On macOS, openocd has runtime dependencies on libftdi and libcapstone. I needed to install them manually using brew install.
Before manual installation:
$ ls -lart ~/.pico-sdk/openocd/0.12.0+dev total 9320 drwxr-xr-x 3 my_username staff 96 Sep 2 18:28 .. -rw-r--r-- 1 my_username staff 76592 Sep 2 18:28 libhidapi.dylib -r--r--r-- 1 my_username staff 179152 Sep 2 18:28 libusb-1.0.dylib -rwxr-xr-x 1 my_username staff 4511000 Sep 2 18:28 openocd drwxr-xr-x 15 my_username staff 480 Sep 2 18:28 scripts lrwxr-xr-x 1 my_username staff 59 Sep 2 18:28 openocd.exe -> /Users/my_username/.pico-sdk/openocd/0.12.0+dev/openocd $ otool -L /Users/my_username/.pico-sdk/openocd/0.12.0+dev/openocd /Users/my_username/.pico-sdk/openocd/0.12.0+dev/openocd: /opt/homebrew/opt/libftdi/lib/libftdi1.2.dylib (compatibility version 2.0.0, current version 2.5.0) @loader_path/libusb-1.0.dylib (compatibility version 5.0.0, current version 5.0.0) @loader_path/libhidapi.dylib (compatibility version 0.0.0, current version 0.14.0) /usr/lib/libSystem.B.dylib (compatibility version 1.0.0, current version 1345.100.2) /opt/homebrew/opt/capstone/lib/libcapstone.5.dylib (compatibility version 5.0.0, current version 5.0.1) $ ls -l /opt/homebrew/opt/libftdi/lib/libftdi1.2.dylib ls: /opt/homebrew/opt/libftdi/lib/libftdi1.2.dylib: No such file or directory $ ls -l /opt/homebrew/opt/capstone/lib/libcapstone.5.dylib ls: /opt/homebrew/opt/capstone/lib/libcapstone.5.dylib: No such file or directory
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