I decided to get an Ubuntu installation going on my machine using VMWare player and it’s Unity feature. The only problem was: TMG. This was how I got around the issue of allowing my VM to access the internet: Cntlm proxy

(If you cannot install CNTLM using the apt-get command I’d suggest you download the software and SCP it to your VM.)

The other great thing about the cntlm software is that it can create NTLM hashes.

1. Install CNTLM

Update your sources:

apt-get update

Update your installation:

apt-get upgrade

Install application:

apt-get install cntlm

2. Configure CNTLM

Once installed edit the configuration file:

nano /etc/cntlm.conf

Set username, domain, remote proxy, and address with port which local proxy will listen to. Here will listen only in local interface:

Username        testuser
Domain          contoso.com
Proxy           10.0.0.41:8080
Listen          127.0.0.1:3128

Generate password hash:

cntlm -H

You will see something like this:

Password:
PassLM          7F4BB72132BAA2A01FA94BD623A70D3B
PassNT          2C27BB146F74625D159413FC1F30745F
PassNTLMv2      D3972609581D8260868ED588303F0FF0    # Only for user 'testuser', domain 'contoso'

Copy these lines to /etc/cntlm.conf

3. Configure Debian to use the CNTLM proxy:

Execute this line to configure system to use the local proxy:

export http_proxy=http://127.0.0.1:3128/

4. Configure CNTLM to listen external network:

If you need to use CNTLM as a proxy server, add this line to /etc/cntlm.conf (assuming 10.0.0.1 is the local address):

Listen          127.0.0.1:3128
Listen          10.0.0.1:3128

Reference:
https://www.howtoforge.com/linux-ntlm-authentication-proxy-isa-server-with-cntlm

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