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What is the recommended way to set different preferred email addresses for a contact for each of their groups?

Eg. Contact A has a work email address (primary) and a home email address, and is in 'Work' group and 'Home' group.

How can a mailing to 'Work' group go to their work email address, and a mailing to 'Home' group go to their home email address (and not their primary work email address)?

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