Alex,

On 5/19/25 5:37 PM, My Subs wrote:
> I'm using Ubuntu 20.04 with OpenSSL 1.1.1f.

Okay.

In your earlier message, you had a different configuration. This time you haven't 
specified the class name in the "protocol" attribute. Which one are you 
actually using?



I did change the connector configuration because when updating to Tomcat 10.1.40, I could 
no longer use class Http11AprProtocol on the protocol attribute (I learned then that the 
APR connector had been deprecated).  So, I set it to "HTTP/1.1" to get 
automatic selection of the JSSE OpenSSL implementation.



I also set certificateVerification="required" because I found in the logs an error 
message saying that "optional" does not work with HTTP/2.



Besides, I'm now testing on Tomcat 11.0.6.

Okay.

So the above configuration works for all requests that do not try to send a 
client certificate during the handshake? It's only when you try to send a 
client certificate that things stop working?



Actually, the configuration works seamlessly with client certificate 
verification for as long as no CRL verification is set up.  Client certificates 
are accepted and made visible to servlets.



However, as soon as I set on the <SSLHostConfig>, attribute 
certificateRevocationListFile to the CRL file, or certificateRevocationListPath to 
the directory containing the CRL file (properly c_rehashed), all client certificates 
are rejected.

When you have configured a CRL, are *all* requests rejected, or only those which include a client certificate during the handshake? I see you have configured certificateVerification="required" so maybe there are no modes of operation where client certificates are used.

I'm trying to understand whether this is a problem with the whole setup when CRLs are added, or only a problem when a client certificate is actively being checked against the CRL.

When they stop working, does that mean that no more requests are accepted and 
processed, or is it that handshakes fail with client certs but handshakes 
without client certs work okay?



Since certificateVerification is now set to "required", it means that 
handshakes fail with client certs, and therefore, there is no access at all.

Does the connection actually hang, or do you simply get a failed (but complete) handshake?

If you connect to your server like this, what does the output look like:

$ openssl s_client -showcerts -connect https://host/whatever



I get the following:

     CONNECTED(00000003)

     Can't use SSL_get_servername

     depth=0 CN = localhost

     verify error:num=18:self signed certificate

     verify return:1

     depth=0 CN = localhost

     verify return:1

     ---

     Certificate chain

      0 s:CN = localhost

         i:CN = localhost

         -----BEGIN CERTIFICATE-----

         MIIBfzCCASWgAwIBAgIUBtGtuw6cAZvC560e0RVjnI/+tnwwCgYIKoZIzj0EAwIw

         FDESMBAGA1UEAwwJbG9jYWxob3N0MCAXDTI1MDQxNjIyNTg0OFoYDzIxMjUwMzIz

         MjI1ODQ4WjAUMRIwEAYDVQQDDAlsb2NhbGhvc3QwWTATBgcqhkjOPQIBBggqhkjO

         PQMBBwNCAASWvdHleExdyTqn+wXgNY3XueCLjkkpbrtVhw8lB4DsmkTJDUCdszZX

         9ElKT01bP10cX+mrinNNEtgKFPBwcTCXo1MwUTAdBgNVHQ4EFgQUJIQfq2nU9T2J

         uexYvw1bqosji6cwHwYDVR0jBBgwFoAUJIQfq2nU9T2JuexYvw1bqosji6cwDwYD

         VR0TAQH/BAUwAwEB/zAKBggqhkjOPQQDAgNIADBFAiAUmPONFAU4ThvidgLnlXiu

         7XElAkAGfmlXKkN0DgJWwAIhAPkF8ngCXY4G7Y2obrGUS2u80p06O2ZYFtXyrM3+

         UuRN

         -----END CERTIFICATE-----

         ---

         Server certificate

         subject=CN = localhost

         issuer=CN = localhost

         ---

         No client certificate CA names sent

This looks like a problem. Do you have the trusted certificates configured correctly? I would have expected Tomcat to send a list of acceptable certificates back to the client. That's not strictly required by the TLS spec, but it's handy for debugging like this.

If you do not configure the CRL, are any CA certs listed in this output?

I haven't used TLS with Tomcat much, so I'm not entirely sure what to expect.

Just to be clear, this is my current <Connector>:



     <Connector

         protocol="HTTP/1.1"

         port="8443"

         SSLEnabled="true"

         maxParameterCount="1000"

         >

         <SSLHostConfig

             protocols="TLSv1.3"

             certificateVerification="required"

             caCertificatePath="tls/client/certs-ca"

             certificateRevocationListPath="tls/client/crls"

             >

             <Certificate

                 certificateKeyFile="tls/server/localhost-key.pem"

                 certificateFile="tls/server/localhost-cert.pem"

                 />

         </SSLHostConfig>

         <UpgradeProtocol

             className="org.apache.coyote.http2.Http2Protocol"

             />

     </Connector>


Thanks for posting the whole thing.

-chris

---- On Fri, 09 May 2025 13:46:35 -0500 Christopher Schultz 
<ch...@christopherschultz.net> wrote ---



Alex,
On 5/9/25 2:11 PM, My Subs wrote:
I have tested on Tomcat 10.1.40 with Native
Library 1.3.1 running on JDK 21.0.7+6.  The result is exactly the
same as described before.  The connector below works well with client
authentication, until I add the caCertificatePath attribute.  There
are no error messages in the logs.
Thanks for confirming that. It probably does not matter, but what OS are you using, and what version
of OpenSSL are you using?
      <Connector
     protocol="HTTP/1.1"
     port="8443"
     SSLEnabled="true"
     maxParameterCount="1000"
     >
In your earlier message, you had a different configuration. This time
you haven't specified the class name in the "protocol" attribute. Which
one are you actually using?
          <SSLHostConfig
         protocols="TLSv1.3"
         certificateVerification="required"
         caCertificatePath="tls/client/certs-ca"
         >
              <Certificate
         certificateKeyFile="tls/server/localhost-key.pem"
         certificateFile="tls/server/localhost-cert.pem"
         />
          </SSLHostConfig>
     <UpgradeProtocol
         className="org.apache.coyote.http2.Http2Protocol"
         />
      </Connector>


This time around, Firefox only shows "0 B" on the
"Transferred" column of the "Network" tab in
developer tools.

Any ideas on what could be wrong?
So the above configuration works for all requests that do not try to
send a client certificate during the handshake?
It's only when you try to send a client certificate that things stop
working?
When they stop working, does that mean that no more requests are
accepted and processed, or is it that handshakes fail with client certs
but handshakes without client certs work okay?
If you connect to your server like this, what does the output look like: $ openssl s_client -showcerts -connect https://host/whatever This would usually give you a list of allowable client certificates like
this:
"
Acceptable client certificate CA names
(cert 1)
(cert 2)
...
(cert N)
"
I'm interested in what that returns, if anything. -chris
---- On Wed, 07 May 2025 12:37:16 -0500 Chuck Caldarale 
<mailto:n82...@gmail.com> wrote ---




On 2025 May 7, at 11:43, My Subs <mailto:mailto:my.s...@zoho.com.invalid> wrote:

I'm setting up certificate client authentication on Tomcat 10.0.0
running on Java 16+36.


Before doing anything else, you need to upgrade. That version of Tomcat is over 
4 years old, and no 10.0.x version is currently supported. Move up to the 
10.1.x level (current version is 10.1.40) and see if your issue has already 
been addressed.

   - Chuck


I'm having trouble getting it to work with a
CRL.  My SSL connector is:

     <Connector
      protocol="org.apache.coyote.http11.Http11AprProtocol"
      port="8443"
      SSLEnabled="true"
      maxParameterCount="1000"
      >
         <SSLHostConfig
          protocols="TLSv1.3"
          certificateVerification="optional"
          caCertificatePath="conf/ca-certs"
          certificateRevocationListPath="conf/ca-crls"
          >
             <Certificate
          certificateKeyFile="conf/localhost-ec-key.pem"
          certificateFile="conf/localhost-ec-cert.pem"
          />
         </SSLHostConfig>
      <UpgradeProtocol
          className="org.apache.coyote.http2.Http2Protocol"
          />
     </Connector>

In my PKI setup (using OpenSSL), I have a root CA
(cert: root-ca.pem), and a subordinate CA (cert: sub-ca-01.pem),
which signs leaf certificates, and issues a CRL (crl:
sub-ca-01-crl.pem).

File root-ca.pem is in conf/ca-certs.  File
sub-ca-01-crl.pem is in conf/ca-crls, as follows:

0551d8aa.r0 -> sub-ca-01-crl.pem
c79c8ddb.r0 -> sub-ca-01-crl.pem
sub-ca-01-crl.pem -> /home/me/somedir/sub-ca-01-crl.pem

Before adding to <SSLHostConfig>, attribute
«certificateRevocationListPath="conf/ca-crls"», client
authentication works fine.  The servlet can see a valid client
certificate and extract its attributes from the X509Certificate
object returned by
request.getAttribute("jakarta.servlet.request.X509Certificate").

However, once I add attribute
certificateRevocationListPath, the connector stops responding to
requests that present a client certificate regardless of whether the
certificate is valid or revoked —it still responds though if the
request does not present a client certificate.

Firefox only shows error NS_ERROR_FAILURE on the
"Transferred" column of the "Network" tab in
developer tools.

The CRL is not expired (and it won't be for long),
as its printout shows:

Certificate Revocation List (CRL):
         Version 2 (0x1)
         Signature Algorithm: ecdsa-with-SHA256
         Issuer: CN = Sub CA 01
         Last Update: May  6 21:53:22 2025 GMT
         Next Update: Apr 12 21:53:22 2125 GMT
         CRL extensions:
             X509v3 CRL Number:
                 4097
Revoked Certificates:
     Serial Number: 82AB03509A91A8DCCBA0CE62A67417B6
         Revocation Date: May  6 21:51:40 2025 GMT
         CRL entry extensions:
             X509v3 CRL Reason Code:
                 Unspecified
     Signature Algorithm: ecdsa-with-SHA256
          30:45:02:21:00:f7:98:07:1f:2f:cf:d5:ad:b7:5e:20:61:de:
          1b:7b:1f:c7:74:f9:80:33:d8:a2:cc:3a:75:28:4c:64:65:93:
          c1:02:20:5b:3e:e9:dd:52:9e:11:9b:45:5a:53:fc:2f:bb:b3:
          f4:db:52:64:f6:ea:13:54:43:d6:54:2b:f3:28:03:ae:6f

The problem persists if I drop attribute
certificateRevocationListPath, and replace it with
«certificateRevocationListFile="conf/ca-crls/sub-ca-01-crl.pem"».
It persists as well if I add to  conf/ca-crls a CRL for the root CA.

I found nothing helpful in the logs.  The source
of the problem escapes me.  How can I get certificate client
authentication to work with CRLs in Tomcat?

Help is appreciated.  Thank you.


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