the message
security service. You want to be sure that your org hierarchy includes special
organizations for users who should not be synchronized, so those users won’t be
deleted. Decide which users go in which organizations. If you want to specify
different organizations for many different users, you can populate a user attribute
on your LDAP directory server that shows the exact name of the message
security service organization for that user. This requires changing your LDAP
settings.
Mail Server: The SMTP mail server to use for notifications. The directory sync
utility does not include an outbound mail server, and will connect to the mail server
you specify. You will need the domain name or IP address of a mail server that will
relay messages from the directory sync server. If the SMTP server you plan to use
requires SMTP authentication, you will need to find or create a username and
password for SMTP authentication as well.
Once you have collected this information and decided on how you want to
synchronize users in different organizations, you’re ready to begin with
Configuration Manager.
If you begin using Configuration Manager and find you need more information,
save your configuration file. You can return to Configuration Manager and load
your XML file after you collect the needed information.
Preparation 17
Useful LDAP Tools
By default, most LDAP directory servers do not include a way to view or modify
your LDAP structure directly. To collect information about your LDAP structure,
download and install an LDAP browser. Two such browsers are listed below.
Note that these are third-party browsers, and this document does not include
instructions or support on the use of an LDAP browser.
Softerra LDAP Administrator

To download Softerra LDAP Administrator, go to:
http://www.ldapbrowser.com
JXplorer
To download the JXplorer Java Ldap Browser, go to:
http://www.jxplorer.org
LDAP Queries
The directory sync utility uses the LDAP query language to gather information
from your directory server. The LDAP query language is a flexible standard that
supports complex and powerful logical queries.
To build your LDAP queries, you will need to know your LDAP structure. The best
way to collect directory server information is an LDAP browser. For more
information, see “Useful LDAP Tools” on page 18.
Google Apps Directory Sync strictly adheres to RFC 2254, which defines
international standards on LDAP filters.
Most of the search rules in the directory sync utility use LDAP queries for
information. The only exception to this are Exception Rules, which use substring
or regular expressions based on the text of email addresses, not LDAP fields.
Note: The support team cannot write LDAP queries for your environment or debug
your LDAP queries. While this document lists the most common queries, every
directory server is different, and many store information in different fields or
formats. To develop these queries, consult standard LDAP documentation and
review your LDAP structure with an LDAP browser.

Syntax
The following syntax is used in LDAP filters:
Name of
Operator Character Use
Equals = Creates a filter which requires a field to have a

given value.
Any * Wildcard to represent that a field can equal

anything except NULL.
Parentheses () Separates filters to allow other logical

operators to function.
And & Joins filters together. All conditions in the

series must be true.
Or | Joins filters together. At least one condition in

the series must be true.
Not ! Excludes all objects that match the filter.
For examples of how these operators are used, see the common LDAP queries
below.
Common LDAP Queries

The examples below show the most common LDAP queries. These queries are
the most common queries used, and are designed to work with most directory
server environments.
All objects (this may cause load problems):
objectclass=*.
All user objects that are designated as a “person”
(&(objectclass=user)(objectcategory=person))
Distribution Lists only
(objectcategory=group)
Public Folders only
(objectcategory=publicfolder)
Preparation 19
All user objects except for ones with primary email addresses that begin with
test
(&(&(objectclass=user)(objectcategory=person))(!(mail=test*)))
All user objects except for ones with primary email addresses that end with test
(&(&(objectclass=user)(objectcategory=person))(!(mail=*test)))
All user objects except for ones with primary email addresses that contain the
word “test”
(&(&(objectclass=user)(objectcategory=person))(!(mail=*test*)))
All user objects (users and aliases) that are designated as a “person” and all
group objects (distribution lists)
(|(&(objectclass=user)(objectcategory=person))(objectcategory=grou
p))
All user objects that are designated as a “person”, all group objects and all
contacts, except those with any value defined for extensionAttribute9:
(&(|(|(&(objectclass=user)(objectcategory=person))(objectcategory=
group))(objectclass=contact))(!(extensionAttribute9=*)))
All users, but exclude disabled users:
(&(&(objectclass=user)(objectcategory=person))(!(userAccountContro
l=514)))
Active Directory LDAP: All users
(objectClass=person)
Active Directory LDAP: All email users (alternate)
(&(objectclass=user)(objectcategory=person))
OpenLDAP: All users
(objectClass=inetOrgPerson)
Lotus Domino LDAP: All users
(objectClass=dominoPerson)
Lotus Domino LDAP: All objects with a mail address defined that are designated
as a “person “or “group”:
(&(|(objectclass=dominoPerson)(objectclass=dominoGroup)(objectclas
s=dominoServerMailInDatabase))(mail=*))

Planning for Large or Complex Deployments
If your deployment is large enough or complex enough to require multiple
configuration files, you may need extra planning and preparation.
Synchronizing for a very large or complex organization may require special

consideration. This may be the case for two reasons:
• A complex deployment may include many different sub-groups which need to

be synchronized using separate rules or message security service
organizations.
• A large deployment may be system-intensive and may require special work to

be sure it runs quickly.
A common way to handle a large deployment is to create multiple configuration

files for different parts of your company. This allows greater customization and
may speed up your synchronization.
When you set up multiple configuration files for a large deployment, consider the
following:
• If you are scheduling synchronization, schedule each configuration file

separately.
• Every configuration file must synchronize to a different organization in the

message security service. If two configuration files affect the same
organization on the message security service, the directory sync utility may
overwrite or delete users.
• You must include some kind of LDAP user search in every configuration file.
• The directory sync utility can move users from other organizations to
complete synchronization.
One particular way to enhance performance is to separate mailing lists to a

separate search. If a large synchronization is going slowly, consider creating a
separate organization for mailing lists, and running a separate synchronization for
that organization. However, remember that you must include some kind of LDAP
user search in every configuration file; if you’re only synchronizing mailing lists,
add a placeholder LDAP search rule that will not return any results, such as
(objectclass = thisisnotavalidclass).
If your organization has multiple LDAP servers, or multiple base DNs, set up
separate XML configuration files and run separate synchronizations. Create a
separate organization in the message security service Administration Console for
each separate LDAP server or base DN.
If you are using multiple configuration files, consider assigning a different

administrator to each. Then, set the permissions for
Preparation 21
Chapter 4
Installation Chapter 4
About Installation
To run Google Apps Directory Sync, install the directory sync utility on your server.
The directory sync utility is designed to run on Windows, Linux or Solaris
machines.
The installer is an executable program that installs all needed components on the
server, including managing libraries, classpath variables, and other components.
The installer also uninstalls any existing version of the directory sync utility in the
same directory.
The sections below contain instructions on how to install, upgrade or uninstall the
directory sync utility on your server.
Installation 23
System Requirements
Using Google Apps Directory Sync requires the following:
• A server on which to install Google Apps Directory Sync, running Microsoft

Windows (tested on XP and Vista), Linux or Solaris.
• Sufficient disk space on the server. You should have at least 5G of disk space
for log files and data. If you are running with DEBUG or INFO level of logging,
you may need more free space than this for additional log data.
• Sufficient memory on the server. The minimum amount of RAM needed to run
the tool is 256MB free. Suggested is 1G free if you have less than 10,000
users, 2G free if you have more than 10,000 users. For very large
organizations (over 250,000) further tuning may be needed.
• An LDAP server with user information which is accessible to the directory

sync utility. All versions of the LDAP protocol are supported.
• Read and execute administrative access over the appropriate OU structure of

the LDAP server.
• Network access to the message security service through HTTPS, directly or

through a proxy server.
• An administrator account on the message security service.
• A mail server able to accept and relay notifications from the directory sync
utility.
Install Google Apps Directory Sync

To install the directory sync utility:
1. In a web browser, go to http://www.postini.com/dir_sync.
2. Choose the operating system of the server where you plan to run the directory
sync utility.

3. Download and run the installer.
4. When you have completed all the steps of the installer, the directory sync
utility has been installed.
The installer contains all needed components and can be run offline without any
outside connection.
Upgrade Google Apps Directory Sync

In Release 1.3.13 or later, Google Apps Directory Sync automatically checks to
see if there are any updates available. If updates are available, you will be
prompted to upgrade when you start Configuration Manager.
Installation 25
You can also update manually. The latest version of the directory sync utility is
always accessible on the Google Apps Directory Sync website. To upgrade to the
latest version, go to this site, and download and run the directory sync utility.
Configuration files are backward-compatible. Future versions of the directory sync

utility cans run configuration files created in earlier versions.
The installer wizard automatically detects and uninstalls previous versions of the
software in the same directory.
To reinstall the utility.
1. In a web browser, go to http://www.postini.com/dir_sync.
2. Choose the operating system of the server where you plan to run the directory
sync utility.
3. Download and run the installer.
4. Select a directory on your server to install the directory sync utility.
5. Complete the installer wizard.
Uninstall Google Apps Directory Sync

The directory sync utility also includes an uninstaller.
To remove the directory sync utility:
1. Open a command line interface and go to the directory that contains the
directory sync utility
2. Run the following command:

uninstall
3. In the uninstaller, click Next to uninstall the directory sync utility.
4. Once uninstallation has completed close the uninstaller.
All directory sync utility files and all libraries not used by other programs will be
removed. Log files and XML configuration files will not be deleted.

Chapter 5
Configuration Chapter 5
About Configuration
Configuration Manager is a step-by-step graphical user interface that walks you
through creating and testing an XML configuration file for Google Apps Directory
Sync.
Note: Before you use Configuration Manager, collect information about your LDAP
directory server and your message security service organizations. For more
information, see “Checklist: Before You Begin” on page 16.‘
In Configuration Manager, you can:
• Set up and test a connection to the message security service.
• Configure which users and orgs in the message security service to

synchronize.
• Set up and test a connection to your LDAP server.
• Configure LDAP search criteria for synchronization.
• Set up notifications and logging.
• Run a simulated synchronization to verify your settings.
Once you have set up your configuration in Configuration Manager, you can run
your actual synchronization from the command line. See “Synchronization” on
page 67.
Configuration Manager does not change the data in your LDAP directory server or
the message security service. It is strictly used to configure and simulate
synchronization.
Google Apps Directory Sync settings are stored as XML configuration files.
Configuration Manager can also load and edit existing configuration files for the
directory sync utility.
Configuration Manager walks you through each step of configuring Google Apps
Directory Sync. Once you have finished each page, click Next to go to the next
step. You can also go back to previous steps with the Previous button, or jump
directly to any step using the left side navigation menu.
Configuration 27
The directory sync utility includes several ways to customize search rules and
filters. When collecting information from your LDAP server, you can define LDAP
queries to extract information. The directory sync utility supports RFC 2254, the
international standard on LDAP Filters. For the details, see RFC 2254:
http://www.ietf.org/rfc/rfc2254.txt
The directory sync utility also includes some non-LDAP filters. In these, you can
use regular expressions to filter for patterns of text. Regular expressions use
standard Java regular expression syntax, which is similar to most standard regular
expression syntax standards.
Configuration Files
In Configuration Manager, you can save or load configuration files to manage
multiple configuration files and store settings for later. All configuration files are
XML files.
To save configuration settings under a new name, select File->Save As from the
top menu and specify the directory and filename you wish to use. If you overwrite
an existing file, Configuration Manager will save the existing file as a copy with the
timestamp in the file name.
To save configuration settings under the existing name, select File->Save from
the top menu. If you haven’t saved yet, this option will be greyed out. If you
overwrite an existing file, Configuration Manager will save the previous file as a
copy with the timestamp of when the file was overwritten.
To open a configuration file, select File->Open from the top menu and choose the
configuration file. The user interface will then show the settings for that
configuration file. To open a recent configuration file, select File->Open Recent
and choose the configuration file.
To start a new configuration file, select File->New from the top menu.
Configuration Manager will load a new file with no configuration rules specified.

Message Security Service Settings
The Message Security Settings section governs how the directory sync utility
connects to the message security service, and how the directory sync utility
generates your message security service user list for comparison.
Before you enter information in the Message Security Service Settings pages,
collect the information from the message security service. You may need to create
new organizations or administrators in the message security service.
Configuration 29
Message Security Service Authentication
Enter your message security service login and connection information in this
section.
Specify the following:
Authentication Setting Description
Admin Email The email address used to log into the Administration
Console. This address should be a valid user on the
Administration Console with administrative privileges
over the user organizations you want to synchronize.
The administrator needs read authority for All Standard

Privileges, and write authority for all Help Desk and
User Settings.
Example: admin@mixateria.com
Password or Xauth The password (if using passwords) or XAuth hash

Hash String string (if using XAuth) for the Admin Email.
Example: swordFISH23
Passwords are stored in an encrypted format.
Authentication The authentication method used.
If you have set up XAuth (cross-authentication) with

the Administration Console, and you wish to use XAuth
to connect, select XAuth. Otherwise, leave this setting
as Password.
Example: Password

Authentication Setting Description
SSL Proxy Host If your server is running behind a firewall that requires
Name an SSL Proxy to connect to an outside server, enter
the proxy host name here.
(if needed)
If you can connect directly to the internet from this
machine, leave this field blank.
Example: httpproxy.mixateriacorp.com
SSL Proxy Host Port If your server is running behind a firewall that requires
an SSL Proxy to connect to an outside server, enter
(if needed) the proxy host port here. Otherwise, leave this field
blank. The usual port for SSL proxy is 8080.
Example: 8080
Immediately send a Typically, the message security service sends welcome

welcome message notifications to new users within 24 hours, but not
to new users immediately. This is to prevent a flood of welcome that
may overload your mail server.
If you want to send all the notifications immediately,

check the box labelled “Immediately send a welcome
message to new users.”
Test Connection
Once you have configured Server settings, click Test Connection. Configuration
Manager will connect to the message security service and attempt to log in.
If the test fails, verify your admin email and password, and confirm that you are
able to connect to the Internet from the machine.
Configuration 31
Message Security Service Orgs
On this page, specify which orgs in the message security service to synchronize.
The directory sync utility will use these orgs to generate user lists as a basis for
comparison with your LDAP user list.
Any existing user in the specified orgs will be deleted if they are not in the user list
generated from your LDAP server. Any users not in these orgs will be added (or
moved from another org) if they are in the user list generated from your LDAP
server. After synchronization, your users in the message security service will be
the same as your users on your LDAP server. You make exceptions to this
behavior by using exclusion filters.
Choose which orgs to synchronize:
• All users in all orgs under your Postini account: All organizations visible
to the administrator account (specified in the Server section) are included in
synchronization.
• Hierarchy: All organizations under an organization you specify here are

included in the synchronization. Enter the org name (not IID) here. The org
name is case sensitive. Match the same case as the org name in the
• Specific orgs: Only the specified organizations are included in the

synchronization. Enter each org name (not IID) and click Add to add it to the
list. To remove an organization from synchronization, select that organization
on the list and click Remove. Org names are case sensitive. Match the same
case as the corresponding org name in the message security service.

Exclusion Filters for Service Settings
If you have any users on your message security service user list who should not
be deleted or moved by the synchronization, add an exclusion filter to protect
those users.
Other exclusion filters you might want to include are:
• Default users
• Administrators who are not in your LDAP system in the OUs you specify
• Mailing list administrators
• Users in the message security service who are listed on a different LDAP
server
Exclusion rules are based on string values and regular expressions, not LDAP
settings.
This page shows the list of exclusion filters. In a new configuration, this will
contain two filters for default users. To add new exclusion filters, click the Add
Exclusion Filter button at the bottom of the screen.
On the list of Exclusion Filters, you can change existing filters as follows:
• Reorganize: Click the up arrow or down arrow icon to change the order of
exclusion filters.
• Edit: Click the notepad icon to edit the settings of an exclusion filter.
• Delete: Click the X icon to delete the exclusion filter.
Configuration 33
Add Exclusion Filter
Click Add Exclusion Filter at the bottom of the page to exclude a user or
organization from synchronization.
Exclusion Rule Setting Description
Type Sets what type of exclusion filter to create, Primary

Address or Postini Org.
• Primary Address: Check the user’s primary

address and exclude any users that match.
• Postini Org: check the organization name on the

message security service and exclude all users in
organizations that match.

Match Type The type of rule to match for the filter.
• Exact Match: The address or organization name

must match the rule exactly.
User Example: For a user, user1@mixateria.com

would exclude that single user.
Org Example: For an org, “Mixateria Florida Sales”

would exclude all users in that single org.
• Substring Match: The address or organization

name must contain the text of the rule as a
substring.
User Example: For a user, pdefault would exclude

pdefaultsales55@mixateria.com and
pdefault@sales.mixateria.com.
Org Example: For an org, “Sales” would exclude all

users in “Mixateria Florida Sales” and “Sales
Teams”.
• Regular Expression: The address or organization

must match the regular expression in the rule.
User Example: For a user, the regular expression

team[3-9]@mixateria.com would exclude
team3@mixateria.com through
team9@mixateria.com.
Org Example: For an org, the regular expression

Local Group - [A-Z][A-Z] would exclude all
users in the “Local Group - NJ” and “Local Group -
AZ” organizations.
Exclusion Rule The text of the match or regular expression to

compare.
See above for examples for these rules.
Users that meet the requirements for an exclusion filter

will not be deleted or moved. If they are listed on the
LDAP server, the directory sync utility will attempt to
add the user and fail
Sample Message Security Exclusion Rules

Listed below are samples of common exclusion rules. Note that the exact text of
these rules will vary based on your needs.
Configuration 35
Default Users
If your search includes your pdefault users, the directory sync utility will try to
delete these users unless they are in your LDAP server. Therefore, every new
configuration file includes the following two exclusion filters when created.
First rule:
• Type: Primary Address
• Match Type: Substring Match
• Exclusion Rule: pdefault@
Second rule:
• Exclusion Rule: postinidefault@
Special Administrations
If you have administrative accounts on the message security service that are not
part of your LDAP query, you may want to exclude them from synchronization so
they won’t be moved or deleted.
Add a separate rule for each special administrator:
First rule:
• Match Type: Exact Match
• Exclusion Rule: spam.administrator@mixateria.com
Second rule:
• Rule: virus.administrator@mixateria.com
Mailing List Org
If you have a separate organization devoted to mailing lists, and you want to
exclude it from synchronization, create an org rule. Note the exact organization
name from the Administration Console.
• Type: Postini Org
• Exclusion Rule: Mixteria Mailing List Users

Alternate Offices
The company has two other offices with separate LDAP servers. The three offices
have intermingled org structures, but all orgs in the other two offices are labeled
as “Dubai” or “London” in the org name in the Administration Console.
• Type: Postini Org
• Match Type: Regular Expression
• Exclusion Rule: [Dubai|London]
LDAP Settings
The LDAP Settings section configures how the directory sync utility connects to
your LDAP directory server and generates your LDAP user list for comparison.
You may need to collect information from your LDAP directory server before you
can enter details in this section.
Configuration 37
LDAP Connection
Specify your LDAP connection and authentication in this page.
LDAP Connection
Setting Description
Connection Type Choose whether to use an encrypted connection.
If your LDAP server supports an SSL connection and

you wish to use it, choose LDAP + SSL. Otherwise,
choose Standard LDAP.
Example: Standard
Host Name Enter the domain name or IP address of your LDAP

directory server.
Example: ad.mixateria.com, or 10.22.1.1.
Port Specify the host port. The default is 389.
Example: 389
Base DN Enter the base DN for the subtree to sycnrhonize. Do

not include spaces between commas. If you don’t
know the base DN, consult your LDAP administrator or
check an LDAP browser.
Example:
ou=test,ou=sales,ou=melbourne,dc=ad,dc=mixateri
a,dc=com

LDAP Connection
Setting Description
Authentication Type The authentication method for your LDAP server
If your LDAP server allows anonymous connections

and you want to connect anonymously, select
Anonymous. Otherwise, select Simple.
Example: Simple
Authorized User Enter the user to use when connecting to the server.
This user should have read and execute permissions
for the whole subtree.
If needed, include the domain for the user as well.
Example: admin1
Password Enter the password for the authorized user.
Example: swordfish
Test Connection
Once you have configured LDAP Authentication settings, click Test Connection.
Configuration Manager will connect to your LDAP server and attempt to log in, to
verify the settings you entered.
Configuration 39
LDAP Users
The LDAP Settings section configures how Google Apps Directory Sync
generates your LDAP user list for comparison. You may need to collect
information from your LDAP directory server before you can enter details in this
section.
Note: You must add at least one LDAP User Sync rule to run Google Apps
Directory Sync. This determines which users are synchronized and added in the

LDAP User Attributes
Specify what attributes Google Apps Directory Sync will use when generating the
LDAP user list.
LDAP User Attribute

Setting Description
Server Type The type of LDAP server that you are using with the
directory sync utility.
If you are using a Lotus Domino, Microsoft Active

Directory, or Open LDAP directory server, select that
server type. Otherwise, select Other.
Example: Microsoft Active Directory
Email Address The LDAP attribute that contains a user’s primary

Attribute email address.
Example: The default is mail.
Configuration 41
LDAP User Attribute
Setting Description
Non-Address An LDAP attribute with a unique key other than an

Primary Key email address.
Attribute
This field is optional. If a user’s email address on your
(Optional) LDAP server changes (for instance, because of a
name change), Google Apps Directory Sync will
rename the user in the message security service
without losing any quarantined mail or user settings.
Example: sAMAccountName
Note: Use an attribute that contains a valid string. An

attribute that contains raw binary data will not work as
a Non-Address Primary Key Attribute. Do not use the
objectGUID attribute for this field.
Mail List Attribute An LDAP attribute that specifies the address of a

mailing list. The directory sync utility will use this
attribute to look up the email address for any mailing
lists detected with Mail List rules. For most servers, this
value will be the same as the Email Address attribute.
Example: mail
Alias Address One or more attributes used to hold alias addresses.

Attributes These addresses will be placed as aliases to the
primary address listed in the Email Address Attribute
(if needed) field.
Example: proxyAddresses
Domino Alias Only for Lotus Domino servers. One or more attributes
Address Attribute used to hold internal Domino alias attributes, which are
stored as usernames without domain information.
(if needed) These addresses will be formatted as email addresses
and placed as aliases to the primary address listed in
the Email Address Attribute field.
If you are using a Lotus Domino server but your alias

address attribute stores full SMTP email addresses, list
the attribute in Alias Address Attributes, not Domino
Alias Address Attributes.
Example: uid
Domino Only for Lotus Domino servers. If an address contains

Replacement a space, Google Apps Directory Sync will substitute
Character this character instead.
Example: The most common values are dot (“.”) and

underscore (“_”).

Use Defaults
Click this button to use the default values for your server type, as follows:
• Lotus Domino: Email Address Attribute mail, Domino Alias Address

Attribute uid.
• MS Active Directory: Email Address Attribute mail, Alias Address Attribute

proxyAddresses.
• OpenLDAP: Email Address Attribute mail.
• Other: Email Address Attribute mail.
LDAP User Sync

This shows a list of rules used when generating the LDAP user list.
By default, all users that match these search rules will be added to the message
security service user list (or moved if they are in a different organization) and all
users that do not match these search rules will be removed. You can change this
behavior with exclusion filters.
This page shows the list of search rules. In a new configuration, this will be an
empty list. To add a search rule, click the Add Search Rule button at the bottom
of the screen.
Note: You cannot create an LDAP rule to exclude a specific OU in your LDAP
directory. Instead, limit the authority of the LDAP Administrator you use, removing
access to any OUs you do not want to synchronize.
Configuration 43
On the list of Search Rules, you can change existing rules:
search rules.
• Edit: Click the notepad icon to edit the settings of a search rule.
• Delete: Click the X icon to delete a search rule.
Search rules are processed in the order listed. If you would like one search rule to
take priority over another, move that search rule up using the up arrow icon on this
page. If two rules contradict each other, the first rule takes precedence.
Add Search Rule
To add a new search rule, click Add Search Rule.

LDAP User Sync

Setting Description
Org Name Select Org Name or Org name defined by this LDAP
attribute and enter an appropriate value.
Configure where to put users in your message security

service org hierarchy. The directory sync utility adds all
users that match this rule into the specified org in the
Example: mixateria-com users
WARNING: Synchronization does not create new orgs

in the message security service. If you need to add
new organizations in the message security service,
add them before you use the directory sync utility.
Org name defined Select Org Name or Org name defined by this LDAP
by this LDAP attribute and enter an appropriate value.
attribute
For each user, the directory sync utility reads the value
an LDAP attribute you specify, and adds the user to the
message security service organization specified in this
LDAP attribute.
Collect this information from the message security

service and your LDAP server. For more information,
see “Checklist: Before You Begin” on page 16.
Example: extensionAttribute5
For instance, if the value for Org name defined by

this attribute is extensionAttribute5, the directory
sync utility will look up each user’s
extensionAttribute5 attribute. If that attribute is set to
“mixateria-com sales” then the directory sync utility will
attempt to add the user to “mixateria-com sales” in the
If the value of the Org Mapping Attribute is blank, the

directory sync utility will not add the user, and will
attempt to delete the user from the message security
system if it is there.Configure where to put users in
your message security service org hierarchy.
WARNING: Synchronization does not create new orgs

in the message security service, nor does it populate
fields in your LDAP server. If you need to add new
organizations in the message security service, or new
fields on your LDAP server, add them before you use
the directory sync utility.
Configuration 45
LDAP User Sync
Setting Description
Use Default Filter Only usable if you are using “Org name defined by
this LDAP attribute.”
(optional)
The “use default filter” check box sets the scope to
“Subtree” and the rule to objectclass=*.
WARNING: This setting is not recommended for large

deployments because it may cause extreme load.
Scope This determines where in the LDAP directory this rule

applies. This could be an entire subtree, one level, or a
single object.
• Subtree: All objects matched by the search, and

anything under those objects. (recursive)
• One-level: All objects matched by the search, and

anything one level underneath them. Does not look
further than one level.
• Object: Only objects directly matched by the

search. No recursion of any kind.
Choosing which option to use:
Subtree gives the broadest search, but for very large

organizations this can be load-intensive and cause
system problems.
One-level provides a limited search that will avoid

causing extreme load for very large organizations.
Object is rarely used except with very complex LDAP

searches. It allows a search only on the specified
object.
Example: Subtree

LDAP User Sync
Setting Description
Rule This is the search rule used. This rule uses standard
LDAP filtering language, and allows sophisticated logic
and complex rules for searching. For more information
about LDAP search filters, see “LDAP Queries” on
page 18.
Example 1: To match all objects (this may cause load

problems):
objectclass=*.
Example 2: To match all human users:
• For OpenLDAP:
(objectClass=inetOrgPerson)
• For Active Directory:

(objectClass=person)
• for Lotus Domino:

(objectClass=dominoPerson)
LDAP User Exclusion Rules

If you have any users on your LDAP directory server that match your search rules
but should not be added, add an exclusion rule here. This might include:
• Internal users who do not have outside email addresses
• Printers, conference rooms, and other non-user resources
• Users who should not receive mail filtering
Configuration 47
settings.
Note: To exclude individual users, add a separate rule for each user.
This page shows the list of exclusion filters. In a new configuration, this will be an
empty list. To add exclusion filters, click the Add Exclusion Filter button at the
bottom of the screen.
On the list of Exclusion Filters, you can change existing filters as follows:
exclusion filters.

Click the Add Exclusion Filter at the bottom of the page to exclude a user or
organization in your LDAP server from synchronization.
Match Type The type of rule to use for the filter.
• Exact Match: The address must match the rule

exactly.
Example: maria@mixateria.com would exclude

only the user maria@mixateria.com.

substring.
Example: “test” would exclude

testadmin@mixateria.com and
salestest1@mixateria.com.

must match the regular expression specified.
Example: internal.*@mixateria.com would

exclude internalhelpdesk@mixateria.com and
internal@mixateria.com.
Configuration 49
Exclude Type What kind of LDAP data to exclude.
• Primary Address: Directory Sync will exclude

primary addresses that match this rule.
• Alias Address: Directory Sync will exclude aliases

that match this rule.
If you want to exclude both primary addresses and

alias addresses, create two exclusion rules.
Rule The match string or regular expression for the

exclusion rule. Behavior of this field depends on the
Match Type you choose.
Addresses that contain this string (or match this

regular expression) will not be added to the message
security service, and will be deleted if found.
Examples:
• Exact Match: maria@mixateria.com
• Substring Match: listinternal
• Regular Expression: internal.*@mixateria.com
Sample LDAP User Exclusion Rules

Sample Substring Match: Printers
In this example, printers are listed as LDAP users and would match the LDAP
query given. However, the printers all have the word “printer” in the name. The
rule looks for that substring.
• Exclude Type: Primary Address
• Rule: printer
Sample Exact Match: Opt-Out Users
Two users have opted out of mail filtering and should not be synchronized.
Add a separate rule for each special user.

First rule:
• Rule: atif@mixateria.com
Second rule:
• Rule: svetlana@mixateria.com
Sample Regular Expression Match: Test Users
About five hundred test users are listed in LDAP, but they are only used for
internal load testing. All the test users follow the same name pattern: internal-
testX, where X is a number, and all test users are in the same domain.
• Rule: internal-test[0-9]*@mixateria.com
LDAP Mailing List Overview

The LDAP Settings section configures how Google Apps Directory Sync
generates a list of mailing lists from your LDAP directory server. You may need to
collect information from your LDAP directory server before you can enter details in
this section.
Configuration 51
Mailing lists are often handled separately, because if a mailing list is added as a
user, all recipients of the mailing list will receive notifications. This can cause
confusion. To avoid this problem, Google Apps Directory Sync can import mailing
lists as aliases to a user you specify.
This section is optional. Fill out the information in this section if you wish to import
mailing lists as aliases to a central user in the message security service.

LDAP Mailing List Sync
Mailing lists are a special kind of email address that direct mail to many addresses
at once. Most administrators prefer to create mailing lists as aliases to a separate
user in the message security service, to avoid administrative notifications and
quarantine summaries going out to all the members of a mailing list.
This page shows the list of LDAP mail list rules. In a new configuration, this will be
an empty list. To add mail lists, click the Add Mail List button at the bottom of the
screen.
On the list of Mail List rules, you can change existing filters as follows:
exclusion filters.
Configuration 53
Add Mail List
Click the Add Mail List at the bottom of the page to synchronize one or more
addresses as mailing lists.
Mailing List Setting Description
Mail list owner The email address of the user who will manage the
mailing list. If this user is not a user in the message
security service, the directory sync utility will add this
user in the specified Mail list owner org.
Example: admin@mixateria.com
Mail list owner org If the mailing list owner does not exist on your LDAP
server, the directory sync utility will add it to this
organization. If the mailing list owner already exists this
field is not used.
Example: Mixateria Special Administrators

Mailing List Setting Description
Scope Where to apply the mail list rule. This could be a whole
subtree, a single level, or a single object.
• Subtree: All objects matched by the search, and

anything under those objects. (recursive)
• One-level: All objects matched by the search, and

anything one level underneath them. Does not look
further than one level.
• Object: Only objects directly matched by the

search. No recursion of any kind.
Choosing which option to use:
Subtree gives the broadest search, but for very large

organizations this can be load-intensive and cause
system problems.
One-level provides a limited search that will avoid

causing load for very large organizations.
Object is rarely used except with very complex LDAP

searches. It allows a search only on the specified
object.
Example: Subtree
Rule This is the search rule used. This rule uses standard
LDAP filtering language, and allows sophisticated logic
and complex rules for searching. For more information
about LDAP search filter language, consult your LDAP
documentation.
Example: (objectclass=dominoGroup)
LDAP Mailing List Exclusion Rules

You can exclude particular addresses from being treated as mailing lists.
If you have any entries in your directory server that match a mail list rule, but
should not be treated as a mailing list, list them here. This might include:
• Internal mailing lists that do not have outside email addresses
• Printers, conference rooms, and other non-user resources
• Mailing lists that should be treated as individual users, with separate archives
and quarantines.
Configuration 55
settings.
This page shows the list of exclusion filters. In a new configuration, this will be an
empty list. To add exclusion filters, click the Add Exclusion Filter button at the
bottom of the screen.
On the list of exclusion filters, you can change existing filters as follows:
exclusion filters.

Click Add Exclusion Filter at the bottom of the page to prevent an address from
being treated as a mailing list.
Match Type The type of rule to use for the filter.
• Exact Match: The address or organization name

must match the rule exactly.

substring.

must match the regular expression specified.
Rule The text of the match or regular expression to

compare.
Addresses that meet the requirements for an exclusion

filter (or users in orgs that meet the requirements) will
not be added as mailing lists.
Sample LDAP User Exclusion Rules

Configuration 57
Sample Substring Match: Internal Mailing Lists
Several mailing lists are devoted to internal use only. Those lists all have “internal”
in the address.
• Rule: internal
Sample Exact Match: Secure Mailing Lists
Three small-distribution mailing lists are top security and should not be archived
with other mailing lists.
Add a separate rule for each special mailing list.
First rule:
• Rule: finance-early-statements@mixateria.com
Second rule:
• Rule: internal-security@mixateria.com
Third rule:
• Rule: legal-confidential@mixateria.com
Sample Regular Expression Match: Test Users
About five hundred test users are listed in LDAP, but they are only used for
internal load testing. All the test users follow the same name pattern: internal-
testX, where X is a number, and all test users are in the same domain.
• Rule: internal-test[0-9]*@mixateria.com
Notifications
You can set Configuration Manager so that every time synchronization occurs,
Google Apps Directory Sync will send out a notification to a list of users.

Consider adding a notification to send mail to your own address, and possibly the
addresses of any concerned parties in your company.
Note: Notifications do not support TLS.
Notifications Setting Description
Send notifications Enter the “From:” address for the notification mail.
from address Recipients will see this address as the notification
sender. For instance, you might use your own email
address.
Example: dirsync@mixateria.com
Send notifications Notifications will be sent to all addresses on this list.

to the following Enter any valid email address on any domain. Enter
addresses each recipient email address individually, then click the
Add button.
Depending on your mail server settings, the directory

sync utility may be unable to send mail to external
email addresses. Run a test notification to confirm that
mail is sent properly.
Example: dirsync-admins@mixateria.com
Configuration 59
Notifications Setting Description
SMTP Relay Host The SMTP mail server to use for notifications. The
directory sync utility uses this mail server as a relay
host.
Example: 172.0.0.1 to run the mail server on the

same machine.
Example: mail.mixateria.com
Username If the SMTP server you specify requires SMTP

authentication, enter the user name to use here.
(if needed)
Example: admin5
Password If the SMTP server you specify requires SMTP

authentication, enter the Password to use here.
(if needed)
Example: swordfish
Do not include in You can limit the information sent in notifications by

notifications checking any of the three checkboxes. All checkboxes
are optional.
(Optional)
• Extra details: Google Apps Directory Sync
notifications will not include extra details and
potentially extraneous information.
• Warnings: Google Apps Directory Sync

notifications will not include warning messages.
• Errors: Google Apps Directory Sync notifications

will not include error messages.
Test Notification
Click this button to test notifications. Configuration Manager will connect to the
SMTP server you specified and send a test notification to the addresses you list.
Delete Limits
As a safeguard, you can limit how many users Google Apps Directory Sync can
delete during synchronization. This is recommended as a way to prevent
accidental mass deletion.

The directory sync utility checks to be sure that synchronization will not delete too
many users. If the synchronization would delete more users than the delete limits
allow, the entire synchronization fails and no users are added, moved or deleted.
This will be noted in the notifications email.
Note: Delete limits apply during synchronization, but not during simulation.
Simulation results will not include delete limits.
To set a delete limit, specify one of the following:
Delete Limits Setting Description
Delete no more than Specify a maximum percentage of users that can be

deleted. This is a percentage of the users registered on
% of users the message security service, not a percentage of
users on your LDAP server.
(Optional)
If no delete limit is specified, the default is 5%.
If youset the delete limit to 100%, delete limits will not

apply.
You can suppress delete limits from the command line.
Example: 5%
Delete no more than Specify a maximum number of users that can be

deleted.
users
Example: 25
(Optional)
Configuration 61
Log Files
You can specify the file name and level of detail of logging for Google Apps
Directory Sync.
Logging Setting Description
File name Enter the directory and file name to use for the log file
or click Browse to browse your file system.
Example: sync.log
Log Detail The level of detail of the log. Options are FATAL,
ERROR, WARN, INFO, DEBUG, and TRACE.
The level of detail is cumulative: each level includes all

the details of previous levels. ERROR includes all
ERROR and FATAL messages, and so on.
• FATAL only logs fatal operations.
• ERROR only logs errors and fatal operations.
• WARN only logs warnings, errors and fatal

operations.
• INFO logs summary information.
• DEBUG logs more extensive details.
• TRACE logs all possible details.

Logging Setting Description
Maximum Log Size The maximum size of the log file, in gigabytes. When
this file reaches half capacity, it is saved as a backup
file (which overwrites any existing backup file) and a
new file is created. At any time, the total size of these
two files (the log file and the backup log file) will not
exceed the total maximum size.
Example: 4
Simulate Sync
After you enter configuration information, use this section to verify and test your
Google Apps Directory Sync settings.
Note: Configuration Manager does not check for valid LDAP syntax. To find invalid
LDAP queries, use Simulate Sync. Invalid LDAP queries will cause errors.
Simulate Sync
When you first go to this page, you will see Validation Results. This page will show
a checklist of all the Configuration Manager sections. If you are missing required
information, you will see error messages showing what needs to be added.
Important: This checklist confirms only the minimum needed for synchronization.
You may need to configure additional filters or rules to be sure the results are what
you expect.
Configuration 63
Once you’ve completed all required fields, you will be able to use the Simulate
Sync button to simulate a synchronization.
Once you’re ready, click Simulate Sync. You will see the Simulate Sync page.
During simulation, Configuration Manager will:
• Connect to the message security service and generate a registered user list.
• Connect to your LDAP server and generate an LDAP user list.
• Generate a list of differences.
• Log all events.
• If connection was successful, show a Proposed Change Report which shows

what changes would have been made to your message security service user
list.
Note: Simulate Sync will never update or change your LDAP server or your users
in the message security service. The simulation is strictly for configuration and
testing. To run an actual synchronization, use the command line. See
“Synchronization” on page 67 for more.

Review the Simulation Results to confirm that the simulation occurred correctly
without any unexpected results.
If any errors occur, check the error text. Most error text is human readable, but
some error text may contain Java stack trace errors. If you need help
troubleshooting these errors, see “Troubleshooting” on page 71.
If the synchronization was successful, check the Proposed Change Report and
review it for unexpected results.
Note: The Proposed Change Report doesn’t check your delete limits.
If you see any errors or unexpected results, you can go back and change your
configuration to try again. To change your configuration, click on any of the
headings on the left navigation bar.
You can switch between the Validation Results and Simulation Results pages
using the buttons at the bottom of the page. You can also run another simulation
from either page by clicking the Simulate Sync button at the bottom.
Once you are finished, save your configuration file and run synchronization. See
“Synchronization” on page 67.
Configuration 65
Chapter 6
Synchronization Chapter 6
About Synchronization
Run the synchronization command to push your LDAP directory server user
information to the message security service.
The directory sync utility uses the command sync-cmd to run synchronization.
This simple command line interface gives you the flexibility to incorporate
synchronization into any scheduling or batch script you wish to use.
Before you can synchronize the message security service with your LDAP
directory server, you must create rules that detail how to connect to both servers,
and what filters and rules to use. These rules are stored in an XML file. To create
this XML file, run Configuration Manager. For more information about
Configuration Manager, see “Configuration” on page 27.
Most administrators run their first synchronization manually to test the process,
import an initial set of users, and confirm the changes. After initial synchronization
with the command line, you can set up automatic scheduling for future
synchronization.
Command Line Synchronization

Before you can run synchronization, create a Configuration XML file using the
Configuration Manager user interface. For more information, see For more
information about Configuration Manager, see “Configuration” on page 27.
The command line to use for all platforms is
sync-cmd
Run without any arguments, this command gives an error and directs you to run
sync-cmd -h for help.
To synchronize, use the following command line to read a configuration file,

connect to both servers, generate a list of changes, and apply those changes:
sync-cmd -a -c [filename]
Synchronization 67
Replace [filename] with the name of the XML file you created in the
Synchronization options
The table below describes the possible arguments to the sync-cmd command. You
can also see this information by running the following:
sync-cmd -h
in the directory where the directory sync utility is installed.
Option Values
-r,--report-out Write reports to the specified output file, in

addition to writing them to the log.
-a,--apply Apply detected changes.
-V Display detailed application version
information.
-c,--config [filename] Specify the configuration to load.
Synchronization will not occur without a valid
XML file for this argument.
-d, --deletelimits Ignores any configured delete limits.
-f, --flush For support troubleshooting only (slows sync)
WARNING: This option is intended only to

resolve specific troubleshooting issues.
Improper use can cause performance
degradation. Do not use this option unless
directed by support.
-g, --groups Do not analyze groups.
Note: Do not use this option. It is intended for

other versions of the directory sync utility, and
will have no effect.
-h,--help View this information and exit.
-l,--loglevel [level] Override the default and/or configured log
level with the specified value. Valid values (in
increasing order of verbosity) are FATAL,
ERROR, WARN, INFO, DEBUG, and TRACE.
In most cases, the recommended log level is

INFO.
-s, --sharedcontacts Do not analyze shared contacts.
Note: Do not use this option. It is intended for

other versions of the directory sync utility, and
will have no effect.

Option Values
-u, --users Do not analyze users.
Note: If you use this option, Google Apps

Directory Sync will not add, move or delete
users.
-v Display short application version information.
Scheduling Synchronization
Once you have successfully run a manual synchronization, you can set up
automatic synchronization. Use existing third-party scheduling software to
automate synchronization.
In most cases, scheduling twice a week is recommended. The exact timing will
vary based on the number of users you have and how often you need to update
them. A large company with many users changing frequently may need to run the
directory sync utility daily, while a small company with few changes may not need
to run the utility more than once a week.
The exact method to schedule this task depends on the operating system in which
the directory sync utility is installed. In Microsoft Windows, use Scheduled Tasks.
In Linux or Solaris, use cron. Steps for how to do this are listed below. You can
also use any other scheduling software that can launch commands from the
command line interface.
Microsoft Windows: Scheduled Tasks

In Microsoft Windows, schedule synchronization using Scheduled Tasks.
Note: These steps apply to most common Microsoft Windows configurations.

Scheduled Tasks is a third-party product and is not supported directly by the
Google (or Postini) team. In the event of a Scheduled Tasks issue, contact your
Windows administrator.
To schedule a task
1. In Control Panel, open Scheduled Tasks.
2. Double-click Add Scheduled Task.
Synchronization 69
3. Complete the Scheduled Task wizard using the following information. (Steps
may vary depending on your version of Microsoft Windows.)
• Choose the program sync-cmd.exe, located where the directory sync

utility is installed.
• The frequency of the task depends on your synchronization needs. For
most environments, twice per week is appropriate.
• Use Advanced Properties to specify an exact command line. The
appropriate command line is:
[path]\sync-cmd -a -c [filename]
Replace [path] with the path where the directory sync utility was
installed. Replace [filename] with the name of the XML file you created
in the Configuration Manager.
4. Test the scheduled task by running manually once. In the Scheduled Tasks
window, right-click the task you created and select Run from the right-click
menu. Check the log file for errors.
Linux and Solaris: cron

In Linux and Solaris environments, schedule synchronization using crontab.
Note: These steps apply to most common Linux and Solaris configurations. Linux
and Solaris are third-party products and are not supported directly by the Google
(or Postini) team. In the event of an issue with cron, contact your administrator.
To add a cron job
1. Run crontab -e to update the crontab file.
2. Add a line in the crontab file for the following command:

sync-cmd -a -c [filename]
The syntax of this line will depend on your operating system and version of
cron. For instance, to schedule the task to run at 3:30 AM twice per week, on
Monday and Thursday, add the following entry:
30 3 * * 1,4 [path]/sync-cmd -a -c [filename]
Replace [path] with the path where the directory sync utility was
installed.Replace [filename] with the name of the XML file you created in the
3. Save the crontab file and exit your text editor.

Chapter 7
Troubleshooting Chapter 7
About Troubleshooting
This chapter covers information about how to troubleshoot problems that may
occur with Google Apps Directory Sync.
Troubleshooting information includes information about common issues, system

tests and researching issues.
For information about LDAP queries, see “LDAP Queries” on page 18.
Common Issues
The following describes common issues and questions related to Google Apps
Directory Sync.
A mailing list rule or exclusion rule doesn’t seem to be doing anything.
Check the scope of the rule. You may need to set the scope to SUBTREE.
A mailing list rule generates errors.
Check the Mailing List Attribute in LDAP Configuration. This is the field that
contains the email address of a mailing list. In most cases, this will be mail.
The proxy environment requires a password challenge for external web access.
The directory sync utility can use a proxy server but cannot respond to password
challenges. To run synchronization, you will need to change your network setup to
allow the directory sync utility to connect without a password challenge, or without
a proxy server.
The base DN information doesn’t seem to be correct.
Check to be sure your base DN doesn’t include any spaces.
Troubleshooting 71
How do I find out information about my LDAP server fields?
You will need to download an LDAP browser. An LDAP browser allows you to
browse through an LDAP directory server and identify all fields and values. Most
directory servers do not include a complete LDAP browser.
For information about LDAP browsers, see “Useful LDAP Tools” on page 18.
I cannot simulate a synchronization because the notifications server not

specified.
To run a simulated synchronization, you will need a server capable of sending

mail. If you are running directory sync on a mail server machine, you can use the
IP address 127.0.0.1 for your mail server. Otherwise, contact your mail
administrator for the correct mail information.
How securely are passwords stored?
Google Apps Directory Sync stores passwords using a two-way encryption

scheme. This protects your sensitive information from casual snooping or reverse
engineering.
This is a change from previous versions. Before 1.3.11, passwords were stored
unencrypted in plain text in configuration files.
To convert a configuration file to the new format with encrypted passwords:
1. Open the file in Configuration Manager.
2. Save the file again.
You can also upgrade the file with the following command-line executable:
upgrade-config -c [filename]
where [filename] is the name of the XML configuration file to upgrade.
Note: Configuration files for version 1.3.11 or later are not compatible with earlier
versions.
How can I exclude a specific LDAP organization?
You cannot create an LDAP rule to exclude users in a specific LDAP organization.
Instead, limit the authority of the LDAP Administrator you use, removing access to
any OUs you do not want to synchronize.
Is there a way to change the Non-Address Primary Key Attribute for users
manually once the directory sync utility has synced users in the message
security service?
The purpose of this field is to store something stable and unique from LDAP
directory and then use that to compare users later.
If you use the optional field for Non-Address Primary Key Attribute, and then you
change this attribute to something other than the original Non-Address Primary
Key Attribute, the directory sync utility will delete users and add them again.

There is no workaround for this. This stored information is only available to DSS
and is not available via batch or the GUI.
After a user is deleted, then added again, non-fatal errors occur during
synchronization.
You can safely ignore non-fatal error messages that directory sync tried to add an
alias that already exists.
The directory sync utility preserves alias information after deleting a user, and
keeps that information for a period of time. If the user is added again, the user still
has all the same aliases, which can cause a warning message when the directory
sync utility tries to add them again.
Some users on the LDAP server have aliases in another domain that is not listed
in the message security service. Is there a way to exclude aliases from
synchronization?
No. The directory sync utility will attempt to add these aliases and fail. If this
happens, you can safely ignore the warning messages.
How can I set up the directory sync utility to use a Global Catalog?
Set Configuration Manager to connect to port 3268 instead of 389. You will also
need to set up your LDAP scope and queries appropriately for the Global Catalog.
For more information on appropriate LDAP queries for a Global Catalog, see your
LDAP server documentation or contact your LDAP administrator.
System Tests
If you encounter problems, use the tests in Configuration Manager to find the
problem:
1. In Configuration Manager, open the XML file you are using for configuration.
2. Under Message Security Service Authentication, click Test Connection to

confirm you can connect to the message security service.
3. Under LDAP Connectons, click Test Connection to confirm you can connect
to your LDAP server.
4. Under Notifications, click Test Notification to confirm you can send a test
notification.
5. Under Simulate Sync, confirm you have filled out all required fields.
6. Under Simulate Sync, click Simulate Sync to confirm that synchronization is

running properly.
If you encounter any problems, note which tests failed and confirm that the
configuration information is correct for those sections of Configuration Manager.
Troubleshooting 73
Escalating Problems
If you are unable to run directory sync, and cannot resolve the problem using
system tests, collect the following information for troubleshooting:
• The most current sync log file, located in the folder where the directory sync
utility is installed.
• The version number of the directory sync utility you are running. You can find
this in the Configuration Manager UI by going to Help->About, or you can run
the command sync-cmd -V.
• The current config file you are using. This is an XML file (default name
sync.xml) located in the same folder where the directory sync utility is
installed.
• The brand and version of the LDAP directory server you're using.
• The operating system on the machine where the directory sync utility is
running.
Once you have collected this information, escalate this using your normal support
channels. For more information about support for the directory sync utility, see the
Google Apps Directory Sync site:
http://www.postini.com/dir_sync

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Google Apps Directory Sync

Release 1.3.25, January 2009

Part number: DSS_1.3.25_09

© Copyright 2008 Google, Inc. All rights reserved.

2 Release 1.3.25, January 2009

About This Guide 7

6 Release 1.3.25, January 2009

What This Guide Contains

• Google Apps Directory Sync features.

• Configuration for the directory sync utility.

• Troubleshooting the directory sync utility.

This guide is a supplement to the Message Security Administration Guide. For

Message Security Administration Guide for the message security

Directory Sync Configuration Instructions for setting up your network

How to Send Comments About This Guide

8 Release 1.3.25, January 2009

About Google Apps Directory Sync

Features and Benefits

• Updates registered users in the message security service to match your

• Can be configured to track user primary address changes, keeping

• Runs on any Windows (XP or Vista), Linux or Solaris server.

• All needed components included in installation.

• Allows sophisticated rules to handle mailing lists, aliases, and exceptions.

• Allows complex mapping for your org hierarchy.

• Extensive tests and simulations to ensure correct synchronization.

This table compares the two methods:

Google Apps Directory Sync Directory Sync Hosted Edition

Runs on a server in your network. Runs within the message security

Configure on your server with the Configure in the Administration

Installation includes all needed Requires complex installation of third

Connects directly to your LDAP server Connects to your DSML server by

Requires administration access on the Requires administration access on the

Allows advanced LDAP queries, Allows advanced LDAP queries,

10 Release 1.3.25, January 2009

12 Release 1.3.25, January 2009

• Configuration Manager - Use this graphical UI to configure how the directory

• XML Configuration File - Save configuration information from Configuration

• Synchronization Command Line - Use the command-line utility sync-cmd to

For information on system requirements, see “System Requirements” on page 24.

2. Install the directory sync utility.

3. Step through Configuration Manager to configure synchronization.

4. In Configuration Manager, simulate a synchronization.

5. Revise your configuration in Configuration Manager based on the simulation.

8. Using your server’s scheduling tools, set up automatic scheduled

• Message Security Org Structure

• Message Security Administrator

• LDAP Structure Information

Each item on the checklist is detailed below.

Message Security Org Structure: Before you configure synchronization, set up

Message Security Administrator: Note the administrator username and

16 Release 1.3.25, January 2009

LDAP Administrator: Collect the username and password of an administrator on

Softerra LDAP Administrator

18 Release 1.3.25, January 2009

Equals = Creates a filter which requires a field to have a

Any * Wildcard to represent that a field can equal

Parentheses () Separates filters to allow other logical

And & Joins filters together. All conditions in the

Or | Joins filters together. At least one condition in

Not ! Excludes all objects that match the filter.

Common LDAP Queries

All objects (this may cause load problems):

All user objects that are designated as a “person”