FULL PRODUCT VERSION :
java version "1.8.0_101"
Java(TM) SE Runtime Environment (build 1.8.0_101-b13)
Java HotSpot(TM) 64-Bit Server VM (build 25.101-b13, mixed mode)

I have also tried the same with the latest java version, as well

ADDITIONAL OS VERSION INFORMATION :
Linux Cent OS
Mac OSX

EXTRA RELEVANT SYSTEM CONFIGURATION :
Just add the parameter com.sun.jndi.ldap.connect.timeout for ldaps (ldap over ssl), i am getting the error, java.net.SocketException: Unconnected sockets not implemented.

It works fine for ldap without ssl.

A DESCRIPTION OF THE PROBLEM :
When i add the parameter com.sun.jndi.ldap.connect.timeout for ldaps (ldap over ssl), i am getting the error, java.net.SocketException: Unconnected sockets not implemented.

The error is hit when calling the function, InitialLdapContext
javax.naming.ldap.InitialLdapContext#InitialLdapContext(java.util.Hashtable<?,?>, javax.naming.ldap.Control[])

It works fine for ldap without ssl.

I believe the root cause is because the createSocket() method is invoked without any parameter when a connect.timeout is specified.

STEPS TO FOLLOW TO REPRODUCE THE PROBLEM :
Set the parameter, com.sun.jndi.ldap.connect.timeout to a value like 30000
Create ldap connection over ssl

<refer to source code for more details>

EXPECTED VERSUS ACTUAL BEHAVIOR :
EXPECTED -
successful ldaps (ldap over ssl) connection should created.

I am expecting the same behavior as ldap without ssl
ACTUAL -
Got exception : Caused by: java.net.SocketException: Unconnected sockets not implemented

ERROR MESSAGES/STACK TRACES THAT OCCUR :
exc: Caused by: javax.naming.CommunicationException: <ip>:<port> [Root exception is java.net.SocketException: Unconnected sockets not implemented] │
  exc: at com.sun.jndi.ldap.Connection.<init>(Connection.java:216) │
  exc: at com.sun.jndi.ldap.LdapClient.<init>(LdapClient.java:137) │
  exc: at com.sun.jndi.ldap.LdapClient.getInstance(LdapClient.java:1614) │
  exc: at com.sun.jndi.ldap.LdapCtx.connect(LdapCtx.java:2746) │
  exc: at com.sun.jndi.ldap.LdapCtx.<init>(LdapCtx.java:319) │
  exc: at com.sun.jndi.ldap.LdapCtxFactory.getUsingURL(LdapCtxFactory.java:192) │
  exc: at com.sun.jndi.ldap.LdapCtxFactory.getUsingURLs(LdapCtxFactory.java:210) │
  exc: at com.sun.jndi.ldap.LdapCtxFactory.getLdapCtxInstance(LdapCtxFactory.java:153) │
  exc: at com.sun.jndi.ldap.LdapCtxFactory.getInitialContext(LdapCtxFactory.java:83) │
  exc: at javax.naming.spi.NamingManager.getInitialContext(NamingManager.java:684) │
  exc: at javax.naming.InitialContext.getDefaultInitCtx(InitialContext.java:313) │
  exc: at javax.naming.InitialContext.init(InitialContext.java:244) │
  exc: at javax.naming.ldap.InitialLdapContext.<init>(InitialLdapContext.java:154) │
  exc: at com.snaplogic.snaps.ad.ADBasicAuth.connect(ADBasicAuth.java:93) │
  exc: ... 46 more │
  exc: Caused by: java.net.SocketException: Unconnected sockets not implemented │
  exc: at javax.net.SocketFactory.createSocket(SocketFactory.java:125) │
  exc: at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method) │
  exc: at sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:62) │
  exc: at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43) │
  exc: at java.lang.reflect.Method.invoke(Method.java:498) │
  exc: at com.sun.jndi.ldap.Connection.createSocket(Connection.java:303) │
  exc: at com.sun.jndi.ldap.Connection.<init>(Connection.java:203) │
  exc: ... 59 more │
  exc: Caused by: java.lang.UnsupportedOperationException │
  exc: at javax.net.SocketFactory.createSocket(SocketFactory.java:123) │
  exc: ... 65 more │
  exc:

REPRODUCIBILITY :
This bug can be reproduced always.

---------- BEGIN SOURCE ----------
import java.net.Socket;
import java.net.ServerSocket;
import javax.net.ServerSocketFactory;
import javax.net.ssl.SSLServerSocketFactory;
import java.io.*;
import javax.naming.*;
import javax.naming.directory.*;
import java.util.Hashtable;

public class ReadTimeoutTest {
  
static boolean ssl = false;

    public static void main(String[] args) throws Exception {
  
boolean passed = false;

if (args.length > 0 && args[0].equalsIgnoreCase("SSL")) {
System.out.println("SSL on");
ssl = true;
} else {
System.out.println("SSL off");
ssl = false;
}

// Set up the environment for creating the initial context
Hashtable env = new Hashtable(11);
env.put(Context.INITIAL_CONTEXT_FACTORY,
"com.sun.jndi.ldap.LdapCtxFactory");
env.put("com.sun.jndi.ldap.connect.timeout", "2000");
if (ssl) {
        env.put(Context.PROVIDER_URL, "ldaps://localhost:2001");
  } else {
        env.put(Context.PROVIDER_URL, "ldap://localhost:2001");
  }

Server s = new Server();

try {

// start the server
s.start();

// Create initial context
DirContext ctx = new InitialDirContext(env);
System.out.println("LDAP Client: Connected to the Server");

// Close the context when we're done
ctx.close();
} catch (NamingException e) {
e.printStackTrace();
}
s.interrupt();
    }

    static class Server extends Thread {

        static int serverPort = 2001;

Server() {
}

public void run() {
try {
        ServerSocket serverSock;
        
        if (ssl) {
          SSLServerSocketFactory ssocketFactory = (SSLServerSocketFactory) SSLServerSocketFactory.getDefault();
          serverSock = ssocketFactory.createServerSocket(serverPort);
        } else {
          serverSock = new ServerSocket(serverPort);
        }
           Socket socket = serverSock.accept();
             System.out.println("Server: Connection accepted");

             BufferedInputStream bin = new BufferedInputStream(socket.
                                getInputStream());
             while (true) {
// bin.read(); // If uncommented, bug does not appear.
             }
} catch (IOException e) {
e.printStackTrace();
// ignore
}
       }
    }
}
---------- END SOURCE ----------
---------- END SOURCE ----------

CUSTOMER SUBMITTED WORKAROUND :
None.

I am not setting connection timeout to avoid the issue.

SUPPORT :
YES