Bash SSH Shell Script – How to Write a Script to Log onto Another Machine

I think you missed a level of quotes escaping. At this high level of escaping, it is best to simply make a little script for every stage where otherwise quotes would be required.

Otherwise, you could try this modified version (but mind you, I don't encourage this coding style!)

function _remoteInstallation(){
    local retval=1
    local debToInstall=$(basename "$1")
    local remoteMachine="$2"
    spawned=$(expect -d -c "
          set timeout 1800
          spawn \"/usr/bin/ssh -t borrajax@$remoteMachine /usr/bin/sudo /usr/bin/dpkg -i /home/borrajax/Documents/$debToInstall\"
          expect {
                \"Are you sure you want to continue connecting\" { send \"yes\r\"; exp_continue }
                \"password\" { send \"myPassword\r\";  exp_continue }
                \"[sudo] password\" { send \"myPassword\r\";  exp_continue }
                default { exit 1 }
          }
    " )
    retval=$?
    return $retval
}

On a system, the only thing that is really persistent is a file. That's pretty much what you should use. Here's an solution using an init.d script.

Let's consider the following (simple) script, /etc/init.d/myupdate :

#! /bin/sh

### BEGIN INIT INFO
# Provides:          myupdate
### END INIT INFO

PATH=/sbin:/bin:/usr/sbin:/usr/bin

case "$1" in
    start)
        /path/to/update/script
        ;;
    stop|restart|reload)
        ;;
esac

If you activate it with update-rc.d myupdate defaults, the start action will be executed upon boot. Now, when your update script calls for a reboot:

touch /var/run/rebooting-for-updates
sudo reboot

With this solution, you can divide your update script into two parts :

before_reboot(){
    # Do stuff
}

after_reboot(){
    # Do stuff
}

if [ -f /var/run/rebooting-for-updates ]; then
    after_reboot
    rm /var/run/rebooting-for-updates
    update-rc.d myupdate remove
else
    before_reboot
    touch /var/run/rebooting-for-updates
    update-rc.d myupdate defaults
    sudo reboot
fi

It'll execute the before_reboot code section, create a file in /var/run, and reboot. Upon boot, the script will be called again, but since the file exists, after_reboot will be called instead of before_reboot.

Note that update-rc.d requires root privileges.

Without using a file (from Stephen Ostermiller's comment):

If you are familiar with the getopts utility, you may want to use options instead of files. In the init script, call the script with:

/path/to/update/script -r

And in your script, check for options instead of files. Call your script once without the option, and init.d will call it again on boot, this time with -r.

# Set AFTER_REBOOT according to options (-r).

if [ "x$AFTER_REBOOT" = "xyes" ]; then
    # After reboot
else
    # Before reboot
fi

You'll find more information about option handling here (for short options only). I also edited my script with calls to update-rc.d to keep this a one-time job (from another comment).