How can I send the current working directory from bash to Terminal?
Did you change PROMPT_COMMAND? The default PROMPT_COMMAND is defined in /etc/bashrc:

# Tell the terminal about the working directory at each prompt.
if [ "$TERM_PROGRAM" == "Apple_Terminal" ] &amp;&amp; [ -z "$INSIDE_EMACS" ]; then
    update_terminal_cwd() {
        # Identify the directory using a "file:" scheme URL,
        # including the host name to disambiguate local vs.
        # remote connections. Percent-escape spaces.
        local SEARCH=' '
        local REPLACE='%20'
        local PWD_URL="file://$HOSTNAME${PWD//$SEARCH/$REPLACE}"
        printf '\e]7;%s\a' "$PWD_URL"
    }
    PROMPT_COMMAND="update_terminal_cwd; $PROMPT_COMMAND"
fi