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The IIS Orchestrator treats the certificates bound (actively in use) on a Microsoft Internet Information Server (IIS) as a Keyfactor certificate store. Inventory, Management, and Reenrollment jobs are supported. The orchestrator replaces the IIS orchestrator that ships with Keyfactor Command (which did not support binding.)

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Windows Certificate Universal Orchestrator Extension

Integration Status: production Release Issues GitHub Downloads (all assets, all releases)

Support · Installation · License · Related Integrations

Overview

The Windows Certificate Orchestrator Extension is a multi-purpose integration that can remotely manage certificates on a Windows Server's Local Machine Store. This extension currently manages certificates for the current store types:

  • WinCert - Certificates defined by path set for the Certificate Store
  • WinIIS - IIS Bound certificates
  • WinSQL - Certificates that are bound to the specified SQL Instances

By default, most certificates are stored in the “Personal” (My) and “Web Hosting” (WebHosting) stores. For a complete list of local machine cert stores you can execute the PowerShell command:

Get-ChildItem Cert:\LocalMachine

The returned list will contain the actual certificate store name to be used when entering store location.

This extension implements four job types: Inventory, Management Add/Remove, and Reenrollment.

The Keyfactor Universal Orchestrator (UO) and WinCert Extension can be installed on either Windows or Linux operating systems. A UO service managing certificates on remote servers is considered to be acting as an Orchestrator, while a UO Service managing local certificates on the same server running the service is considered an Agent. When acting as an Orchestrator, connectivity from the orchestrator server hosting the WinCert extension to the orchestrated server hosting the certificate stores(s) being managed is achieved via either an SSH (for Linux orchestrated servers) or WinRM (for Windows orchestrated servers) connection. When acting as an agent (Windows only), WinRM may still be used, OR the certificate store can be configured to bypass a WinRM connection and instead directly access the orchestrator server's certificate stores.

Please refer to the READMEs for each supported store type for more information on proper configuration and setup for these different stores. The supported configurations of Universal Orchestrator hosts and managed orchestrated servers are detailed below:

UO Installed on Windows UO Installed on Linux
Orchestrated Server hosting certificate store(s) on remote Windows server WinRM connection SSH connection
Certificate store(s) on same server as orchestrator service (Agent) WinRM connection or local file system Not Supported

WinRM is used to remotely manage the certificate stores and IIS bindings on Windows machines only. WinRM must be properly configured to allow the orchestrator on the server to manage the certificates. Setting up WinRM is not in the scope of this document.

Note: In version 2.0 of the IIS Orchestrator, the certificate store type has been renamed and additional parameters have been added. Prior to 2.0 the certificate store type was called “IISBin” and as of 2.0 it is called “IISU”. If you have existing certificate stores of type “IISBin”, you have three options:

  1. Leave them as is and continue to manage them with a pre 2.0 IIS Orchestrator Extension. Create the new IISU certificate store type and create any new IIS stores using the new type.
  2. Delete existing IIS stores. Delete the IISBin store type. Create the new IISU store type. Recreate the IIS stores using the new IISU store type.
  3. Convert existing IISBin certificate stores to IISU certificate stores. There is not currently a way to do this via the Keyfactor API, so direct updates to the underlying Keyfactor SQL database is required. A SQL script (IIS-Conversion.sql) is available in the repository to do this. Hosted customers, which do not have access to the underlying database, will need to work Keyfactor support to run the conversion. On-premises customers can run the script themselves, but are strongly encouraged to ensure that a SQL backup is taken prior running the script (and also be confident that they have a tested database restoration process.)

Note: There is an additional (and deprecated) certificate store type of “IIS” that ships with the Keyfactor platform. Migration of certificate stores from the “IIS” type to either the “IISBin” or “IISU” types is not currently supported.

Note: If Looking to use GMSA Accounts to run the Service Keyfactor Command 10.2 or greater is required for No Value checkbox to work

The Windows Certificate Universal Orchestrator extension implements 3 Certificate Store Types. Depending on your use case, you may elect to use one, or all of these Certificate Store Types. Descriptions of each are provided below.

Compatibility

This integration is compatible with Keyfactor Universal Orchestrator version 10.1 and later.

Support

The Windows Certificate Universal Orchestrator extension If you have a support issue, please open a support ticket by either contacting your Keyfactor representative or via the Keyfactor Support Portal at https://support.keyfactor.com.

To report a problem or suggest a new feature, use the Issues tab. If you want to contribute actual bug fixes or proposed enhancements, use the Pull requests tab.

Requirements & Prerequisites

Before installing the Windows Certificate Universal Orchestrator extension, we recommend that you install kfutil. Kfutil is a command-line tool that simplifies the process of creating store types, installing extensions, and instantiating certificate stores in Keyfactor Command.

Using the WinCert Extension on Linux servers:
  1. General SSH Setup Information: PowerShell 6 or higher and SSH must be installed on all computers. Install SSH, including ssh server, that's appropriate for your platform. You also need to install PowerShell from GitHub to get the SSH remoting feature. The SSH server must be configured to create a SSH subsysten to host a PowerShell process on the remote computer. It is suggested to turn off password authentication as this extension uses key-based authentication.

  2. SSH Authentication: When creating a Keyfactor certificate store for the WinCert orchestrator extension, the only protocol supported to communicate with Windows servers is ssh. When providing the user id and password, the connection is attempted by creating a temporary private key file using the contents in the Password textbox. Therefore, the password field must contain the full SSH Private key.

Using the WinCert Extension on Windows servers:
  1. When orchestrating management of external (and potentially local) certificate stores, the WinCert Orchestrator Extension makes use of WinRM to connect to external certificate store servers. The security context used is the user id entered in the Keyfactor Command certificate store. Make sure that WinRM is set up on the orchestrated server and that the WinRM port (by convention, 5585 for HTTP and 5586 for HTTPS) is part of the certificate store path when setting up your certificate stores jobs. If running as an agent, managing local certificate stores, local commands are run under the security context of the user account running the Keyfactor Universal Orchestrator Service.

Please consult with your company's system administrator for more information on configuring SSH or WinRM in your environment.

PowerShell Requirements

PowerShell is extensively used to inventory and manage certificates across each Certificate Store Type. Windows Desktop and Server includes PowerShell 5.1 that is capable of running all or most PowerShell functions. If the Orchestrator is to run in a Linux environment using SSH as their communication protocol, PowerShell 6.1 or greater is required (7.4 or greater is recommended).
In addition to PowerShell, IISU requires additional PowerShell modules to be installed and available. These modules include: WebAdministration and IISAdministration, versions 1.1.

Security and Permission Considerations

From an official support point of view, Local Administrator permissions are required on the target server. Some customers have been successful with using other accounts and granting rights to the underlying certificate and private key stores. Due to complexities with the interactions between Group Policy, WinRM, User Account Control, and other unpredictable customer environmental factors, Keyfactor cannot provide assistance with using accounts other than the local administrator account.

For customers wishing to use something other than the local administrator account, the following information may be helpful:

  • The WinCert extensions (WinCert, IISU, WinSQL) create a WinRM (remote PowerShell) session to the target server in order to manipulate the Windows Certificate Stores, perform binding (in the case of the IISU extension), or to access the registry (in the case of the WinSQL extension).

  • When the WinRM session is created, the certificate store credentials are used if they have been specified, otherwise the WinRM session is created in the context of the Universal Orchestrator (UO) Service account (which potentially could be the network service account, a regular account, or a GMSA account)

  • WinRM needs to be properly set up between the server hosting the UO and the target server. This means that a WinRM client running on the UO server when running in the context of the UO service account needs to be able to create a session on the target server using the configured credentials of the target server and any PowerShell commands running on the remote session need to have appropriate permissions.

  • Even though a given account may be in the administrators group or have administrative privileges on the target system and may be able to execute certificate and binding operations when running locally, the same account may not work when being used via WinRM. User Account Control (UAC) can get in the way and filter out administrative privledges. UAC / WinRM configuration has a LocalAccountTokenFilterPolicy setting that can be adjusted to not filter out administrative privledges for remote users, but enabling this may have other security ramifications.

  • The following list may not be exhaustive, but in general the account (when running under a remote WinRM session) needs permissions to:

    • Instantiate and open a .NET X509Certificates.X509Store object for the target certificate store and be able to read and write both the certificates and related private keys. Note that ACL permissions on the stores and private keys are separate.
    • Use the Import-Certificate, Get-WebSite, Get-WebBinding, and New-WebBinding PowerShell CmdLets.
    • Create and delete temporary files.
    • Execute certreq commands.
    • Access any Cryptographic Service Provider (CSP) referenced in re-enrollment jobs.
    • Read and Write values in the registry (HKLM:\SOFTWARE\Microsoft\Microsoft SQL Server) when performing SQL Server certificate binding.

Certificate Store Types

To use the Windows Certificate Universal Orchestrator extension, you must create the Certificate Store Types required for your usecase. This only needs to happen once per Keyfactor Command instance.

The Windows Certificate Universal Orchestrator extension implements 3 Certificate Store Types. Depending on your use case, you may elect to use one, or all of these Certificate Store Types.

WinCert

Click to expand details

The Windows Certificate Certificate Store Type, known by its short name 'WinCert,' enables the management of certificates within the Windows local machine certificate stores. This store type is a versatile option for general Windows certificate management and supports functionalities including inventory, add, remove, and reenrollment of certificates.

The store type represents the various certificate stores present on a Windows Server. Users can specify these stores by entering the correct store path. To get a complete list of available certificate stores, the PowerShell command Get-ChildItem Cert:\LocalMachine can be executed, providing the actual certificate store names needed for configuration.

Key Features and Considerations

  • Functionality: The WinCert store type supports essential certificate management tasks, such as inventorying existing certificates, adding new certificates, removing old ones, and reenrolling certificates.

  • Caveats: It's important to ensure that the Windows Remote Management (WinRM) is properly configured on the target server. The orchestrator relies on WinRM to perform its tasks, such as manipulating the Windows Certificate Stores. Misconfiguration of WinRM may lead to connection and permission issues.

  • Limitations: Users should be aware that for this store type to function correctly, certain permissions are necessary. While some advanced users successfully use non-administrator accounts with specific permissions, it is officially supported only with Local Administrator permissions. Complexities with interactions between Group Policy, WinRM, User Account Control, and other environmental factors may impede operations if not properly configured.

Supported Operations

Operation Is Supported
Add âś… Checked
Remove âś… Checked
Discovery 🔲 Unchecked
Reenrollment âś… Checked
Create 🔲 Unchecked

Store Type Creation

Using kfutil:

kfutil is a custom CLI for the Keyfactor Command API and can be used to created certificate store types. For more information on kfutil check out the docs

Click to expand WinCert kfutil details
Using online definition from GitHub:

This will reach out to GitHub and pull the latest store-type definition

# Windows Certificate
kfutil store-types create WinCert
Offline creation using integration-manifest file:

If required, it is possible to create store types from the integration-manifest.json included in this repo. You would first download the integration-manifest.json and then run the following command in your offline environment.

kfutil store-types create --from-file integration-manifest.json

Manual Creation

Below are instructions on how to create the WinCert store type manually in the Keyfactor Command Portal

Click to expand manual WinCert details

Create a store type called WinCert with the attributes in the tables below:

Basic Tab
Attribute Value Description
Name Windows Certificate Display name for the store type (may be customized)
Short Name WinCert Short display name for the store type
Capability WinCert Store type name orchestrator will register with. Check the box to allow entry of value
Supports Add âś… Checked Check the box. Indicates that the Store Type supports Management Add
Supports Remove âś… Checked Check the box. Indicates that the Store Type supports Management Remove
Supports Discovery 🔲 Unchecked Indicates that the Store Type supports Discovery
Supports Reenrollment âś… Checked Indicates that the Store Type supports Reenrollment
Supports Create 🔲 Unchecked Indicates that the Store Type supports store creation
Needs Server âś… Checked Determines if a target server name is required when creating store
Blueprint Allowed 🔲 Unchecked Determines if store type may be included in an Orchestrator blueprint
Uses PowerShell 🔲 Unchecked Determines if underlying implementation is PowerShell
Requires Store Password 🔲 Unchecked Enables users to optionally specify a store password when defining a Certificate Store.
Supports Entry Password 🔲 Unchecked Determines if an individual entry within a store can have a password.

The Basic tab should look like this:

WinCert Basic Tab

Advanced Tab
Attribute Value Description
Supports Custom Alias Forbidden Determines if an individual entry within a store can have a custom Alias.
Private Key Handling Optional This determines if Keyfactor can send the private key associated with a certificate to the store. Required because IIS certificates without private keys would be invalid.
PFX Password Style Default 'Default' - PFX password is randomly generated, 'Custom' - PFX password may be specified when the enrollment job is created (Requires the Allow Custom Password application setting to be enabled.)

The Advanced tab should look like this:

WinCert Advanced Tab

For Keyfactor Command versions 24.4 and later, a Certificate Format dropdown is available with PFX and PEM options. Ensure that PFX is selected, as this determines the format of new and renewed certificates sent to the Orchestrator during a Management job. Currently, all Keyfactor-supported Orchestrator extensions support only PFX.

Custom Fields Tab

Custom fields operate at the certificate store level and are used to control how the orchestrator connects to the remote target server containing the certificate store to be managed. The following custom fields should be added to the store type:

Name Display Name Description Type Default Value/Options Required
spnwithport SPN With Port Internally set the -IncludePortInSPN option when creating the remote PowerShell connection. Needed for some Kerberos configurations. Bool false 🔲 Unchecked
WinRM Protocol WinRM Protocol Multiple choice value specifying which protocol to use. Protocols https or http use WinRM to connect from Windows to Windows Servers. Using ssh is only supported when running the orchestrator in a Linux environment. MultipleChoice https,http,ssh âś… Checked
WinRM Port WinRM Port String value specifying the port number that the Windows target server's WinRM listener is configured to use. Example: '5986' for HTTPS or '5985' for HTTP. By default, when using ssh in a Linux environment, the default port number is 22. String 5986 âś… Checked
ServerUsername Server Username Username used to log into the target server for establishing the WinRM session. Example: 'administrator' or 'domain\username'. Secret 🔲 Unchecked
ServerPassword Server Password Password corresponding to the Server Username used to log into the target server. When establishing a SSH session from a Linux environment, the password must include the full SSH Private key. Secret 🔲 Unchecked
ServerUseSsl Use SSL Determine whether the server uses SSL or not (This field is automatically created) Bool true âś… Checked

The Custom Fields tab should look like this:

WinCert Custom Fields Tab

Entry Parameters Tab
Name Display Name Description Type Default Value Entry has a private key Adding an entry Removing an entry Reenrolling an entry
ProviderName Crypto Provider Name Name of the Windows cryptographic provider to use during reenrollment jobs when generating and storing the private keys. If not specified, defaults to 'Microsoft Strong Cryptographic Provider'. This value would typically be specified when leveraging a Hardware Security Module (HSM). The specified cryptographic provider must be available on the target server being managed. The list of installed cryptographic providers can be obtained by running 'certutil -csplist' on the target Server. String 🔲 Unchecked 🔲 Unchecked 🔲 Unchecked 🔲 Unchecked
SAN SAN String value specifying the Subject Alternative Name (SAN) to be used when performing reenrollment jobs. Format as a list of <san_type>=<san_value> entries separated by ampersands; Example: 'dns=www.example.com&dns=www.example2.com' for multiple SANs. Can be made optional if RFC 2818 is disabled on the CA. String 🔲 Unchecked 🔲 Unchecked 🔲 Unchecked ✅ Checked

The Entry Parameters tab should look like this:

WinCert Entry Parameters Tab

IISU

Click to expand details

The IIS Bound Certificate Certificate Store Type, identified by its short name 'IISU,' is designed for the management of certificates bound to IIS (Internet Information Services) servers. This store type allows users to automate and streamline the process of adding, removing, and reenrolling certificates for IIS sites, making it significantly easier to manage web server certificates.

Key Features and Representation

The IISU store type represents the IIS servers and their certificate bindings. It specifically caters to managing SSL/TLS certificates tied to IIS websites, allowing bind operations such as specifying site names, IP addresses, ports, and enabling Server Name Indication (SNI). By default, it supports job types like Inventory, Add, Remove, and Reenrollment, thereby offering comprehensive management capabilities for IIS certificates.

Limitations and Areas of Confusion

  • Caveats: It's important to ensure that the Windows Remote Management (WinRM) is properly configured on the target server. The orchestrator relies on WinRM to perform its tasks, such as manipulating the Windows Certificate Stores. Misconfiguration of WinRM may lead to connection and permission issues.

    When performing Inventory, all bound certificates regardless to their store location will be returned.

    When executing an Add or Renew Management job, the Store Location will be considered and place the certificate in that location.

  • Limitations: Users should be aware that for this store type to function correctly, certain permissions are necessary. While some advanced users successfully use non-administrator accounts with specific permissions, it is officially supported only with Local Administrator permissions. Complexities with interactions between Group Policy, WinRM, User Account Control, and other environmental factors may impede operations if not properly configured.

  • Custom Alias and Private Keys: The store type does not support custom aliases for individual entries and requires private keys because IIS certificates without private keys would be invalid.

Supported Operations

Operation Is Supported
Add âś… Checked
Remove âś… Checked
Discovery 🔲 Unchecked
Reenrollment âś… Checked
Create 🔲 Unchecked

Store Type Creation

Using kfutil:

kfutil is a custom CLI for the Keyfactor Command API and can be used to created certificate store types. For more information on kfutil check out the docs

Click to expand IISU kfutil details
Using online definition from GitHub:

This will reach out to GitHub and pull the latest store-type definition

# IIS Bound Certificate
kfutil store-types create IISU
Offline creation using integration-manifest file:

If required, it is possible to create store types from the integration-manifest.json included in this repo. You would first download the integration-manifest.json and then run the following command in your offline environment.

kfutil store-types create --from-file integration-manifest.json

Manual Creation

Below are instructions on how to create the IISU store type manually in the Keyfactor Command Portal

Click to expand manual IISU details

Create a store type called IISU with the attributes in the tables below:

Basic Tab
Attribute Value Description
Name IIS Bound Certificate Display name for the store type (may be customized)
Short Name IISU Short display name for the store type
Capability IISU Store type name orchestrator will register with. Check the box to allow entry of value
Supports Add âś… Checked Check the box. Indicates that the Store Type supports Management Add
Supports Remove âś… Checked Check the box. Indicates that the Store Type supports Management Remove
Supports Discovery 🔲 Unchecked Indicates that the Store Type supports Discovery
Supports Reenrollment âś… Checked Indicates that the Store Type supports Reenrollment
Supports Create 🔲 Unchecked Indicates that the Store Type supports store creation
Needs Server âś… Checked Determines if a target server name is required when creating store
Blueprint Allowed 🔲 Unchecked Determines if store type may be included in an Orchestrator blueprint
Uses PowerShell 🔲 Unchecked Determines if underlying implementation is PowerShell
Requires Store Password 🔲 Unchecked Enables users to optionally specify a store password when defining a Certificate Store.
Supports Entry Password 🔲 Unchecked Determines if an individual entry within a store can have a password.

The Basic tab should look like this:

IISU Basic Tab

Advanced Tab
Attribute Value Description
Supports Custom Alias Forbidden Determines if an individual entry within a store can have a custom Alias.
Private Key Handling Required This determines if Keyfactor can send the private key associated with a certificate to the store. Required because IIS certificates without private keys would be invalid.
PFX Password Style Default 'Default' - PFX password is randomly generated, 'Custom' - PFX password may be specified when the enrollment job is created (Requires the Allow Custom Password application setting to be enabled.)

The Advanced tab should look like this:

IISU Advanced Tab

For Keyfactor Command versions 24.4 and later, a Certificate Format dropdown is available with PFX and PEM options. Ensure that PFX is selected, as this determines the format of new and renewed certificates sent to the Orchestrator during a Management job. Currently, all Keyfactor-supported Orchestrator extensions support only PFX.

Custom Fields Tab

Custom fields operate at the certificate store level and are used to control how the orchestrator connects to the remote target server containing the certificate store to be managed. The following custom fields should be added to the store type:

Name Display Name Description Type Default Value/Options Required
spnwithport SPN With Port Internally set the -IncludePortInSPN option when creating the remote PowerShell connection. Needed for some Kerberos configurations. Bool false 🔲 Unchecked
WinRM Protocol WinRM Protocol Multiple choice value specifying which protocol to use. Protocols https or http use WinRM to connect from Windows to Windows Servers. Using ssh is only supported when running the orchestrator in a Linux environment. MultipleChoice https,http,ssh âś… Checked
WinRM Port WinRM Port String value specifying the port number that the Windows target server's WinRM listener is configured to use. Example: '5986' for HTTPS or '5985' for HTTP. By default, when using ssh in a Linux environment, the default port number is 22. String 5986 âś… Checked
ServerUsername Server Username Username used to log into the target server for establishing the WinRM session. Example: 'administrator' or 'domain\username'. Secret 🔲 Unchecked
ServerPassword Server Password Password corresponding to the Server Username used to log into the target server. When establishing a SSH session from a Linux environment, the password must include the full SSH Private key. Secret 🔲 Unchecked
ServerUseSsl Use SSL Determine whether the server uses SSL or not (This field is automatically created) Bool true âś… Checked

The Custom Fields tab should look like this:

IISU Custom Fields Tab

Entry Parameters Tab
Name Display Name Description Type Default Value Entry has a private key Adding an entry Removing an entry Reenrolling an entry
Port Port String value specifying the IP port to bind the certificate to for the IIS site. Example: '443' for HTTPS. String 443 🔲 Unchecked 🔲 Unchecked 🔲 Unchecked 🔲 Unchecked
IPAddress IP Address String value specifying the IP address to bind the certificate to for the IIS site. Example: '*' for all IP addresses or '192.168.1.1' for a specific IP address. String * 🔲 Unchecked ✅ Checked ✅ Checked ✅ Checked
HostName Host Name String value specifying the host name (host header) to bind the certificate to for the IIS site. Leave blank for all host names or enter a specific hostname such as 'www.example.com'. String 🔲 Unchecked 🔲 Unchecked 🔲 Unchecked 🔲 Unchecked
SiteName IIS Site Name String value specifying the name of the IIS web site to bind the certificate to. Example: 'Default Web Site' or any custom site name such as 'MyWebsite'. String Default Web Site 🔲 Unchecked ✅ Checked ✅ Checked ✅ Checked
SniFlag SSL Flags A 128-Bit Flag that determines what type of SSL settings you wish to use. The default is 0, meaning No SNI. For more information, check IIS documentation for the appropriate bit setting.) String 0 🔲 Unchecked 🔲 Unchecked 🔲 Unchecked 🔲 Unchecked
Protocol Protocol Multiple choice value specifying the protocol to bind to. Example: 'https' for secure communication. MultipleChoice https 🔲 Unchecked ✅ Checked ✅ Checked ✅ Checked
ProviderName Crypto Provider Name Name of the Windows cryptographic provider to use during reenrollment jobs when generating and storing the private keys. If not specified, defaults to 'Microsoft Strong Cryptographic Provider'. This value would typically be specified when leveraging a Hardware Security Module (HSM). The specified cryptographic provider must be available on the target server being managed. The list of installed cryptographic providers can be obtained by running 'certutil -csplist' on the target Server. String 🔲 Unchecked 🔲 Unchecked 🔲 Unchecked 🔲 Unchecked
SAN SAN String value specifying the Subject Alternative Name (SAN) to be used when performing reenrollment jobs. Format as a list of <san_type>=<san_value> entries separated by ampersands; Example: 'dns=www.example.com&dns=www.example2.com' for multiple SANs. Can be made optional if RFC 2818 is disabled on the CA. String 🔲 Unchecked 🔲 Unchecked 🔲 Unchecked ✅ Checked

The Entry Parameters tab should look like this:

IISU Entry Parameters Tab

WinSql

Click to expand details

The WinSql Certificate Store Type, referred to by its short name 'WinSql,' is designed for the management of certificates used by SQL Server instances. This store type allows users to automate the process of adding, removing, reenrolling, and inventorying certificates associated with SQL Server, thereby simplifying the management of SSL/TLS certificates for database servers.

Caveats and Limitations

  • Caveats: It's important to ensure that the Windows Remote Management (WinRM) is properly configured on the target server. The orchestrator relies on WinRM to perform its tasks, such as manipulating the Windows Certificate Stores. Misconfiguration of WinRM may lead to connection and permission issues.

  • Limitations: Users should be aware that for this store type to function correctly, certain permissions are necessary. While some advanced users successfully use non-administrator accounts with specific permissions, it is officially supported only with Local Administrator permissions. Complexities with interactions between Group Policy, WinRM, User Account Control, and other environmental factors may impede operations if not properly configured.

Supported Operations

Operation Is Supported
Add âś… Checked
Remove âś… Checked
Discovery 🔲 Unchecked
Reenrollment 🔲 Unchecked
Create 🔲 Unchecked

Store Type Creation

Using kfutil:

kfutil is a custom CLI for the Keyfactor Command API and can be used to created certificate store types. For more information on kfutil check out the docs

Click to expand WinSql kfutil details
Using online definition from GitHub:

This will reach out to GitHub and pull the latest store-type definition

# WinSql
kfutil store-types create WinSql
Offline creation using integration-manifest file:

If required, it is possible to create store types from the integration-manifest.json included in this repo. You would first download the integration-manifest.json and then run the following command in your offline environment.

kfutil store-types create --from-file integration-manifest.json

Manual Creation

Below are instructions on how to create the WinSql store type manually in the Keyfactor Command Portal

Click to expand manual WinSql details

Create a store type called WinSql with the attributes in the tables below:

Basic Tab
Attribute Value Description
Name WinSql Display name for the store type (may be customized)
Short Name WinSql Short display name for the store type
Capability WinSql Store type name orchestrator will register with. Check the box to allow entry of value
Supports Add âś… Checked Check the box. Indicates that the Store Type supports Management Add
Supports Remove âś… Checked Check the box. Indicates that the Store Type supports Management Remove
Supports Discovery 🔲 Unchecked Indicates that the Store Type supports Discovery
Supports Reenrollment 🔲 Unchecked Indicates that the Store Type supports Reenrollment
Supports Create 🔲 Unchecked Indicates that the Store Type supports store creation
Needs Server âś… Checked Determines if a target server name is required when creating store
Blueprint Allowed âś… Checked Determines if store type may be included in an Orchestrator blueprint
Uses PowerShell 🔲 Unchecked Determines if underlying implementation is PowerShell
Requires Store Password 🔲 Unchecked Enables users to optionally specify a store password when defining a Certificate Store.
Supports Entry Password 🔲 Unchecked Determines if an individual entry within a store can have a password.

The Basic tab should look like this:

WinSql Basic Tab

Advanced Tab
Attribute Value Description
Supports Custom Alias Forbidden Determines if an individual entry within a store can have a custom Alias.
Private Key Handling Optional This determines if Keyfactor can send the private key associated with a certificate to the store. Required because IIS certificates without private keys would be invalid.
PFX Password Style Default 'Default' - PFX password is randomly generated, 'Custom' - PFX password may be specified when the enrollment job is created (Requires the Allow Custom Password application setting to be enabled.)

The Advanced tab should look like this:

WinSql Advanced Tab

For Keyfactor Command versions 24.4 and later, a Certificate Format dropdown is available with PFX and PEM options. Ensure that PFX is selected, as this determines the format of new and renewed certificates sent to the Orchestrator during a Management job. Currently, all Keyfactor-supported Orchestrator extensions support only PFX.

Custom Fields Tab

Custom fields operate at the certificate store level and are used to control how the orchestrator connects to the remote target server containing the certificate store to be managed. The following custom fields should be added to the store type:

Name Display Name Description Type Default Value/Options Required
spnwithport SPN With Port Internally set the -IncludePortInSPN option when creating the remote PowerShell connection. Needed for some Kerberos configurations. Bool false 🔲 Unchecked
WinRM Protocol WinRM Protocol Multiple choice value specifying which protocol to use. Protocols https or http use WinRM to connect from Windows to Windows Servers. Using ssh is only supported when running the orchestrator in a Linux environment. MultipleChoice https,http,ssh âś… Checked
WinRM Port WinRM Port String value specifying the port number that the Windows target server's WinRM listener is configured to use. Example: '5986' for HTTPS or '5985' for HTTP. By default, when using ssh in a Linux environment, the default port number is 22. String 5986 âś… Checked
ServerUsername Server Username Username used to log into the target server for establishing the WinRM session. Example: 'administrator' or 'domain\username'. Secret 🔲 Unchecked
ServerPassword Server Password Password corresponding to the Server Username used to log into the target server. When establishing a SSH session from a Linux environment, the password must include the full SSH Private key. Secret 🔲 Unchecked
ServerUseSsl Use SSL Determine whether the server uses SSL or not (This field is automatically created) Bool true âś… Checked
RestartService Restart SQL Service After Cert Installed Boolean value (true or false) indicating whether to restart the SQL Server service after installing the certificate. Example: 'true' to enable service restart after installation. Bool false âś… Checked

The Custom Fields tab should look like this:

WinSql Custom Fields Tab

Entry Parameters Tab
Name Display Name Description Type Default Value Entry has a private key Adding an entry Removing an entry Reenrolling an entry
InstanceName Instance Name String value specifying the SQL Server instance name to bind the certificate to. Example: 'MSSQLServer' for the default instance or 'Instance1' for a named instance. String 🔲 Unchecked 🔲 Unchecked 🔲 Unchecked 🔲 Unchecked
ProviderName Crypto Provider Name Optional string value specifying the name of the Windows cryptographic provider to use during reenrollment jobs when generating and storing private keys. Example: 'Microsoft Strong Cryptographic Provider'. String 🔲 Unchecked 🔲 Unchecked 🔲 Unchecked 🔲 Unchecked
SAN SAN String value specifying the Subject Alternative Name (SAN) to be used when performing reenrollment jobs. Format as a list of <san_type>=<san_value> entries separated by ampersands; Example: 'dns=www.example.com&dns=www.example2.com' for multiple SANs. String 🔲 Unchecked 🔲 Unchecked 🔲 Unchecked ✅ Checked

The Entry Parameters tab should look like this:

WinSql Entry Parameters Tab

Installation

  1. Download the latest Windows Certificate Universal Orchestrator extension from GitHub.

    Navigate to the Windows Certificate Universal Orchestrator extension GitHub version page. Refer to the compatibility matrix below to determine whether the net6.0 or net8.0 asset should be downloaded. Then, click the corresponding asset to download the zip archive.

    Universal Orchestrator Version Latest .NET version installed on the Universal Orchestrator server rollForward condition in Orchestrator.runtimeconfig.json iis-orchestrator .NET version to download
    Older than 11.0.0 net6.0
    Between 11.0.0 and 11.5.1 (inclusive) net6.0 net6.0
    Between 11.0.0 and 11.5.1 (inclusive) net8.0 Disable net6.0
    Between 11.0.0 and 11.5.1 (inclusive) net8.0 LatestMajor net8.0
    11.6 and newer net8.0 net8.0

    Unzip the archive containing extension assemblies to a known location.

    Note If you don't see an asset with a corresponding .NET version, you should always assume that it was compiled for net6.0.

  2. Locate the Universal Orchestrator extensions directory.

    • Default on Windows - C:\Program Files\Keyfactor\Keyfactor Orchestrator\extensions
    • Default on Linux - /opt/keyfactor/orchestrator/extensions
  3. Create a new directory for the Windows Certificate Universal Orchestrator extension inside the extensions directory.

    Create a new directory called iis-orchestrator.

    The directory name does not need to match any names used elsewhere; it just has to be unique within the extensions directory.

  4. Copy the contents of the downloaded and unzipped assemblies from step 2 to the iis-orchestrator directory.

  5. Restart the Universal Orchestrator service.

    Refer to Starting/Restarting the Universal Orchestrator service.

  6. (optional) PAM Integration

    The Windows Certificate Universal Orchestrator extension is compatible with all supported Keyfactor PAM extensions to resolve PAM-eligible secrets. PAM extensions running on Universal Orchestrators enable secure retrieval of secrets from a connected PAM provider.

    To configure a PAM provider, reference the Keyfactor Integration Catalog to select an extension and follow the associated instructions to install it on the Universal Orchestrator (remote).

The above installation steps can be supplemented by the official Command documentation.

Defining Certificate Stores

The Windows Certificate Universal Orchestrator extension implements 3 Certificate Store Types, each of which implements different functionality. Refer to the individual instructions below for each Certificate Store Type that you deemed necessary for your use case from the installation section.

Windows Certificate (WinCert)

Store Creation

Manually with the Command UI

Click to expand details
  1. Navigate to the Certificate Stores page in Keyfactor Command.

    Log into Keyfactor Command, toggle the Locations dropdown, and click Certificate Stores.

  2. Add a Certificate Store.

    Click the Add button to add a new Certificate Store. Use the table below to populate the Attributes in the Add form.

    Attribute Description
    Category Select "Windows Certificate" or the customized certificate store name from the previous step.
    Container Optional container to associate certificate store with.
    Client Machine Hostname of the Windows Server containing the certificate store to be managed. If this value is a hostname, a WinRM session will be established using the credentials specified in the Server Username and Server Password fields. For more information, see Client Machine.
    Store Path Windows certificate store path to manage. The store must exist in the Local Machine store on the target server, e.g., 'My' for the Personal Store or 'Root' for the Trusted Root Certification Authorities Store.
    Orchestrator Select an approved orchestrator capable of managing WinCert certificates. Specifically, one with the WinCert capability.
    spnwithport Internally set the -IncludePortInSPN option when creating the remote PowerShell connection. Needed for some Kerberos configurations.
    WinRM Protocol Multiple choice value specifying which protocol to use. Protocols https or http use WinRM to connect from Windows to Windows Servers. Using ssh is only supported when running the orchestrator in a Linux environment.
    WinRM Port String value specifying the port number that the Windows target server's WinRM listener is configured to use. Example: '5986' for HTTPS or '5985' for HTTP. By default, when using ssh in a Linux environment, the default port number is 22.
    ServerUsername Username used to log into the target server for establishing the WinRM session. Example: 'administrator' or 'domain\username'.
    ServerPassword Password corresponding to the Server Username used to log into the target server. When establishing a SSH session from a Linux environment, the password must include the full SSH Private key.
    ServerUseSsl Determine whether the server uses SSL or not (This field is automatically created)

Using kfutil CLI

Click to expand details
  1. Generate a CSV template for the WinCert certificate store

    kfutil stores import generate-template --store-type-name WinCert --outpath WinCert.csv
  2. Populate the generated CSV file

    Open the CSV file, and reference the table below to populate parameters for each Attribute.

    Attribute Description
    Category Select "Windows Certificate" or the customized certificate store name from the previous step.
    Container Optional container to associate certificate store with.
    Client Machine Hostname of the Windows Server containing the certificate store to be managed. If this value is a hostname, a WinRM session will be established using the credentials specified in the Server Username and Server Password fields. For more information, see Client Machine.
    Store Path Windows certificate store path to manage. The store must exist in the Local Machine store on the target server, e.g., 'My' for the Personal Store or 'Root' for the Trusted Root Certification Authorities Store.
    Orchestrator Select an approved orchestrator capable of managing WinCert certificates. Specifically, one with the WinCert capability.
    Properties.spnwithport Internally set the -IncludePortInSPN option when creating the remote PowerShell connection. Needed for some Kerberos configurations.
    Properties.WinRM Protocol Multiple choice value specifying which protocol to use. Protocols https or http use WinRM to connect from Windows to Windows Servers. Using ssh is only supported when running the orchestrator in a Linux environment.
    Properties.WinRM Port String value specifying the port number that the Windows target server's WinRM listener is configured to use. Example: '5986' for HTTPS or '5985' for HTTP. By default, when using ssh in a Linux environment, the default port number is 22.
    Properties.ServerUsername Username used to log into the target server for establishing the WinRM session. Example: 'administrator' or 'domain\username'.
    Properties.ServerPassword Password corresponding to the Server Username used to log into the target server. When establishing a SSH session from a Linux environment, the password must include the full SSH Private key.
    Properties.ServerUseSsl Determine whether the server uses SSL or not (This field is automatically created)
  3. Import the CSV file to create the certificate stores

    kfutil stores import csv --store-type-name WinCert --file WinCert.csv

PAM Provider Eligible Fields

Attributes eligible for retrieval by a PAM Provider on the Universal Orchestrator

If a PAM provider was installed on the Universal Orchestrator in the Installation section, the following parameters can be configured for retrieval on the Universal Orchestrator.

Attribute Description
ServerUsername Username used to log into the target server for establishing the WinRM session. Example: 'administrator' or 'domain\username'.
ServerPassword Password corresponding to the Server Username used to log into the target server. When establishing a SSH session from a Linux environment, the password must include the full SSH Private key.

Please refer to the Universal Orchestrator (remote) usage section (PAM providers on the Keyfactor Integration Catalog) for your selected PAM provider for instructions on how to load attributes orchestrator-side.

Any secret can be rendered by a PAM provider installed on the Keyfactor Command server. The above parameters are specific to attributes that can be fetched by an installed PAM provider running on the Universal Orchestrator server itself.

The content in this section can be supplemented by the official Command documentation.

IIS Bound Certificate (IISU)

Store Creation

Manually with the Command UI

Click to expand details
  1. Navigate to the Certificate Stores page in Keyfactor Command.

    Log into Keyfactor Command, toggle the Locations dropdown, and click Certificate Stores.

  2. Add a Certificate Store.

    Click the Add button to add a new Certificate Store. Use the table below to populate the Attributes in the Add form.

    Attribute Description
    Category Select "IIS Bound Certificate" or the customized certificate store name from the previous step.
    Container Optional container to associate certificate store with.
    Client Machine Hostname of the Windows Server containing the IIS certificate store to be managed. If this value is a hostname, a WinRM session will be established using the credentials specified in the Server Username and Server Password fields. For more information, see Client Machine.
    Store Path Windows certificate store path to manage. Choose 'My' for the Personal store or 'WebHosting' for the Web Hosting store.
    Orchestrator Select an approved orchestrator capable of managing IISU certificates. Specifically, one with the IISU capability.
    spnwithport Internally set the -IncludePortInSPN option when creating the remote PowerShell connection. Needed for some Kerberos configurations.
    WinRM Protocol Multiple choice value specifying which protocol to use. Protocols https or http use WinRM to connect from Windows to Windows Servers. Using ssh is only supported when running the orchestrator in a Linux environment.
    WinRM Port String value specifying the port number that the Windows target server's WinRM listener is configured to use. Example: '5986' for HTTPS or '5985' for HTTP. By default, when using ssh in a Linux environment, the default port number is 22.
    ServerUsername Username used to log into the target server for establishing the WinRM session. Example: 'administrator' or 'domain\username'.
    ServerPassword Password corresponding to the Server Username used to log into the target server. When establishing a SSH session from a Linux environment, the password must include the full SSH Private key.
    ServerUseSsl Determine whether the server uses SSL or not (This field is automatically created)

Using kfutil CLI

Click to expand details
  1. Generate a CSV template for the IISU certificate store

    kfutil stores import generate-template --store-type-name IISU --outpath IISU.csv
  2. Populate the generated CSV file

    Open the CSV file, and reference the table below to populate parameters for each Attribute.

    Attribute Description
    Category Select "IIS Bound Certificate" or the customized certificate store name from the previous step.
    Container Optional container to associate certificate store with.
    Client Machine Hostname of the Windows Server containing the IIS certificate store to be managed. If this value is a hostname, a WinRM session will be established using the credentials specified in the Server Username and Server Password fields. For more information, see Client Machine.
    Store Path Windows certificate store path to manage. Choose 'My' for the Personal store or 'WebHosting' for the Web Hosting store.
    Orchestrator Select an approved orchestrator capable of managing IISU certificates. Specifically, one with the IISU capability.
    Properties.spnwithport Internally set the -IncludePortInSPN option when creating the remote PowerShell connection. Needed for some Kerberos configurations.
    Properties.WinRM Protocol Multiple choice value specifying which protocol to use. Protocols https or http use WinRM to connect from Windows to Windows Servers. Using ssh is only supported when running the orchestrator in a Linux environment.
    Properties.WinRM Port String value specifying the port number that the Windows target server's WinRM listener is configured to use. Example: '5986' for HTTPS or '5985' for HTTP. By default, when using ssh in a Linux environment, the default port number is 22.
    Properties.ServerUsername Username used to log into the target server for establishing the WinRM session. Example: 'administrator' or 'domain\username'.
    Properties.ServerPassword Password corresponding to the Server Username used to log into the target server. When establishing a SSH session from a Linux environment, the password must include the full SSH Private key.
    Properties.ServerUseSsl Determine whether the server uses SSL or not (This field is automatically created)
  3. Import the CSV file to create the certificate stores

    kfutil stores import csv --store-type-name IISU --file IISU.csv

PAM Provider Eligible Fields

Attributes eligible for retrieval by a PAM Provider on the Universal Orchestrator

If a PAM provider was installed on the Universal Orchestrator in the Installation section, the following parameters can be configured for retrieval on the Universal Orchestrator.

Attribute Description
ServerUsername Username used to log into the target server for establishing the WinRM session. Example: 'administrator' or 'domain\username'.
ServerPassword Password corresponding to the Server Username used to log into the target server. When establishing a SSH session from a Linux environment, the password must include the full SSH Private key.

Please refer to the Universal Orchestrator (remote) usage section (PAM providers on the Keyfactor Integration Catalog) for your selected PAM provider for instructions on how to load attributes orchestrator-side.

Any secret can be rendered by a PAM provider installed on the Keyfactor Command server. The above parameters are specific to attributes that can be fetched by an installed PAM provider running on the Universal Orchestrator server itself.

The content in this section can be supplemented by the official Command documentation.

WinSql (WinSql)

Store Creation

Manually with the Command UI

Click to expand details
  1. Navigate to the Certificate Stores page in Keyfactor Command.

    Log into Keyfactor Command, toggle the Locations dropdown, and click Certificate Stores.

  2. Add a Certificate Store.

    Click the Add button to add a new Certificate Store. Use the table below to populate the Attributes in the Add form.

    Attribute Description
    Category Select "WinSql" or the customized certificate store name from the previous step.
    Container Optional container to associate certificate store with.
    Client Machine Hostname of the Windows Server containing the SQL Server Certificate Store to be managed. If this value is a hostname, a WinRM session will be established using the credentials specified in the Server Username and Server Password fields. For more information, see Client Machine.
    Store Path Fixed string value 'My' indicating the Personal store on the Local Machine. This denotes the Windows certificate store to be managed for SQL Server.
    Orchestrator Select an approved orchestrator capable of managing WinSql certificates. Specifically, one with the WinSql capability.
    spnwithport Internally set the -IncludePortInSPN option when creating the remote PowerShell connection. Needed for some Kerberos configurations.
    WinRM Protocol Multiple choice value specifying which protocol to use. Protocols https or http use WinRM to connect from Windows to Windows Servers. Using ssh is only supported when running the orchestrator in a Linux environment.
    WinRM Port String value specifying the port number that the Windows target server's WinRM listener is configured to use. Example: '5986' for HTTPS or '5985' for HTTP. By default, when using ssh in a Linux environment, the default port number is 22.
    ServerUsername Username used to log into the target server for establishing the WinRM session. Example: 'administrator' or 'domain\username'.
    ServerPassword Password corresponding to the Server Username used to log into the target server. When establishing a SSH session from a Linux environment, the password must include the full SSH Private key.
    ServerUseSsl Determine whether the server uses SSL or not (This field is automatically created)
    RestartService Boolean value (true or false) indicating whether to restart the SQL Server service after installing the certificate. Example: 'true' to enable service restart after installation.

Using kfutil CLI

Click to expand details
  1. Generate a CSV template for the WinSql certificate store

    kfutil stores import generate-template --store-type-name WinSql --outpath WinSql.csv
  2. Populate the generated CSV file

    Open the CSV file, and reference the table below to populate parameters for each Attribute.

    Attribute Description
    Category Select "WinSql" or the customized certificate store name from the previous step.
    Container Optional container to associate certificate store with.
    Client Machine Hostname of the Windows Server containing the SQL Server Certificate Store to be managed. If this value is a hostname, a WinRM session will be established using the credentials specified in the Server Username and Server Password fields. For more information, see Client Machine.
    Store Path Fixed string value 'My' indicating the Personal store on the Local Machine. This denotes the Windows certificate store to be managed for SQL Server.
    Orchestrator Select an approved orchestrator capable of managing WinSql certificates. Specifically, one with the WinSql capability.
    Properties.spnwithport Internally set the -IncludePortInSPN option when creating the remote PowerShell connection. Needed for some Kerberos configurations.
    Properties.WinRM Protocol Multiple choice value specifying which protocol to use. Protocols https or http use WinRM to connect from Windows to Windows Servers. Using ssh is only supported when running the orchestrator in a Linux environment.
    Properties.WinRM Port String value specifying the port number that the Windows target server's WinRM listener is configured to use. Example: '5986' for HTTPS or '5985' for HTTP. By default, when using ssh in a Linux environment, the default port number is 22.
    Properties.ServerUsername Username used to log into the target server for establishing the WinRM session. Example: 'administrator' or 'domain\username'.
    Properties.ServerPassword Password corresponding to the Server Username used to log into the target server. When establishing a SSH session from a Linux environment, the password must include the full SSH Private key.
    Properties.ServerUseSsl Determine whether the server uses SSL or not (This field is automatically created)
    Properties.RestartService Boolean value (true or false) indicating whether to restart the SQL Server service after installing the certificate. Example: 'true' to enable service restart after installation.
  3. Import the CSV file to create the certificate stores

    kfutil stores import csv --store-type-name WinSql --file WinSql.csv

PAM Provider Eligible Fields

Attributes eligible for retrieval by a PAM Provider on the Universal Orchestrator

If a PAM provider was installed on the Universal Orchestrator in the Installation section, the following parameters can be configured for retrieval on the Universal Orchestrator.

Attribute Description
ServerUsername Username used to log into the target server for establishing the WinRM session. Example: 'administrator' or 'domain\username'.
ServerPassword Password corresponding to the Server Username used to log into the target server. When establishing a SSH session from a Linux environment, the password must include the full SSH Private key.

Please refer to the Universal Orchestrator (remote) usage section (PAM providers on the Keyfactor Integration Catalog) for your selected PAM provider for instructions on how to load attributes orchestrator-side.

Any secret can be rendered by a PAM provider installed on the Keyfactor Command server. The above parameters are specific to attributes that can be fetched by an installed PAM provider running on the Universal Orchestrator server itself.

The content in this section can be supplemented by the official Command documentation.

Client Machine Instructions

Prior to version 2.6, this extension would only run in the Windows environment. Version 2.6 and greater is capable of running on Linux, however, only the SSH protocol is supported.

If running as an agent (accessing stores on the server where the Universal Orchestrator Services is installed ONLY), the Client Machine can be entered, OR you can bypass a WinRM connection and access the local file system directly by adding "|LocalMachine" to the end of your value for Client Machine, for example "1.1.1.1|LocalMachine". In this instance the value to the left of the pipe (|) is ignored. It is important to make sure the values for Client Machine and Store Path together are unique for each certificate store created, as Keyfactor Command requires the Store Type you select, along with Client Machine, and Store Path together must be unique. To ensure this, it is good practice to put the full DNS or IP Address to the left of the | character when setting up a certificate store that will be accessed without a WinRM connection.

License

Apache License 2.0, see LICENSE.

Related Integrations

See all Keyfactor Universal Orchestrator extensions.

About

The IIS Orchestrator treats the certificates bound (actively in use) on a Microsoft Internet Information Server (IIS) as a Keyfactor certificate store. Inventory, Management, and Reenrollment jobs are supported. The orchestrator replaces the IIS orchestrator that ships with Keyfactor Command (which did not support binding.)

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