Since TailwindCSS generates the expected CSS code perfectly, the issue is that the expected CSS code itself does not work properly. The expected CSS code is correct:

Input

<div class="cursor-pointer">...</div>

Generated CSS (check yourself: Playground)

.cursor-pointer {
  cursor: pointer;
}

Since the syntax is correct and other overrides can be ruled out, the only remaining explanation is: a browser bug.

Some external sources mentioning a similar browser bug in Safari:

• https://discussions.apple.com/thread/250283073?sortBy=rank
• https://www.reddit.com/r/osx/comments/b9fc3x/safari_cursor_not_changing_to_a_hand
• https://forums.macrumors.com/threads/mouse-pointer-not-changing-to-hand-or-text-cursor-macos-14-2.2415236/
• https://www.reddit.com/r/webdev/comments/1fj36kf/comment/mnrz3ad (latest? 4 months ago)