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The Amnesic Incognito Live System (TAILS) is a live CD/USB distribution preconfigured so that everything is safely routed through Tor and leaves no trace on the local system.

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Any concerns with online upgrade of tails? Should new ISO be downloaded instead?

I don't see how running a Tails virtual machine (if that is what you mean by "... unless you are running something like VMWare or VirtualBox."), has any mitigating impact on my scenario/concern. … I believe that anything that could be done to a physical instance of Tails (hack/snoop/sniff/etc.), can be done to a virtual instance of Tails, can it not? …
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