I have a TCP Client where calling a regular connect on a tcp socket works fine. However, the call to async_connect never fires the handler. They both use almost the same code. The difference is just the call to connect vs async_connect.
Header
#ifndef TCPCLIENT_H
#define TCPCLIENT_H
#include <boost/bind.hpp>
#include <boost/shared_ptr.hpp>
#include <boost/enable_shared_from_this.hpp>
#include <boost/asio.hpp>
#include <boost/thread/thread.hpp> 
#include <boost/thread/mutex.hpp>
using boost::asio::ip::tcp;
//How about an interface for outputting errors
class BoostTCPDebugOutputInterface
{
public:
    virtual void outputError(std::string& error)=0;
    virtual void outputDebug(std::string& debug) = 0;
    virtual void outputWarning(std::string& warning) = 0;
    virtual void outputInfo(std::string& info) = 0;
};
class ShutdownCallback
{
public:
    virtual void shutdown() = 0;
};
class BoostTCPConnection 
    : public boost::enable_shared_from_this<BoostTCPConnection>
{
public:
    typedef boost::shared_ptr<BoostTCPConnection> Connection_ptr;
    static Connection_ptr create(boost::asio::io_service& io_service, BoostTCPDebugOutputInterface* output, ShutdownCallback* shutdowner)
    {
        return Connection_ptr(new BoostTCPConnection(io_service, output, shutdowner));
    }
    virtual ~BoostTCPConnection(void);
    void start();
    bool isRunning();
    void setRunning(bool running);
    void enqueueMessageToSend(boost::shared_ptr<std::string>& message);
    boost::asio::ip::tcp::socket& socket()
    {
        return socket_;
    }
    void getQueueSize(unsigned long& tcpToSend, unsigned long& tcpRead);
    void getMessages(std::list< boost::shared_ptr<std::string> >& messages);
protected:
    BoostTCPConnection(boost::asio::io_service& io_service, BoostTCPDebugOutputInterface* output, ShutdownCallback* shutdowner) : socket_(io_service), errorOutput_(output), shutdowner_(shutdowner) {}
    void send();
    void handleWrite(const boost::system::error_code& error,size_t bytes_transferred);
    void handleReceive(const boost::system::error_code& error,size_t bytes_transferred);
    void readMessage();
    void handleReceive();
    std::string hostIP_;
    unsigned int hostPort_;
    boost::asio::io_service io_service_;
    boost::asio::ip::tcp::socket socket_;
    boost::mutex runningMutex_;
    bool running_;
    boost::mutex readMutex_;
    std::list< boost::shared_ptr<std::string> > receivedMsgs_;
    boost::mutex sendMutex_;
    std::list< boost::shared_ptr<std::string> > sendMsgs_;
    BoostTCPDebugOutputInterface* errorOutput_;
    ShutdownCallback* shutdowner_;
    static const size_t HEADERSIZE = 4;
};
class TCPClient
{
public:
    TCPClient();
    virtual ~TCPClient();
    bool start(std::string& hostIP,  unsigned int& hostPort, BoostTCPDebugOutputInterface* output, ShutdownCallback* shutdowner);
    void stop();
    void getQueueSize(unsigned long& tcpToSend, unsigned long& tcpRead);
    void send(boost::shared_ptr<std::string>& message);
    void getMessages(std::list< boost::shared_ptr<std::string> >& messages);
protected:
    void threadAction();
    void handleConnect(const boost::system::error_code& error);
    BoostTCPConnection::Connection_ptr connection_;
    boost::thread_group worker_threads_;
    boost::asio::io_service io_service_;
    BoostTCPDebugOutputInterface* errorOutput_;
    ShutdownCallback* shutdowner_;
};
#endif
CPP File
#include "TCPClient.h"
#include <iostream>
BoostTCPConnection::~BoostTCPConnection(void)
{
}
void BoostTCPConnection::start()
{
    setRunning(true);
    while (isRunning())
    {
        bool readData(false);
        bool wroteData(false);
        if (!socket_.is_open())
        {
            std::string info("BoostTCPConnection::start() socket is no longer open.  ");
            errorOutput_->outputError(info);
            shutdowner_->shutdown();
            //Stop this NOW!!!
        }
        //Check if there are 4 bytes for packet size 
        //If there are read the size and then do an read to get the packet
        //The handler function should put the packet on a queue.
        boost::asio::socket_base::bytes_readable command(true);
        socket_.io_control(command);
        std::size_t bytes_readable = command.get();
        if ( bytes_readable >= HEADERSIZE )
        {
            readMessage();
            readData=true;
        }
        size_t sendSize(0);
        {
            boost::mutex::scoped_lock(sendMutex_);
            sendSize = sendMsgs_.size();
        }
        if ( sendSize > 0)
        {
            send();
        }
        if ( !readData && !wroteData )
            boost::this_thread::sleep(boost::posix_time::milliseconds(5)); 
    }
}
void BoostTCPConnection::readMessage()
{
    size_t messageSize(0);
    char temp[4]="";
    std::vector<char> header(4);
    boost::system::error_code ec;
    //Read the header which is the size
    size_t read=boost::asio::read(socket_, boost::asio::buffer(header), ec);
    if (ec)
    {       
        std::string info("BoostTCPConnection::readMessage errorcode ");
        info+=ec.message();
        errorOutput_->outputError(info);
        shutdowner_->shutdown();
        //TODO Signal the GUI to stop
        return;
    }
    memcpy((void*)(&messageSize),(void*)header.data(),4);
    std::vector<char> rcvBuffer(messageSize);
    read=boost::asio::read(socket_, boost::asio::buffer(rcvBuffer),ec);
    if (ec)
    {
        std::string info("BoostTCPConnection::readMessage errorcode ");
        info+=ec.message();
        errorOutput_->outputError(info);
        shutdowner_->shutdown();
        //TODO Signal the GUI to stop
        return;
    }
    rcvBuffer.push_back('\0');
    std::string test(rcvBuffer.begin(),rcvBuffer.end());
    boost::shared_ptr<std::string> message(new std::string(rcvBuffer.begin(),rcvBuffer.end()));
    receivedMsgs_.push_back(message);
}
void BoostTCPConnection::getMessages(std::list< boost::shared_ptr<std::string> >& messages)
{
    if (messages.size() > 0)
        messages.clear();
    {
        boost::mutex::scoped_lock lock(readMutex_); 
        receivedMsgs_.swap(messages);
    }
}
void BoostTCPConnection::handleReceive(const boost::system::error_code& error, size_t bytes_transferred)
{
    if (error)
    {
        std::ostringstream oss;
        oss<< "BoostTCPConnection::handleReceive got an error Code of "<<error.value()<<" and message "<<error.message()<<" bytes_transferred = "<<bytes_transferred<<std::endl;
        errorOutput_->outputError(oss.str());
        shutdowner_->shutdown();
        return;
    }
}
bool BoostTCPConnection::isRunning()
{
    boost::mutex::scoped_lock lock(runningMutex_);
    return running_;
}
void BoostTCPConnection::setRunning(bool running)
{
    boost::mutex::scoped_lock lock(runningMutex_);
    running_=running;
}
void BoostTCPConnection::enqueueMessageToSend(boost::shared_ptr<std::string>& message)
{
    boost::mutex::scoped_lock lock(sendMutex_);
    sendMsgs_.push_back(message);
}
void BoostTCPConnection::getQueueSize(unsigned long& tcpToSend, unsigned long& tcpRead)
{
    {
        boost::mutex::scoped_lock lock(sendMutex_);
        tcpToSend=sendMsgs_.size();
    }
    {
        boost::mutex::scoped_lock lock(readMutex_);
        tcpRead=receivedMsgs_.size();
    }
}
void BoostTCPConnection::send()
{
    if (sendMsgs_.empty())
        return;
    boost::shared_ptr<std::string> message;
    {
        message=sendMsgs_.front();
        sendMsgs_.pop_front();
    }
    char temp[4];
    size_t messageSize=message->size();
    memcpy(temp,&messageSize, 4);
    message->insert(0,temp, 4);
    boost::asio::async_write(socket_, boost::asio::buffer(*message),
        boost::bind(&BoostTCPConnection::handleWrite, shared_from_this(),
        boost::asio::placeholders::error,
        boost::asio::placeholders::bytes_transferred));
}
void BoostTCPConnection::handleWrite(const boost::system::error_code& error,size_t bytes_transferred)
{
    //Success
    if (error.value() == 0) 
        return;
    std::ostringstream oss;
    oss<< "BoostTCPConnection::handleWrite  got an error Code of "<<error.value()<<" and message "<<error.message()<<" with bytes_transferred = "<<bytes_transferred<<std::endl;
    errorOutput_->outputError(oss.str());
    shutdowner_->shutdown();
}
//***************************************************
//              TCPClient
//***************************************************
TCPClient::TCPClient()
{
}
TCPClient::~TCPClient()
{
}
void TCPClient::threadAction()
{
    io_service_.run();
}
bool TCPClient::start(std::string& hostIP,  unsigned int& hostPort, BoostTCPDebugOutputInterface* output, ShutdownCallback* shutdowner)
{
    bool bResult(false);
    errorOutput_=output;
    connection_ = BoostTCPConnection::create(io_service_, output, shutdowner);
    shutdowner_=shutdowner;
    //Use multiple threads to do my bidding
    for( int x = 0; x < 3; ++x )
    {
        worker_threads_.create_thread( 
            boost::bind( &TCPClient::threadAction, this )
            );
    }
    boost::system::error_code ec;
    try
    {
        boost::asio::ip::tcp::endpoint ep( boost::asio::ip::address_v4::from_string(hostIP), hostPort);
        if (connection_)
        {
            connection_->socket().async_connect(ep,
                                                boost::bind(&TCPClient::handleConnect, 
                                                this, boost::asio::placeholders::error));
                            //Synchronous code that works fine
                            //boost::system::error_code ec;         
            //connection_->socket().connect(ep, ec);
            /*if (!ec)
            {
                worker_threads_.create_thread( 
                    boost::bind( &TCPClient::handleConnect, this, ec ));
                bResult=true;
            }
            else
            {
                std::ostringstream oss;
                oss<< "BoostTCPConnection::start has an error "<<ec.message()<<std::endl;
                errorOutput_->outputError(oss.str());
            }*/
        }
    }
    catch (std::exception& e)
    {
        std::ostringstream oss;
        oss<< "BoostTCPConnection::start received the exception "<<e.what()<<std::endl;
        errorOutput_->outputError(oss.str());
    }
    return bResult;
}
void TCPClient::handleConnect(const boost::system::error_code& error)
{
    if (error )
    {
        std::ostringstream oss;
        oss<< "BoostTCPConnection::handleConnect received the error "<<error.message()<<std::endl;
        errorOutput_->outputError(oss.str());
        shutdowner_->shutdown();
        return;
    }
    if (connection_)
        connection_->start();
}
void TCPClient::stop()
{
    if (connection_)
        connection_->setRunning(false);
    io_service_.stop();
    worker_threads_.join_all();
}
void TCPClient::getQueueSize(unsigned long& tcpToSend, unsigned long& tcpRead)
{
    if (connection_)
        connection_->getQueueSize(tcpToSend, tcpRead);
    else
    {
        tcpToSend=0;
        tcpRead=0;
    }
}
void TCPClient::send(boost::shared_ptr<std::string>& message)
{
    if (connection_)
        connection_->enqueueMessageToSend(message);
}
void TCPClient::getMessages(std::list< boost::shared_ptr<std::string> >& messages)
{ 
    if (connection_)
        connection_->getMessages(messages);
}
 
     
     
    