What version of Winfax and ACT!? Are you on Exchange? (If ACT! is set up to use Exchange and you are using ACT! for the database, WinFax in certain versions won't work). It was always a pretty reliable solution for me, but I haven't used the combination for a couple years.
If you have email addresses for most of your contacts, a good solution that we have started using is CoolerEmail (
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