Cheapest priced copy (The Brothers' War): $2.79 at Card Kingdom, near mint, their price list as of .
Painful Quandary 
Enchantment · Rare · Foundations · #179
Whenever an opponent casts a spell, that player loses 5 life unless they discard a card.
Legal inCommanderBrawlStandardPioneerModernLegacyVintage
Not legal inPauper
7 printings · $2.79 to $12.99 at Card Kingdom
| Set | Number | Rarity | Card Kingdom | Foil |
|---|---|---|---|---|
| The Brothers' War | 111 | Rare | $2.79 | $2.99 |
| The Brothers' War | 331 | Rare | $4.99 | $4.99 |
| Foundations | 179 | Rare | $2.79 | $2.99 |
| The Brothers' War Promos | 111p | Rare | $3.49 | $3.49 |
| The Brothers' War Promos | 111s | Rare | — | $4.99Out of stock |
| Foundations Promos | 179s | Rare | — | $5.49 |
| Scars of Mirrodin | 73 | Rare | $4.49 | $12.99 |
2 rulings from Wizards of the Coast
- 1 January 2011Whenever an opponent casts a spell, Painful Quandary's ability triggers and goes on the stack on top of it. It will resolve before the spell does.
- 14 October 2022Whenever an opponent casts a spell, Painful Quandary's ability triggers and goes on the stack on top of it. It will resolve before the spell does.