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Teleport

Troubleshooting Desktop Access

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Common issues and resolution steps.

Certificate expired or not yet valid

In order for remote desktop access to work correctly, certificates issued by Teleport must be validated by several different components. If these components do not agree what the current time is, then you will likely encounter certificate validation errors which prevent Teleport from working correctly.

These errors can manifest in several different ways depending on which system(s) have an incorrect system clock.

For example, you may see that Teleport starts a remote desktop session, but that the login screen on the remote desktop shows an error similar to:

The smartcard certificate used for authentication has expired. Please contact your system administrator.

Alternatively, you may see an error in the Teleport Web UI before the remote desktop connection is established:

Remote error tls expired certificate

Solution: Check the system clock on all systems

In order to fix these issues, it is important for the system clocks on the following components to be synchronized:

  • the Teleport Auth Service
  • the Teleport Proxy Service
  • the Teleport Windows Desktop Service
  • the target Windows hosts

We recommend using NTP on these systems to ensure that the system clock remains accurate. On Linux systems running systemd, you can verify the system clock settings with the following command:

timedatectl

The following is an example of a correctly configured system:

               Local time: Wed 2024-09-11 13:45:17 UTC
           Universal time: Wed 2024-09-11 13:45:17 UTC
                 RTC time: Wed 2024-09-11 13:45:17
                Time zone: Etc/UTC (UTC, +0000)
System clock synchronized: yes
              NTP service: active
          RTC in local TZ: no

In this example, you can see that NTP service is marked active and that the system clock is synchronized. If your output differs from the above then your clock settings may need to be reconfigured.

Auto-login does not work

Smart card service not running

You connect to a Windows host from the Teleport UI, land on the Windows login screen and nothing happens.

You can click on the username, click Sign-in options and click on the smart card icon. The error message is: "No Valid Certificates Were Found on This Smart Card".

Solution: Enable the Smart Card Service

Usually, this means that the Smart Card service is not running on the target host.

First, make sure that you enable the Smart Card service in Group Policy.

If that doesn't help, log into the target host directly, open the "Services" program from the "Start" menu and check that the "Smart Card" service is in the "Running" state.

If the "Smart Card" service is not running, open PowerShell and run gpupdate.exe /force. This forces a Group Policy sync and should pick up the service changes.

Smart card PIN not detected

Teleport uses a cryptographically secure random number generator to generate a smart card PIN for each new desktop session. In order to prevent the smart card certificate from being used for any purpose other than the initial login, this PIN is never shared with the Teleport user.

Teleport provides this PIN to the desktop during the RDP connection phase. If your group policy prevents the desktop from seeing this PIN, the user will remain at the login screen even though the smart card was detected.

Solution: Ensure that group policy allows specifying credentials during RDP connection establishment.

Expand Computer Configuration, Administrative Templates, Windows Components, Remote Desktop Services, and Remote Desktop Session Host.

Under Remote Desktop Session Host, select Security.

Right-click Always prompt for password upon connection, select Edit, select Disabled, then click OK.

Note: despite mention of passwords in the name of this policy, no passwords are sent on the wire. This mechanism is used only to send the smart card PIN.

Third-party smart card drivers prevent automatic login

Some third-party smart card drivers such as HID ActivID ActivClient may prevent the automatic login process from working correctly. To check for the presence of third-party drivers, connect to the host where automatic logon is not working and view the contents of the Computer\HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Cryptography\Calais\SmartCards\Identity Device (NIST SP 800-73 [PIV]) entry.

On a correctly configured system, you expect to see an entry pointing at a DLL for the default Windows driver: C:\Windows\System32\msclmd.dll. On a system with custom drivers installed, you will typically see this path overridden to point to a DLL under C:\Program Files.

Solution: Disable or uninstall any third party smart card tools that may be interfering with the logon process. Ensure that the registry entry mentioned above points to msclmd.dll after completing the uninstall.

Smart card not supported for Account

You connect to a Windows host and get the error message: "Signing in with a smart card isn't supported for your account." or similar.

Solution: Review the Security-Kerberos Log on the Windows host for causes.

The Security-Kerberos Windows Event Log provides information on smart card-based authentication attempts. This Event Log is not enabled by default. Open the Windows Event Log and navigate to Event Viewer, Application and Services Logs, Microsoft, Windows, Security-Kerberos, Operational. Enable this Event Log and attempt to connect with Teleport Web UI to review log entries.

Smart card certificate not trusted

You connect to a Windows host from the Teleport UI, land on the Windows login screen and see an error message: "The smartcard certificate used for authentication was not trusted" (or similar).

Solution: Import the Teleport CA

This means that the host does not trust the Teleport CA.

First, make sure that you import the Teleport CA into Group Policy. Note that if you have rotated the Teleport CA since the last import, you need to fetch the new CA using the following command, replacing teleport.example.com with the address of your Teleport cluster:

curl.exe -fo user-ca.cer https://teleport.example.com/webapi/auth/export?type=windows

If that doesn't help, log into the target host directly, open PowerShell and run gpupdate.exe /force. This forces a Group Policy update and should pick up the new CA.

New session "hangs"

Host unreachable

You click Connect on a Windows host from the Teleport Web UI, and a new tab opens, but nothing is displayed other than the top bar. After a while, an error is displayed about a failed connection. In most case, this error occurs when the windows_desktop_service can't reach the target Windows host.

Solution: Modify firewall rules to allow inbound RDP traffic

First, make sure that you open the RDP port and allow remote desktop connections in the group policy object you have configured for Teleport connections.

If that does not help, check if the target host is online and try to ping it from the Linux server that runs windows_desktop_service. If the host is online but not reachable, there is some other networking barrier in the way, specific to your infrastructure.

Hostname does not resolve

Connections to Windows Desktops hang during connection establishment, or the Teleport debug logs show errors of the form couldn't resolve winserver.example.com.

Solution: Ensure Firewall Permits DNS Traffic

For desktops that are automatically discovered via LDAP, Teleport makes DNS queries against the LDAP server in order to resolve the hostname to an IP address.

Ensure that your firewalls allow inbound DNS traffic on port 53 from the instance(s) running Teleport's Windows Desktop Service to the LDAP server (Active Directory Domain Controller).

Teleport fails to start

Incorrect domain

Teleport fails to start with an error similar to:

LDAP Result Code 10 "Referral": 0000202B: RefErr: DSID-0310082F, data 0, 1 access points
"\tref 1: 'xample.com'"
"\x00"

Solution: Correct Domain

This means that your domain name is likely wrong. Double-check the domain field in the ldap section of windows_desktop_service.

Domain controller unreachable

Teleport fails to start with an error similar to:

LDAP Result Code 200 "Network Error": dial tcp ad.example.com:636: i/o timeout

Solution: Check LDAP Address

This means that your domain controller is down or unreachable. Double-check the addr field in the ldap section of windows_desktop_service. If it's correct, check that the domain controller is up and reachable from the server that runs windows_desktop_service.

Cannot initialize LDAP over TLS

Teleport fails to connect to LDAP on startup. You may see errors similar to:

LDAP Result Code 52 "Unavailable": 00000000: LdapErr: DSID-0C090F78, comment: Error initializing SSL/TLS, data 0, v2580\x00

or

connecting to LDAP server: unable to read LDAP response packet: read tcp 172.18.0.5:35970->;172.18.0.4:636: read: connection reset by peer

Solution: Enable LDAPS

This means you do not have an LDAP certificate installed on your LDAP servers, or you are trying to make an insecure connection on port 389. Teleport requires secure LDAPS connections, which are typically on port 636. First, confirm that you are connecting to the correct LDAPS port. If that doesn't resolve your issue, you can install Active Directory Certificate Services (AD CS) or import your own third party certificate. Note that Active Directory is extremely picky so take care to generate your certificates correctly.

Desktops are not discovered via LDAP

LDAP not yet initialized

Teleport is running, but desktops do not show up in the Web UI. The logs contain errors similar to:

skipping desktop discovery: LDAP not yet initialized

Solution: Confirm Teleport certificate is installed

The Teleport Desktop Service uses a Teleport-issued certificate to authenticate with the LDAP server. This error occurs when Teleport is unable to authenticate, which is often due to its certificate authority not being trusted by Active Directory.

First, verify that the Teleport CA is present in the LDAP NTAuth store. Run the following command, modifying the DN for your domain (in this command we use a domain of example.com)

$ certutil -viewstore "ldap:///CN=NTAuthCertificates,CN=Public Key Services,CN=Services,CN=Configuration,DC=example,DC=com?caCertificate"

You should see a popup window that shows the Teleport CA certificate. If the Teleport certificate is not present, import it with:

$ certutil -dspublish -f <path-to-cert> NTAuthCA

Once you've verified that the Teleport certificate is present in LDAP, you should check whether it has propagated to all desktops. From a desktop that you would like to connect to, run the following:

$ certutil -viewstore -enterprise NTAuth

If the popup window does not show the Teleport certificate, and it was present in LDAP, you can force the desktop to sync with the following command:

$ certutil -pulse

If you have verified that the Teleport CA certificate is properly installed and are still seeing this error, check for any security tools or addons that may be interfering with the mTLS connection. Tools such as CrowdStrike's LDAP inspection or Silverfort's AD adapter are known to terminate TLS and drop the client certificate, which prevents Teleport from authenticating.

Manually validate a client certificate

Another helpful troubleshooting step is to issue a client certificate using tctl and attempt to validate it on the Windows side.

First, generate a client certificate with tctl, being sure to replace the --windows-user, --windows-sid, and --windows-domain flags with values appropriate for your environment:

NOTE: To issue Windows certificates, you must run 'tctl auth sign' locally
on the same machine as the Teleport auth_service. Running this command remotely
with an identity issued by 'tsh' will result in 'ERROR: access denied'
tctl auth sign \    --windows-user=svc-teleport \    --windows-sid=S-1-5-21-3788279871-1068139173-3054872986-500 \    --windows-domain=domain.example.com \    --format=windows \    --out=test

This will generate a certificate file named test.svc-teleport.der.

Next, copy this certificate to one of your domain controllers and attempt to verify it:

$ certutil -urlfetch -verify test.svc-teleport.der

A successful verification should end with output similar to the following:

------------------------------------
Verified Application Policies:
    1.3.6.1.5.5.7.3.2 Client Authentication
    1.3.6.1.4.1.311.20.2.2 Smart Card Logon
Cert is an End Entity certificate
Leaf certificate revocation check passed
CertUtil: -verify command completed successfully.

If you do not see similar results, scan the output for errors which may indicate why the certificate cannot be verified.

Connection attempts fail

RDP server only uses Standard RDP Security

Attempts to connect to a desktop fail with an error similar to

client advertised SSL, but server selected STANDARD_RDP_SECURITY

Solution: Enable Enhanced RDP security

Standard RDP Security is based on RC4 encryption and is the least secure way to connect to a Windows host over RDP. Teleport's RDP client requires enhanced RDP security with TLS.

Enhanced RDP Security is typically enabled by default, but your environment may be configured to require the legacy security methods.

This configuration is available via group policy at:

Computer Configuration > Administrative Templates > Windows Components > Remote Desktop Services > Remote Desktop Session Host > Security

Look for the "Require use of a specific security layer for remote (RDP) connections" setting. The setting should be set to Negotiate or SSL, not RDP.

RDP connection failed

You click Connect on a Windows host from the Teleport Web UI, a new tab opens but nothing is displayed other than the top bar. You see an error that refers to a failed RDP connection. You may also see errors similar to:

Rdp(Io(Os { code: 54, kind: ConnectionReset, message: "Connection reset by peer" }))

Solution: Configure a certificate for RDP connections

This means that the desktop does not support secure cipher suites for TLS connections.

Make sure that you configure a certificate for RDP connections.

Enhanced RDP security with CredSSP required

Attempts to connect to a desktop fail, and the logs show an error similar to:

Error during negotiation step: the server requires that the client support enhanced RDP security with CredSSP

Solution: Disable Network Level Authentication (NLA)

This means that the RDP server is requiring NLA. Teleport currently requires that NLA is disabled in order to perform its certificate-based passwordless login.

To disable NLA, follow the instructions to allow remote desktop connections in the group policy object you have configured for Teleport connections. If you are still encountering this error after disabling NLA in Active Directory, run the following command from the Windows Command prompt as an administrator to force the policy update:

gpupdate.exe /force

Directory Sharing

Failed to share directory

Attempts to share a directory fail and a warning is presented that says:

Failed to share directory, drive redirection may be disabled on the RDP server.

Solution: Ensure that device redirection is enabled.

Teleport's directory sharing feature leverages RDP device redirection. If device redirection is not enabled or allowed by the RDP server then the operation will fail.

Device redirection is typically enabled by default, but may be disabled in group policy. The relevant settings are located under:

Computer configuration > Administrative Templates > Windows Components > Remote Desktop Services > Remote Desktop Session Host > Device and Resource Redirection

Make sure that the option for Do not allow drive redirection is unset or disabled.