I posted this on the freenas forums..

Here’s a short write-up on how I got SSL going with LDAPS against AD for authentication. I used the plugin and am working out of / in the jail.
keytool is located at /usr/pbi/subsonic-amd64/bin
1) Create a cnf file to be used for generating the csr.

[ req ]
default_bits = 2048
distinguished_name = req_distinguished_name
req_extensions = v3_req
x509_extensions = v3_req
[ req_distinguished_name ]
countryName = Country Name (2 letter code)
countryName_default = US
countryName_min = 2
countryName_max = 2
stateOrProvinceName = State or Province Name (full name)
stateOrProvinceName_default = Texas
localityName = Locality Name (eg, city)
localityName_default = San Antonio
0.organizationName = Organization Name (eg, company)
0.organizationName_default = Company
organizationalUnitName = Organizational Unit Name (eg, section)
organizationalUnitName_default = Department
commonName = Common Name (hostname)
commonName_default = subsonic
commonName_max = 64
emailAddress = Email Address
emailAddress_default = email@domain.com
emailAddress_max = 64
[ v3_req ]
basicConstraints = CA:FALSE
keyUsage = nonRepudiation, digitalSignature, keyEncipherment
subjectAltName=@alt_names
[alt_names]
DNS.1 = subsonic
DNS.2 = subsonic.domain.com
IP.1 = 192.168.0.1

2) Generate the csr and private key

openssl req -new -sha256 -out subsonic.csr -config subsonic.cnf -newkey rsa:2048 -nodes -keyout subsonic.key

3) Submit the CSR to your CA. I used a Windows CA and received the subsonic.cer certificate.
4) Generate a PKCS12 file to be used for the Web SSL Java Keystore. I could not get this working using the sytem keystore, so this one is just for https.

openssl pkcs12 -export -out subsonic.pfx -inkey subsonic.key -in subsonic.cer -certfile CA-Certificate.cer

5) Create the Java Keystore to be used for SSL access.

./keytool -importkeystore -srckeystore subsonic.pfx -destkeystore subsonic.keystore -srcstoretype PKCS12 -srcalias 1 -destalias subsonic.domain.com

6) Add your CA certificate to the system Java Keystore as well. This will be used for LDAPS authentication. The default password is ‘changeit’ You should probably change that as well.

./keytool -import -trustcacerts -alias CA-domain.com -file /CA-Certificate.cer -keystore /usr/pbi/subsonic-amd64/openjdk7/jre/lib/security/cacerts

7) Enable LDAP Authentcation under Settings\Advanced

LDAP URL: ldaps://server.domain.com:636/dc=domain,dc=com
LDAP search filter: (&(sAMAccountName={0})(&(objectCategory=user)(memberof=cn=subsonic,ou=groups,dc=domain,dc=com)))
LDAP Manager: DOMAIN\user (non privileged!)

8) The default user cache is too high. Edit it in /var/db/subsonic/jetty/4427/webapp/WEB-INF/classes/ehcache.xml

<cache name="userCache"
maxElementsInMemory="1000"
eternal="false"
timeToIdleSeconds="3600"
timeToLiveSeconds="3600"
overflowToDisk="false"
diskSpoolBufferSizeMB="1"
statistics="true"/>