Single sign-on, directories and Kerberos

A typical employee uses dozens of applications a day. If each demanded its own password, users would reuse one weak password everywhere or write them all down, help desks would drown in reset requests and leavers would keep accounts in systems nobody remembered. Single sign-on, SSO, lets a user authenticate once and then reach many systems without re-entering credentials. It improves usability and security together, but it concentrates risk: whoever controls the SSO session controls everything behind it. This lesson covers directory services, the different forms of SSO, and Kerberos, the ticket-based protocol at the heart of Windows domains and many Unix environments. Lesson 6 covers federated SSO across organizations with SAML and OpenID Connect.

Directory services

A directory is a specialized database of identities and their attributes, optimized for frequent reads. It holds user accounts, groups, devices, service accounts and policies, and answers questions such as whether a user exists, which groups they belong to and what their email address is. The X.500 standards defined the hierarchical naming model most directories use, in which every entry has a distinguished name built from its position in a tree, for example cn=Priya Singh,ou=Payroll,dc=example,dc=ca. The Lightweight Directory Access Protocol, LDAP, is the standard way applications query and update directories; it runs on TCP port 389, and LDAPS or StartTLS should be used so that bind passwords are not sent in clear text.

Microsoft Active Directory Domain Services, the most widely deployed enterprise directory, combines an LDAP directory, Kerberos authentication, DNS integration and Group Policy for configuring computers. Its security boundary is the forest, its administrative units are domains and organizational units, and its most sensitive accounts, such as members of Domain Admins and Enterprise Admins, can control every joined computer. Cloud identity providers such as Microsoft Entra ID, Okta and Google Cloud Identity play the same role for cloud applications and are often synchronized with an on-premises directory, which makes the synchronization server itself a highly privileged system.

Because directory and authentication services can grant access to everything, many organizations use a tiered administration model. Tier 0 contains the identity infrastructure itself: domain controllers, identity providers, synchronization servers and the accounts that administer them. Tier 1 contains servers and applications; Tier 2 contains user workstations. Administrators use separate accounts for each tier and never sign in to a lower-tier machine with a higher-tier account, so that malware on a workstation cannot capture domain administrator credentials. Lesson 8 extends this with privileged access management.

Forms of single sign-on

SSO takes several forms. Enterprise or desktop SSO, typical of a Windows domain, uses the user's sign-in to the workstation to obtain Kerberos tickets that authenticate them to file servers, intranet sites and email without further prompts. Web SSO uses an identity provider and browser redirects: the user signs in to the identity provider once, and each web application accepts a signed assertion or token from it, which lesson 6 covers. Password vaulting or form-filling SSO, sometimes called legacy SSO, stores each application's password and types it in for the user; it improves convenience but leaves separate passwords in place. Reduced sign-on is the realistic goal in most organizations: as few authentications as possible, each one strong.

SSO's security trade-off must be managed explicitly. The benefits are fewer passwords to reuse or forget, one place to enforce strong and phishing-resistant authentication, one place to see every sign-in and, crucially, one place to revoke access when a person leaves. The risks are that a stolen SSO session or credential opens every connected application, and that an outage of the identity provider stops work everywhere. The answers are strong authentication at the identity provider, short session lifetimes with step-up for sensitive actions, protection of session tokens, high availability for identity services and a documented break-glass procedure for when they fail.

How Kerberos works

Kerberos, developed at MIT and specified in RFC 4120, provides mutual authentication over an untrusted network without sending passwords across it. It relies on a trusted third party, the key distribution center, KDC, which shares a long-term secret key with every principal, meaning every user and service, in its realm. The KDC has two logical parts: the authentication service, AS, which verifies users and issues ticket-granting tickets, and the ticket-granting service, TGS, which issues tickets for specific services. In Active Directory, every domain controller runs a KDC.

The exchange runs as follows. First, the user's workstation sends the AS a request; with pre-authentication, the request includes a timestamp encrypted with a key derived from the user's password, proving the user knows it without sending it. Second, the AS returns a ticket-granting ticket, TGT, encrypted with the key of the special krbtgt account so the user cannot read or alter it, together with a session key encrypted with the user's key. Third, when the user wants a service, the workstation sends the TGT and an authenticator, a timestamp encrypted with the session key, to the TGS. Fourth, the TGS returns a service ticket encrypted with that service's long-term key, plus a new session key for talking to the service. Fifth, the workstation presents the service ticket and a fresh authenticator to the service, which decrypts the ticket with its own key, finds the session key inside and checks the authenticator. Optionally, sixth, the service replies with proof that it too knew the session key, giving mutual authentication.

Several properties follow. The password is used only at the start, to derive a key; afterwards the user holds tickets with limited lifetimes, typically ten hours for a TGT, renewable up to a maximum such as seven days. Authenticators contain timestamps, so all parties need synchronized clocks, and requests outside the allowed skew, five minutes by default, are rejected to stop replay. Services never contact the KDC to validate a ticket, which makes Kerberos scale, but also means a stolen ticket works until it expires. Group memberships travel inside the ticket in Windows as the privilege attribute certificate, PAC, which services use for authorization.

import hmac, hashlib, json
# Toy model: a 'sealed' blob is data plus an HMAC under a key the KDC and service share.
# Real Kerberos uses encryption (AES), not just integrity, but the trust logic is the same.
def seal(key, data):
    body = json.dumps(data, sort_keys=True).encode()
    return body, hmac.new(key, body, hashlib.sha256).hexdigest()
def open_sealed(key, sealed):
    body, tag = sealed
    if not hmac.compare_digest(tag, hmac.new(key, body, hashlib.sha256).hexdigest()):
        raise ValueError('ticket integrity check failed')
    return json.loads(body)
file_server_key = b'long-term key shared by KDC and file server'
ticket = seal(file_server_key, {'client': 'priya@EXAMPLE.CA', 'service': 'cifs/files01', 'session_key': 'k-7f3a', 'start': 1767254400, 'end': 1767254400 + 10 * 3600})
SKEW = 300
def service_accepts(sealed, now, authenticator_time):
    t = open_sealed(file_server_key, sealed)
    if not (t['start'] <= now <= t['end']):
        return 'reject: ticket expired or not yet valid'
    if abs(now - authenticator_time) > SKEW:
        return 'reject: clock skew exceeds 5 minutes'
    return 'accept ' + t['client']
print(service_accepts(ticket, 1767258000, 1767258030))
print(service_accepts(ticket, 1767258000, 1767257400))
print(service_accepts(ticket, 1767254400 + 11 * 3600, 1767254400 + 11 * 3600))
tampered = (ticket[0].replace(b'priya', b'admin'), ticket[1])
try:
    service_accepts(tampered, 1767258000, 1767258000)
except ValueError as e:
    print('reject:', e)

accept priya@EXAMPLE.CA
reject: clock skew exceeds 5 minutes
reject: ticket expired or not yet valid
reject: ticket integrity check failed

Kerberos weaknesses and defenses

Kerberos is robust, but its design creates well-known attack paths, all of which depend on obtaining keys or tickets after an initial compromise. The krbtgt key signs every TGT, so an attacker who steals it can forge TGTs for any user with any group membership, a so-called golden ticket; the defense is protecting domain controllers as Tier 0 assets and resetting the krbtgt password twice, with replication between resets, after any suspected compromise. A service account's key encrypts its service tickets, so an attacker who obtains that key can forge service tickets for that service, a silver ticket. Any authenticated user can request a service ticket for an account with a service principal name and then try to guess the service account's password offline, an attack known as Kerberoasting; long, random, managed passwords for service accounts and AES-only encryption make it impractical. Accounts that do not require pre-authentication expose material for offline guessing too. Lesson 10 discusses pass-the-ticket and related attacks.

Older Windows authentication, NTLM, uses a challenge-response based on a hash of the user's password. It does not support mutual authentication well, is vulnerable to relay and pass-the-hash attacks and is being phased out by Microsoft in favor of Kerberos. Organizations should audit NTLM use, block it where possible and require signing and channel binding where it remains.

Thinking like a manager

SSO and Kerberos questions test whether you see identity infrastructure as the most critical asset. The best answers protect the identity provider and domain controllers as Tier 0, require strong authentication at the point of single sign-on, keep sessions and tickets short-lived, plan for identity outages and manage service account secrets carefully. Remember the Kerberos vocabulary, KDC, AS, TGS, TGT, service ticket, authenticator, realm, and that Kerberos depends on synchronized time and on keeping long-term keys secret.