Microsoft Entra application proxy frequently asked questions

This page answers frequently asked questions about Microsoft Entra application proxy.


Can I modify an App Proxy app from the **App registrations** page in the Microsoft Entra admin center?

No, the following configuration items are being used by app proxy and should not be altered or deleted:

  • Enable/Disable “Allow public clients flows”.
  • CWAP_AuthSecret (Client secrets).
  • API Permissions. Modifying any of the above configuration items on the App registration page will break pre-authentication for Azure AD Application Proxy.

Can I delete an App Proxy app from the App registrations page in the Microsoft Entra admin center?

No. You should delete an App Proxy app from the Enterprise applications area of the Microsoft Entra admin center. If you delete the App Proxy app from the App registrations area of the Microsoft Entra admin center then you could experience issues.

What license is required to use Microsoft Entra application proxy?

To use Microsoft Entra application proxy, you must have a Microsoft Entra ID P1 or P2 license. For more information about licensing, see Microsoft Entra pricing

What happens to Microsoft Entra application proxy in my tenant, if my license expires?

If your license expires, Application Proxy will automatically be disabled. Your application information will be saved for up to one year.

Why is the "Enable Application Proxy button grayed out?

Make sure you have at least a Microsoft Entra ID P1 or P2 license and a Microsoft Entra application proxy Connector installed. After you successfully install your first connector, the Microsoft Entra application proxy service will be enabled automatically.

Connector configuration

Why is my connector still using an older version and not auto-upgraded to latest version?

This may be due to either the updater service not working correctly or if there are no new updates available that the service can install.

The updater service is healthy if it’s running and there are no errors recorded in the event log (Applications and Services logs -> Microsoft -> AadApplicationProxy -> Updater -> Admin).


Only major versions are released for auto-upgrade. We recommend updating your connector manually only if it's necessary. For example, you cannot wait for a major release, because you must fix a known problem or you want to use a new feature. For more information on new releases, the type of the release (download, auto-upgrade), bug fixes and new features see, Microsoft Entra application proxy: Version release history.

To manually upgrade a connector:

  • Download the latest version of the connector. (You will find it under Application Proxy on the Microsoft Entra admin center. You can also find the link at Microsoft Entra application proxy: Version release history.
  • The installer restarts the Azure AD Application Proxy Connector services. In some cases, a reboot of the server might be required if the installer cannot replace all files. Therefore we recommend closing all applications (i.e. Event Viewer) before you start the upgrade.
  • Run the installer. The upgrade process is quick and does not require providing any credentials and the connector will not be re-registered.

Can Application Proxy Connector services run in a different user context than the default?

No, this scenario isn't supported. The default settings are:

  • Microsoft Entra application proxy Connector - WAPCSvc - Network Service
  • Microsoft Entra application proxy Connector Updater - WAPCUpdaterSvc - NT Authority\System

Can a guest user with the Global Administrator or the Application Administrator role register the connector for the (guest) tenant?

No, currently, this isn't possible. The registration attempt is always made on the user's home tenant.

My back-end application is hosted on multiple web servers and requires user session persistence (stickiness). How can I achieve session persistence? 

Is TLS termination (TLS/HTTPS inspection or acceleration) on traffic from the connector servers to Azure supported?

The Application Proxy Connector performs certificate-based authentication to Azure. TLS Termination (TLS/HTTPS inspection or acceleration) breaks this authentication method and isn't supported. Traffic from the connector to Azure must bypass any devices that are performing TLS Termination.

Is TLS 1.2 required for all connections?

Yes. To provide the best-in-class encryption to our customers, the Application Proxy service limits access to only TLS 1.2 protocols. These changes were gradually rolled out and effective since August 31, 2019. Make sure that all your client-server and browser-server combinations are updated to use TLS 1.2 to maintain connection to Application Proxy service. These include clients your users are using to access applications published through Application Proxy. See Preparing for TLS 1.2 in Office 365 for useful references and resources.

Can I place a forward proxy device between the connector server(s) and the back-end application server?

Yes, this scenario is supported starting from the connector version 1.5.1526.0. See Work with existing on-premises proxy servers.

Should I create a dedicated account to register the connector with Microsoft Entra application proxy?

There's no reason to. Any Global Administrator or application administrator account will work. The credentials entered during installation aren't used after the registration process. Instead, a certificate is issued to the connector, which is used for authentication from that point on.

How can I monitor the performance of the Microsoft Entra application proxy connector?

There are Performance Monitor counters that are installed along with the connector. To view them:

  1. Select Start, type "Perfmon", and press ENTER.
  2. Select Performance Monitor and click the green + icon.
  3. Add the Microsoft Entra application proxy Connector counters you want to monitor.

Does the Microsoft Entra application proxy connector have to be on the same subnet as the resource?

The connector isn't required to be on the same subnet. However, it needs name resolution (DNS, hosts file) to the resource and the necessary network connectivity (routing to the resource, ports open on the resource, etc.). For recommendations, see Network topology considerations when using Microsoft Entra application proxy.

What versions of Windows Server can I install a connector on?

Application Proxy requires Windows Server 2012 R2 or later. There is currently a limitation on HTTP2 for Windows Server 2019. In order to successfully use the connector on Windows Server 2019, you will need to add the following registry key and restart the server:

HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows\CurrentVersion\Internet Settings\WinHttp\EnableDefaultHttp2 (DWORD) Value: 0 

Why is the connector still showing in Microsoft Entra admin center after I uninstalled the connector from the Server?

When a connector is running, it remains active as it connects to the service. Uninstalled /Unused connectors are tagged as inactive and are removed after 10 days of inactivity from the portal. There is no way to remove the Inactive connector manually from the Microsoft Entra admin center.

Application configuration

Can I use the domain suffixes [tenantname] or [tenantname] in the external URL?

Although these suffixes appear in the suffix list, you should not use them. These domain suffixes are not meant to be used with Microsoft Entra application proxy. If you use these domain suffixes, the created Microsoft Entra application proxy application won't work. You can use either the standard domain suffix or a custom domain.

I am receiving an error about an invalid certificate or possible wrong password

After you uploaded the SSL certificate, you receive the message "Invalid certificate, possible wrong password" on the portal.

Here are some tips for troubleshooting this error:

  • Check for problems with the certificate. Install it on your local computer. If you don't experience any issues then the certificate is good.
  • Ensure that the password does not contain any special characters. For testing, the password should only contain the characters 0-9, A-Z, and a-z.
  • If the certificate was created with Microsoft Software Key Storage Provider, the RSA algorithm must be used.

What is the length of the default and "long" backend timeout? Can the timeout be extended?

The default length is 85 seconds. The "long" setting is 180 seconds. The timeout limit can't be extended.

Can a service principal manage Application Proxy using PowerShell or Microsoft Graph APIs?

No, this is currently not supported.

What happens if I delete CWAP_AuthSecret (the client secret) in the app registration?

The client secret, also called CWAP_AuthSecret, is automatically added to the application object (app registration) when the Microsoft Entra application proxy app is created.

The client secret is valid for one year. A new one-year client secret is automatically created before the current valid client secret expires. Three CWAP_AuthSecret client secrets are kept in the application object at all times.


Deleting CWAP_AuthSecret breaks pre-authentication for Azure AD Application Proxy. Don't delete CWAP_AuthSecret.

I'm using or want to use Microsoft Entra application proxy. Can I replace the `` fallback domain of my tenant in Microsoft 365 as suggested in the article [Add and replace your fallback domain in Microsoft 365](../../microsoft-365/admin/setup/add-or-replace-your-onmicrosoftcom-domain?view=o365-worldwide)?

No. You must use the original fallback domain.

How do I change the landing page my application loads?

From the Application Registrations page, you can change the homepage URL to the desired external URL of the landing page. The specified page will load when the application is launched from My Apps or the Office 365 Portal. For configuration steps, see Set a custom home page for published apps by using Microsoft Entra application proxy

Why do I get redirected to a truncated URL when I try to access my published application whenever the URL contains a "#" (hashtag) character?

If Microsoft Entra pre-authentication is configured, and the application URL contains a “#” character when you try to access the application for the first time, you get redirected to Microsoft Entra ID ( for the authentication. Once you complete the authentication you get redirected to the URL part prior to the ”#” character and everything that comes after the “#“ seems to be ignored/ removed. For example if the URL is, once the Microsoft Entra authentication is done the user will be redirected to This behavior is by design due to how the “#” character is handled by the browser.

Possible solutions/ alternatives:

  • Setup a redirection from to The user must first access
  • The URL used for the first access attempt must include the “#” character in encoded form (%23). The published server might not accept this.
  • Configure passthrough pre-authentication type (not recommended).

Can only IIS-based applications be published? What about web applications running on non-Windows web servers? Does the connector have to be installed on a server with IIS installed?

No, there's no IIS requirement for applications that are published. You can publish web applications running on servers other than Windows Server. However, you might not be able to use pre-authentication with a non-Windows Server, depending on if the web server supports Negotiate (Kerberos authentication). IIS isn't required on the server where the connector is installed.

Can I configure Application Proxy to add the HSTS header?

Application Proxy does not automatically add the HTTP Strict-Transport-Security header to HTTPS responses, but it will maintain the header if it is in the original response sent by the published application. Proving a setting to enable this functionality is on the roadmap.

Can I use a custom port number in the external URL?

No, if the protocol http is configured in the external URL then the Microsoft Entra application proxy endpoint accepts incoming request on the port TCP 80, if the protocol https then on the port TCP 443.

Can I use a custom port number in the internal URL?

Yes, some examples for internal URLs including ports: http://app.contoso.local:8888/, https://app.contoso.local:8080/, https://app.contoso.local:8081/test/.

What are the challenges, if the external and the internal URLs are different?

Some responses sent by the published web applications might contain hard-coded URLs. In this case it must be ensured by using a link translation solution that the client always uses the correct URL. Link translation solutions might be complex and might not work in all the scenarios. You can find here our documented solutions for link translation.

As best practice it is advised to use identical external and internal URLs. External and internal URLs are considered to be identical, if the protocol://hostname:port/path/ in both URLs are identical.

This can be achieved by using the Custom Domains feature.



External URL:
Internal URL:

Not identical:

External URL:
Internal URL:

External URL:
Internal URL:

External URL:
Internal URL:

Making the external and internal URLs identical is not possible at all, if the internal URL contains a non-standard port (other than TCP 80 / 443).

In some scenarios changes must be done in the configuration of the web app.

Integrated Windows authentication

When should I use the PrincipalsAllowedToDelegateToAccount method when setting up Kerberos Constrained Delegation (KCD)?

The PrincipalsAllowedToDelegateToAccount method is used when connector servers are in a different domain from the web application service account. It requires the use of Resource-based Constrained Delegation. If the connector servers and the web application service account are in the same domain, you can use Active Directory Users and Computers to configure the delegation settings on each of the connector machine accounts, allowing them to delegate to the target SPN.

If the connector servers and the web application service account are in different domains, Resource-based delegation is used. The delegation permissions are configured on the target web server and web application service account. This method of Constrained Delegation is relatively new. The method was introduced in Windows Server 2012, which supports cross-domain delegation by allowing the resource (web service) owner to control which machine and service accounts can delegate to it. There's no UI to assist with this configuration, so you'll need to use PowerShell. For more information, see the whitepaper Understanding Kerberos Constrained Delegation with Application Proxy.

Does NTLM authentication work with Microsoft Entra application proxy?

NTLM authentication can’t be used as a pre-authentication or single sign-on method. NTLM authentication can be used only when it can be negotiated directly between the client and the published web application. Using NTLM authentication usually causes a sign-in prompt to appear in the browser.

Can I use the logon identity “On-premises user principal name” or “On-premises SAM account name” in a B2B IWA single sign-on scenario?

No, this won’t work, because a guest user in Microsoft Entra ID doesn't have the attribute that is required by any of the logon identities mentioned above.

In this case there will be a fallback to “User principal name”. For more details on the B2B scenario please read Grant B2B users in Microsoft Entra ID access to your on-premises applications.

Pass-through authentication

Can I use Conditional Access Policies for applications published with pass-through authentication?

Conditional Access Policies are only enforced for successfully pre-authenticated users in Microsoft Entra ID. Pass-through authentication doesn’t trigger Microsoft Entra authentication, so Conditional Access Policies can't be enforced. With pass-through authentication, MFA policies must be implemented on the on-premises server, if possible, or by enabling pre-authentication with Microsoft Entra application proxy.

Can I publish a web application with client certificate authentication requirement?

No, this scenario isn't supported because Application Proxy will terminate TLS traffic.

Remote Desktop Gateway publishing

How can I publish Remote Desktop Gateway over Microsoft Entra application proxy?

Can I use Kerberos Constrained Delegation (Single Sign-On - Windows Integrated Authentication) in the Remote Desktop Gateway publishing scenario?

No, this scenario isn't supported.

My users don't use Internet Explorer 11 and the pre-authentication scenario doesn’t work for them. Is this expected?

Yes, it’s expected. The pre-authentication scenario requires an ActiveX control, which isn't supported in third-party browsers.

Is the Remote Desktop Web Client (HTML5) supported?

Yes, this scenario is currently in public preview. Refer to Publish Remote Desktop with Microsoft Entra application proxy.

After I configured the pre-authentication scenario, I realized that the user has to authenticate twice: first on the Microsoft Entra sign-in form, and then on the RDWeb sign-in form. Is this expected? How can I reduce this to one sign-in?

Yes, it's expected. If the user’s computer is Microsoft Entra joined, the user signs in to Microsoft Entra ID automatically. The user needs to provide their credentials only on the RDWeb sign-in form.

Can I use the Resources Launch Method option "Download the rdp file" under Settings on the Remote Desktop Web Client Portal in Microsoft Entra pre-authentication scenario?

This option enables the user to download the rdp file and use it by another RDP client (outside of the Remote Desktop Web Client). Typically, another RDP clients (like the Microsoft Remote Desktop Client) cannot handle the pre-authentication natively. That's why this will not work.

SharePoint publishing

How can I publish SharePoint over Microsoft Entra application proxy?

Can I use the SharePoint mobile app (iOS/ Android) to access a published SharePoint Server?

The SharePoint mobile app does not support Microsoft Entra pre-authentication currently.

Active Directory Federation Services (AD FS) publishing

Can I use Microsoft Entra application proxy as AD FS proxy (like Web Application Proxy)?

No. Microsoft Entra application proxy is designed to work with Microsoft Entra ID and doesn’t fulfill the requirements to act as an AD FS proxy.

Can I use Microsoft Entra application proxy to publish any AD FS endpoint (like /adfs/portal/updatepassword/)?

No, this is not supported.


Does Microsoft Entra application proxy support the WebSocket protocol?

Applications that use the WebSocket protocol, for example QlikSense and Remote Desktop Web Client (HTML5), are now supported. The following are known limitations:

  • Application proxy discards the cookie that is set on the server response while opening the WebSocket connection.
  • There is no SSO applied to the WebSocket request.
  • Features (Eventlogs, PowerShell and Remote Desktop Services) in the Windows Admin Center (WAC) do not work through Azure AD Application Proxy.

The WebSocket application doesn't have any unique publishing requirements, and can be published the same way as all your other Application Proxy applications.

Yes. Link translation affects performance. The Application Proxy service scans the application for hardcoded links and replaces them with their respective, published external URLs before presenting them to the user.

For best performance, we recommend using identical internal and external URLs by configuring custom domains. If using custom domains isn't possible, you can improve link translation performance by using the My Apps Secure Sign in Extension or Microsoft Edge Browser on mobile. See Redirect hardcoded links for apps published with Microsoft Entra application proxy.


How do I use wildcards to publish two applications with the same custom domain name but with different protocols, one for HTTP and one for HTTPS?

This scenario isn't supported directly. Your options for this scenario are:

  1. Publish both the HTTP and HTTPS URLs as separate applications with a wildcard, but give each of them a different custom domain. This configuration will work since they have different external URLS.

  2. Publish the HTTPS URL through a wildcard application. Publish the HTTP applications separately using these Application Proxy PowerShell cmdlets: