Apostrophe becomes ? when copy and pasting into text attachments

We have an issue when we attach text notes (attachments) to quotes, repair orders, etc., that when we copy and paste into the text screen from a word document, the apostrophe changes to question mark after we save and exit the document. At the time we save the apostrophe does not change to a question mark, but when we exit the document and query it back up, then click on the attachment paperclip on the toolbar, the apostrophe is now a question mark. Has anyone encountered this before or perhaps have a solution they can share?

Example: The PO's need to be would change to the PO?s need to be.