SMIME signature verify+decrypt is not working

Client side //encrypt SomeJSON (simple POJO) EnvelopedOutput output = new EnvelopedOutput( new SomeJSON( "test" ), MediaType.APPLICATION_JSON_TYPE); output.setCertificate(<certificate>); //sign encrypted SomeJSON SignedOutput signed = new SignedOutput(output, "application/pkcs7-mime" ); signed.setCertificate(<certificate>); signed.setPrivateKey(<privateKey>); Response res = target.request().post(Entity.entity(signed, "multipart/signed" )); Server side @POST @Path( "/{somepath}" ) public SignedOutput status(@PathParam( "somepath" ) final String somepath,SignedInput<EnvelopedInput<SomeJSON>> input) throws Exception { //get encrypted content - it is OK final EnvelopedInput<SomeJSON> envelop = input.getEntity(); //verify signature - it is OK if (!input.verify(<certificate>)) throw new WebApplicationException(500); //encrypt content - FAILED final SomeJSON someJSON = envelop.getEntity(<privateKey>,<certificate>); ...... } The 'envelop.getEntity(<privateKey>,<certificate>)' method fails with: stacktrace 17:25:31,888 ERROR [org.apache.catalina.core.ContainerBase.[jboss.web].[ default -host].[/edc- rest -service-0.0.1].[com.testapp.edc. rest .service.EDCApplication]] (http-localhost-127.0.0.1-8080-1) Servlet.service() for servlet com.testapp.edc. rest .service.EDCApplication threw exception: org.jboss.resteasy.spi.UnhandledException: java.lang.RuntimeException: org.bouncycastle.cms.CMSException: Malformed content. at org.jboss.resteasy.core.ExceptionHandler.handleApplicationException(ExceptionHandler.java:76) [resteasy-jaxrs-3.0.4.Final.jar:] at org.jboss.resteasy.core.ExceptionHandler.handleException(ExceptionHandler.java:212) [resteasy-jaxrs-3.0.4.Final.jar:] at org.jboss.resteasy.core.SynchronousDispatcher.writeException(SynchronousDispatcher.java:149) [resteasy-jaxrs-3.0.4.Final.jar:] at org.jboss.resteasy.core.SynchronousDispatcher.invoke(SynchronousDispatcher.java:372) [resteasy-jaxrs-3.0.4.Final.jar:] at org.jboss.resteasy.core.SynchronousDispatcher.invoke(SynchronousDispatcher.java:179) [resteasy-jaxrs-3.0.4.Final.jar:] at org.jboss.resteasy.plugins.server.servlet.ServletContainerDispatcher.service(ServletContainerDispatcher.java:220) [resteasy-jaxrs-3.0.4.Final.jar:] at org.jboss.resteasy.plugins.server.servlet.HttpServletDispatcher.service(HttpServletDispatcher.java:56) [resteasy-jaxrs-3.0.4.Final.jar:] at org.jboss.resteasy.plugins.server.servlet.HttpServletDispatcher.service(HttpServletDispatcher.java:51) [resteasy-jaxrs-3.0.4.Final.jar:] at javax.servlet.http.HttpServlet.service(HttpServlet.java:847) [jboss-servlet-api_3.0_spec-1.0.0.Final.jar:1.0.0.Final] at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:329) [jbossweb-7.0.13.Final.jar:] at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:248) [jbossweb-7.0.13.Final.jar:] at org.jboss.weld.servlet.ConversationPropagationFilter.doFilter(ConversationPropagationFilter.java:62) [weld-core-1.1.5.AS71.Final.jar:2012-02-10 15:31] at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:280) [jbossweb-7.0.13.Final.jar:] at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:248) [jbossweb-7.0.13.Final.jar:] at org.apache.catalina.core.StandardWrapperValve.invoke(StandardWrapperValve.java:275) [jbossweb-7.0.13.Final.jar:] at org.apache.catalina.core.StandardContextValve.invoke(StandardContextValve.java:161) [jbossweb-7.0.13.Final.jar:] at org.jboss.as.web.security.SecurityContextAssociationValve.invoke(SecurityContextAssociationValve.java:153) [jboss-as-web-7.1.1.Final.jar:7.1.1.Final] at org.apache.catalina.core.StandardHostValve.invoke(StandardHostValve.java:155) [jbossweb-7.0.13.Final.jar:] at org.apache.catalina.valves.ErrorReportValve.invoke(ErrorReportValve.java:102) [jbossweb-7.0.13.Final.jar:] at org.apache.catalina.core.StandardEngineValve.invoke(StandardEngineValve.java:109) [jbossweb-7.0.13.Final.jar:] at org.apache.catalina.connector.CoyoteAdapter.service(CoyoteAdapter.java:368) [jbossweb-7.0.13.Final.jar:] at org.apache.coyote.http11.Http11Processor.process(Http11Processor.java:877) [jbossweb-7.0.13.Final.jar:] at org.apache.coyote.http11.Http11Protocol$Http11ConnectionHandler.process(Http11Protocol.java:671) [jbossweb-7.0.13.Final.jar:] at org.apache.tomcat.util.net.JIoEndpoint$Worker.run(JIoEndpoint.java:930) [jbossweb-7.0.13.Final.jar:] at java.lang. Thread .run(Unknown Source) [rt.jar:1.6.0_27] Caused by: java.lang.RuntimeException: org.bouncycastle.cms.CMSException: Malformed content. at org.jboss.resteasy.security.smime.EnvelopedInputImpl.getEntity(EnvelopedInputImpl.java:166) [resteasy-crypto-3.0.4.Final.jar:] at org.jboss.resteasy.security.smime.EnvelopedInputImpl.getEntity(EnvelopedInputImpl.java:123) [resteasy-crypto-3.0.4.Final.jar:] at com.testapp.edc. rest .service.EDCRestService.status(EDCRestService.java:87) [classes:] at com.testapp.edc. rest .service.EDCRestService$Proxy$_$$_WeldClientProxy.status(EDCRestService$Proxy$_$$_WeldClientProxy.java) [classes:] at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method) [rt.jar:1.6.0_27] at sun.reflect.NativeMethodAccessorImpl.invoke(Unknown Source) [rt.jar:1.6.0_27] at sun.reflect.DelegatingMethodAccessorImpl.invoke(Unknown Source) [rt.jar:1.6.0_27] at java.lang.reflect.Method.invoke(Unknown Source) [rt.jar:1.6.0_27] at org.jboss.resteasy.core.MethodInjectorImpl.invoke(MethodInjectorImpl.java:137) [resteasy-jaxrs-3.0.4.Final.jar:] at org.jboss.resteasy.core.ResourceMethodInvoker.invokeOnTarget(ResourceMethodInvoker.java:280) [resteasy-jaxrs-3.0.4.Final.jar:] at org.jboss.resteasy.core.ResourceMethodInvoker.invoke(ResourceMethodInvoker.java:234) [resteasy-jaxrs-3.0.4.Final.jar:] at org.jboss.resteasy.core.ResourceMethodInvoker.invoke(ResourceMethodInvoker.java:221) [resteasy-jaxrs-3.0.4.Final.jar:] at org.jboss.resteasy.core.SynchronousDispatcher.invoke(SynchronousDispatcher.java:356) [resteasy-jaxrs-3.0.4.Final.jar:] ... 21 more Caused by: org.bouncycastle.cms.CMSException: Malformed content. at org.bouncycastle.cms.CMSUtils.readContentInfo(Unknown Source) [bcmail-jdk16-1.46.jar:1.46.0] at org.bouncycastle.cms.CMSUtils.readContentInfo(Unknown Source) [bcmail-jdk16-1.46.jar:1.46.0] at org.bouncycastle.cms.CMSEnvelopedData.<init>(Unknown Source) [bcmail-jdk16-1.46.jar:1.46.0] at org.bouncycastle.mail.smime.SMIMEEnveloped.<init>(Unknown Source) [bcmail-jdk16-1.46.jar:1.46.0] at org.jboss.resteasy.security.smime.EnvelopedInputImpl.getEntity(EnvelopedInputImpl.java:156) [resteasy-crypto-3.0.4.Final.jar:] ... 33 more Caused by: java.lang.IllegalArgumentException: unknown object in factory: org.bouncycastle.asn1.DERApplicationSpecific at org.bouncycastle.asn1.cms.ContentInfo.getInstance(Unknown Source) [bcprov-jdk16-1.46.jar:1.46.0] ... 38 more