So it has come the day when I stop lurking and write down my first post on this sub.

[TL;DR] I am using Proxychains, Tor, Nmap and Macchanger to understand how to hide myself while using Wireshark to disect my scan. I’d like some insights to understand if I have the right approach while studying to become a Pentester.

[Personal Context] I am one of the many students out there who are learning about cybersecurity who would like to become a Pentester in the near future. Right now I am learning about the “Scanning Phase” with the given tools on my Kali Linux VM, so I am working on the following scenario:

[Scenario & Approach] I am using Nmap & Proxychains4 along with Tor to hide my VM’s ip, and I am using Wireshark as well on a Windows 11 VM to capture all traffic coming from it. I have also decided to use macchanger in order to spoof my MAC address as well.

My current train of thought is:

• Thought 1. I can make use of proxychains to hide my real ip by configuring Tor and add some other proxies in there as well. Would that be necessary if I am already within the same network, or is it okay given that I can pull TCP requests from other ips other than mine?
• Thought 2. Will spoofing my MAC Address provide another layer of anonymity if Wireshark tries to locate my ARP request?
• Thought 3. Whenever I use macchanger and try to either connect to a website or use proxychains, it won’t allow me. Proxychains prompts a message about socket error/timeout. Would macchanger be that necessary to anonymize myself? If I use nmap along with proxychains, would it be easier if I just use –spoof-mac while performing the scan?

[Goals] The main idea is to understand how this would look from both Red & Blue teams perspective. Although Wireshark might not be an IDS, it allows me to disect how my scan is working and what could be used to identify myself.