SSL certificate compatibility issues when accessing the ArcGIS Web Adaptor configuration page

Description

When attempting to configure ArcGIS Web Adaptor, the configuration page fails to load over Hypertext Transfer Protocol Secure (HTTPS). The web browser displays the following error:

Error:
ERR_SSL_KEY_USAGE_INCOMPATIBLE

This prevents access to the ArcGIS Web Adaptor configuration page and blocks completion of the configuration process. The issue has been observed in web browsers such as Google Chrome.

Cause

The self-signed Secure Sockets Layer (SSL) certificate configured in Internet Information Services (IIS) for the HTTPS (443) binding used by Web Adaptor is incompatible with the browser's SSL validation. As a result, the Web Adaptor configuration page fails to load and returns the error. In some cases, the required certificate key usages, such as DigitalSignature, are missing. Refer to ArcGIS Enterprise: Self-signed certificates for more information.

Solution or Workaround

Create a new SSL certificate with the required key usage attribute and bind it to the website hosting Web Adaptor

Note:
In this workflow, PowerShell is used to create an explicit SSL certificate with the required key usage attribute (DigitalSignature), which is enforced by web browsers such as Google Chrome for HTTPS connections.

1. Create a new self-signed SSL certificate using Windows PowerShell. 

New-SelfSignedCertificate -FriendlyName <Certificate_Name> -DnsName <Server_Name> -KeyUsage DigitalSignature -NotAfter (Get-Date).AddYears(20)

2. On the hosting machine, open Internet Information Services (IIS) Manager.
3. In the Connections pane, expand the machine name and expand Sites. Click Default Web Site.
4. In the Actions pane, click Bindings.
5. In the Site Bindings dialog box, select the https binding on port 443 and click Edit.
6. Select the certificate created in Step 1 and click OK.