Regarding isReachable() - it's only a best effort API. The documentation points out that it tries to send an ICMP echo request or create a TCP connection to port 7 on the destination host, both of which are highly likely to be blocked by a firewall. Is this happening in your case?
As for the acknowledgement, there's nothing in Netty that provides this as standard, but it shouldn't be too difficult to implement. Firstly each message needs to be uniquely identifible by some sort of identifier, possibly a sequence number but a globally unique identifier means you can potentially recover across disconnections. Then you want to create a combined handler that implements both ChannelInboundHandler and ChannelOutboundHandler (assuming Netty 4). When a message is sent
- add the message to a map indexed by its id
- create a timer associated with the message id. Add it to another map indexed by message id
- forward the message
When the ACK is received cancel the timer and remove the timer and message from their respective maps. If the timer fires use the associated id to decide what to do with the timer and message (possibly retransmit and reset the timer).
Netty provides a HashedWheelTimer for efficiently managing lots of timers with a resolution suitable for this kind of activity.
You may also want to consider putting a limit on the number of retries so you can stop and raise an error rather than continually indefinitely.