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https://issues.apache.org/jira/browse/JAMES-3488?page=com.atlassian.jira.plugin.system.issuetabpanels:comment-tabpanel&focusedCommentId=17262774#comment-17262774
 ] 

Raphael Ouazana commented on JAMES-3488:
----------------------------------------

Thank you for your report I opened a PR to upgrade Bouncy Castle on master: 
https://github.com/linagora/james-project/pull/4207

> SSL/TLS with IMAP & SMTP
> ------------------------
>
>                 Key: JAMES-3488
>                 URL: https://issues.apache.org/jira/browse/JAMES-3488
>             Project: James Server
>          Issue Type: Bug
>          Components: IMAPServer, SMTPServer
>    Affects Versions: 3.5.0
>         Environment: Ubuntu 20.04.1 
>            Reporter: Nikša Antišić
>            Priority: Blocker
>             Fix For: 3.5.0
>
>
> I can't make JAMES work with SSL/TLS configured. When I use JAMES without 
> SSL/TLS everything works as expected, but when I switch to SSL/TLS nothing 
> works. I am using self signed certificate which I created.
> Output from the keytool:
> Keystore type: JKS
>  Keystore provider: SUN
> Your keystore contains 1 entry
> Alias name: james
>  Creation date: Jan 6, 2021
>  Entry type: PrivateKeyEntry
>  Certificate chain length: 1
>  Certificate[1]:
>  Owner: CN=VMUbuntu, OU=me, O=org, C=HR
>  Issuer: CN=VMUbuntu, OU=me, O=org, C=HR
>  Serial number: 630c2cd7
>  Valid from: Wed Jan 06 15:12:47 CET 2021 until: Tue Apr 06 16:12:47 CEST 2021
>  Certificate fingerprints:
>  SHA1: ED:22:F8:A7:C4:5C:EA:C9:10:04:7C:FD:3E:CE:7E:7E:5C:CD:94:9F
>  SHA256: 
> F4:9F:F5:11:1A:7B:8D:A2:A7:42:FF:5F:41:64:2B:D2:58:85:3E:11:F4:C1:82:9B:91:9A:E5:92:CA:F4:B9:1E
>  Signature algorithm name: SHA384withRSA
>  Subject Public Key Algorithm: 4096-bit RSA key
>  Version: 3
> Extensions:
> #1: ObjectId: 2.5.29.17 Criticality=false
>  SubjectAlternativeName [
>  IPAddress: 127.0.0.1
>  ]
> #2: ObjectId: 2.5.29.14 Criticality=false
>  SubjectKeyIdentifier [
>  KeyIdentifier [
>  0000: ED 16 4A 36 E6 DA 28 3A F1 DB A9 A0 5A 24 21 A2 ..J6..(:....Z$!.
>  0010: 01 5E 78 00 .^x.
>  ]
>  ]
> ************************************************************************************
> When I try to connect to smtp server from the openssl, openssl just "hangs":
> OpenSSL> s_client -connect VMUbuntu:465 -starttls smtp
>  CONNECTED(00000003)
>  Can't use SSL_get_servername
>  depth=0 C = HR, O = org, OU = me, CN = VMUbuntu
>  verify error:num=18:self signed certificate
>  verify return:1
>  depth=0 C = HR, O = org, OU = me, CN = VMUbuntu
>  verify return:1
> Thunderbird also can't connect (sending/receiving), and the wrapper.log is 
> full of errors
> ************************************************************************************
> and this is the error from the wrapper.log:
> INFO | jvm 1 | 2021/01/06 15:18:22 | 06-Jan-2021 15:18:22.864 INFO 
> [smtpserver-executor-16] 
> org.apache.james.protocols.netty.BasicChannelUpstreamHandler.channelConnected:93
>  - Connection established from 127.0.0.1
>  INFO | jvm 1 | 2021/01/06 15:18:22 | 06-Jan-2021 15:18:22.878 ERROR 
> [smtpserver-executor-22] 
> org.apache.james.protocols.netty.BasicChannelUpstreamHandler.exceptionCaught:228
>  - Unable to process request
>  INFO | jvm 1 | 2021/01/06 15:18:22 | *java.lang.NullPointerException:* null
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> org.bouncycastle.crypto.signers.PSSSigner.generateSignature(Unknown Source) 
> ~[bcprov-jdk15on-1.62.jar:1.62.0]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> org.bouncycastle.jcajce.provider.asymmetric.rsa.PSSSignatureSpi.engineSign(Unknown
>  Source) ~[bcprov-jdk15on-1.62.jar:1.62.0]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> java.security.Signature$Delegate.engineSign(Signature.java:1404) ~[?:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> java.security.Signature.sign(Signature.java:713) ~[?:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> sun.security.ssl.CertificateVerify$T13CertificateVerifyMessage.<init>(CertificateVerify.java:932)
>  ~[?:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> sun.security.ssl.CertificateVerify$T13CertificateVerifyProducer.onProduceCertificateVerify(CertificateVerify.java:1106)
>  ~[?:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> sun.security.ssl.CertificateVerify$T13CertificateVerifyProducer.produce(CertificateVerify.java:1099)
>  ~[?:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> sun.security.ssl.SSLHandshake.produce(SSLHandshake.java:436) ~[?:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> sun.security.ssl.ClientHello$T13ClientHelloConsumer.goServerHello(ClientHello.java:1234)
>  ~[?:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> sun.security.ssl.ClientHello$T13ClientHelloConsumer.consume(ClientHello.java:1170)
>  ~[?:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> sun.security.ssl.ClientHello$ClientHelloConsumer.onClientHello(ClientHello.java:852)
>  ~[?:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> sun.security.ssl.ClientHello$ClientHelloConsumer.consume(ClientHello.java:813)
>  ~[?:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> sun.security.ssl.SSLHandshake.consume(SSLHandshake.java:392) ~[?:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> sun.security.ssl.HandshakeContext.dispatch(HandshakeContext.java:444) ~[?:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> sun.security.ssl.SSLEngineImpl$DelegatedTask$DelegatedAction.run(SSLEngineImpl.java:1074)
>  ~[?:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> sun.security.ssl.SSLEngineImpl$DelegatedTask$DelegatedAction.run(SSLEngineImpl.java:1061)
>  ~[?:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> java.security.AccessController.doPrivileged(Native Method) ~[?:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> sun.security.ssl.SSLEngineImpl$DelegatedTask.run(SSLEngineImpl.java:1008) 
> ~[?:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> org.jboss.netty.handler.ssl.SslHandler.runDelegatedTasks(SslHandler.java:1393)
>  ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> org.jboss.netty.handler.ssl.SslHandler.unwrap(SslHandler.java:1256) 
> ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> org.jboss.netty.handler.ssl.SslHandler.decode(SslHandler.java:852) 
> ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> org.jboss.netty.handler.codec.frame.FrameDecoder.callDecode(FrameDecoder.java:425)
>  ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> org.jboss.netty.handler.codec.frame.FrameDecoder.messageReceived(FrameDecoder.java:303)
>  ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> org.jboss.netty.channel.SimpleChannelUpstreamHandler.handleUpstream(SimpleChannelUpstreamHandler.java:70)
>  ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> org.jboss.netty.channel.DefaultChannelPipeline.sendUpstream(DefaultChannelPipeline.java:564)
>  ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> org.jboss.netty.channel.DefaultChannelPipeline.sendUpstream(DefaultChannelPipeline.java:559)
>  ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> org.jboss.netty.channel.Channels.fireMessageReceived(Channels.java:268) 
> ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> org.jboss.netty.channel.Channels.fireMessageReceived(Channels.java:255) 
> ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> org.jboss.netty.channel.socket.nio.NioWorker.read(NioWorker.java:88) 
> ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> org.jboss.netty.channel.socket.nio.AbstractNioWorker.process(AbstractNioWorker.java:108)
>  ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> org.jboss.netty.channel.socket.nio.AbstractNioSelector.run(AbstractNioSelector.java:337)
>  ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> org.jboss.netty.channel.socket.nio.AbstractNioWorker.run(AbstractNioWorker.java:89)
>  ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> org.jboss.netty.channel.socket.nio.NioWorker.run(NioWorker.java:178) 
> ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> org.jboss.netty.util.ThreadRenamingRunnable.run(ThreadRenamingRunnable.java:108)
>  ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> org.jboss.netty.util.internal.DeadLockProofWorker$1.run(DeadLockProofWorker.java:42)
>  ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> java.util.concurrent.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1128)
>  [?:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> java.util.concurrent.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:628)
>  [?:?]
>  INFO | jvm 1 | 2021/01/06 15:18:22 | at 
> java.lang.Thread.run(Thread.java:834) [?:?]
> ************************************************************************************
> INFO | jvm 1 | 2021/01/06 16:02:54 | 06-Jan-2021 16:02:54.405 ERROR 
> [smtpserver-executor-13] 
> org.apache.james.protocols.netty.BasicChannelUpstreamHandler.exceptionCaught:228
>  - Unable to process request
>  INFO | jvm 1 | 2021/01/06 16:02:54 | javax.net.ssl.SSLHandshakeException: 
> *Received fatal alert: bad_certificate*
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> sun.security.ssl.Alert.createSSLException(Alert.java:131) ~[?:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> sun.security.ssl.Alert.createSSLException(Alert.java:117) ~[?:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> sun.security.ssl.TransportContext.fatal(TransportContext.java:337) ~[?:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> sun.security.ssl.Alert$AlertConsumer.consume(Alert.java:293) ~[?:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> sun.security.ssl.TransportContext.dispatch(TransportContext.java:186) ~[?:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> sun.security.ssl.SSLTransport.decode(SSLTransport.java:171) ~[?:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> sun.security.ssl.SSLEngineImpl.decode(SSLEngineImpl.java:681) ~[?:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> sun.security.ssl.SSLEngineImpl.readRecord(SSLEngineImpl.java:636) ~[?:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> sun.security.ssl.SSLEngineImpl.unwrap(SSLEngineImpl.java:454) ~[?:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> sun.security.ssl.SSLEngineImpl.unwrap(SSLEngineImpl.java:433) ~[?:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> javax.net.ssl.SSLEngine.unwrap(SSLEngine.java:637) ~[?:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> org.jboss.netty.handler.ssl.SslHandler.unwrap(SslHandler.java:1219) 
> ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> org.jboss.netty.handler.ssl.SslHandler.decode(SslHandler.java:852) 
> ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> org.jboss.netty.handler.codec.frame.FrameDecoder.callDecode(FrameDecoder.java:425)
>  ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> org.jboss.netty.handler.codec.frame.FrameDecoder.messageReceived(FrameDecoder.java:303)
>  ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> org.jboss.netty.channel.SimpleChannelUpstreamHandler.handleUpstream(SimpleChannelUpstreamHandler.java:70)
>  ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> org.jboss.netty.channel.DefaultChannelPipeline.sendUpstream(DefaultChannelPipeline.java:564)
>  ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> org.jboss.netty.channel.DefaultChannelPipeline.sendUpstream(DefaultChannelPipeline.java:559)
>  ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> org.jboss.netty.channel.Channels.fireMessageReceived(Channels.java:268) 
> ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> org.jboss.netty.channel.Channels.fireMessageReceived(Channels.java:255) 
> ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> org.jboss.netty.channel.socket.nio.NioWorker.read(NioWorker.java:88) 
> ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> org.jboss.netty.channel.socket.nio.AbstractNioWorker.process(AbstractNioWorker.java:108)
>  ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> org.jboss.netty.channel.socket.nio.AbstractNioSelector.run(AbstractNioSelector.java:337)
>  ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> org.jboss.netty.channel.socket.nio.AbstractNioWorker.run(AbstractNioWorker.java:89)
>  ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> org.jboss.netty.channel.socket.nio.NioWorker.run(NioWorker.java:178) 
> ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> org.jboss.netty.util.ThreadRenamingRunnable.run(ThreadRenamingRunnable.java:108)
>  ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> org.jboss.netty.util.internal.DeadLockProofWorker$1.run(DeadLockProofWorker.java:42)
>  ~[netty-3.10.6.Final.jar:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> java.util.concurrent.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1128)
>  [?:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> java.util.concurrent.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:628)
>  [?:?]
>  INFO | jvm 1 | 2021/01/06 16:02:54 | at 
> java.lang.Thread.run(Thread.java:834) [?:?]
> ************************************************************************************************************
>  



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