I have had spent some time recently making netty 3.6 sending some message when connection has been established.

What documentation suggests to do is to extend SimpleChannelUpstreamHandler and override method channelConnected(...). It works fine unless SslHandler is used in the pipeline. If handler is present, channelConnected() was never called on my handler.

The problem was caused by client, which did not initialized SSL handshake on connection. Until handshake completed, no other ChannelHandlers are notified. Hopefully, there is a convenient way to initiate handshake on the client. Netty documentation states:

Handshake

If isIssueHandshake() is false (default) you will need to take care of calling handshake() by your own. In most situations were SslHandler is used in ‘client mode’ you want to issue a handshake once the connection was established. if setIssueHandshake(boolean) is set to true you don’t need to worry about this as the SslHandler will take care of it. http://netty.io/3.6/api/org/jboss/netty/handler/ssl/SslHandler.html

So, you should set isIssueHandshake on SslHandler before establishing the connection:

SslHandler sslHandler = new SslHandler(engine);
setIssueHandshake(true);
pipeline.addLast("ssl", sslHandler);

After that, server got hadshaked and SslHandler fired connected ChannelStateEvent to other UpstreamHandlers.