diff --git a/datafusion/optimizer/src/simplify_expressions/expr_simplifier.rs b/datafusion/optimizer/src/simplify_expressions/expr_simplifier.rs
index b491a3529f353..95af4c6bb86b1 100644
--- a/datafusion/optimizer/src/simplify_expressions/expr_simplifier.rs
+++ b/datafusion/optimizer/src/simplify_expressions/expr_simplifier.rs
@@ -1436,33 +1436,49 @@ 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
+            // CASE WHEN false THEN A END --> NULL
+            // CASE WHEN false THEN A ELSE B END --> B
+            // CASE WHEN X THEN A WHEN false THEN B END --> CASE WHEN X THEN A ELSE B END
             Expr::Case(Case {
                 expr: None,
-                mut when_then_expr,
-                else_expr: _,
-                // 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())) => {
+                when_then_expr,
+                mut else_expr,
             }) if when_then_expr
                 .iter()
-                .any(|(when, _)| is_true(when.as_ref())) =>
+                .any(|(when, _)| is_true(when.as_ref()) || is_false(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_));
+                let out_type = info.get_data_type(&when_then_expr[0].1)?;
+                let mut new_when_then_expr = Vec::with_capacity(when_then_expr.len());
+
+                for (when, then) in when_then_expr.into_iter() {
+                    if is_true(when.as_ref()) {
+                        // Skip adding the rest of the when-then expressions after WHEN true
+                        // CASE WHEN X THEN A WHEN TRUE THEN B ... END --> CASE WHEN X THEN A ELSE B END
+                        else_expr = Some(then);
+                        break;
+                    } else if !is_false(when.as_ref()) {
+                        new_when_then_expr.push((when, then));
+                    }
+                    // else: skip WHEN false cases
+                }
+
+                // Exclude CASE statement altogether if there are no when-then expressions left
+                if new_when_then_expr.is_empty() {
+                    // CASE WHEN false THEN A ELSE B END --> B
+                    if let Some(else_expr) = else_expr {
+                        return Ok(Transformed::yes(*else_expr));
+                    // CASE WHEN false THEN A END --> NULL
+                    } else {
+                        let null =
+                            Expr::Literal(ScalarValue::try_new_null(&out_type)?, None);
+                        return Ok(Transformed::yes(null));
+                    }
                 }
 
-                // 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_),
+                    when_then_expr: new_when_then_expr,
+                    else_expr,
                 }))
             }
 
@@ -3810,53 +3826,53 @@ mod tests {
 
     #[test]
     fn simplify_expr_case_when_first_true() {
-        // CASE WHEN true THEN 1 ELSE x END --> 1
+        // CASE WHEN true THEN 1 ELSE c1 END --> 1
         assert_eq!(
             simplify(Expr::Case(Case::new(
                 None,
                 vec![(Box::new(lit(true)), Box::new(lit(1)),)],
-                Some(Box::new(col("x"))),
+                Some(Box::new(col("c1"))),
             ))),
             lit(1)
         );
 
-        // CASE WHEN true THEN col("a") ELSE col("b") END --> col("a")
+        // CASE WHEN true THEN col('a') ELSE col('b') END --> col('a')
         assert_eq!(
             simplify(Expr::Case(Case::new(
                 None,
-                vec![(Box::new(lit(true)), Box::new(col("a")),)],
-                Some(Box::new(col("b"))),
+                vec![(Box::new(lit(true)), Box::new(lit("a")),)],
+                Some(Box::new(lit("b"))),
             ))),
-            col("a")
+            lit("a")
         );
 
-        // CASE WHEN true THEN col("a") WHEN col("x") > 5 THEN col("b") ELSE col("c") END --> col("a")
+        // CASE WHEN true THEN col('a') WHEN col('x') > 5 THEN col('b') ELSE col('c') END --> col('a')
         assert_eq!(
             simplify(Expr::Case(Case::new(
                 None,
                 vec![
-                    (Box::new(lit(true)), Box::new(col("a"))),
-                    (Box::new(col("x").gt(lit(5))), Box::new(col("b"))),
+                    (Box::new(lit(true)), Box::new(lit("a"))),
+                    (Box::new(lit("x").gt(lit(5))), Box::new(lit("b"))),
                 ],
-                Some(Box::new(col("c"))),
+                Some(Box::new(lit("c"))),
             ))),
-            col("a")
+            lit("a")
         );
 
-        // CASE WHEN true THEN col("a") END --> col("a") (no else clause)
+        // CASE WHEN true THEN col('a') END --> col('a') (no else clause)
         assert_eq!(
             simplify(Expr::Case(Case::new(
                 None,
-                vec![(Box::new(lit(true)), Box::new(col("a")),)],
+                vec![(Box::new(lit(true)), Box::new(lit("a")),)],
                 None,
             ))),
-            col("a")
+            lit("a")
         );
 
-        // Negative test: CASE WHEN a THEN 1 ELSE 2 END should not be simplified
+        // Negative test: CASE WHEN c2 THEN 1 ELSE 2 END should not be simplified
         let expr = Expr::Case(Case::new(
             None,
-            vec![(Box::new(col("a")), Box::new(lit(1)))],
+            vec![(Box::new(col("c2")), Box::new(lit(1)))],
             Some(Box::new(lit(2))),
         ));
         assert_eq!(simplify(expr.clone()), expr);
@@ -3869,10 +3885,10 @@ mod tests {
         ));
         assert_ne!(simplify(expr), lit(1));
 
-        // Negative test: CASE WHEN col("x") > 5 THEN 1 ELSE 2 END should not be simplified
+        // Negative test: CASE WHEN col('c1') > 5 THEN 1 ELSE 2 END should not be simplified
         let expr = Expr::Case(Case::new(
             None,
-            vec![(Box::new(col("x").gt(lit(5))), Box::new(lit(1)))],
+            vec![(Box::new(col("c1").gt(lit(5))), Box::new(lit(1)))],
             Some(Box::new(lit(2))),
         ));
         assert_eq!(simplify(expr.clone()), expr);
@@ -3880,76 +3896,124 @@ mod tests {
 
     #[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
+        // CASE WHEN c3 > 0 THEN 'a' WHEN true THEN 'b' ELSE 'c' END --> CASE WHEN c3 > 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"))),
+                    (Box::new(col("c3").gt(lit(0))), Box::new(lit("a"))),
+                    (Box::new(lit(true)), Box::new(lit("b"))),
                 ],
-                Some(Box::new(col("c"))),
+                Some(Box::new(lit("c"))),
             ))),
             Expr::Case(Case::new(
                 None,
-                vec![(Box::new(col("x").gt(lit(0))), Box::new(col("a")))],
-                Some(Box::new(col("b"))),
+                vec![(Box::new(col("c3").gt(lit(0))), Box::new(lit("a")))],
+                Some(Box::new(lit("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
+        // CASE WHEN c3 > 0 THEN 'a' WHEN c4 < 0 THEN 'b' WHEN true THEN 'c' WHEN c3 = 0 THEN 'd' ELSE 'e' END
+        // --> CASE WHEN c3 > 0 THEN 'a' WHEN c4 < 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"))),
+                    (Box::new(col("c3").gt(lit(0))), Box::new(lit("a"))),
+                    (Box::new(col("c4").lt(lit(0))), Box::new(lit("b"))),
+                    (Box::new(lit(true)), Box::new(lit("c"))),
+                    (Box::new(col("c3").eq(lit(0))), Box::new(lit("d"))),
                 ],
-                Some(Box::new(col("e"))),
+                Some(Box::new(lit("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"))),
+                    (Box::new(col("c3").gt(lit(0))), Box::new(lit("a"))),
+                    (Box::new(col("c4").lt(lit(0))), Box::new(lit("b"))),
                 ],
-                Some(Box::new(col("c"))),
+                Some(Box::new(lit("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
+        // CASE WHEN c3 > 0 THEN 1 WHEN c4 < 0 THEN 2 WHEN true THEN 3 END (no else)
+        // --> CASE WHEN c3 > 0 THEN 1 WHEN c4 < 0 THEN 2 ELSE 3 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("c3").gt(lit(0))), Box::new(lit(1))),
+                    (Box::new(col("c4").lt(lit(0))), Box::new(lit(2))),
+                    (Box::new(lit(true)), Box::new(lit(3))),
                 ],
                 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"))),
+                    (Box::new(col("c3").gt(lit(0))), Box::new(lit(1))),
+                    (Box::new(col("c4").lt(lit(0))), Box::new(lit(2))),
                 ],
-                Some(Box::new(col("c"))),
+                Some(Box::new(lit(3))),
             ))
         );
 
-        // Negative test: CASE WHEN x > 0 THEN a WHEN y < 0 THEN b ELSE c END should not be simplified
+        // Negative test: CASE WHEN c3 > 0 THEN c3 WHEN c4 < 0 THEN 2 ELSE 3 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"))),
+                (Box::new(col("c3").gt(lit(0))), Box::new(col("c3"))),
+                (Box::new(col("c4").lt(lit(0))), Box::new(lit(2))),
             ],
-            Some(Box::new(col("c"))),
+            Some(Box::new(lit(3))),
+        ));
+        assert_eq!(simplify(expr.clone()), expr);
+    }
+
+    #[test]
+    fn simplify_expr_case_when_any_false() {
+        // CASE WHEN false THEN 'a' END --> NULL
+        assert_eq!(
+            simplify(Expr::Case(Case::new(
+                None,
+                vec![(Box::new(lit(false)), Box::new(lit("a")))],
+                None,
+            ))),
+            Expr::Literal(ScalarValue::Utf8(None), None)
+        );
+
+        // CASE WHEN false THEN 2 ELSE 1 END --> 1
+        assert_eq!(
+            simplify(Expr::Case(Case::new(
+                None,
+                vec![(Box::new(lit(false)), Box::new(lit(2)))],
+                Some(Box::new(lit(1))),
+            ))),
+            lit(1),
+        );
+
+        // CASE WHEN c3 < 10 THEN 'b' WHEN false then c3 ELSE c4 END --> CASE WHEN c3 < 10 THEN b ELSE c4 END
+        assert_eq!(
+            simplify(Expr::Case(Case::new(
+                None,
+                vec![
+                    (Box::new(col("c3").lt(lit(10))), Box::new(lit("b"))),
+                    (Box::new(lit(false)), Box::new(col("c3"))),
+                ],
+                Some(Box::new(col("c4"))),
+            ))),
+            Expr::Case(Case::new(
+                None,
+                vec![(Box::new(col("c3").lt(lit(10))), Box::new(lit("b")))],
+                Some(Box::new(col("c4"))),
+            ))
+        );
+
+        // Negative test: CASE WHEN c3 = 4 THEN 1 ELSE 2 END should not be simplified
+        let expr = Expr::Case(Case::new(
+            None,
+            vec![(Box::new(col("c3").eq(lit(4))), Box::new(lit(1)))],
+            Some(Box::new(lit(2))),
         ));
         assert_eq!(simplify(expr.clone()), expr);
     }