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This setting is a "guess" so it is perfectly fine if it failed to "guess". We use https://github.com/aadsm/jschardet as library for detection so feel free to report an issue to them with detailed steps how to reproduce.
Problem: When I open a file, I have to guess the encoding or open with another text editor
I set this settings:
"files.autoGuessEncoding": true
This not autodetected ISO-8859-1 encoding in vsCode
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