Tiny Epic Kingdoms

When an alliance is broken and I choose to retreat with multiple meeples, do I need to pay the cost of retreat for each meeple separately?

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Yes
For each meeple you have in a region with your former ally, you must choose separately to either lose the meeple or to retreat with it, paying 1 food for each of your meeples in play at the time this meeple is retreating. You may choose the order you resolve this for each meeple. So you may lose one meeple first to reduce the retreating cost for another meeple.
Related Rule(s)