Hack #2: Running Skype, Zoom, and Microsoft Teams on Tails OS (Two Methods); One Method Involves Running a Guest Operating System Within a Virtual Environment with Tails OS as the Host OS

Short answer: You cannot do this. Skype, Zoom, and MS Teams use UDP (User Datagram Protocol), which the Tor network does not support at the time of this writing (June 2024). All traffic within Tails OS is routed through the Tor network, which means that Internet services that rely on UDP do not work. The Unsafe Browser won't work either because UDP callbacks are disallowed in the Unsafe Browser.

Long answer: You can do this, but you have to be creative. There are two ways: a really hard way (involving emulation) and a (somewhat) easier way. The easy way comes first.

(1) Boot the computer into Tails OS and enable persistent storage and an administrative password.  Connect to the Internet and configure a Tor connection like normal.

(2) Open the "Root Terminal" app (located in the "System Tools" tab of the Applications menu) and type and enter the following command:

(If you cannot view the text of the command, you can download the PDF version of this guide here.  The password to open the PDF document is "aboutwes.com")

(3) Wait for the proxychains to finish installing.  Decide whether you want proxychains to install in the future.  If you want proxychains to install in the future, select "Install Every Time" when prompted.  If you do not select "Install Every Time" then proxychains will not re-install when you power down and turn the computer back on given the non-persistent nature deliberately inherent in Tails OS.

(4) Type and enter the following the command:

(5) Type and enter the following command:

(6) A long string of text appears.  Highlight all the text that appears below the previous command and above the prompter.  Right click with your mouse and select "copy" to copy all that text.

(7) Open the Text Editor app and create a new text document.  Paste all the text you copied from step 6.  Save the file to your Persistent folder.  This is a backup.

(8) Create a new text document in the Text Editor app.  Paste the text again into the new text document.  In most programming languages, the # mark indicates that the line of code is to be ignored by the compiler or interpreter.  Notice the options that have a # mark before them.  The hash mark means that the option following the # mark is disabled.

(9) Remove the # mark before "dynamic_chain"

(10) Add a # mark before "strict_chain"

(11) Add a # mark before "proxy_dns"

(12) Change "socks4" to "socks5" but leave everything else the same

(13) Highlight the entire document you've been working in.  Right click and copy the text.

(14) Go back to the Root Terminal app and type and enter the following command:

(15) Right click and paste.

(16) Press control + D to exit the cat editor.  Note that when you use the "cat >" command, you delete the contents of the file and are replacing those contents with new contents.

(17) Close out the Root Terminal app and the Text Editor app.  I recommend you save the modified settings you created in the Text Editor app to your persistent folder so you can easily paste those settings into the proxychains.conf preference file in the future (when you restart tails the proxychains.conf file will be changed back to the defaults).

(18) Open the Synaptic Package Manager app, which is located under the Applications menu.  Wait for the app to launch and download updated packages.

(19) There's a button with a magnifying glass that says "Search" in the upper right corner of the window.  Click on the button and search for "Firefox"

(20) Scroll down the list of search results until you find "firefox-esr"

(21) Check "firefox-esr" then press the "Apply" button (this button has gears on it and is located in the upper middle of the window).

(22) Wait for "firefox-esr" to finish installing.  Decide whether you want to install Firefox each time you restart Tails OS.  If you do not select "install each time" then Firefox will be lost the next time you power down and restart your computer.

(23) Close out the Synaptic Package Manager app and open the NORMAL, non-Root, Terminal.  The NORMAL Terminal app is located in the "Utilities" tab in the Applications menu.

(24) In the non-root terminal, type and enter the following command:

(25) Next type and enter the following command:

(26) Firefox should launch.  In the address bar type and enter:

(27) You should be able to launch your Zoom meeting.  You should also be able to launch MS Teams and Skype using those companies' web apps as well within the Firefox ESR browser, provided you launched the Firefox ESR browser from the terminal using proxychains.  HOWEVER!  For Microsoft Teams accounts that are managed by a company other than Microsoft, the company that manages the MS Teams account can (and sometimes does) restrict access to the account from specific sets of IP addresses.  If your MS Teams account is subject to an organization policy that restricts certain IP addresses, you might not be able to access MS Teams.  Sorry.  There's no way around that one.

THAT WAS THE "EASY" WAY.

KEEP READING -> : Hack #2.5, Virtual Machines with Tails OS as Host

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