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It doesn't matter what service is used to send the emails because what service is receiving the emails is equally as important. Unless this person has control over both ends--sending and delivery--there is no guarantee of delivery using email. Even when you do control both ends stuff just happens, like the Internet being out at the delivery end of things. Note how the IRS and certain companies will send snail mail reminders of certain things even if you have signed up for e-delivery.
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