Hi Matthew

Here are some ideas that alone or together might help.

First, you could put all paragraphs with a Ticked box bullet into a
paragraph style called "Ticked", and all the paragraphs with an Unticked
bullet into a style called "NotTicked". Then, after you've copied and pasted
the text, re-create the numbering scheme in code so that all paragraphs in
style Ticked have a ticked box and all paragraphs in style Unticked have an
un-ticked box.

Alternatively, working on a copy of your document, you could use
ActiveDocument.ConvertNumbersToText. That will change all automatic
numbering to plain text (including bullets). After you copy the text, you
could search for the appropriate bullet characters and apply the appropriate
bulleting. Note that doing .ConvertNumbersToText is irreversible: you can't
get your automatic numbering back again without re-applying it.

Finaly, you could find out what is actually causing the problem in the first
place. It is probably because of style issues, and the following may help:
Why does text change format when I copy it into another document?
http://www.ShaunaKelly.com/word/styles/FormatOfTextChanges.html

Once you've discovered the underlying cause of the problem, the solution may
be obvious.

Hope this helps.

Shauna Kelly.  Microsoft MVP.
http://www.shaunakelly.com/word