HowTo Troubleshoot AD LDAPS Connection Issues

In this article we cover how to troubleshoot bind issues when connecting to Active Directory using LDAPS.  Typically when a LDAPS connection fails, very little information is provided on the reason for the failure. We will look at using NetTools to help troubleshoot the bind process and identify the reason for the LDAPS bind failure.

There are a few troubleshooting options available, including bypassing the standard certificate revocation process, display the certificate chain with the details of the revocation process and finally displaying the certificate that is installed on the servers used for the connection.

We will use the LDAP Search option in NetTools to test the LDAPS connection. For details on the SSL option see here.

Troubleshooting Steps

    Check a Certificate is Installed

    First, we want to confirm that there is a certificate installed on the domain controller and its being used for the LDAPS.  These tests can be performed remotely or on the domain controller being tested.

    In the server field enter the FQDN of the domain controller, and then select the SSL Bind option, port 636 will be appended to the end of the server name, you will then need to uncheck the Verify Certs and click Go.

    If the connection works and there are no bind errors are returned, then a certificate is installed on the domain controller and Active Directory is using it for LDAPS.

    If you do receive a connection failure error:

    Here are a few checks to determine why the certificate is not being used.

        • Check name resolution and the FQDN can be resolved, see DsGetDCName
        • Use the DC Resolution feature to confirm the port is not blocked
        • On the domain controller check the Directory Services eventlog for event id 1220, Source: ActiveDirectory_DomainService, which means that AD was unable to find a suitable certificate to use.
        • To confirm that a certificate is available, open MMC on the domain controller and add the Certificates snap-in, select Service Account and select Active Directory Domain Services. Check under the NTDS\Personal, Certificates and confirm that a certificate is listed.
        • If the certificate exists:
              • Check the certificate has the private key
              • Confirm that the Enhanced Key Usage includes Server Authentication (
              • Open the certificate and confirm on the Certification Path tab that the certificate is trusted
        • If no certificate is listed, check your certificate delivery mechanism, or manually install a suitable certificate.

    Verify the Certificate

    If the first test worked, then we now repeat the test but with the Verify Certs option selected, this time the standard Windows certificate revocation process will check the certificate, if this fails, then the connection will also fail. Select Verify Certs and click Go.

    2020-08-30 21_56_43- - Remote Desktop Connection

    If you receive the following error, Error: ldap_sslinit failed with error: Error: (0x51) Cannot contact the LDAP server, then the Windows revocation process has identified an issue with the certificate and this has caused the connection to fail.

    Common Certificate Issues

    To help identify what has caused the issue with the certificate, if we select the select the Display Results option, which will display the results of certificate revocation process.

    2020-09-01 12_52_48- - Remote Desktop Connection

    Here are a couple of common examples of the errors that can occur.  In these examples the test domain controller has a self-signed certificate and means only one certificate is shown in the certificate chain in the examples.  If your domain controller has a certificate that has been issued by a root CA or an intermediate CA, your certificate chain will have multiple certificates, in this case each of these would be display and tested.  At the end of the certificate chain output if an issue has been found, an ERR: message will be displayed.

    FQDN of the server doesn’t match the certificate

    In this example the server name that has been entered does not match the subject or SAN, in the output the subject and SAN are displayed and an ERR message is returned stating that Certificate name does not match the host name

    Multiple Certificate Errors

    In this example the certificate chain has three errors: 1- the certificate has expired, 2 – the certificate is not trusted, 3 – the entered server name does not match the subject or SAN in the certificate

    This is output for a certificate that has passed the certificate revocation process

    Display the Certificate

    We also have the option to display the certificate in the normal Certificate dialog, by selecting the Display Cert option, the certificate will be displayed, and we can look at the additional properties of the certificate. NetTools will pause until the certificate dialog is closed.

    In the dialog you can also confirm that the certificate is trusted by the local machine by viewing the Certification Path tab.

    During a logon attempt, the user’s security context accumulated too many security IDs.

    This error occurs when the user's access token exceeds 1015 entries, and at which point the user is blocked from logging on with the above error.  The user’s access token contains an entry for each group the user is a member of, either directly or through nested groups. On top of the entries that are added by group membership, a number of additional entries are added by the system.

    There are a number of reasons that can cause this issue, the two most common are nested groups and migration or more specifically the use of SID History. 

    A complex nested group configuration can cause the number of groups assigned to the increase very quickly.  Due to the nesting, the user could only be a member of handful of groups but due to the nesting the actual number of SIDs in the user’s access token can exceed 1015 entries.  

    The other common cause of this issue is a domain migration using SID History, when SID History is used the user’s access token can double in size, so a user who’s access token contains only 600 groups before migration, it can exceed the 1015 limit post migration, preventing the user from logging on.

    The Token Size option in NetTools allows you to scan domain and report the number of SIDs in the user’s access token. See Token Size.  This report can be tailored to report on specific objects, i.e. trying to find groups that have a high number of nested groups.

    The screenshot below shows that Aaron's access token has exceed the 1015 limit and will not be able to log on. While Abby has only 1006 SID in her access token, and it will depend on the number of additional SIDs that are added to her access token by the workstation when she logs on, which will determine if she will see the error or not.

    Bree from the screenshot above, is shown as having 405 SIDs in her access token, looking at the memberof details of her account it shows that she is only a member of 4 groups, nearly all the SIDs are coming from nested groups.

    If we use the Display SID Inheritance option from the context menu on her account in the list, we can see the high SID count is a result of Group4 and Group5, both of which have 200 nested groups.  Obviously this is a test environment and in a production environment the number of groups and their distribution will be different, but from the Token Size List dialog we can see which groups are causing the problem, we can also drill down further by double clicking on an entry in the list, which will display the SID Inheritance for that item, in this case Group5.

    Another method to see the nested group membership for a user is to use the Group Inheritance option,  The simplest way to access this option is to use the Resolver window.  For the selected object in the list, select the Add to Resolver from the content menu, this will display the Resolver window and add the user we are interested in.

    Once added to the Resolver window select Use With -> Group Inheritance ->MemberOf from the context menu

    This will display the nested groups details in a tree view to allow you to see visually the nested group membership.

    So this has shown you how you can identify which groups have caused the problem, but unfortunately there is no magic fix, in the case of nested groups, you will just need to reduce the number of groups in the user access token, this could be as simple as removing some of the groups that are no longer needed or could require a complete redesign of your groups and resource allocation. 

    In the case of SID history causing the token bloat, the only way to resolve this one is to remove the SID History from the domain, and manage the resulting cleanup, as SID History normally still exists post migration because someone was too scared to remove it.

    HowTo: Retrieve LAPS Password

    Local Administrator Password Solution (LAPS) is a Microsoft component that provides automatic management of the local administrator passwords on domain joined machines, details on LAPS can be found here

    In this article we will show how to use NetTools to display the password that LAPS has assigned to the local administrator account on workstations or servers. With NetTools it is very simple to retrieve the LAPS password, from the Users - Search enter the name of the machine of which you want to retrieve the LAPS password, make sure that the Return Users Only option is deselected and click Go.

    In the dialog select the LAPS tab.

    Note: the LAPS tab will only be displayed if the computer object has a password set and you have rights to read the ms-Mcs-AdmPwd attribute.

    Workaround for SmartScreen

    When running NetTools on a Windows 10 machine, it can sometimes trigger the Microsoft Defender SmartScreen and block the execution of NetTools.  This is because NetTools is not signed and SmartScreen blocks apps that have been downloaded.  This is an example of the SmartScreen dialog that is be displayed.

    To prevent SmartScreen from blocking NetTools, open the properties of NetTools.exe and check the Unblock option and click OK.

    NetTools V1.28.0

    NetTools V1.28.1 - minor fix in LDAP Browser

    NetTools no longer uses the ADSI APIs, all queries against the AD now only use the LDAP API, this provides a small performance increase but more importantly it provides consistency across all features.
    The toolbar is now always displayed at the top of NetTools, and includes buttons for navigation, Connection Profiles, Resolver and Help and quick search by default, Pin items are displayed to the right of these buttons.

    Connection Profiles  *** New ***
    With previous versions of NetTools, it would use the current user's credentials and domain join information of the workstation running NetTools to authenticate and select the directory that would be interrogated and there were only a few features that supported the use of different credentials via the Use LDAP Search Credentials option.  This version introduces a new feature called Connection Profiles, which adds the extra capability to define the server connection and credentials that will be used by the tests and features and provides a common method to define and access the AD across all tests.  See Connection Profiles.

    Circular References  *** New ***
    A new feature to test if there are any infinite loops in your group memberships. See Circular References

    Resolver *** New ***
    A quick way to search for a single or multiple items, just copy and paste a a single or list of items that you want to find, and it will search the AD for the items and display if they exist in the directory or not.  The copy and pasted list can be displayname, samaccountname, DN, SID, UPN, or email address.  See Resolver

    AD Properties Dialog
    Added an extra tab to display the TokenGroups for user and computer objects

    AD Site ISTG
    A complete rewrite of the function from ADSI to LDAP API

    Compare Objects
    Updated to include the NTSecurityDescriptor attribute 

    LDAP Browser
    Added an additional feature to display the attribute values as a hex dump
    Fixed issue with the filter limiting the number of items displayed (v1.28.1)

    LDAP Search
    Table view context menu updated to include a Use Column with option to allow data in the column for common dialogs
    Removed the Credential option, you now use Connection Profiles to specific different credentials and authentication methods
    Updated Tab views so selected items count on the status bar is updated when a tab is selected

    A complete rewrite of the function from ADSI to LDAP API

    NetTools V1.27.7

    A new Pin context menu option is available in the left hand option selector, which is used to create shortcut buttons for your commonly used options.  See Basics
    Default Copy to clipboard shortcut key has been changed to Ctrl-C, to align with standard copy and paste keys. now in any of the table views if one or more rows are selected and Ctrl-C is pressed, contents of the column directly under the cursor is copied to the clipboard

    AD Properties
    Updated to display Kerberos DES-CDC-CRC, DES-CDC-MD5, RC4 encryption options
    Updated to use the LDAP enum decode function so attribute decodes are common across all dialogs 

    Compare Objects
    Added a Compare Values context menu option which displays a visual side by side comparison of the values with the difference highlighted. See Compare Objects

    LDAP Browser
    Fixed bug in LDAP browser, where intermittently it would display the attribute values twice

    LDAP Search
    Updated the LDAP Session options to fix a bug with the GetDsName flags
    Updated enums to support LargeInteger (int64) values
    Updated the MsExchRecipientTypeDetails, msExchRemoteRecipientType, msExchModerationFlags, and MsExchRecipientDisplayType enums with O365 values
    Updated the OmSyntax enums values 
    Added new Base64 Decode Type, to allow attribute values to be outputted in base64 format

    RID Pool
    Added an extra column to display the number of RID that are left in the pool for each domain controller

    NetTools v1.27.0

    Compare Objects  *** New ***
    A new option to provide the ability to compare two object, or the changes that have been made on a single object based on a previous snapshot. See Compare Objects

    LDAP Browser  *** New ***
    I've copied the LDAP Browser feature from the LDAP Search option and now added it as it own item in the left hand pane. See LDAP Browser

    AD Properties Dialog
    Updated to display AES128 and AES256 encryption options

    Attribute Replication
    Added option to check attribute replication for objects in the the global catalog context

    Find Trustee
    Fixed intermittent exception error when checking for ownership permissions

    LDAP Search
    Added a tab output option, so results from each query is displayed on a new tab
    Added enum decodes for msDs-SupportedEncryptionTypes
    Updated the conditional attributes function so that meta data information is supported for both variable and results.
        e.g.   Validate;{if: meta.time.unicodepwd == pwdlastset : "Valid" : "Error"}

    HowTo: Check that a user has actually changed their password

    This is in response to a query raised on maillist about how to check if a user has actually changed their password and not just toggled the pwdlastset attribute to make it look like they have changed their password.   When a user changes their password a number of attributes are updated as a result of the password change, these include dbcspwd, lmpwdhistory, ntpwdhistory, pwdlastset, supplementalcredentials, and unicodepwd.  To be able to determine if the password has actually been changed, we have to look at the meta data for the object and check the last change date of the unicodepwd attribute, which contains the hash of the user’s password. 

    NetTools provides a couple of ways to view the meta data of an object, via Meta data dialog, running an LDAP query, or in this use case the Last Logon, will display all the details required.

    For a single user the Last Logon option will display both the pwdlastset and change date for the unicodepwd in the meta time column. This screenshot shows the results of a normal account password change, both the pwdlastset and meta time are the same.

    For this user the pwdlastset has been toggled, and it shows that the pwdlastset and meta data times don't match

    You can view the meta data on an object via the Meta Data Dialog, this option is provided throughout NetTools as a context menu option called Meta Data.  The easiest place to demonstrate this on the User Search option, search the account in question and then right click on the user and select Meta Data from the right click context menu.

    This shows an account that has had it's password changed. 

    This shows that the pwdlastset has changed but the other attributes have not changed, which is caused by the pwdlastset being toggled.

    The above options are for single accounts, but it is also possible in to check multiple accounts at once.  The LDAP Search option includes an option to return meta data as if it's an attribute of the object.  This is done using the meta option in the attributes field.  We can use an Input Mode of the LDAP Search to provide a list of the samaccountnames to check.

    In this example we are checking the details of the five user accounts, and it shows that user1 meta data doesn't match the pwdlastset date and time.

    Here is the favorite for the above query, see Favorites on how to import 

    [PwdLastSet Meta Data]
    Attributes=meta.time.unicodepwd, pwdlastset

    With the introduction of v1.27, there is new query option that can be used to simplify this task.  In v1.27 the conditional attributes have been extended to support meta data queries.  This means we can do the checking in the query itself without any additional post query work.

    [PwdLastSet Meta Data] 
    Server= BaseDN=##default 
    Attributes=samaccountname, Pwd_Change;{if:meta.time.unicodepwd;date!=pwdlastset:"Invalid":"Valid"} 


    Related Articles
    User Search
    LDAP Search
    LDAP Search Input Mode
    Meta Data Dialog
    Troubleshoot account lockouts

    HowTo: Find Active Accounts

    Finding which accounts are active should be simple, however, there are numerous ways to define if an account is active or not.  There is the simple method of checking if the accounts are enable or not, however, things get more complicated quickly after that, i.e. when was the account last used, has the account expired, has the account ever been used.

    This article provides a number of sample LDAP queries that can be used to determine if accounts are active or not, or you can combine these queries to generate a more complex query to meet your requirements.  The first part of the article shows fragment of the query and the last section shows how to combine these to create the final query.

    Account Enabled
    With AD an account is active based on a value stored in UserAccountControl attribute, however, the attribute uses bit logic to represent a number of different values, so you can't check for a specific value.  Details of the attribute can be here. The second bit of the UserAccountControl indicates if the account is enabled or not,  when not set (0) the account is active, when set (2) the account is disabled.  Using Matching Rule OID we can check the status of the individual bits in the attribute.  i.e. (useraccountcontrol:1.2.840.113556.1.4.802:=2).  The NetTools substitutions simplifies the entry of matching rules with a single character. See Substitutions.

    Account is disabled          (useraccountcontrol|=2)    
    Account is enabled           (!useraccountcontrol|=2)

    Account Expired
    Accounts can be set to automatically expire after a specified date, after which point the user will no longer be able to logon.  The date is stored in the AccountExpires attribute, this attribute uses a 64 bit integer to store the date.  To add to the complexity the attribute can contain more than just a date, it might not be set, or contains a 0 (zero), or 9223372036854775807 then account is not set to expire.  So a query check for expiry has to check for all the possible values to confirm if the account is active or not. Again the use of substitutions can simplify the entry of the Int64 date. 

    Account Expired            (&(!accountExpires={-1:})(!accountExpires=0)(accountExpires<={idate:now})) 
    Account not Expired     (|(!accountExpires=*)(accountExpires={-1:})(accountExpires=0)(accountExpires>={idate:now}))  

    Last Logon
    Most account audits state that if an account has not been used to a set period of time, the account should be consider inactive.  The last time the user logs on is stored in the LastLogon attribute, however this attribute is not replicated between domain controllers, so using this attribute you have to collect the LastLogon attribute from all domain controllers to determine the last logon.  There is another attribute that is replicated between domain controllers called LastLogonTimeStamp, however this attribute has a specific replication cycle which means that it may not contain the most recent logon date (more details here), but is usually close enough for most cases.  Again this attribute uses a 64 bit integer to store the date.

    Not logged on for 60 days        (lastlogontimestamp<={idate:now-60})
    Logged on in the last 30 days   (lastlogontimestamp>={idate:now-30})

    Password Changes
    In some cases the logonTime or the LastLogonTimeStamp will not be updated when a users logs on, these are normally associated to LDAP Simple binds or access through SharePoint.  another method to determine if an account is still being used to check the last time the user's password was changed, this assumes that an account password expires.

    Password change in the last 60 days     (pwdlastset>={idate:now-60})

    Unused New Accounts
    In this scenario an account is created but has not used since it was created.  The queries that is used to find these accounts depends on user provisioning process and which query should be used, if the user is required to change their password at first logon (scenario 1), or not (scenario 2).  If the user is required to change their password, then we check to see when the password was changed, if not, we check if the lastlogontimestamp has been set.

    Scenario 1
    Not used in the last 60 days            (&(whencreated>={zdate:now-60})(pwdlastset=0))
    has been used in the last 60 days    (&(whencreated>={zdate:now-60})(pwdlastset>={idate:now-60}))

    Scenario 2
    Not used in the last 60 days                          (&(whencreated>={zdate:now-60})(!lastlogontimestamp=*))
    Created in the last 60 days and been used    (&(whencreated>={zdate:now-60})(lastlogontimestamp=*))

    Type of Accounts and indices
    When creating queries it's best to create a query that limits the number of object that need to be searched and the number of attributes that are returned.  Building a query using attributes that are indexed will increase the performance of the query, reduce the load on the server executing the query, and reduce the amount of network traffic generated (See this Microsoft article for details). Some of the queries shown above use attributes that are not indexed, so using these queries in the format show could be very inefficient.  Limiting the queries to only search for specific object types will significantly increase the performance of the query, i.e only look at user account or computer accounts and the more indices that are used the better. 

    Users account               (&(objectCategory=user)(objectclass=user))
    Computer Accounts      (&(objectCategory=computer)(objectclass=computer))

    Combined Queries
    This section shows a number of the above query fragments combination to create the full query:

    Find active user accounts:

    Find disabled user accounts

    Find active accounts, that have not expired

    Find all inactive accounts, including expired, password not changed or logon in the last 60 days
    (&(objectCategory=user)(objectclass=user) (!useraccountcontrol|=2)(lastlogontimestamp<={idate:now-60})(pwdlastset>={idate:now-60})(&(!accountExpires={-1:})(!accountExpires=0)(accountExpires<={idate:now})))

    NetTools includes a number of predefined queries covering user accounts, see Predefined Queries

    See Favorites for more examples

    HowTo: Find what Schema updates have been performed

    The AD schema can be extended by installing additional schema extensions, which add additional classes and\or attributes.  There is no builtin method to determine what schema extensions have been installed.  NetTools, however, does have an option to display the schema updates that have been added to the AD.

    The Schema History option uses the WhenCreated attribute to determine when changes were made to the AD, and then using it's internal database to try and retrieve the name of the update based on what attributes or classes have been added.

    See Schema History List