Hi Christopher,


I'm very sorry for not having seen your prompt reply.  Somehow, it ended up in 
the wrong mail folder.  My apologies.  Please find my responses below.



> It probably does not matter, but what OS are you using, and what version of 
> OpenSSL are you using?



I'm using Ubuntu 20.04 with OpenSSL 1.1.1f.



> 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.



> 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 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.



> 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

        Requested Signature Algorithms: 
ECDSA+SHA256:ECDSA+SHA384:ECDSA+SHA512:Ed25519:Ed448:RSA-PSS+SHA256:RSA-PSS+SHA384:RSA-PSS+SHA512:RSA-PSS+SHA256:RSA-PSS+SHA384:RSA-PSS+SHA512:RSA+SHA256:RSA+SHA384:RSA+SHA512:ECDSA+SHA224:RSA+SHA224

        Shared Requested Signature Algorithms: 
ECDSA+SHA256:ECDSA+SHA384:ECDSA+SHA512:Ed25519:Ed448:RSA-PSS+SHA256:RSA-PSS+SHA384:RSA-PSS+SHA512:RSA-PSS+SHA256:RSA-PSS+SHA384:RSA-PSS+SHA512:RSA+SHA256:RSA+SHA384:RSA+SHA512

        Peer signing digest: SHA256

        Peer signature type: ECDSA

        Server Temp Key: X25519, 253 bits

        ---

        SSL handshake has read 826 bytes and written 393 bytes

        Verification error: self signed certificate

        ---

        New, TLSv1.3, Cipher is TLS_AES_256_GCM_SHA384

        Server public key is 256 bit

        Secure Renegotiation IS NOT supported

        Compression: NONE

        Expansion: NONE

        No ALPN negotiated

        Early data was not sent

        Verify return code: 18 (self signed certificate)

        ---

        140001294333248:error:1409445C:SSL routines:ssl3_read_bytes:tlsv13 
alert certificate required:../ssl/record/rec_layer_s3.c:1552:SSL alert number 
116





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 again for your attention.



Alex










---- 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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