Thanks to everyone who helped me. Since it was a struggle for me, I thought that I would post how I did it in case others have the same problems that I had. Maybe it will help someone else. My Setup: Fedora Core 4 Fedora Directory Server 1.0.2 Windows 2000 Server Install FDS ( or reinstall: rpm -qa | grep fedora-ds | xargs rpm -e; rm -rf /opt/fedora-ds ; rpm -i fedora-ds-1.0.2 ) create certificates, etc.. I used this simple script that I wrote: (cd to /opt/fedora-ds/alias) ----------------------------------------------------------------------- echo -n "Creating password and noise file..." echo "8904859034905834-580943502385430958430958049385" > /opt/fedora-ds/alias/pwdfile.txt echo "8374893jkhsdfjkhdjksfah89dskjfkdghkjdfhguiert9348khkfhgkjfd79" > /opt/fedora-ds/alias/noise.txt echo -n "Creating Databases..." $serverroot/shared/bin/certutil -N -d . -f pwdfile.txt echo -n "Generating encryption key..." $serverroot/shared/bin/certutil -G -d . -z noise.txt -f pwdfile.txt echo -n "Generating self-signed certificate..." $serverroot/shared/bin/certutil -S -n "CA certificate" -s "cn=CAcert" -x -t "CT,," -m 1000 -v 120 -d . -z noise.txt -f pwdfile.txt echo -n "Generating server certificate.." $serverroot/shared/bin/certutil -S -n "Server-Cert" -s "cn=msas.msd.lbl.gov" -c "CA certificate" -t "u,u,u" -m 1001 -v 120 -d . -z noise.txt -f pwdfile.txt mv key3.db slapd-msas-key3.db mv cert8.db slapd-msas-cert8.db ln -s slapd-msas-key3.db key3.db ln -s slapd-msas-cert8.db cert8.db echo -n "Setting permissions.." chown nobody.nobody /opt/fedora-ds/alias/slapd-msas* echo -n "Exporting certificate.." $serverroot/shared/bin/certutil -L -d . -n "CA certificate" -r > cacert.der echo "Converting certificate.." openssl x509 -inform DER -in cacert.der -outform PEM -out cacert.pem echo "Copying cacert.pem to /etc/openldap/cacerts.." cp cacert.pem /etc/openldap/cacerts/ echo -n "Enabling SSL in FDS" echo "" echo -n "Please enter Manager password..(twice)" ldapmodify -x -D cn=Manager -W -f /tmp/ssl_enable.ldif ldapmodify -x -D cn=Manager -W -a -f /tmp/addRSA.ldif --------------------------------------------------------- restart FDS Test SSL connections and ldapsearch netstat -an | grep 636 Install Active Directory on Windows Server Install Certificate Services --> Enterprise root CA reboot Enable SSL on AD 1. Install Certificate Services on Windows 2000 Server and an Enterprise Certificate Authority in the Active Directory Domain. Make sure you install an Enterprise Certificate Authority. 2. Create a Security (Group) Policy to direct Domain Controllers to get an SSL certificate from the Certificate Authority (CA). 1. Open the Active Directory Users and Computers Administrative tool. 2. Under the domain, right-click on Domain Controllers. 3. Select Properties. 4. In the Group Policy tab, click to edit the Default Domain Controllers Policy. 5. Go to Computer Configuration->Windows Settings->Security Settings->Public Key Policies. 6. Right click Automatic Certificate Request Settings. 7. Select New. 8. Select Automatic Certificate Request. 9. Run the wizard. Select the Certificate Template for a Domain Controller. 10. Select your Enterprise Certificate Authority as the CA. Selecting a third-party CA works as well. 11. Complete the wizard. 12. All Domain Controllers now automatically request a certificate from the CA, and support LDAP using SSL on port 636. 3. Retrieve the Certificate Authority Certificate 1. Open a Web browser on the AD machine 2. Go to http://localhost/certsrv/ 3. Select the task Retrieve the CA certificate or certificate revocation list. 4. Click Next. 5. The next page automatically highlights the CA certificate. Click Download CA certificate. 6. A new download window opens. Save the file to the hard drive. Save in DER mode Copy file to FDS server, convert to PEM format openssl x509 -inform DER -in ad-cert.der -outform PEM -out ad-cert.pem Import AD CA cert into FDS certutil -A -d . -P slapd-instance- -t "CT,CT,CT" -a -i ad-cert.pem check certs ( from /opt/fedora-ds/alias) certutil -L -d . -P slapd-instance Check ldapsearch from FDS to AD ldapsearch -Z -P <RHDS-cert8.db> -h <AD/NT Hostname> -p <AD SSL port> -D "<sync manager user> -w < sync manager password> -s <scope> -b "<AD base>" "<filter>" Install PassSync on Windows machine. Follow directions from Howto:WindowsSync (certificate creation) restart AD server Enable Replication in Directory Server Console: Go to configuration tab --> Replication --> enable changelog --> default Expand Replication, click UserRoot Check "Enable Replica" Single-master Right Click UserRoot --> Create new windows sync agreement Up log level in FDS: dn: cn=config changetype: modify replace: nsslapd-errorlog-level nsslapd-errorlog-level: 8192 ldapmodify -x -D "cn=directory manager" -a -f repl_log.ldif restart FDS right click win sync agreement --> Initiate Full Sync check error logs (/opt/fedora/slapd-instance/logs/errors) In order for users to be created on the Windows side, users must have certain attributes. e.g. dn: uid=TBird,ou=People, dc=server,dc=com givenName: Tweetie ntUserCreateNewAccount: true objectClass: top objectClass: person objectClass: organizationalPerson objectClass: inetorgperson objectClass: ntuser objectClass: posixAccount facsimileTelephoneNumber: 510-555-5555 uid: TBird mail: tbird at server.com uidNumber: 71209 cn: Tweetie Bird ntUserComment: Tweetie Bird User Account telephoneNumber: 510-555-5555 loginShell: /bin/bash ntUserDomainId: tbird gidNumber: 5000 ntUserDeleteAccount: true gecos: Tweetie Bird homeDirectory: /home/tbird sn: Bird userPassword:: I hope that I have this right.