An insurance enrollment and underwriting method includes providing a first user interface with one or more controls for enabling a user to specify one or more health conditions in an enrollment application for pet health insurance. Data representing one or more health conditions specified through the first user interface is received. That data is electronically processed. Each condition is electronically flagged as a condition that is acceptable, precluded, or for manual review. A dollar limit of coverage for each of a plurality of diagnoses in lieu of one or more exclusions is calculated. The plurality of diagnoses include one or more diagnoses related to one or more of the health conditions. Where all conditions are and flagged as acceptable or determined to be acceptable following a manual review, an active policy is packaged to include coverage for each of the plurality of diagnoses up to each diagnosis' corresponding dollar limit of coverage.