In the realm of network security and Active Directory assessment, efficient reconnaissance is paramount.

This article explores the installation and utilization of ‘ldeep,’ a powerful tool equipped with Kerberos authentication for advanced Active Directory analysis.

Learn how to enhance your network security and streamline your reconnaissance efforts using this comprehensive guide.

If you want to use Kerberos authentication you will need additional packages.:

sudo apt-get install -y libkrb5-dev krb5-config

ldeep is using Python3.:

pip3 install git+https://github.com/franc-pentest/ldeep

For Kerberos, you will also need to configure the /etc/krb5.conf.:

[realms]
      CORP.LOCAL = {
              kdc = DC01.CORP.LOCAL
      }

LDEEP

Help is self-explanatory. Let’s check it out:

$ ldeep -h
usage: ldeep [-h] [-o OUTFILE] {ldap,cache} ...

optional arguments:
    -h, --help            show this help message and exit
    -o OUTFILE, --outfile OUTFILE
                      Store the results in a file
    --security_desc   Enable the retrieval of security descriptors in ldeep
                      results


Modes:
    Available modes

    {ldap,cache}          Mode to query

Ldeep can either run against an Active Directory LDAP server or locally on saved files:

$ ldeep ldap -u Administrator -p 'password' -d winlab -s ldap://10.0.0.1 all backup/winlab
[+] Retrieving auth_policies output
[+] Retrieving auth_policies verbose output
[+] Retrieving computers output
[+] Retrieving conf output
[+] Retrieving delegations output
[+] Retrieving delegations verbose output
[+] Retrieving delegations verbose output
[+] Retrieving delegations verbose output
[+] Retrieving delegations verbose output
[+] Retrieving domain_policy output
[+] Retrieving gmsa output
[+] Retrieving gpo output
[+] Retrieving groups output
[+] Retrieving groups verbose output
[+] Retrieving machines output
[+] Retrieving machines verbose output
[+] Retrieving ou output
[+] Retrieving pkis output
[+] Retrieving pkis verbose output
[+] Retrieving pso output
[+] Retrieving silos output
[+] Retrieving silos verbose output
[+] Retrieving subnets output
[+] Retrieving subnets verbose output
[+] Retrieving trusts output
[+] Retrieving users output
[+] Retrieving users verbose output
[+] Retrieving users verbose output
[+] Retrieving users verbose output
[+] Retrieving users verbose output
[+] Retrieving users verbose output
[+] Retrieving users verbose output
[+] Retrieving users verbose output
[+] Retrieving users verbose output
[+] Retrieving users verbose output
[+] Retrieving zones output
[+] Retrieving zones verbose output

$ ldeep cache -d backup -p winlab users
Administrator
[...]

These two modes have different options:

LDAP

$ ldeep ldap -h
usage: ldeep ldap [-h] -d DOMAIN -s LDAPSERVER [-b BASE] [-t {ntlm,simple}] [-u USERNAME] [-p PASSWORD] [-H NTLM] [-k] [--pfx-file PFX_FILE] [--cert-pem CERT_PEM] [--key-pem KEY_PEM] [-a]
                    {auth_policies,computers,conf,delegations,domain_policy,gmsa,gpo,groups,machines,ou,pkis,pso,silos,smsa,subnets,trusts,users,zones,from_guid,from_sid,memberships,membersof,object,sddl,silo,zone,all,enum_users,search,add_to_group,modify_password,remove_from_group,unlock}
                    ...

LDAP mode

optional arguments:
  -h, --help            show this help message and exit
  -d DOMAIN, --domain DOMAIN
                        The domain as NetBIOS or FQDN
  -s LDAPSERVER, --ldapserver LDAPSERVER
                        The LDAP path (ex : ldap://corp.contoso.com:389)
  -b BASE, --base BASE  LDAP base for query (by default, this value is pulled from remote Ldap)
  -t {ntlm,simple}, --type {ntlm,simple}
                        Authentication type: ntlm (default) or simple
  --throttle THROTTLE   Add a throttle between queries to sneak under detection
                        thresholds (in seconds between queries: argument to the sleep
                        function)
  --page_size PAGE_SIZE
                        Configure the page size used by the engine to query the LDAP
                        server (default: 1000)


NTLM authentication:
  -u USERNAME, --username USERNAME
                        The username
  -p PASSWORD, --password PASSWORD
                        The password used for the authentication
  -H NTLM, --ntlm NTLM  NTLM hashes, format is LMHASH:NTHASH

Kerberos authentication:
  -k, --kerberos        For Kerberos authentication, ticket file should be pointed by $KRB5CCNAME env variable

Certificate authentication:
  --pfx-file PFX_FILE   PFX file
  --cert-pem CERT_PEM   User certificate
  --key-pem KEY_PEM     User private key

Anonymous authentication:
  -a, --anonymous       Perform anonymous binds

commands:
  available commands

  {auth_policies,computers,conf,delegations,domain_policy,gmsa,gpo,groups,machines,ou,pkis,pso,silos,smsa,subnets,trusts,users,zones,from_guid,from_sid,memberships,membersof,object,sddl,silo,zone,all,enum_users,search,add_to_group,modify_password,remove_from_group,unlock}
    auth_policies       List the authentication policies configured in the Active Directory.
    bitlockerkeys       Extract the bitlocker recovery keys.
    computers           List the computer hostnames and resolve them if --resolve is specify.
    conf                Dump the configuration partition of the Active Directory.
    delegations         List accounts configured for any kind of delegation.
    domain_policy       Return the domain policy.
    gmsa                List the gmsa accounts and retrieve NT hash if possible.
    gpo                 Return the list of Group policy objects.
    groups              List the groups.
    machines            List the machine accounts.
    ou                  Return the list of organizational units with linked GPO.
    pkis                List pkis.
    pso                 List the Password Settings Objects.
    silos               List the silos configured in the Active Directory.
    smsa                List the smsa accounts and the machines they are associated with.
    subnets             List sites and associated subnets.
    trusts              List the domain's trust relationships.
    users               List users according to a filter.
    zones               List the DNS zones configured in the Active Directory.
    from_guid           Return the object associated with the given `guid`.
    from_sid            Return the object associated with the given `sid`.
    memberships         List the group for which `account` belongs to.
    membersof           List the members of `group`.
    object              Return the records containing `object` in a CN.
    sddl                Returns the SDDL of an object given it's CN.
    silo                Get information about a specific `silo`.
    zone                Return the records of a DNS zone.
    all                 Collect and store computers, domain_policy, zones, gpo, groups, ou, users, trusts, pso information
    enum_users          Anonymously enumerate users with LDAP pings.
    search              Query the LDAP with `filter` and retrieve ALL or `attributes` if specified.
    add_to_group        Add `user` to `group`.
    modify_password     Change `user`'s password.
    remove_from_group   Remove `user` from `group`.
    unlock              Unlock `user`.

CACHE

$ ldeep cache -h
usage: ldeep cache [-h] [-d DIR] -p PREFIX
                     {auth_policies,computers,conf,delegations,domain_policy,gmsa,gpo,groups,machines,ou,pkis,pso,silos,smsa,subnets,trusts,users,zones,from_guid,from_sid,memberships,membersof,object,sddl,silo,zone}
                     ...

Cache mode

optional arguments:
  -h, --help            show this help message and exit
  -d DIR, --dir DIR     Use saved JSON files in specified directory as cache
  -p PREFIX, --prefix PREFIX
                        Prefix of ldeep saved files

commands:
  available commands

  {auth_policies,computers,conf,delegations,domain_policy,gmsa,gpo,groups,machines,ou,pkis,pso,silos,smsa,subnets,trusts,users,zones,from_guid,from_sid,memberships,membersof,object,sddl,silo,zone}
    auth_policies       List the authentication policies configured in the Active Directory.
    computers           List the computer hostnames and resolve them if --resolve is specify.
    conf                Dump the configuration partition of the Active Directory.
    delegations         List accounts configured for any kind of delegation.
    domain_policy       Return the domain policy.
    gmsa                List the gmsa accounts and retrieve NT hash if possible.
    gpo                 Return the list of Group policy objects.
    groups              List the groups.
    machines            List the machine accounts.
    ou                  Return the list of organizational units with linked GPO.
    pkis                List pkis.
    pso                 List the Password Settings Objects.
    silos               List the silos configured in the Active Directory.
    smsa                List the smsa accounts and the machines they are associated with.
    subnets             List sites and associated subnets.
    trusts              List the domain's trust relationships.
    users               List users according to a filter.
    zones               List the DNS zones configured in the Active Directory.
    from_guid           Return the object associated with the given `guid`.
    from_sid            Return the object associated with the given `sid`.
    memberships         List the group for which `account` belongs to.
    membersof           List the members of `group`.
    object              Return the records containing `object` in a CN.
    sddl                Returns the SDDL of an object given it's CN.
    silo                Get information about a specific `silo`.
    zone                Return the records of a DNS zone.

USAGE

Listing users without verbosity:

$ ldeep ldap -u Administrator -p 'password' -d winlab.local -s ldap://10.0.0.1 users
userspn2
userspn1
gobobo
test
krbtgt
DefaultAccount
Guest
Administrator

Listing users with reversible password encryption enable and with verbosity:

$ ldeep ldap -u Administrator -p 'password' -d winlab.local -s ldap://10.0.0.1 users reversible -v
[
  {
    "accountExpires": "9999-12-31T23:59:59.999999",
    "badPasswordTime": "1601-01-01T00:00:00+00:00",
    "badPwdCount": 0,
    "cn": "User SPN1",
    "codePage": 0,
    "countryCode": 0,
    "dSCorePropagationData": [
      "1601-01-01T00:00:00+00:00"
    ],
    "displayName": "User SPN1",
    "distinguishedName": "CN=User SPN1,CN=Users,DC=winlab,DC=local",
    "dn": "CN=User SPN1,CN=Users,DC=winlab,DC=local",
    "givenName": "User",
    "instanceType": 4,
    "lastLogoff": "1601-01-01T00:00:00+00:00",
    "lastLogon": "1601-01-01T00:00:00+00:00",
    "logonCount": 0,
    "msDS-SupportedEncryptionTypes": 0,
    "name": "User SPN1",
    "objectCategory": "CN=Person,CN=Schema,CN=Configuration,DC=winlab,DC=local",
    "objectClass": [
      "top",
      "person",
      "organizationalPerson",
      "user"
    ],
    "objectGUID": "{593cb08f-3cc5-431a-b3d7-9fbad4511b1e}",
    "objectSid": "S-1-5-21-3640577749-2924176383-3866485758-1112",
    "primaryGroupID": 513,
    "pwdLastSet": "2018-10-13T12:19:30.099674+00:00",
    "sAMAccountName": "userspn1",
    "sAMAccountType": "SAM_GROUP_OBJECT | SAM_NON_SECURITY_GROUP_OBJECT | SAM_ALIAS_OBJECT | SAM_NON_SECURITY_ALIAS_OBJECT | SAM_USER_OBJECT | SAM_NORMAL_USER_ACCOUNT | SAM_MACHINE_ACCOUNT | SAM_TRUST_ACCOUNT | SAM_ACCOUNT_TYPE_MAX",
    "servicePrincipalName": [
      "HOST/blah"
    ],
    "sn": "SPN1",
    "uSNChanged": 115207,
    "uSNCreated": 24598,
    "userAccountControl": "ENCRYPTED_TEXT_PWD_ALLOWED | NORMAL_ACCOUNT | DONT_REQ_PREAUTH",
    "userPrincipalName": "userspn1@winlab.local",
    "whenChanged": "2018-10-22T18:04:43+00:00",
    "whenCreated": "2018-10-13T12:19:30+00:00"
  }
]

Listing GPOs:

$ ldeep -u Administrator -p 'password' -d winlab.local -s ldap://10.0.0.1 gpo
{6AC1786C-016F-11D2-945F-00C04fB984F9}: Default Domain Controllers Policy
{31B2F340-016D-11D2-945F-00C04FB984F9}: Default Domain Policy

Getting all things:

$ ldeep ldap -u Administrator -p 'password' -d winlab.local -s ldap://10.0.0.1 all /tmp/winlab.local_dump
[+] Retrieving computers output
[+] Retrieving domain_policy output
[+] Retrieving gpo output
[+] Retrieving groups output
[+] Retrieving groups verbose output
[+] Retrieving ou output
[+] Retrieving pso output
[+] Retrieving trusts output
[+] Retrieving users output
[+] Retrieving users verbose output
[+] Retrieving zones output
[+] Retrieving zones verbose output

Using this last command line switch, you have persistent output in both verbose and non-verbose mode saved:

$ ls winlab.local_dump_*
winlab.local_dump_computers.lst      winlab.local_dump_groups.json  winlab.local_dump_pso.lst     winlab.local_dump_users.lst
winlab.local_dump_domain_policy.lst  winlab.local_dump_groups.lst   winlab.local_dump_trusts.lst  winlab.local_dump_zones.json
winlab.local_dump_gpo.lst            winlab.local_dump_ou.lst       winlab.local_dump_users.json  winlab.local_dump_zones.lst

The the cache mode can be used to query some other information.

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