First of all, let's clarify that the setting of "Update automatically" in
the Insert | Date and Time dialog has nothing to do with existing dates or
fields; this check box just governs whether the date inserted using this
dialog is plain text or a DATE field.
As for why the date doesn't update in the given document, I would imagine
that the date appears in the document body on the first page and in the
header on subsequent pages. Fields in general (including the DATE field) are
no longer updated on opening a document. All fields in the header and footer
are updated each time the document is repaginated (which happens frequently
in Print Layout view), but fields in the document body are not updated till
you print or Print Preview (unless you update them manually using F9).
Suzanne S. Barnhill
Microsoft MVP (Word)
Words into Type
Fairhope, Alabama USA