Shell – How to use SSH to run a shell script on a remote 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
}

With the first one there is no tty for ssh since stdin is not connected to the terminal, it is a here file. In fact if I try to run a similar command (on Debian) I get the following error:

Pseudo-terminal will not be allocated because stdin is not a terminal.

To get it to work you can do something like:

ssh -tt 192.168.1.100 <<EOF
sudo -S id
password
EOF

Although this is not a good idea since the password will be in plain text.

Update

I stumbled across an easy solution to this that avoids encoding the password in plain text, you can use a graphical program to enter the password:

ssh -X 192.168.1.100 <<EOF
SUDO_ASKPASS=/usr/lib/ssh/x11-ssh-askpass sudo -A id
EOF

Of course the ssh-askpass program must be installed in the given location and you must be running an X session on the machine you are working on. There are a few variations on the ssh-askpass program which should also work (Gnome/KDE versions). Also a graphical sudo replacement program like gksu or kdesudo should do the job too.