Let me start by saying that I have explicitly designed my jump bag with 3 primary goals in mind:
Must contain the basics for all of the common types of assignments I get (penetration test, vulnerability scan, configuration audit, physical penetration test, WiFi).
Tools must be separated into compact boxes / containers so that if I don’t need (or can’t take) everything, I can quickly grab the kits relevant for the job.
Taking all the things is cumbersome when I’m bouncing around between Data Centres and Offices in the CBD without a car; my main bag is therefore a briefcase on wheels (an ordinary travel bag would also work).
The jump-bag contains:
Message Tin
Ethernet Cable
Thunderbolt to Ethernet Adapter (I have a MacOSX Host)
Red Box
Rubber Ducky USB Human Interface Device
Labelled slots for the Micro SD cards that contain Rubber Ducky scripts
On-the-go (OTG) adapter
Black Box
SD to Micro SD adapter
Various USB drives:
Kali 32-bit on a persistant, encrypted, USB drive
Common Exploitation / Post Exploitation Code (WAR files exposing web shells, privilege escalation scripts, etc)
Securely Encrypted USB drives for storing housing penetration test data
Blanks incase I need to transfer custom software from clients to use for testing etc
Backup images for my phone, pre-rooted ROMs with KonBoot preinstalled etc
Tiny Micro USB to USB cable
Misc waterproof bag
Spare USB thumb drive enclosures
Spare Micro USB to USB cables
Spare OTG adapters
TP-Link TL-WN722N WiFi Adapter
Black Tin / Wallet
Several spare blank SIM cards of all sizes for Australia & USA
Backup Rubber Ducky (I have two now because the first one I purchased broke =/)
Portable Power Bank (to charge my phone; I added this after a trip to a Data Centre which had no power-points - my boss/client became rather frustrated because he couldn’t get a hold of me when my phone died…)
My computer
MacOSX Host (Macbook Pro Hardware):
Kali 64-bit VM
Kali 32-bit VM
Windows 7 VM
Windows XP Vm
Portable Southord Lock-picking set on my key ring
My Android phone (this is my primary phone that goes everywhere I do):
KonBoot (dual image for both Mac & Windows systems.
Nethunter (Kali for Android; this is a full Kali installation with Metasploit etc).
This sounds like a lot, but it’s actually not that much.