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That last part of the sentence is the key, however- as you type them. This controls whether Word converts your quote marks and apostrophes as you type them. The control you want to pay attention to is the “Straight Quotes” with “Smart Quotes” check box.

The AutoFormat As You Type tab of the AutoCorrect dialog box. The tab you want to look at on the dialog box is called AutoFormat As You Type. In later versions of Word display the File tab of the ribbon and then click Options.) At the left side of the dialog box click Proofing, and then click AutoCorrect Options. (In Word 2007 click the Office button and then click Word Options. To do this, display the Word Options dialog box. You can see this by displaying the AutoCorrect dialog box. You see, it is part of AutoFormat, which can be considered a portion of the AutoCorrect capabilities of the program. The "why" of what is going on is rooted in how Word implements the smart quotes feature of the program.

If he types "I've," Word uses a smart apostrophe just fine, but if he lets AutoCorrect do the replacement, Word doesn't replace the regular apostrophe with a smart one. Eugene has created an AutoCorrect entry that replaces "ive" with "I've." The problem is that AutoCorrect always seems to do the replacing using a regular apostrophe instead of a smart apostrophe.