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name Punditsdkoslkdosdkoskdo

SSL connection issue with s_client

I'm trying to configure SSL on two machines (on LAN) from a local CA I created and am hitting an issue when testing with s_client, I can't seem to locate helpful info w/ my google-fu skills. I'm trying to familiarize myself with info security and seemed like a good place to start. My scenario is

host1: ubuntu 12.04, tomcat7

host2: ubuntu 12.04, tomcat7

configured tomcat w/ ssl on both hosts, and can reach the tomcat homepage @ https://{host}:8443 from either machine. I configured the connector w/ my keystore & pass, I believe tomcat is happy w/ the params as earlier I had tomcat startup errors not being able to extract the private key but that is resolved. here's what I did

// create tomcat server keystore
1. sudo keytool -genkey -alias tomcat7 -keyalg rsa -keystore     /etc/tomcat7/keystore/host1.jks

2. openssl genrsa -aes256 -out host1_key.pem 2048

3. openssl req -new -key host1_key.pem -out host1.csr

4. openssl x509 -req -days 3650 -in host1.csr -CA root_ca.cer -CAkey root_ca_key.pem -    CAcreateserial -setalias host1 -addtrust serverAuth -addtrust clientAuth -extensions client -outform PEM -out host1.cer

// export to keystore
5. openssl pkcs12 -export -in host1.cer -inkey host1_key.pem -out host1.p12 -name "host1"

// import keystore
6. sudo keytool -importkeystore -srckeystore host1.p12 -destkeystore     /etc/tomcat7/keystore/host1.jks -srcstoretype pkcs12
dest passwd: 
src passwd: 
Entry for alias host1 successfully imported
Import command completed: 1 entries successfully imported, 0 entries failed or cancelled

7. view keystore host1.jks
Enter keystore password:  

Keystore type: JKS
Keystore provider: SUN

Your keystore contains 2 entries

tomcat7, Feb 18, 2013, PrivateKeyEntry, 
Certificate fingerprint (MD5): 2A:F1:5A:D1:5B:B1:24:5E:C7:96:3F:71:C8:17:09:E8
host1, Feb 18, 2013, PrivateKeyEntry, 
Certificate fingerprint (MD5): 3F:81:FD:79:78:85:98:32:72:C4:42:8F:D6:2F:DD:09

8. Configure connector in tomcat w/ this keystore.  restart tomcat. Boots w/out error.


Browse to https://host1:8443 from host2 and will get to "It Works!" page

The next step I did was test the connection from one machine to the other

host2: openssl s_client -connect host1:8443
CONNECTED(00000003)
140310470641312:error:14077438:SSL routines:SSL23_GET_SERVER_HELLO:tlsv1 alert internal error:s23_clnt.c:724:
---
no peer certificate available
---
No client certificate CA names sent
---
SSL handshake has read 7 bytes and written 226 bytes
---
New, (NONE), Cipher is (NONE)
Secure Renegotiation IS NOT supported
Compression: NONE
Expansion: NONE
---

In Wireshark I set my filter for all TLS protocol ("ssl.record.version == 0x0301") and I don't even see a request go out when I run the above command. I think that means openssl can't extract my certificate? I'm not sure where to look from here, if I change my keystore password to something invalid in my tomcat connector, i'll see errors in tomcat when it boots. Otherwise I should have seen the handshaking requests in wireshark.

I'll see the same if I try from my other host.

I've read about 'truststores' when trying to resolve my issue, would that be another keystore w/ the other server's .p12 imported and my local CA?

Thanks, any direction would be helpful.

      • 1
    • If I force ssl3 via -ssl3 I get a successful connection; I see my server cert and a massive list of acceptable CA names. I guess this means I don't have an issue and must use ssl3.. would this be something I specify in the tomcat connector?

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