Sharing files from Finder to Simulator doesn't work

I'm trying to copy some files from the Finder on macOS 14 to several Simulator instances running iOS 16 and 17. When I right-click the file in the Finder, I can select Share > Simulator, then a share dialog pops up where I select the relevant Simulator and click on Send. According to this official help topic, the Files app should open allowing me to choose the destination, but instead nothing happens and the shared file is nothing to be seen. What's the issue?

Sharing files from Finder to Simulator doesn't work
 
 
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