https://bz.apache.org/bugzilla/show_bug.cgi?id=61445

            Bug ID: 61445
           Summary: Unable to start SSL using SunMSCAPI
           Product: Tomcat 8
           Version: 8.5.20
          Hardware: PC
            Status: NEW
          Severity: normal
          Priority: P2
         Component: Connectors
          Assignee: dev@tomcat.apache.org
          Reporter: radek.ne...@solitea.cz
  Target Milestone: ----

Created attachment 35250
  --> https://bz.apache.org/bugzilla/attachment.cgi?id=35250&action=edit
Catalina log with SSL problem

I have this Connector in server.xml:

<Connector port="8443" protocol="org.apache.coyote.http11.Http11NioProtocol"
maxThreads="150" SSLEnabled="true" scheme="https" secure="true">
    <SSLHostConfig truststoreProvider="SunMSCAPI" truststoreType="Windows-Root"
protocols="+TLSv1.2,+TLSv1.1,+TLSv1">
        <Certificate certificateKeystoreProvider="SunMSCAPI"
certificateKeystoreFile="" certificateKeystoreType="Windows-MY"
certificateKeyAlias="my-web-cz" type="RSA" />
    </SSLHostConfig>
</Connector>

Tomcat is running as a service under account "ServiceAccount". In Tomcat 8.5.14
the site is functioning normally and certificate from LocalMachine
(Windows-Root) is accessed and used.
Setting certificateKeystoreFile="" is correct for SunMSCAPI, not an error,
without it the "java.lang.IllegalArgumentException: Illegal character in opaque
part at index 2: C:\Users\ServiceAccount/.keystore" occurs.

However after upgrading 8.5.14 to 8.5.20, this error appears in log (see
attachment for full log):

...
17-Aug-2017 16:41:45.976 INFO [main]
org.apache.catalina.core.AprLifecycleListener.lifecycleEvent Loaded APR based
Apache Tomcat Native library [1.2.12] using APR version [1.5.2].
17-Aug-2017 16:41:45.976 INFO [main]
org.apache.catalina.core.AprLifecycleListener.lifecycleEvent APR capabilities:
IPv6 [true], sendfile [true], accept filters [false], random [true].
17-Aug-2017 16:41:45.976 INFO [main]
org.apache.catalina.core.AprLifecycleListener.lifecycleEvent APR/OpenSSL
configuration: useAprConnector [false], useOpenSSL [true]
17-Aug-2017 16:41:46.633 INFO [main]
org.apache.catalina.core.AprLifecycleListener.initializeSSL OpenSSL
successfully initialized [OpenSSL 1.0.2k  26 Jan 2017]
17-Aug-2017 16:41:46.836 INFO [main] org.apache.coyote.AbstractProtocol.init
Initializing ProtocolHandler ["https-openssl-nio-8443"]
17-Aug-2017 16:41:47.398 SEVERE [main] org.apache.coyote.AbstractProtocol.init
Failed to initialize end point associated with ProtocolHandler
["https-openssl-nio-8443"]
 java.lang.IllegalArgumentException: java.security.KeyStoreException: Cannot
get key bytes, not PKCS#8 encoded
        at
org.apache.tomcat.util.net.AbstractJsseEndpoint.createSSLContext(AbstractJsseEndpoint.java:114)
        at
org.apache.tomcat.util.net.AbstractJsseEndpoint.initialiseSsl(AbstractJsseEndpoint.java:85)
        at org.apache.tomcat.util.net.NioEndpoint.bind(NioEndpoint.java:225)
        at
org.apache.tomcat.util.net.AbstractEndpoint.init(AbstractEndpoint.java:982)
        at
org.apache.tomcat.util.net.AbstractJsseEndpoint.init(AbstractJsseEndpoint.java:244)
        at org.apache.coyote.AbstractProtocol.init(AbstractProtocol.java:620)
        at
org.apache.coyote.http11.AbstractHttp11Protocol.init(AbstractHttp11Protocol.java:66)
        at
org.apache.catalina.connector.Connector.initInternal(Connector.java:997)
        at org.apache.catalina.util.LifecycleBase.init(LifecycleBase.java:107)
        at
org.apache.catalina.core.StandardService.initInternal(StandardService.java:549)
...

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