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public class RecoverableTimerTask extends TimerTask {
    int numOfRetry;
    ConnectInfo connectInfo;
    Socket socket;
 
    RecoverableTimerTask(int numOfRetry, ConnectInfo connectInfo){
         this.numOfRetry = numOfRetry;
         this.connectInfo = connectInfo;
    }
 
    private void initialSocket(){
        ...
        socket = new ...
    }
 
    @Override
    public void run() {
        for(int i=0; i < numOfRetry; i++){
            try {
                initialSocket();
                //business logic
                //thorw exeption
                return; 
            } catch (SSLHandshakeException e) {
                // clean error state
                continue;
            } finally{
                socket.close();
            }
        }
    }
}

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Future result = ScheduledExecutorService.schedule(...)
try{
    result.get()
} catch (SSLHandshakeException e) {
    ...
}