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Yes, it is possible, but this approach alone could monitor only new unique characters, subsequent characters does not produce requests. I proposed perhaps it could be worked around if subsequent CSS updates defined new font stack for input consisting of one font covering known input value in single ligature and as a fallback classical "keylogging" font.
So instead of requesting a bg image, you would use @fontface
I think you can also use font subsetting to request fonts for certain characters
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