{"id":122306,"date":"2023-01-31T06:23:33","date_gmt":"2023-01-31T06:23:33","guid":{"rendered":"https:\/\/www.stellarinfo.com\/blog\/?p=122306"},"modified":"2025-05-21T02:38:22","modified_gmt":"2025-05-21T02:38:22","slug":"how-to-fix-the-exchange-server-2019-upgrade-error-5506","status":"publish","type":"post","link":"https:\/\/www.stellarinfo.com\/blog\/how-to-fix-the-exchange-server-2019-upgrade-error-5506\/","title":{"rendered":"How to Fix the Exchange Server 2019 Upgrade Error 5506?"},"content":{"rendered":"

A user has reported encountering an error when upgrading the Exchange Server 2019 to the Cumulative Update (CU). During the installation, the setup failed, showing the below error message:<\/p>

The following error was generated when \"$error.Clear();
 Install-ExchangeCertificate -services IIS -DomainController $RoleDomainController
 if ($RoleIsDatacenter -ne $true -And $RoleIsPartnerHosted -ne $true)
 { Install-AuthCertificate -DomainController $RoleDomainController } \" was run: \"Microsoft.Exchange.Management.Clients.FormsAuthenticationMarkPathUnknownSetError: An unexpected error occurred while modifying the forms authentication settings for path \/LM\/W3SVC\/1. The error returned was 5506. at Microsoft.Exchange.Configuration.Tasks.Task.ThrowError(Exception exception, ErrorCategory errorCategory, Object target, String helpUrl) at Microsoft.Exchange.Configuration.Tasks.Task.WriteError(Exception exception, ErrorCategory category, Object target) at Microsoft.Exchange.Management.SystemConfigurationTasks.InstallExchangeCertificate.EnableForServices(X509Certificate2 cert, AllowedServices services) at Microsoft.Exchange.Management.SystemConfigurationTasks.InstallExchangeCertificate.InternalProcessRecord() at Microsoft.Exchange.Configuration.Tasks.Task.<ProcessRecord>b__91_1() at Microsoft.Exchange.Configuration.Tasks.Task.InvokeRetryableFunc(String funcName, Action func, Boolean terminatePipelineIfFailed)\".<\/code><\/p>

\"Exchange<\/figure>

Due to this error, the installation gets failed, leaving the Exchange Server unusable with services unable to start and a bunch of issues in the Event Viewer.<\/p>

Below, we’ll be discussing the possible solutions to fix this error and to bring back the services in minimum time.<\/p>

Solutions to Fix Exchange Server 2019 Error 5506<\/h2>

Though you can re-run the update, it will surely fail and you may end up getting your Exchange in an even worst situation. If your only Exchange Server becomes accessible, then you need to restore the services as soon as possible with minimum impact.<\/p>

From the error message, it looks that the issue is related to the certificates. There is a possibility that the CU installation failed due to an expired certificate. Therefore, the first thing to do is check the certificates and ensure that they are not expired. For best practice, it’s suggested to never allow the certificates and renew them beforehand.<\/p>

Next, you can check the IIS and the default Web Site HTTPS bindings. You can try to replace the one from the certificate authority with the self-signed certificate provided by default during the installation. Here is how to do so:<\/p>