The issue relates to the algorithm that converts straight quotes to smart quotes. However if you enter the required character directly from the keyboard, the correct required character is not subject to the conversion.
Workarounds include typing ALT+0146 on the numeric keypad, or do that then save the character as a formatted autocorrect entry using an easily remembered key combination as a trigger e.g. on a UK pattern keyboard #' works for me.
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Graham Mayor - MS MVP (Word) (2002-2019)
Visit my web site for more programming tips and ready made processes www.gmayor.com
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