I tried upgrading from Tomcat 8.0.14 to 8.0.24 over the weekend and could not 
get it working (using Tomcat Native)… Here is what I see in catalina.out:
———
SEVERE [main] org.apache.catalina.core.AprLifecycleListener.init An 
incompatible version 1.1.31 of the APR based Apache Tomcat Native library is 
installed, while Tomcat requires version 1.1.32

SEVERE [main] org.apache.tomcat.util.net.jsse.JSSESocketFactory.getStore Failed 
to load keystore type JKS with path /var/root/.keystore due to 
/var/root/.keystore (No such file or directory)
 java.io.FileNotFoundException: /var/root/.keystore (No such file or directory)

SEVERE [main] org.apache.coyote.AbstractProtocol.init Failed to initialize end 
point associated with ProtocolHandler ["http-nio-8443"]
 java.io.FileNotFoundException: /var/root/.keystore (No such file or directory)

SEVERE [main] 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]]
———
Here are the steps I performed in the upgrade (Mac running OS 10.9.5):

### upgrade APR
cd /usr/local/src/apr-1.5.2 
./configure 
make
sudo make install
### upgrade OpenSSL
cd /usr/local/src/openssl-1.0.1p 
./configure darwin64-x86_64-cc
make
make test
sudo make install
openssl version
### compile Native
cd /usr/local/apache-tomcat-8.0.24/bin/
tar -xvf tomcat-native.tar.gz 
cd tomcat-native-1.1.33-src/jni/native/
./configure --with-apr=/usr/local/apr --with-ssl=/usr/local/ssl/ 
--with-java-home=/Library/Java/JavaVirtualMachines/jdk1.8.0_45.jdk/Contents/Home
make
sudo make install

Did not see any errors in the compiling that stopped the build of APR, OpenSSL, 
or Native…
Copied server.xml, tomcat-users.xml, setenv.sh, 2 libraries for db access, and 
SSL certificates over to the new Tomcat instance.
Started new Tomcat instance. Opened browser and connected to Manager. Deployed 
WAR files.
Upon opening an application that needed SSL, the browser just stalled.
Looking in catalina.out, I saw the errors posted above…

Thoughts?

Brian



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