diff --git a/crates/oxc_prettier/src/doc.rs b/crates/oxc_prettier/src/doc.rs
index 987f14849b63d..155c22e791e16 100644
--- a/crates/oxc_prettier/src/doc.rs
+++ b/crates/oxc_prettier/src/doc.rs
@@ -77,12 +77,19 @@ impl Line {
 pub struct Group<'a> {
     pub contents: Vec<'a, Doc<'a>>,
     pub should_break: bool,
+    pub expanded_states: Option<Vec<'a, Doc<'a>>>,
     pub id: Option<GroupId>,
 }
 
 impl<'a> Group<'a> {
     pub fn new(contents: Vec<'a, Doc<'a>>, should_break: bool) -> Self {
-        Self { contents, should_break, id: None }
+        Self { contents, should_break, id: None, expanded_states: None }
+    }
+    pub fn new_conditional_group(
+        contents: Vec<'a, Doc<'a>>,
+        expanded_states: Vec<'a, Doc<'a>>,
+    ) -> Self {
+        Self { contents, should_break: false, id: None, expanded_states: Some(expanded_states) }
     }
     pub fn with_id(mut self, id: GroupId) -> Self {
         self.id = Some(id);
@@ -244,6 +251,10 @@ fn print_doc_to_debug(doc: &Doc<'_>) -> std::string::String {
             string.push_str("])");
         }
         Doc::Group(group) => {
+            if group.expanded_states.is_some() {
+                string.push_str("conditionalGroup([\n");
+            }
+
             string.push_str("group([\n");
             for (idx, doc) in group.contents.iter().enumerate() {
                 string.push_str(&print_doc_to_debug(doc));
@@ -257,6 +268,17 @@ fn print_doc_to_debug(doc: &Doc<'_>) -> std::string::String {
                 string.push_str(&format!(", id: {id}"));
             }
             string.push_str(" })");
+
+            if let Some(expanded_states) = &group.expanded_states {
+                string.push_str(",\n");
+                for (idx, doc) in expanded_states.iter().enumerate() {
+                    string.push_str(&print_doc_to_debug(doc));
+                    if idx != expanded_states.len() - 1 {
+                        string.push_str(", ");
+                    }
+                }
+                string.push(']');
+            }
         }
         Doc::Line(Line { soft, hard, .. }) => {
             if *soft {
diff --git a/crates/oxc_prettier/src/macros.rs b/crates/oxc_prettier/src/macros.rs
index a6219495e3a6a..3196ecc7c472d 100644
--- a/crates/oxc_prettier/src/macros.rs
+++ b/crates/oxc_prettier/src/macros.rs
@@ -98,6 +98,35 @@ macro_rules! group {
     };
 }
 
+#[macro_export]
+macro_rules! conditional_group {
+    ($p:ident, $c: expr, $( $x:expr ),* $(,)?) => {
+        {
+            use $crate::doc::DocBuilder;
+            let mut temp_vec = $p.vec();
+            $(
+                temp_vec.push($x);
+            )*
+            let contents = $p.vec_single($c);
+            Doc::Group($crate::doc::Group::new_conditional_group(contents, temp_vec))
+        }
+    };
+}
+
+#[macro_export]
+macro_rules! group_break {
+    ($p:ident, $( $x:expr ),* $(,)?) => {
+        {
+            use $crate::doc::DocBuilder;
+            let mut temp_vec = $p.vec();
+            $(
+                temp_vec.push($x);
+            )*
+            Doc::Group($crate::doc::Group::new(temp_vec, true))
+        }
+    };
+}
+
 #[macro_export]
 macro_rules! if_break {
     ($p:ident, $s:expr, $flat:expr, $group_id:expr) => {{
diff --git a/crates/oxc_prettier/src/printer/mod.rs b/crates/oxc_prettier/src/printer/mod.rs
index 231e301de2ea6..66024e26d42c8 100644
--- a/crates/oxc_prettier/src/printer/mod.rs
+++ b/crates/oxc_prettier/src/printer/mod.rs
@@ -140,13 +140,28 @@ impl<'a> Printer<'a> {
                     self.cmds.push(Command::new(indent, Mode::Flat, cmd.doc));
                 } else {
                     let Doc::Group(group) = cmd.doc else { unreachable!() };
-                    self.cmds.extend(
-                        group
-                            .contents
-                            .into_iter()
-                            .rev()
-                            .map(|doc| Command::new(indent, Mode::Break, doc)),
-                    );
+
+                    if let Some(mut expanded_states) = group.expanded_states {
+                        let most_expanded = expanded_states.pop().unwrap();
+                        if group.should_break {
+                            self.cmds.push(Command::new(indent, Mode::Break, most_expanded));
+                            return;
+                        }
+                        for state in expanded_states {
+                            let cmd = Command::new(indent, Mode::Flat, state);
+                            if self.fits(&cmd, remaining_width) {
+                                self.cmds.push(cmd);
+                                return;
+                            }
+                        }
+                        self.cmds.push(Command::new(indent, Mode::Break, most_expanded));
+                    } else {
+                        self.cmds.push(Command::new(
+                            indent,
+                            Mode::Break,
+                            Doc::Array(group.contents),
+                        ));
+                    }
                 }
                 self.set_group_mode_from_last_cmd(group_id);
             }
@@ -360,9 +375,16 @@ impl<'a> Printer<'a> {
                 }
                 Doc::Group(group) => {
                     let mode = if group.should_break { Mode::Break } else { mode };
-                    for d in group.contents.iter().rev() {
-                        queue.push_front((mode, d));
-                    }
+                    if group.expanded_states.is_some() && mode.is_break() {
+                        queue.push_front((
+                            mode,
+                            group.expanded_states.as_ref().unwrap().last().unwrap(),
+                        ));
+                    } else {
+                        for d in group.contents.iter().rev() {
+                            queue.push_front((mode, d));
+                        }
+                    };
                 }
                 Doc::IfBreak(if_break_doc) => {
                     let group_mode = if_break_doc
@@ -413,11 +435,20 @@ impl<'a> Printer<'a> {
     /// Reference:
     /// * https://github.com/prettier/prettier/blob/main/src/document/utils.js#L156-L185
     pub fn propagate_breaks(doc: &mut Doc<'_>) -> bool {
+        let check_array = |arr: &mut oxc_allocator::Vec<'_, Doc<'_>>| {
+            arr.iter_mut().rev().any(|doc| Self::propagate_breaks(doc))
+        };
+
         match doc {
             Doc::BreakParent => true,
             Doc::Group(group) => {
-                let should_break =
-                    group.contents.iter_mut().rev().any(|doc| Self::propagate_breaks(doc));
+                let mut should_break = false;
+                if let Some(expanded_states) = &mut group.expanded_states {
+                    should_break = expanded_states.iter_mut().rev().any(Self::propagate_breaks);
+                }
+                if !should_break {
+                    should_break = check_array(&mut group.contents);
+                }
                 if should_break {
                     group.should_break = should_break;
                 }
@@ -426,9 +457,7 @@ impl<'a> Printer<'a> {
             Doc::IfBreak(d) => Self::propagate_breaks(&mut d.break_contents),
             Doc::Array(arr)
             | Doc::Indent(arr)
-            | Doc::IndentIfBreak(IndentIfBreak { contents: arr, .. }) => {
-                arr.iter_mut().any(|doc| Self::propagate_breaks(doc))
-            }
+            | Doc::IndentIfBreak(IndentIfBreak { contents: arr, .. }) => check_array(arr),
             _ => false,
         }
     }