Hello @richmond eric-okolai ,
Welcome to the Microsoft Q&A Platform! Thank you for asking your question here.
To troubleshoot the Thumbprint challenge failure, log the thumbprint of the incoming certificate in your APIM policy. This will allow you to compare the thumbprint of the incoming request with the one specified in your policy.
Here's how you can do it first use the trace policy to log the thumbprint of the incoming certificate and below is an example of how you can modify your APIM policy to include logging:
<choose>
<when condition="@(context.Request.Certificate == null)">
<return-response>
<set-status code="403" reason="Missing client certificate" />
</return-response>
</when>
<when condition="@(context.Request.Certificate.Thumbprint != "expected_thumbprint")">
<return-response>
<set-status code="403" reason="Certificate present but Thumbprint Challenge Failed" />
</return-response>
</when>
<otherwise>
<trace>
<message>Incoming certificate thumbprint: @(context.Request.Certificate.Thumbprint)</message>
</trace>
<!-- Your existing policy logic -->
</otherwise>
</choose>
Now trace policy logs the thumbprint of the incoming certificate.
You can then check the logs to see the thumbprint and compare it with the expected thumbprint specified in your policy also, ensure that the thumbprint specified in your APIM policy matches the thumbprint of the certificate you uploaded.
And make sure that the certificate you are using is still valid and has not expired.
if you have any further query do let us know.
Thankyou.