From mboxrd@z Thu Jan  1 00:00:00 1970
From: Nick Dokos <ndokos@gmail.com>
Subject: Re: Getting checkboxes in HTML output?
Date: Wed, 27 Nov 2013 11:03:38 -0500
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Peter Davis <pfd@pfdstudio.com> writes:

> I noticed that HTML output contains "[ ]" and "[X]", just like the
> mark-up. Wouldn't it make sense to use actual unchecked or checked
> checkboxes in HTML?
>
> Is there a simple way to do this that I've overlooked?
>

A cursory glance through ox-html.el uncovered this:

--8<---------------cut here---------------start------------->8---
(defun org-html-checkbox (checkbox)
  "Format CHECKBOX into HTML."
  (case checkbox (on "<code>[X]</code>")
	(off "<code>[&#xa0;]</code>")
	(trans "<code>[-]</code>")
	(t "")))
--8<---------------cut here---------------end--------------->8---

Maybe you can redefine this function to do what you want?

Nick