This is quite a post. I needed to transfer files back and forth to an ssh server behind bastion on azure. Alas, its not too terribly well documented, so I thought I would make a document explaining how to do it. First I am going to define some terms.

Referencing the microsoft destination here are the cli arguments explained (they do a TERRIBLE job of this)

az network bastion ssh --auth-type
                 [--ids] = horrible slashy thing with evil vm resource ids (not necessary)
                 [--name] = Name of the actual (not vm!) bastion server
                 [--resource-group] = Resource group of the bastion server
                 [--resource-port] (not applicable for ssh)
                 [--ssh-key] (your local key, I just use ssh-agent)
                 [--subscription] the subscription with the proper bastion/vm
                 [--target-ip-address] n/a
                 [--target-resource-id] VERY EVIL long path you get from properties of vm
                 [--username] remote username of the local user on the VM

Here is an example with everything filled out:

az network bastion ssh --name MyHappyPastion-eus-VNet-bastion --resource-group MyHappyResourceGroupforBastion --target-resource-id /subscriptions/<subscriptionguid>/resourceGroups/<resource group>-RG/providers/Microsoft.Compute/virtualMachines/<vmname> --auth-type PASSWORD --username <vmuser> --subscription my-sub-name

This is 1/2 of the magic. You can get the resource vm by going to the vm and finding its "resource ID" which is that evil path I talked about. This also assumes you are properly logged into said sub with appropriate az login commands.

Now for the Cool part: Zmodem transfer w/o portforwarding OR any scp/sftp subsystems and NO direct connectivity to remote network

Install lrzsz on the remote vm (it might be a different package name, basically zmodem on unix).
Install lrzsz on your mac (alas this doesn't work as nicely for unix!) brew install lrzsz
Follow this guide (assuming you have iterm2 installed!)
PROFIT!

Appendix 1: saved text of github in case it disappears

#!/usr/bin/env bash

#
# iterm2-zmodem
#
# copyright (c) 2013 by Harald Lapp <harald@octris.org>
#
# AppleScript portion from:
# http://stackoverflow.com/questions/4309087/cancel-button-on-osascript-in-a-bash-script
# licensed under cc-wiki with attribution required 
#

#
# This script can be found at:
# https://github.com/aurora/iterm2-zmodem
#

#
# This is a re-implementation of the shell scripts "iterm2-recv-zmodem.sh" and
# "iterm2-send-zmodem.sh" found at https://github.com/mmastrac/iterm2-zmodem
#

# usage
if [[ $1 != "sz" && $1 != "rz" ]]; then
    echo "usage: $0 sz|rz"
    exit
fi

# send Z-Modem cancel sequence
function cancel {
    echo -e \\x18\\x18\\x18\\x18\\x18
}

# send notification using growlnotify
function notify {
    local msg=$1

    if command -v growlnotify >/dev/null 2>&1; then
        growlnotify -a /Applications/iTerm.app -n "iTerm" -m "$msg" -t "File transfer"
    else
        echo "# $msg" | tr '\n' ' '
    fi
}

#setup
[[ $LRZSZ_PATH != "" ]] && LRZSZ_PATH=":$LRZSZ_PATH" || LRZSZ_PATH=""

PATH=$(command -p getconf PATH):/usr/local/bin$LRZSZ_PATH
ZCMD=$(
    if command -v $1 >/dev/null 2>&1; then
        echo "$1"
    elif command -v l$1 >/dev/null 2>&1; then
        echo "l$1"
    fi
)

# main
if [[ $ZCMD = "" ]]; then
    cancel
    echo

    notify "Unable to find Z-Modem tools"
    exit
elif [[ $1 = "rz" ]]; then
    # receive a file
    DST=$(
        osascript \
            -e "tell application \"iTerm\" to activate" \
            -e "tell application \"iTerm\" to set thefile to choose folder with prompt \"Choose a folder to place received files in\"" \
            -e "do shell script (\"echo \"&(quoted form of POSIX path of thefile as Unicode text)&\"\")"
    )

    if [[ $DST = "" ]]; then
        cancel
        echo 
    fi

    cd "$DST"

    notify "Z-Modem started receiving file"

    $ZCMD -e -y
    echo 

    notify "Z-Modem finished receiving file"
else
    # send a file
    SRC=$(
        osascript \
            -e "tell application \"iTerm\" to activate" \
            -e "tell application \"iTerm\" to set thefile to choose file with prompt \"Choose a file to send\"" \
            -e "do shell script (\"echo \"&(quoted form of POSIX path of thefile as Unicode text)&\"\")"
    )

    if [[ $SRC = "" ]]; then
        cancel
        echo 
    fi

    notify "Z-Modem started sending
$SRC"

    $ZCMD -e "$SRC"
    echo 

    notify "Z-Modem finished sending
$SRC"
fi

Z-Modem integration for iTerm2- backup in case github blows up

Preface

The purpose of this script is to add Z-Modem file transfer support to (in theory) any ssh session from within iTerm2.

This script is inspired by and would probably not exist without the scripts "iterm2-recv-zmodem.sh" and "iterm2-send-zmodem.sh" (c) by Matt Mastracci, https://github.com/mmastrac/iterm2-zmodem.

The motivation to not forking but rewriting the scripts was mainly to put the functionality into a single shell script to make it possible to share common code used by both sending and receiving funtionality and to make it more easy to extend the functionality in future.

Installation

Prework

For sending and receiving files the Z-Modem tools are required on both machines involved in the transfer. I recommend installing the lrzsz package which should be available in most Linux distributions or which can be downloaded and build from source from:

http://ohse.de/uwe/software/lrzsz.html

A recent version of iTerm2 is required for Mac OS X to make things work, downloadable from:

http://www.iterm2.com/

Optionally the script supports Growl notifications. For this to work the Growl application and the additional tool "growlnotify" is needed.

Installation and configuration

The script iterm2-zmodem should by copied to /usr/local/bin.

It's required to setup the following "Triggers" in iTerm2:

Regular expression: \*\*B0100
Action:             Run Coprocess
Parameters:         /usr/local/bin/iterm2-zmodem sz

Regular expression: \*\*B00000000000000
Action:             Run Coprocess
Parameters:         /usr/local/bin/iterm2-zmodem rz

The script "iterm2-zmodem" tries to determine the names (lrz, rz, lsz, sz) and locations of the binaries of growlnotify and the Z-Modem tools. The pathes searched are:

/usr/bin:/bin:/usr/sbin:/sbin:/usr/local/bin

If the Z-Modem tools are installed in some unusual place, the path can be specified when configuring the triggers using the LRZSZ_PATH environment variable, the "Parameters" setting of the trigger has to be modified in this case to become for example:

Parameters:         LRZSZ_PATH=/opt/lrzsz/bin /usr/local/bin/iterm2-zmodem rz

Usage

The file transfer is initiated on the remote machine by executing rz respectively lrz (for receiving a file on the remote machine) or by executing sz respectively lsz (for sending a file to the remote machine). See the command usage information of the Z-Modem tools for additional details.

Note, that sending files will overwrite the destination file on the local machine, if it already exists.

Disclaimer

Use with caution. This software may contain serious bugs. I can not be made responsible for any damage the software may cause to your system or files.

License

iterm2-zmodem

This program is free software: you can redistribute it and/or modify it under the terms of the GNU General Public License as published by the Free Software Foundation, either version 3 of the License, or (at your option) any later version.

This program is distributed in the hope that it will be useful, but WITHOUT ANY WARRANTY; without even the implied warranty of MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the GNU General Public License for more details.

You should have received a copy of the GNU General Public License along with this program. If not, see http://www.gnu.org/licenses/.

3rd party code

The AppleScript portion included in the script is inspired by http://stackoverflow.com/questions/4309087/cancel-button-on-osascript-in-a-bash-script licensed under cc-wiki with attribution required

How to ssh with azure cli and use zmodem to transfer with iterm2 and mac