That's pretty weird, maybe the SD card does not persist the data.
Same problem as Lappy and Derick. Do you think I should replace the card? I'm using a ScanDisk that came with the kit.
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."
Curiously, mine does the same! But only after booting the PI from it. A normal write, unmount, mount, read, works fine!
I was facing the same. This worked for me in wpa_supplicant.conf:
I also made sure, the file has unix line endings. Using vim, write the file using ':w ++ff=unix'.
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