This tutorial shows how to resolve the Advanced Insights certificate expired problem. After upgrading my Configuration Manager lab to version 2409, I was unable to access the Advanced Insights portal. My browser reported Net::ERR_CERT_DATE_INVALID error when accessing the portal, indicating that the certificate created for the Advanced Insights IIS website was expired.

Advanced Insights is a dashboard portal for reporting on a ConfigMgr data set developed by Patch My PC. It is basically an Internet Information Server-based application that runs locally on the server. You can refer to my guide on setting up the Advanced Insights for Configuration Manager.

Admittedly, I had Advanced Insights installed a long time ago, but I never updated this application to the most recent version. I was under the impression it would automatically update to the latest version, but that’s not the case.

Install and Update Third Party Applications with Patch My PC
Install and Update Third Party Applications with Patch My PC

Advanced Insights IIS Website Certificate Expired

Launching the Advanced Insights tool launches a browser from where you sign in and access the dashboard. My browser reported that the dashboard URL was not secure and did not even display the login screen.

Advanced Insights Portal Certificate Expired
Advanced Insights Portal Certificate Expired

Checking the certificate details revealed that the IIS certificate configured for the Advanced Insights website was indeed expired. Note that this certificate was a self-signed certificate created during the setup.

Advanced Insights Portal Certificate Expired
Advanced Insights Certificate Expired

Fix Advanced Insights Certificate Expired

Advanced Insights requires a valid SSL certificate to bind to the application websites. If the certificate is expired for Advanced Insights, you can resolve it by assigning a new valid certificate. Most importantly, if your advanced insights version is not up-to-date, upgrade to the most recent version first. I am covering both the solutions here.

My lab was running an older version of Advanced Insights, version 1.0.27, and the latest version was 2.3.7. So I had to first upgrade the software and then change the certificate. The ability to change the SSL certificate using the modify feature is supported in version 2.1.0 and later.

Step 1: Upgrade the Advanced Insights

To begin, download the latest version of Advanced Insights. Run the executable on the server where an older version of Advanced Insights is already installed. Accept the license terms and click Next.

Upgrade the Advanced Insights
Upgrade the Advanced Insights

Here, the installer will display any warnings related to the certificate currently used with the Advanced Insights IIS website. You can change the website port from the default 444 to a custom one. In the below screenshot, we see the Advanced Insights IIS website certificate is expired, and we will change it after we upgrade. Click Next.

Upgrade the Advanced Insights
Upgrade the Advanced Insights

That’s it. The Advanced Insights software has been upgraded to the latest version. Click Finish.

Upgrade the Advanced Insights
Upgrade the Advanced Insights

Step 2: Assign Certificate to Advanced Insights IIS Website

In this step, I will show you how to change the SSL certificate used for an existing Advanced Insights deployment. We’ll replace the expired certificate with a valid certificate by modifying the insights configuration. For my lab, I created a new server host standard certificate exclusively for Advanced Insights.

Go to Control Panel > Programs and Features and locate the Advanced Insights program and select Change.

Modify Advanced Insights Configuration
Modify Advanced Insights Configuration

Click Modify to alter the advanced configurations.

Modify Advanced Insights Configuration
Modify Advanced Insights Configuration

On the configuration modification page, select the checkbox for ‘SSL Certificate‘ and then click the ‘Change Certificate‘ button.

Fix Advanced Insights Certificate Expired Issue
Change SSL Certificate of IIS Website

Use the dropdown list to select the SSL certificate that represents the CNAME/Alias you wish to use. Click Next.

Fix Advanced Insights Certificate Expired Issue
Change SSL Certificate of IIS Website

Once you have assigned the new certificate, click Install.

Fix Advanced Insights Certificate Expired Issue
Fix Advanced Insights Certificate Expired Issue

We have successfully assigned a new certificate for the Advanced Insights IIS website. Click Finish.

Fix Advanced Insights Certificate Expired Issue
Fix Advanced Insights Certificate Expired Issue

I recommend restarting the server after making the above changes. Log in to the server and launch the Patch My PC Advanced Insights. The browser opens the Advanced Insights URL with a login screen. I hope this guide helps!!

Fix Advanced Insights Portal Certificate Expired Issue
Fix Advanced Insights Portal Certificate Expired Issue

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Prajwal Desai

Prajwal Desai is a technology expert and 10 time Dual Microsoft MVP (Most Valuable Professional) with a strong focus on Microsoft Intune, SCCM, Windows 365, Enterprise Mobility, and Windows. He is a renowned author, speaker, & community leader, known for sharing his expertise & knowledge through his blog, YouTube, conferences, webinars etc.