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From Don Flinn <fl...@alum.mit.edu>
Subject Re: Trying to understand How Tomcat uses Keystore for SSL
Date Sun, 26 Nov 2017 21:54:01 GMT
Didn't read closely enough.  The protocol that I used is no longer
applicable for Tomcat 9.

Don

On Sun, Nov 26, 2017 at 3:15 PM, Don Flinn <flinn@alum.mit.edu> wrote:

> 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(Standa
> rdService.java:549)
> at org.apache.catalina.util.LifecycleBase.init(LifecycleBase.java:107)
> at org.apache.catalina.core.StandardServer.initInternal(Standar
> dServer.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.cre
> ate(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.getImplemente
> dProtocols(OpenSSLUtil.java:61)
> at org.apache.tomcat.util.net.SSLUtilBase.<init>(SSLUtilBase.java:46)
> at org.apache.tomcat.util.net.openssl.OpenSSLUtil.<init>(OpenSS
> LUtil.java:41)
> at org.apache.tomcat.util.net.openssl.OpenSSLImplementation.get
> SSLUtil(OpenSSLImplementation.java:36)
> at org.apache.tomcat.util.net.AbstractJsseEndpoint.initialiseSs
> l(AbstractJsseEndpoint.java:82)
> at org.apache.tomcat.util.net.NioEndpoint.bind(NioEndpoint.java:261)
> at org.apache.tomcat.util.net.AbstractEndpoint.init(AbstractEnd
> point.java:798)
> at org.apache.coyote.AbstractProtocol.init(AbstractProtocol.java:547)
> at org.apache.coyote.http11.AbstractHttp11Protocol.init(Abstrac
> tHttp11Protocol.java:66)
> at org.apache.catalina.connector.Connector.initInternal(Connect
> or.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 <
> chris@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/~markt/presentations/2017-05-16-b-tomcat-ssl.pdf>
>>
>> http://people.apache.org/~schultz/ApacheCon%20NA%202017/Let's%20Encrypt%
>> 20Apache%20Tomcat.pdf
>> <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/
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>> =IHty
>> -----END PGP SIGNATURE-----
>>
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>

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