diff --git a/sql/catalyst/src/main/scala/org/apache/spark/sql/catalyst/optimizer/RewriteWithExpression.scala b/sql/catalyst/src/main/scala/org/apache/spark/sql/catalyst/optimizer/RewriteWithExpression.scala
index 5d85e89e1eab..424f04b2c8c2 100644
--- a/sql/catalyst/src/main/scala/org/apache/spark/sql/catalyst/optimizer/RewriteWithExpression.scala
+++ b/sql/catalyst/src/main/scala/org/apache/spark/sql/catalyst/optimizer/RewriteWithExpression.scala
@@ -186,6 +186,8 @@ object RewriteWithExpression extends Rule[LogicalPlan] {
           case With(child, defs) =>
             // For With in the conditional branches, they may not be evaluated at all and we can't
             // pull the common expressions into a project which will always be evaluated. Inline it.
+            // SPARK-58902: Inlining nondeterministic expressions can cause multiple evaluations
+            // per row. Lazy per-row memoization is recommended for multi-referenced expressions.
             val refToExpr = defs.map(d => d.id -> d.child).toMap
             child.transformWithPruning(_.containsPattern(COMMON_EXPR_REF)) {
               case ref: CommonExpressionRef => refToExpr(ref.id)
diff --git a/sql/catalyst/src/test/scala/org/apache/spark/sql/catalyst/optimizer/RewriteWithExpressionSuite.scala b/sql/catalyst/src/test/scala/org/apache/spark/sql/catalyst/optimizer/RewriteWithExpressionSuite.scala
index 8918b58ca1b5..4ff7404554cf 100644
--- a/sql/catalyst/src/test/scala/org/apache/spark/sql/catalyst/optimizer/RewriteWithExpressionSuite.scala
+++ b/sql/catalyst/src/test/scala/org/apache/spark/sql/catalyst/optimizer/RewriteWithExpressionSuite.scala
@@ -500,4 +500,19 @@ class RewriteWithExpressionSuite extends PlanTest {
     val plan = testRelation.select(expr.as("col"))
     comparePlans(Optimizer.execute(plan), testRelation.select((a + a + 1).as("col")))
   }
+
+  test("SPARK-58902: inlines With expression inside conditional branches") {
+    val a = testRelation.output.head
+    val exprDef = CommonExpressionDef(a + a)
+    val exprRef = new CommonExpressionRef(exprDef)
+    // CaseWhen with With inside the ELSE branch
+    val withExpr = With(exprRef > 0 && exprRef < 10, Seq(exprDef))
+    val caseWhenExpr = CaseWhen(Seq((a < 0, Literal(false))), Some(withExpr))
+    val plan = testRelation.select(caseWhenExpr.as("col")).analyze
+
+    val expectedPlan = testRelation.select(
+      CaseWhen(Seq((a < 0, Literal(false))), Some((a + a > 0) && (a + a < 10))).as("col")
+    ).analyze
+    comparePlans(Optimizer.execute(plan), expectedPlan)
+  }
 }