Potential answers for "Gives a hard time"

⭐⭐⭐⭐ RAGSON
⭐⭐ IRONAGE
⭐⭐ DIS
⭐⭐ GRIEF
⭐⭐ TORN
⭐⭐ SARA
⭐⭐ LENDS
⭐⭐ AGONIZES
⭐⭐ JAILSTRETCH

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Hopeful hit   Perplexing problem   Get ready for an exam, perhaps