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When you relaunch a HOBO data logger, the device reverts to the beginning of its memory and starts writing new data over the old.
The attached image shows both the incorrect and correct assembly of a logger coupler to the BASE-U-4 (Optic Base station) and the U-DTW-1 (Waterproof Shuttle).
A few years back, Apple removed traditional USB ports and went to something called USB-C. This makes everything incompatible, including HDMI & Ethernet cables.