Chris Thank you for your excellent reply and references.
I've been doing a lot of reading on SSL, certificates, keys, algorithms, etc. Woo! However I still don't have it correct. I've retrieved certificates from letsencrypt and following your suggestions did the following. Created a pkcs12 store using the following command line. openssl pkcs12 -export -in "domain-chain.crt" -inkey "domain.key" -certfile "ICDTrustRoot.crt" -out "MM.p12" -name tomcat -passout "pass:changeit" where the domain-chain.crt contains two certificates and ICDTrustRoot contains one as shown below - PS C:\users\don\security\letsenc5> openssl x509 -noout -subject -issuer -in domaincert1.crt (the first cert in domain-chain.crt) subject= /CN=info.finwoks.com issuer= /C=US/O=Let's Encrypt/CN=Let's Encrypt Authority X3 PS C:\users\don\security\letsenc5> openssl x509 -noout -subject -issuer -in domaincert2.crt (the second cert in domain-chain.crt) subject= /C=US/O=Let's Encrypt/CN=Let's Encrypt Authority X3 issuer= /O=Digital Signature Trust Co./CN=DST Root CA X3 PS C:\users\don\security\letsenc4> openssl x509 -noout -subject -issuer -in ICDTrustRoot.crt subject= /O=Digital Signature Trust Co./CN=DST Root CA X3 issuer= /O=Digital Signature Trust Co./CN=DST Root CA X3 so I have the three certificates and the private key which is shared with letsencrypt called domain.key My server.xml contains: <Connector protocol="org.apache.coyote.http11.Http11NioProtocol" sslImplementationName="org.apache.tomcat.util.net. openssl.OpenSSLImplementation" port="8443" maxThreads="200" scheme="https" secure="true" SSLEnabled="true" keystoreType="PKCS12" keystoreFile="/users/don/Security/MM.p12" keystorePass="changeit" clientAuth="false" sslProtocol="TLS" /> However when I restart Tomcat is get the following error in the Tomcat error log and of course it fails in the handshake with the browser org.apache.catalina.core.StandardService.initInternal Failed to initialize connector [Connector[HTTP/1.1-8443]] org.apache.catalina.LifecycleException: Failed to initialize component [Connector[HTTP/1.1-8443]] at org.apache.catalina.util.LifecycleBase.init(LifecycleBase.java:112) at org.apache.catalina.core.StandardService.initInternal( StandardService.java:549) at org.apache.catalina.util.LifecycleBase.init(LifecycleBase.java:107) at org.apache.catalina.core.StandardServer.initInternal( StandardServer.java:873) at org.apache.catalina.util.LifecycleBase.init(LifecycleBase.java:107) at org.apache.catalina.startup.Catalina.load(Catalina.java:606) at org.apache.catalina.startup.Catalina.load(Catalina.java:629) at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method) at sun.reflect.NativeMethodAccessorImpl.invoke(Unknown Source) at sun.reflect.DelegatingMethodAccessorImpl.invoke(Unknown Source) at java.lang.reflect.Method.invoke(Unknown Source) at org.apache.catalina.startup.Bootstrap.load(Bootstrap.java:311) at org.apache.catalina.startup.Bootstrap.main(Bootstrap.java:494) Caused by: java.lang.UnsatisfiedLinkError: org.apache.tomcat.jni.Pool. create(J)J at org.apache.tomcat.jni.Pool.create(Native Method) at org.apache.tomcat.util.net.openssl.OpenSSLEngine.<clinit> (OpenSSLEngine.java:75) at org.apache.tomcat.util.net.openssl.OpenSSLUtil.getImplementedProtocols( OpenSSLUtil.java:61) at org.apache.tomcat.util.net.SSLUtilBase.<init>(SSLUtilBase.java:46) at org.apache.tomcat.util.net.openssl.OpenSSLUtil.<init>( OpenSSLUtil.java:41) at org.apache.tomcat.util.net.openssl.OpenSSLImplementation.getSSLUtil( OpenSSLImplementation.java:36) at org.apache.tomcat.util.net.AbstractJsseEndpoint.initialiseSsl( AbstractJsseEndpoint.java:82) at org.apache.tomcat.util.net.NioEndpoint.bind(NioEndpoint.java:261) at org.apache.tomcat.util.net.AbstractEndpoint.init( AbstractEndpoint.java:798) at org.apache.coyote.AbstractProtocol.init(AbstractProtocol.java:547) at org.apache.coyote.http11.AbstractHttp11Protocol.init( AbstractHttp11Protocol.java:66) at org.apache.catalina.connector.Connector.initInternal(Connector.java:1010) at org.apache.catalina.util.LifecycleBase.init(LifecycleBase.java:107) ... 12 more I'm running Tomcat 9 in Amazon Web services using Windows Server. I don't know what I'm doing wrong. Further help will be appreciated. It appears I have the pkcs12 wrong. Don On Tue, Nov 14, 2017 at 4:33 PM, Christopher Schultz < ch...@christopherschultz.net> wrote: > -----BEGIN PGP SIGNED MESSAGE----- > Hash: SHA256 > > Don, > > On 11/14/17 1:57 AM, Don Flinn wrote: > > I've done some reading on SSL and understand the protocol is as > > follows; Client/Browser sends ClientHello and server Tomcat replies > > with ServerHello. This establishes the protocol they will use. The > > server then sends the certificate and the public key - in the > > clear The browser encrypts a message containing the servers domain, > > all encrypted with the server's public key to the CA which the > > browser trusts. The public key is in the certificate. The CA > > de-crypts the message with the server's private key. So the > > server's name/ domain must be not encrypted. If the server can > > decrypt the message it knows the server and it then sends a ack > > message back to the browser encrypted with the client's private > > key. > > Most of that is correct (enough) except for the last part: the server > never has the client's private key. The handshake is done using > public-key/asymmetric encryption and part of that handshake includes > establishing the keys to be used for the bulk encryption -- the > encryption used after the handshake. > > > The browser and Tomcat then establish a secret key to send messages > > back and forth. > > That's the bulk encryption key. Note that it can be re-negotiated at > intervals during the conversation if necessary. > > > If I have the above correct, I must have keystore set up > > incorrectly, since running my scenario I get an error in the Chrome > > debugger,which says > > > > This page is not secure "Valid certificate The connection to this > > site is using a valid, trusted server certificate issued by unknown > > name. Secure resources All resources on this page are served > > securely. " > > > > Note the 'the certificate is valid and it is issued by unknown > > name" Why is the issuer unknown, since the issuer's name is in the > > certificate? > > That message may be misleading. If the certificate is self-signed than > of course the certificate signer is "known" to the client (Chrome) > because it's just identified itself (as itself!). What it means to be > "unknown" is that it is /untrusted/. You haven't told Chrome that you > specifically trust the certificate that signed the server's > certificate. If you e.g. self-sign then the self-signature isn't > recognized as authoritative. If a real CA signs it -- e.g. Verisign, > DigiCert, Let's Encrypt, etc. -- then the browser /will/ recognize it. > > > letsencrypt has an online web site from which one can download a > > ca_bundle, a private key and a certificate for your domain > > Theoretically, you should generate your own private key and then use > LE's tools to obtain a signed certificate. > > > Oracle has an article on keytool which says that keytool can not > > create a pkcs12 keystore but can read it and to use openssl, which > > I did following their instructions. > > OpenSSL will do DER/PEM files and also PKCS12 keystores, but they are > interchangeable and contain the same types of key material... just in > different kinds of packages. > > > Concatenate the CA cert, the private key and the user cert then put > > these in keystore. > > Be careful with terms. Concatenation usually means just slamming bytes > together. This only works with PEM-encoded files like OpenSSL likes to > use -- the ones that start with e.g. "---- BEGIN CERTIFICATE ----". > The other types of files have a very specific format and you can't > just slam them together. > > > The result is shown below. Tomcat isn't able to use this keystore > > to communicate with the browser for some reason. Why? What's > > missing or incorrect? > > > > C:\Users\don\Security\letsenc>%keytool% -list -keystore MMcert.p12 > > -v -storetype pkcs12 Enter keystore password: > > > > Keystore type: PKCS12 Keystore provider: SunJSSE > > > > Your keystore contains 1 entry > > > > Alias name: tomcat Creation date: Nov 13, 2017 Entry type: > > PrivateKeyEntry > > So this is one of the things that makes me angry about keytool: it > tells you there is only a single entry in the keystore and tells you > that it's a "private key". Well... there is also a certificate in > there and it's got signatures on it and stuff. I'd count that as at > least 2 items. Anyway... > > > Certificate chain length: 1 Certificate[1]: Owner: > > CN=info.finwoks.com > > Okay, this is traditionally called the "subject": info.finworks.com. > This is *your certificate*, usually called the "server certificate". > It's usually the last link in a chain of trust going from the CA down > to the server cert. > > > Issuer: CN=Let's Encrypt Authority X3, O=Let's Encrypt, C=US > > Good: you have a certificate that has been issued (aka signed) by > Let's Encrypt. > > You appear to be missing the Let's Encrypt intermediate certificate in > your keystore, which will be required for most browsers to trust the > certificate (chain). > > Might I recommend using Qualys's fine SSL server test tool: > https://www.ssllabs.com/ssltest/ > > It probably would have told you that you have a single certificate in > your chain and that you need to have an intermediate certificate. > > It turns out that it's fairly easy to fix this: just import LE's > intermediate certificate into your keystore, like this: > > $ keytool -import -alias [Authority.intermediate] -trustcacerts \ > -file [authority's intermediate cert file] \ > -keystore yourkeystore.jks > > Once you add this certificate, you will likely have to restart Tomcat > to pick-up the changes. > > You can do this in a single operation to convert from the PEM-encoded > files that LE gives to you into a PKCS12 package like this: > > $ openssl pkcs12 -export -in "${LE_BASE}/cert.pem" \ > -inkey "${LE_BASE}/privkey.pem" \ > -certfile "${LE_BASE}/fullchain.pem" \ > -out "${CATALINA_BASE}/${HOSTNAME}.p12" -name tomcat \ > -passout "pass:changeit" > > Note that this command imports all 3 items (server key, server > certificate, and CA intermediate certs) into a single PKCS12 bundle. > Then you can convert that into a Java keystore. Or just use PKCS12 as > your keystore type from Tomcat and avoid the use of keytool altogether. > > You might find these two presentations informative: > http://people.apache.org/~markt/presentations/2017-05-16-b-tomcat-ssl.pd > f > > http://people.apache.org/~schultz/ApacheCon%20NA%202017/Let's%20Encrypt% > 20Apache%20Tomcat.pdf > > Hope that helps, > - -chris > -----BEGIN PGP SIGNATURE----- > Comment: GPGTools - http://gpgtools.org > Comment: Using GnuPG with Thunderbird - http://www.enigmail.net/ > > iQJRBAEBCAA7FiEEMmKgYcQvxMe7tcJcHPApP6U8pFgFAloLYUYdHGNocmlzQGNo > cmlzdG9waGVyc2NodWx0ei5uZXQACgkQHPApP6U8pFjtxRAAisLpBKPg9VFN5dPH > tEeZQs7Bd6hM3NDBjRXE7RYAJhvBlOE2ImDkWXjRkJGedf00nTTQly6zKWHrusbC > VlJMoEK+T72XeJIv2y5up3K+VmartQZLK6twMCqDEVZBv0gaEz1T7yfe6WC6/G4W > oqGCkcDAF61P2u0K4QXldXBl1I83VCfEWWGpI7Bc1/5u7c/SE3kEN0D/V8Gs0H1r > 8/LF2MzPSpGoJqSuRhyPWzklaK/ks+LSv1d7ur+ZrHHobSeMFtIHuhk6KakbheIL > 3APEHZw3vHv70SFjvhviYg873CYOT52/x8zfzqpxc1z3X9JC/hAqzZUL7qKHPSMd > bbWTSu8Tv7XWARe2BdyRQDKFJSTPnUNFxvyWviekNK5HkJx2sSgcH8iiTJN5lrMQ > uEDZ4RukyT/b3VWn0RWtqvHnxZrLmXjWyV3MWNPFI0LYNuorJu6cROy4WnO7NFOV > dmvDKC79qJ/XOziOmaGKgL11hNGwqYB2pn/aS7G+VCLCG0UGp8B/64j/5mNd9BL5 > a4DZXmonIPoKhjO/OP5H7hte2uqQAprrQgVI1JzKlYAb6wV+f4123nctlM+UeFBM > ytYYVpwyD/TXxeVr0SnmNpOlyPHnO6RRXPXfmiNEbdsjMef+Inljc4DlcLnlbdvK > Fc/zRGoUIB8+LN0T8NxVvXMAGGc= > =IHty > -----END PGP SIGNATURE----- > > --------------------------------------------------------------------- > To unsubscribe, e-mail: users-unsubscr...@tomcat.apache.org > For additional commands, e-mail: users-h...@tomcat.apache.org > >