Images inserted with the 'Save with document' option don't necessarily update automatically. For that, you also need to set Word's 'update automatic links at open' and 'update linked data before printing' options. On PC versions of Word, these are found under File|Options|Advanced>General and File|Options|Display>Printing, respectively.
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Cheers,
Paul Edstein
[Fmr MS MVP - Word]
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