When typing /image and clicking on the contextual menu, instead of opening the file picker, the contextual menu simply disappears. I have the same behavior on my Mac. I tried different browsers without popup blockers.
HiĀ @Antoine Dubucwelcome to the community and thank you for your question.This is indeed a strange behaviour. Is this still happening? Sometimes those hiccups can happen and dissapear as quickly as they came.I can confirm that it works for me on a test site with Chrome on macOS.GreetingsPhilipp
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