Linux Chrome dev channel 55.0.2859.0 (64-bit) have no issues with image paste.
Seems that it is ChromeOS specific issue.
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I'm observing same issue in current ChromeOS 55.0.2858.0 dev branch.
At the same time image paste works in Telegram web client (seems that they use contentEditable div instead of textarea)
Do you know whether it's a chrome os bug or google deprecated DataTransfer.items in new chrome's?