Hello @FallsSchools ,
Unique email addresses are what denotes a unique contact for billing, emailing, compliance (permissions, anti-spam, etc.) For this reason, contacts can only have one active email address.
If you have a singular person with multiple emails addresses, and you want to be able to email all of them, you'd need to import each of those email addresses as an individual contact. This may require you to upload a contact list multiple times, or import contacts with this kind of setup using one of the other available methods.
If you just want to keep records of a person having multiple addresses beyond their primary, you can import those as custom fields you've setup (e.g. Other Email 2, Other Email 3, etc.)
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