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How to have 2 plan enrollments during the same period

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We have 2 plans configured. One is for Medical Insurance Premium while the other one is for Life Insurance Premium. The customer doesnt want to club both the plans in a single program. The customer has different enrollment cycles for each which are overlapping. 

medical Insurance: 01-Jun to 30-Jun

Life Insurance: 15-Jun to 15-Jul.

There is an overlapping period of 15 days between them. When I'm trying to process life insurance plan, its backing out the medical insurance plan. Please let me know if its feasible to have 2 plan enrollments at the same time?

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