Hello @PasadenaCove , The 1 and 2 fields bit was referring to mitchelll121 's original post.
Ultimately, you're going to need to have your contacts (unique email addresses) separated out for the upload. Even if you have several "duplicates" based on physical address, name, etc., it's the unique email addresses that ultimately determine a unique contact for sending, reporting, billing, etc.
You can technically have a single contact with multiple other email addresses listed as custom fields, but only the address listed for a contact's official Email Address field will be available for sending to.
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