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Shadows don't use your CSS variables directly:

.shadow-lg {
  --tw-shadow: inset 0 1px 2px var(--tw-shadow-color, #0000ff70), 0 4px 6px var(--tw-shadow-color, #00000030), 0 6px 10px var(--tw-shadow-color, #00000015);
  box-shadow: var(--tw-inset-shadow), var(--tw-inset-ring-shadow), var(--tw-ring-offset-shadow), var(--tw-ring-shadow), var(--tw-shadow);
}

See how the shadow value is kind of transposed into the value with some modifications. Notice how the var(--shadow-sm) CSS variable does not exist. Hence why the dark version never overrides the shadow.

Some workarounds:

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