Dubbed “The Amnesic Incognito Live System”, Tails is an open source Linux distribution delivered as a single Live CD ISO image that supports only 32-bit instruction set architectures. It can be deployed to a SD card, USB thumb drive, or CD/DVD discs. Tails is a favorite companion tool of Tor. — Roger Dingledine, co-founder of the Tor Project One of the most robust ways of using the Tor network is through a dedicated operating system that enforces strong privacy- and security-protective defaults. That operating system is Tails. — Electronic Frontier Foundation. Sep 22, 2020 Tails 4.11 Tails is a live operating system, that you can start on almost any computer from a DVD, USB stick, or SD card. It aims at preserving your privacy and anonymity on any computer. Tutorial on how to install TAILS on a Mac. Tested on Macbook Pro Mid 2010 and 2015. Works with TAILS 2.4! Some have reported issues with wifi not working!
In this article we show you how to verify and install Tails 4.11 onto a USB Flash drive and browse the web anonymously using the Tor Web Browser. It is easy, anyone can do it and it is completely free, without having to burn any DVD’s.
Because we take web security very seriously at Wisevu we wrote an article and did a video several months ago on How to Install Tails 4.2 on a USB Drive on Mac OS and Launch Tor Browser, it got a lot of attention on our site and on youtube, and so we are doing another article and video on the same topic but this time for the latest version of Tails at the present moment – Tails 4.11 and this time with Tails 4.11 running on 3 of all our tested Mac’s.
You can either watch our video below or read the article.
We Tested Tails 4.11 On The Following Mac Computers
We tested Tails 4.11 on MacBook Pro 2018 with Touch Bar, iMac Late 2013, and MacBook Air 2015. Tails 4.11 worked on all our devices.
However, please note that you may need to use either a wired internet connection using an Ethernet cable or a cheap USB/WiFi adapter to connect to the internet. Many people report that their wifi does not work in Tails 4.11 (as well as earlier versions of Tails) either.
Also if you are using a MacBook Pro with a touch-bar, your built in keyboard and trackpad will not work once you load Tails 4.11. Therefore, you will need an external keyboard and mouse. Doesn’t matter if they are wired or wireless.
Formatting Your USB Drive for Tails 4.11
Step 1: You will need a USB thumb drive that is at least 8GB and it must be formatted using the Mac OS Extended (Journaled) Format. If you also see a Scheme dropdown, select the GUID Partition Map Scheme.
How to Download and Verify Tails 4.11 on Mac OS
Go to https://tails.boum.org/
Scroll down and click the Get Tails 4.11 link, click MACOS link, click INSTALL FROM MACOS link, click the LET’S GO link
Click Download the Tails 4.11 USB Image (1.2GB)
Click ‘Instal Tails Verification Extension’, once installed go back to Tails 4.11 Download page, or click here and refresh the page. You should see a message that says .Tails Verification Extension Installed’ with a green checkmark. If the section is greyed out, click the green text link that says ‘I already downloaded Tails 4.11.
You will see a green ‘Verify Tails 4.11..’ button. Click it, locate the tails-amd64-4.11.img that you already downloaded to your computer and click Open. The extension will verify your Tails. Before doing so, ensure that Tails 4.11 is done downloading to your computer because it is a 1.2GB file and may take some time. If Tails does not verify, you may have to download it again and follow the above steps once more without having to download the browser verification extension again.
Install Tails 4.11
Follow the steps here, or simply click here to Install Etcher for MacOS,
Once Etcher is installed, make sure the USB stick that you want to install Tails 4.11 is plugged into your Mac > Click the ‘Flash From File’ button on the left of the Etcher application and select tails-amd64-4.11.img from your computer that you already downloaded.
Next, click the ‘Select Target’ button and select your USB stick y clicking on the checkbox. Finally click flash and let Etcher do its magic. Once Etcher is done flashing Tails 4.11 to your USB stick you are ready to load Tails 4.11 on you Mac.
With you USB Stick still inserter into your Mac, restart your computer and hold down the alt/option key on your keyboard as the computer starts up.
You will see the various bootable drives, one of them will be the USB Drive with Tails 4.11 on it, the name may say EFI BOOT or Windows or possibly something else. Click it to boot using Tails OS 4.11
If the USB stick does not appear in the list of possible startup disks:
Make sure that you have verified your download of Tails.
Try installing again on the same USB stick.
Try installing on a different USB stick.
Try using the same USB stick to start on a different computer? If the same USB stick works on a different computer, please report the problem to the Tails help desk as per this article.
Once you Click on the Tails startup disk, you may get the following security warning “Security settings do not allow this Mac to use an external startup disk.” read the instructions here or watch our video above which shows you how to fix this issue.
Next, restart your computer again holding down the alt/option key on your keyboard, select the Tails startup disc and wait for Tails 4.11 to load up.
You can now access the Tor browser and surf the web anonymously.
Troubleshooting
Please see below links related to some common problems with installing Tails 4.11 on some Mac computers, as well as Tails 4.2.
If Tails 4.11 disk does not show up when you restart your computer while holding down the alt/option key on your keyboard, Tails may not be compatible with your mac model/version.
Security settings do not allow this Mac to use an external startup disk. – If you get this warning read the instructions in the provided link or watch our video above.
Keyboard and trackpad do not work on Mac Book Pros with touch-bar when Tails loads – The only way to get Tails working on any Mac’s that have a touch-bar is to use an external mouse and an external keyboard.
Connecting to a WiFi network in Tails – If you cannot use an Ethernet cable, USB tethering or USB Wi-Fi adapter and must connect to WiFi to access Tails , you can try disable MAC spoofing to get your Wi-Fi interface to work in Tails. However, this does not always work. Disabling MAC spoofing has security implications, so read carefully the documentation about MAC spoofing before doing so. Note that even if MAC spoofing is disabled, your anonymity on the Internet is preserved. In this reddit thread on Help with Tails WiFi on Mac Book Pro, it is recommended to use a cheap USB/WiFi adapter.
Are you having any issues installing Tails OS on a Jump Drive on your Mac? What do you use Tails OS for? What is your favourite application on Tails OS? Please do share in the comments below.
At Wisevu we take web security seriously, so if you want to learn how to privately and anonymously surf the web in the safest way possible without leaving a trace on your personal or work station, this article will show you exactly how to do this using Tails OS 4.2 and the Tor Web Browser using Apple’s Mac.
UPDATE: We have created a new article and video on Youtube which shows how to install the latest version of Tails 4.11 on a USB stick and run in on Mac computers including the latest Mac Book Pro’s with touch-pads. You can read the article here – How to Install Tails 4.11 on a USB Drive on Mac OS and Launch Tor Browser and watch the new video here – Video How to Install Tails 4.11 on a USB Stick on Mac OS and Launch Tor Anonymously. However, if you still rather learn how to instal Tails 4.2 on your Mac, then check out the article and video below.
Tails 4.2 doesn’t work on several of the latest models of Mac computers, however the latest version of Tails 4.11 does, learn which Mac’s/OS Tails 4.2 works on and on which it doesn’t in the article below, or click here.
Tails Os Virtual Machine
As per Wikipedia,
“Tails or The Amnesic Incognito Live System is a security-focused Debian-based Linux distribution aimed at preserving privacy and anonymity. All its incoming and outgoing connections are forced to go through Tor, and any and all non-anonymous connections are blocked. The system is designed to be booted as a live DVD or live USB, and will leave no digital footprint on the machine unless explicitly told to do so.”
In this article and video, we show you how to Download and Verify Tails OS 4.2 (latest version at the time of writing this article) and install it on a USB drive on Mac OS X, completely free, without having to burn any DVD’s.
Tails 4.2 Does Not Work On All Macs
We tested Tails 4.2 on several different Mac computers. The USB stick with Tails 4.2 works on the iMac Late 2013 model running Mac OS High Sierra Version 10.13.6. It does not load on the following Apple Mac’s – MacBook Pro 2018 model with touch-bar running macOS Catalina Version10.15.7 and Version 10.15.5, MacBook Pro 2018 model running macOS Mojave Version 10.14.5, MacBook Air Early 2015 running macOS Catalina Version 10.15.7 and Version 10.14.6, iMac 2010 model running OS X El Capitan Version 10.11.16 and MacBook Air early 2013 running macOS Mojave Version 10.14.6. Please let us know if it works on your Mac Model/Version so that we can alert tails support. You should also report yourself is as per this article to help improve Tails.
Aside from our above tested Mac models/OS versions, we had Youtube users report that Tails also worked on: 2017 Mac versions Macbook Air 2013 running OS 10.15,
Other Youtube users reported that Tails 4.2 does not work on Macbook Pro with Touchbar (2019) Macbook Pro Late 2016
But we have not tested the above mentioned Macs ourselves, we will however continue testing Tails on newer Mac versions and will provide an update above.
With that said, let’s get started!
Please note that you will need a USB thumb drive that is at least 8GB and it must be formatted using the Mac OS Extended (Journaled) Format with the GUID Partition Map Scheme.
Tails Os For Mac Os
Open Disk Utility > Right click on your flash drive in the left > click Erase > Format Mac OS Extended (Journaled)
How to Download and Verify Tails on Mac OS
Go to https://tails.boum.org/
Click the Install Tails 4.2 link, click Mac OS link, click Install from Mac OS link, click the Let’s Go link
Download the iso image of the latest Tails OS
Click the link that says “See instructions for basic OpenPGP verification.” and then
Download Tails signing key
Download the OpenPGP signature for the Tails 4.2 USB image
Wait until the Tails OS image iso file is downloaded to your computer. Then put all 3 downloaded files in a folder called tails on your desktop.
Go to pgptools.org and download the PGP suite, install it, then click Import and locate the Tails signing key file and double click it.
Open terminal Type: cd ~/Desktop/tails (hit enter) (this is the location of the 3 files you downloaded from the Tails website.
Next type ls into Terminal to list the files in the directory and hit enter. The 3 files mentioned above will be listed (in my case the following 3 files: tails-amd64-4.2.iso, tails-amd64-4.2.iso.sig, tails-signing.key)
Next type gpg —verify tails-amd64-4.2.img.sig tails-amd64-4.2.img (Note the tails file name above will change depending on the version of tails you are installing. You need to enter the name of the .img file from the /Desktop/tails folder.
If the Tails file is legitimate you will get a message that says “Good signature from tails developers <[email protected]>” [unknown]
This message indicates that the downloaded Tails OS is legitimate and you can proceed to burn it to a USB Drive or DVD
How to Burn the Tails OS image iso file to a USB stick on Mac OS
You can use the free Etcher software for Mac. Etcher is free, an open-source, cross-platform solution, which allows users to quickly and efficiently create bootable flash drives. Very simple instructions on how to do this can be found here.
In this article, we will show you how to do it using the Terminal command line on Mac OS. In our video above we show you how to do it using Etcher.
Open terminal type diskutil list (hit enter) (this will list all storage devices)
In our case, the USB drive is named /dev/disk2 (hit enter) You can see the size of the drive as an indication if it is the correct USB drive, and also the name of the USB drive is listed.
Next type diskutil unmount /dev/disk2 (hit enter)
If that doesn’t work then type diskutil unmountDisk /dev/disk2 (hit enter) (this will unmount all the volumes in your USB stick)
Next type sudo dd bs=1m if=~/Desktop/tails/tails-amd64-4.2.iso of=/dev/rdisk2 (hit enter) (note – firs file path is the file path of the iso file, the last part of the code is the usb stick. The letter r is added to speed up the process)
Finally type diskutil eject /dev/disk2 (hit enter) Now you can unplug the USB drive and plug it back in.
Restart your computer and hold down the Option key on your keyboard as the computer starts up.
You will see the various bootable drives, one of them will be the USB Drive, the name may say Windows. Click it to boot using Tails OS
I would like to add that the USB stick does not appear in the list of possible startup disks on all Mac’s. We tested it on 4 different Mac computers. The USB stick with Tails 4.2 appeared on our iMac Late 2013 model running mac OS High Sierra Version 10.13.6. It did not load on the following three Macs – MacBook Pro 2018 model running macOS Mojave Version 10.14.5, iMac 2010 model running OS X El Capitan Version 10.11.16 and Macbook Air early 2013 running macOS Mojave Version 10.14.6. To get it working on your Mac, follow the below instructions.
If the USB stick does not appear in the list of possible startup disks:
Make sure that you have verified your download of Tails.
Try installing again on the same USB stick.
Try installing on a different USB stick.
Try using the same USB stick to start on a different computer.?If the same USB stick works on a different computer, please report the problem to the Tails help desk as per this article.
Troubleshooting
Please see below links related to some common problems with Tails
If Tails disk does not show up when you restart your computer while holding down the alt/option key on your keyboard, Tails may not be compatible with your mac model/version. See here for tested Mac models.
Keyboard and trackpad do not work when Tails loads – The only way to get Tails working on any Mac’s that have a touch-pad is to use an external mouse (preferably wired) and an external keyboard.
Connecting to a WiFi network in Tails – If you cannot use an Ethernet cable, USB tethering or USB Wi-Fi adapter and must connect to WiFi to access Tails , you can try disable MAC spoofing to get your Wi-Fi interface to work in Tails. However, this does not always work. Disabling MAC spoofing has security implications, so read carefully the documentation about MAC spoofing before doing so. Note that even if MAC spoofing is disabled, your anonymity on the Internet is preserved. In this reddit thread on Help with Tails WiFi on Mac Book Pro, it is recommended to use a cheap USB/WiFi adapter.
Are you having any issues installing Tails OS on a Jump Drive on your Mac? What do you use Tails OS for? What is your favourite application on Tails OS? Please do share in the comments below.