When composing documents and emails using Microsoft Word, standard quotation marks are turned into Smart Quotes. Smart Quotes are stored using non-standard special codes which are incompatible with a number of applications including most email clients other than Microsoft Outlook. This problem also effects LetterMark, which will behave like other applications and display the Smart Quotes as question marks as it is unable to process the non-standard codes used by Word in place of standard quotation marks.
This problem effects all versions of Outlook 2007 and Outlook 2010, as well as earlier versions of Outlook when using Word as your email editor (which is the default configuration).
Note: For compatibility reasons, we highly recommend you do not use Word as your editor in Outlook. The use of Word introduces several compatibility problems with other email clients and document management systems. You should not use Word as your email editor if you intend to send messages outside of your organization as the messages will likely be corrupted by the various email systems on the Internet that are unable to process the special non-standard characters word uses.
To resolve this issue, Smart Quotes should be disabled.
To turn this feature on or off:
This information was obtained from the following Microsoft document: