Enable HTTPS with self-signed certificate in Sprin

Question

I'm following this tutorial to enable HTTPS in Spring Boot 2.0 using a self-signed certificate, just for testing purpose. In summary, that tutorial includes these steps:

1.Generate the keystore using keytool.

keytool -genkey -alias tomcat
 -storetype PKCS12 -keyalg RSA -keysize 2048
 -keystore keystore.p12 -validity 3650

2.Enable HTTPS in Spring Boot by adding some properties in the application.properties file.

server.port: 8443
server.ssl.key-store: keystore.p12
server.ssl.key-store-password: mypassword
server.ssl.keyStoreType: PKCS12
server.ssl.keyAlias: tomcat

3.Redirect HTTP to HTTPS (optional). I ignored this part.

But when I start my application, I got these error:

org.apache.catalina.LifecycleException: Failed to start component [Connector[HTTP/1.1-8443]]
    at org.apache.catalina.util.LifecycleBase.start(LifecycleBase.java:167) ~[tomcat-embed-core-8.5.28.jar:8.5.28]
    at org.apache.catalina.core.StandardService.addConnector(StandardService.java:225) ~[tomcat-embed-core-8.5.28.jar:8.5.28]
    at org.springframework.boot.web.embedded.tomcat.TomcatWebServer.addPreviouslyRemovedConnectors(TomcatWebServer.java:255) [spring-boot-2.0.0.RELEASE.jar:2.0.0.RELEASE]
    at org.springframework.boot.web.embedded.tomcat.TomcatWebServer.start(TomcatWebServer.java:197) [spring-boot-2.0.0.RELEASE.jar:2.0.0.RELEASE]
    at org.springframework.boot.web.servlet.context.ServletWebServerApplicationContext.startWebServer(ServletWebServerApplicationContext.java:300) [spring-boot-2.0.0.RELEASE.jar:2.0.0.RELEASE]
    at org.springframework.boot.web.servlet.context.ServletWebServerApplicationContext.finishRefresh(ServletWebServerApplicationContext.java:162) [spring-boot-2.0.0.RELEASE.jar:2.0.0.RELEASE]
    at org.springframework.context.support.AbstractApplicationContext.refresh(AbstractApplicationContext.java:552) [spring-context-5.0.4.RELEASE.jar:5.0.4.RELEASE]
    at org.springframework.boot.web.servlet.context.ServletWebServerApplicationContext.refresh(ServletWebServerApplicationContext.java:140) [spring-boot-2.0.0.RELEASE.jar:2.0.0.RELEASE]
    at org.springframework.boot.SpringApplication.refresh(SpringApplication.java:752) [spring-boot-2.0.0.RELEASE.jar:2.0.0.RELEASE]
    at org.springframework.boot.SpringApplication.refreshContext(SpringApplication.java:388) [spring-boot-2.0.0.RELEASE.jar:2.0.0.RELEASE]
    at org.springframework.boot.SpringApplication.run(SpringApplication.java:327) [spring-boot-2.0.0.RELEASE.jar:2.0.0.RELEASE]
    at org.springframework.boot.SpringApplication.run(SpringApplication.java:1246) [spring-boot-2.0.0.RELEASE.jar:2.0.0.RELEASE]
    at org.springframework.boot.SpringApplication.run(SpringApplication.java:1234) [spring-boot-2.0.0.RELEASE.jar:2.0.0.RELEASE]
    at epic.gwdg.restgraph.RestgraphApplication.main(RestgraphApplication.java:10) [classes/:na]
Caused by: org.apache.catalina.LifecycleException: Protocol handler start failed
    at org.apache.catalina.connector.Connector.startInternal(Connector.java:1021) ~[tomcat-embed-core-8.5.28.jar:8.5.28]
    at org.apache.catalina.util.LifecycleBase.start(LifecycleBase.java:150) ~[tomcat-embed-core-8.5.28.jar:8.5.28]
    ... 13 common frames omitted
Caused by: java.lang.IllegalArgumentException: Private key must be accompanied by certificate chain
    at org.apache.tomcat.util.net.AbstractJsseEndpoint.createSSLContext(AbstractJsseEndpoint.java:116) ~[tomcat-embed-core-8.5.28.jar:8.5.28]
    at org.apache.tomcat.util.net.AbstractJsseEndpoint.initialiseSsl(AbstractJsseEndpoint.java:87) ~[tomcat-embed-core-8.5.28.jar:8.5.28]
    at org.apache.tomcat.util.net.NioEndpoint.bind(NioEndpoint.java:225) ~[tomcat-embed-core-8.5.28.jar:8.5.28]
    at org.apache.tomcat.util.net.AbstractEndpoint.start(AbstractEndpoint.java:1150) ~[tomcat-embed-core-8.5.28.jar:8.5.28]
    at org.apache.coyote.AbstractProtocol.start(AbstractProtocol.java:591) ~[tomcat-embed-core-8.5.28.jar:8.5.28]
    at org.apache.catalina.connector.Connector.startInternal(Connector.java:1018) ~[tomcat-embed-core-8.5.28.jar:8.5.28]
    ... 14 common frames omitted
Caused by: java.lang.IllegalArgumentException: Private key must be accompanied by certificate chain
    at java.base/java.security.KeyStore.setKeyEntry(KeyStore.java:1170) ~[na:na]
    at org.apache.tomcat.util.net.jsse.JSSEUtil.getKeyManagers(JSSEUtil.java:257) ~[tomcat-embed-core-8.5.28.jar:8.5.28]
    at org.apache.tomcat.util.net.AbstractJsseEndpoint.createSSLContext(AbstractJsseEndpoint.java:114) ~[tomcat-embed-core-8.5.28.jar:8.5.28]
    ... 19 common frames omitted

2018-03-16 16:42:30.917  INFO 970 --- [           main] o.apache.catalina.core.StandardService   : Stopping service [Tomcat]
2018-03-16 16:42:30.931  INFO 970 --- [           main] ConditionEvaluationReportLoggingListener : 

Error starting ApplicationContext. To display the conditions report re-run your application with 'debug' enabled.
2018-03-16 16:42:30.933 ERROR 970 --- [           main] o.s.b.d.LoggingFailureAnalysisReporter   : 

***************************
APPLICATION FAILED TO START
***************************

Description:

The Tomcat connector configured to listen on port 8443 failed to start. The port may already be in use or the connector may be misconfigured.

Action:

Verify the connector's configuration, identify and stop any process that's listening on port 8443, or configure this application to listen on another port.

2018-03-16 16:42:30.934  INFO 970 --- [           main] ConfigServletWebServerApplicationContext : Closing org.springframework.boot.web.servlet.context.AnnotationConfigServletWebServerApplicationContext@58ce9668: startup date [Fri Mar 16 16:42:26 CET 2018]; root of context hierarchy
2018-03-16 16:42:30.936  INFO 970 --- [           main] o.s.j.e.a.AnnotationMBeanExporter        : Unregistering JMX-exposed beans on shutdown

Process finished with exit code 1

Basically, the message is:

Private key must be accompanied by certificate chain.

This is a self-signed certificate, so it, of course, doesn't have the trusted chain. How can I fix it?

Here is my current application.properties file:

server.port=8443
server.ssl.enabled=true
server.ssl.key-store=classpath:keystore.p12
server.ssl.key-password=123456
server.ssl.key-store-type=PKCS12
server.ssl.key-alias=tomcat

Thank you so much for your help.

Answer 1

I had the same problem. I made the changes from 2nd answer. But problem wasn't gone. After all I've made, I just included my keystore.p12 certificate to pom.xml in profiles section

    <profiles>
    <!-- DEVELOPMENT PROFILE -->
    <profile>
        <id>dev</id>
        <activation>
            <activeByDefault>true</activeByDefault>
        </activation>
        <build>
            <resources>
                <resource>
                    <directory>src/main/resources</directory>
                    <includes>
                        <include>application.properties</include>
                        <include>keystore.p12</include>
                        <include>data/**</include>
                    </includes>
                </resource>
            </resources>
        </build>
    </profile>
</profiles>

Answer 2

I was getting this horrible Private key must be accompanied by certificate chain error as well on my Spring Boot application with an embedded Tomcat server. It was making me insane.

It turns out a simple typo was my problem:

@Override
public void customize(ConfigurableServletWebServerFactory server) {
    Ssl ssl = new Ssl();
    ssl.setEnabled(true);
    ssl.setKeyStore(keystoreFile);
    ssl.setKeyPassword(keystorePass); // << Should be `setKeyStorePassword` !!!!
    ssl.setKeyStoreType(keystoreType);
    ssl.setKeyAlias(keystoreAlias);

    server.setSsl(ssl);
    server.setPort(sslPort);
}

So the error message is not helpful at all for this case. I hope this helps someone else. Just be sure to verify that you're putting the right passwords (key vs keystore) in the right place. The same issue can happen in a properties based setup - it depends on what you are working with.

Answer 3

The problem is that in your generated keystore you dont have a key pair so there is no private key that's because your using the option -genkey you need to change it by the option -genkeypair :

-genkey generates a Secret Key whereas the -genkeypair generates a key pair (a public key and a private key).

So I think this should work :

keytool -genkeypair -alias tomcat -storetype PKCS12 -keyalg RSA -keysize 2048  -keystore keystore.p12 -validity 3650

In your spring boot configuration change ":" by "=" and add the path to your keystore I suppose that your keystore.p12 is in your resources folder so :

server.ssl.key-store = classpath:keystore.p12
server.ssl.key-store-password = mypassword
server.ssl.key-store-type = PKCS12
server.ssl.key-alias = tomcat

Answer 4

1.use " -genkeypair"

keytool -genkeypair -alias tomcat -storetype PKCS12 -keyalg RSA -keysize 2048  -keystore keystore.p12 -validity 3650

2. change "server.ssl.key-password" to "server.ssl.key-store-password"