Hi Etienne,
I know it’s annoying when the "Insert Image" button does nothing in Outlook signatures, but a few things are worth checking. First, make sure your message format is set to HTML (File > Options > Mail), since images won’t work in plain text or rich text. If you’re on the new Outlook, this may also be a bug, so updating Outlook or temporarily switching back to classic Outlook can help. Try disabling any add-ins or running Outlook in safe mode, because add-ins sometimes block that image dialog from opening. If the button still does nothing, repair your Office installation to fix any broken files, and as a test, create a fresh signature with a small local image to see if it works.
Kind regards,