diff --git a/datafusion/core/tests/dataframe/mod.rs b/datafusion/core/tests/dataframe/mod.rs
index 6e22aeab61089..26de1e23b38e1 100644
--- a/datafusion/core/tests/dataframe/mod.rs
+++ b/datafusion/core/tests/dataframe/mod.rs
@@ -6851,3 +6851,50 @@ async fn test_duplicate_state_fields_for_dfschema_construct() -> Result<()> {
 
     Ok(())
 }
+
+/// Regression test for https://github.com/apache/datafusion/issues/21411
+/// grouping() should work when wrapped in an alias via the DataFrame API.
+///
+/// This bug only manifests through the DataFrame API because `.alias()` wraps
+/// the `grouping()` call in an `Expr::Alias` node at the aggregate expression
+/// level. The SQL planner handles aliasing separately (via projection), so the
+/// `ResolveGroupingFunction` analyzer rule never sees an `Expr::Alias` wrapper
+/// around the aggregate function in SQL queries — making SQL-based tests
+/// insufficient to cover this case.
+#[tokio::test]
+async fn test_grouping_with_alias() -> Result<()> {
+    use datafusion_functions_aggregate::expr_fn::grouping;
+
+    let df = create_test_table("test")
+        .await?
+        .aggregate(vec![col("a")], vec![grouping(col("a")).alias("g")])?
+        .sort(vec![Sort::new(col("a"), true, false)])?;
+
+    let results = df.collect().await?;
+
+    let expected = [
+        "+-----------+---+",
+        "| a         | g |",
+        "+-----------+---+",
+        "| 123AbcDef | 0 |",
+        "| CBAdef    | 0 |",
+        "| abc123    | 0 |",
+        "| abcDEF    | 0 |",
+        "+-----------+---+",
+    ];
+    assert_batches_eq!(expected, &results);
+
+    // Also verify that nested aliases (e.g. .alias("x").alias("g")) work correctly
+    let df = create_test_table("test")
+        .await?
+        .aggregate(
+            vec![col("a")],
+            vec![grouping(col("a")).alias("x").alias("g")],
+        )?
+        .sort(vec![Sort::new(col("a"), true, false)])?;
+
+    let results = df.collect().await?;
+    assert_batches_eq!(expected, &results);
+
+    Ok(())
+}
diff --git a/datafusion/optimizer/src/analyzer/resolve_grouping_function.rs b/datafusion/optimizer/src/analyzer/resolve_grouping_function.rs
index c12d7fd2ec2f6..95649ab8286b7 100644
--- a/datafusion/optimizer/src/analyzer/resolve_grouping_function.rs
+++ b/datafusion/optimizer/src/analyzer/resolve_grouping_function.rs
@@ -97,15 +97,15 @@ fn replace_grouping_exprs(
         .into_iter()
         .zip(columns.into_iter().skip(group_expr_len + grouping_id_len))
     {
+        let grouping_id_type = is_grouping_set
+            .then(|| {
+                schema
+                    .field_with_name(None, Aggregate::INTERNAL_GROUPING_ID)
+                    .map(|f| f.data_type().clone())
+            })
+            .transpose()?;
         match expr {
             Expr::AggregateFunction(ref function) if is_grouping_function(&expr) => {
-                let grouping_id_type = is_grouping_set
-                    .then(|| {
-                        schema
-                            .field_with_name(None, Aggregate::INTERNAL_GROUPING_ID)
-                            .map(|f| f.data_type().clone())
-                    })
-                    .transpose()?;
                 let grouping_expr = grouping_function_on_id(
                     function,
                     &group_expr_to_bitmap_index,
@@ -117,6 +117,24 @@ fn replace_grouping_exprs(
                     column.name,
                 )));
             }
+            Expr::Alias(Alias {
+                ref relation,
+                ref name,
+                ..
+            }) if is_grouping_function(&expr) => {
+                let function = unwrap_alias_to_grouping_function(&expr)?;
+                let grouping_expr = grouping_function_on_id(
+                    function,
+                    &group_expr_to_bitmap_index,
+                    grouping_id_type,
+                )?;
+                // Preserve the outermost user-provided alias
+                projection_exprs.push(Expr::Alias(Alias::new(
+                    grouping_expr,
+                    relation.clone(),
+                    name.clone(),
+                )));
+            }
             _ => {
                 projection_exprs.push(Expr::Column(column));
                 new_agg_expr.push(expr);
@@ -155,10 +173,27 @@ fn analyze_internal(plan: LogicalPlan) -> Result<Transformed<LogicalPlan>> {
     Ok(transformed_plan)
 }
 
+/// Recursively unwrap `Expr::Alias` nodes to reach the inner `AggregateFunction`.
+/// Returns an error if the innermost expression is not an `AggregateFunction`,
+/// which should not happen if `is_grouping_function` returned true.
+fn unwrap_alias_to_grouping_function(expr: &Expr) -> Result<&AggregateFunction> {
+    match expr {
+        Expr::AggregateFunction(function) => Ok(function),
+        Expr::Alias(Alias { expr, .. }) => unwrap_alias_to_grouping_function(expr),
+        _ => plan_err!("Expected grouping aggregate function inside alias, got {expr}"),
+    }
+}
+
 fn is_grouping_function(expr: &Expr) -> bool {
     // TODO: Do something better than name here should grouping be a built
     // in expression?
-    matches!(expr, Expr::AggregateFunction(AggregateFunction { func, .. }) if func.name() == "grouping")
+    match expr {
+        Expr::AggregateFunction(AggregateFunction { func, .. }) => {
+            func.name() == "grouping"
+        }
+        Expr::Alias(Alias { expr, .. }) => is_grouping_function(expr),
+        _ => false,
+    }
 }
 
 fn contains_grouping_function(exprs: &[Expr]) -> bool {