diff --git a/datafusion/optimizer/src/simplify_expressions/expr_simplifier.rs b/datafusion/optimizer/src/simplify_expressions/expr_simplifier.rs
index 97dfc09c4f2a6..3c96f953f0000 100644
--- a/datafusion/optimizer/src/simplify_expressions/expr_simplifier.rs
+++ b/datafusion/optimizer/src/simplify_expressions/expr_simplifier.rs
@@ -1400,13 +1400,35 @@ impl<S: SimplifyInfo> TreeNodeRewriter for Simplifier<'_, S> {
             //
 
             // CASE WHEN true THEN A ... END --> A
+            // CASE WHEN X THEN A WHEN TRUE THEN B ... END --> CASE WHEN X THEN A ELSE B END
             Expr::Case(Case {
                 expr: None,
                 mut when_then_expr,
                 else_expr: _,
-            }) if !when_then_expr.is_empty() && is_true(when_then_expr[0].0.as_ref()) => {
-                let (_, then_) = when_then_expr.swap_remove(0);
-                Transformed::yes(*then_)
+                // if let guard is not stabilized so we can't use it yet: https://github.com/rust-lang/rust/issues/51114
+                // Once it's supported we can avoid searching through when_then_expr twice in the below .any() and .position() calls
+                // }) if let Some(i) = when_then_expr.iter().position(|(when, _)| is_true(when.as_ref())) => {
+            }) if when_then_expr
+                .iter()
+                .any(|(when, _)| is_true(when.as_ref())) =>
+            {
+                let i = when_then_expr
+                    .iter()
+                    .position(|(when, _)| is_true(when.as_ref()))
+                    .unwrap();
+                let (_, then_) = when_then_expr.swap_remove(i);
+                // CASE WHEN true THEN A ... END --> A
+                if i == 0 {
+                    return Ok(Transformed::yes(*then_));
+                }
+
+                // CASE WHEN X THEN A WHEN TRUE THEN B ... END --> CASE WHEN X THEN A ELSE B END
+                when_then_expr.truncate(i);
+                Transformed::yes(Expr::Case(Case {
+                    expr: None,
+                    when_then_expr,
+                    else_expr: Some(then_),
+                }))
             }
 
             // CASE
@@ -3563,7 +3585,7 @@ mod tests {
     }
 
     #[test]
-    fn simplify_expr_case_when_true() {
+    fn simplify_expr_case_when_first_true() {
         // CASE WHEN true THEN 1 ELSE x END --> 1
         assert_eq!(
             simplify(Expr::Case(Case::new(
@@ -3632,6 +3654,82 @@ mod tests {
         assert_eq!(simplify(expr.clone()), expr);
     }
 
+    #[test]
+    fn simplify_expr_case_when_any_true() {
+        // CASE WHEN x > 0 THEN a WHEN true THEN b ELSE c END --> CASE WHEN x > 0 THEN a ELSE b END
+        assert_eq!(
+            simplify(Expr::Case(Case::new(
+                None,
+                vec![
+                    (Box::new(col("x").gt(lit(0))), Box::new(col("a"))),
+                    (Box::new(lit(true)), Box::new(col("b"))),
+                ],
+                Some(Box::new(col("c"))),
+            ))),
+            Expr::Case(Case::new(
+                None,
+                vec![(Box::new(col("x").gt(lit(0))), Box::new(col("a")))],
+                Some(Box::new(col("b"))),
+            ))
+        );
+
+        // CASE WHEN x > 0 THEN a WHEN y < 0 THEN b WHEN true THEN c WHEN z = 0 THEN d ELSE e END
+        // --> CASE WHEN x > 0 THEN a WHEN y < 0 THEN b ELSE c END
+        assert_eq!(
+            simplify(Expr::Case(Case::new(
+                None,
+                vec![
+                    (Box::new(col("x").gt(lit(0))), Box::new(col("a"))),
+                    (Box::new(col("y").lt(lit(0))), Box::new(col("b"))),
+                    (Box::new(lit(true)), Box::new(col("c"))),
+                    (Box::new(col("z").eq(lit(0))), Box::new(col("d"))),
+                ],
+                Some(Box::new(col("e"))),
+            ))),
+            Expr::Case(Case::new(
+                None,
+                vec![
+                    (Box::new(col("x").gt(lit(0))), Box::new(col("a"))),
+                    (Box::new(col("y").lt(lit(0))), Box::new(col("b"))),
+                ],
+                Some(Box::new(col("c"))),
+            ))
+        );
+
+        // CASE WHEN x > 0 THEN a WHEN y < 0 THEN b WHEN true THEN c END (no else)
+        // --> CASE WHEN x > 0 THEN a WHEN y < 0 THEN b ELSE c END
+        assert_eq!(
+            simplify(Expr::Case(Case::new(
+                None,
+                vec![
+                    (Box::new(col("x").gt(lit(0))), Box::new(col("a"))),
+                    (Box::new(col("y").lt(lit(0))), Box::new(col("b"))),
+                    (Box::new(lit(true)), Box::new(col("c"))),
+                ],
+                None,
+            ))),
+            Expr::Case(Case::new(
+                None,
+                vec![
+                    (Box::new(col("x").gt(lit(0))), Box::new(col("a"))),
+                    (Box::new(col("y").lt(lit(0))), Box::new(col("b"))),
+                ],
+                Some(Box::new(col("c"))),
+            ))
+        );
+
+        // Negative test: CASE WHEN x > 0 THEN a WHEN y < 0 THEN b ELSE c END should not be simplified
+        let expr = Expr::Case(Case::new(
+            None,
+            vec![
+                (Box::new(col("x").gt(lit(0))), Box::new(col("a"))),
+                (Box::new(col("y").lt(lit(0))), Box::new(col("b"))),
+            ],
+            Some(Box::new(col("c"))),
+        ));
+        assert_eq!(simplify(expr.clone()), expr);
+    }
+
     fn distinct_from(left: impl Into<Expr>, right: impl Into<Expr>) -> Expr {
         Expr::BinaryExpr(BinaryExpr {
             left: Box::new(left.into()),