After upgrade to Tomcat 8.0.28, the SSL connection failed (Time out). When downgrade back to Tomcat 8.0.27, the SSL connection back to normal. Any other variables are not changed (OS, JVM, configurations). Only change the Tomcat version. I guess this problem is caused by 8.0.28 changed the rule of reading/parsing the path of configuration resources (keystore locations of SSL). e.g. using the format of C:/ or / will cause reading configuration resources fail in the Tomcat 8.0.28 but 8.0.27 works well. Here is my server.xml of Connector part. Other parts of server.xml are the same with default version. <Connector port="443" protocol="org.apache.coyote.http11.Http11Nio2Protocol" maxThreads="150" SSLEnabled="true" scheme="https" secure="true" clientAuth="false" sslProtocol="TLSv1.2" keystoreFile="C:/Users/Administrator/mysite.jks" keystorePass="changeit" /> Note: This bug may related to Bug 56777 https://bz.apache.org/bugzilla/show_bug.cgi?id=56777
This was a regression in bug 56777. This has been fixed in trunk and 8.0.x for 8.0.29.
Potential (untested) workaround: use a "file:" URL to specify your keystore file on the filesystem.