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In September 2020 I published the second edition of my workbook on anonymous and secure digital communication in the English language. It suggests 57 hands on exercises und user tasks.
Among many other privacy tools it also describes Academic Signature and ways to combine this and other tools(GnuPG, I2P, TOR, TAILS, OTR, Onionshare,...) to allow for protected message transfer. Such message transfer will protect content as well as anonymity of recipient and sender against adversaries, which may be powerful enough to have full access to the digital infrastructure used in the communication.
The English language version of the book is called "Surveillance and the Art of Digital Camouflage".

Surveillance and the Art of Digital Camouflage
ISBN 978-3-752994-16-2
epubli GmbH Berlin 2020

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It can be acquired from the publisher here
or e.g. from amazon here.