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Chapter 4a. Proper Start Up and Shut Down Procedures for Whonix

In order for Whonix to function as intended, there is a specific start up and shut down 

procedure that you need to follow in the future. This chapter will explain how to do just that. 

For an easy quick reference, here is the procedure:

1. Boot the Whonix Gateway first.
2. Boot the Whonix Workstation second.
3. Shutdown the Whonix Workstation first.
4. Shutdown the Whonix Gateway second.
5. Shutdown Debian last.

Below are the slightly more detailed instruction.

1. When you have booted into Debian from your USB Flash Drive and reach your Dekstop, 

click on “Applications → Accessories → VirtualBox” to open the VirtualBox Manager.

Chapter 4A - A Beginner Friendly Comprehensive Guide to Installing and Using a Safer Anonymous Operating System
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2. In the VirtualBox Manager, click on “Whonix-Gateway” and click “Start.” Whonix 

Gateway must always be run first or the system won't work.

Chapter 4A - A Beginner Friendly Comprehensive Guide to Installing and Using a Safer Anonymous Operating System
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3. When you reach the Desktop of the Whonix Gateway, go back to the VirtualBox Manager, 

click on “Whonix-Workstation” and click “Start.” 

When you reach the Desktop of the Whonix Workstation, you are ready to being using it as 
you usually would any other computer. 

NOTE: Whonix now uses Guest Additions which allows for a true “full screen” experience. 
If you would like to use the Whonix Workstation in full screen mode, 
press “RIGHT-CTRL+F.” If you need to switch to the VirtualBox Manager or Whonix 
Gateway, you can either return the Whonix Workstation to the windowed version by 
pressing “RIGHT-CTRL+F” again or you can simply press “RIGHT-CTRL” and then 
press “ALT-TAB” to move to other programs running on your Debian host OS.

Chapter 4A - A Beginner Friendly Comprehensive Guide to Installing and Using a Safer Anonymous Operating System
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4. When you are ready to shut down your computer, first make sure you have saved all 

your work in the Whonix Workstation and closed the programs. Then, shut down the 
Whonix-Workstation.  Then, click on the “K” start button in the lower left corner of your 
screen, hover the mouse over the “Leave” icon that appears in the right side of the Start 
Menu and then click on “Shut down.”

5. In the next window that appears, click on “Turn Off Computer.”

Chapter 4A - A Beginner Friendly Comprehensive Guide to Installing and Using a Safer Anonymous Operating System
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6. When the Whonix Workstation window closes from view, it is shut down. You can now 

close the Whonix Gateway. To close the Whonix Gateway, switch over to the Whonix 
Gateway window and
 repeat the choices made in steps 4-5 above. It is the exact same 
process for shutting down the Whonix Gateway as it is for shutting down the Whonix 
Workstation.

Chapter 4A - A Beginner Friendly Comprehensive Guide to Installing and Using a Safer Anonymous Operating System
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7. When the Whonix Gateway window closes from view, it is shut down. Now you can shut 

down Debian. Click on the “user” menu in the upper right corner of your screen and click 
“Shut Down.” 

8. In the window that pops up, click “Shut Down.” Eventually your computer should power 

off.

Once your computer is powered off, you are finished.  This is how you should start up and 
shut down your system every time in the future.

Continue to Chapter 4B - Using the Tor Browser.