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Discussion on: Headless Raspberry Pi Zero W Setup

 
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Dennis Hildenbrand

Probably a little late but the documentation says "When the Pi boots, it looks for the ssh file. If it is found, SSH is enabled and the file is deleted.".

It's similar for wpa_supplicant.conf (see documentation) "Put this file in the boot folder, and when the Pi first boots, it will copy that file into the correct location in the Linux root file system and use those settings to start up wireless networking."