War of the Ring
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When does Worn with Sorrow and Toil trigger?
Only when a Companion is taken as a casualty from a Hunt. The designer confirmed the wording is deliberately narrower than 'eliminated', so a Companion removed by The Lure of the Ring does not trigger it, and neither does a guide separating to cut Hunt damage. The card is not discarded after the first loss; it stays until the Fellowship enters a Free Peoples Stronghold.