diff --git a/crates/oxc_prettier/src/doc.rs b/crates/oxc_prettier/src/doc.rs
index ac83aea56..a6b0ac8ad 100644
--- a/crates/oxc_prettier/src/doc.rs
+++ b/crates/oxc_prettier/src/doc.rs
@@ -21,7 +21,7 @@ pub enum Doc<'a> {
     /// Groups are usually nested, and the printer will try to fit everything on one line,
     /// but if it doesn't fit it will break the outermost group first and try again.
     /// It will continue breaking groups until everything fits (or there are no more groups to break).
-    Group(Vec<'a, Doc<'a>>),
+    Group(Group<'a>),
     /// Specify a line break.
     /// If an expression fits on one line, the line break will be replaced with a space.
     /// Line breaks always indent the next line with the current level of indentation.
@@ -36,6 +36,18 @@ pub enum Doc<'a> {
     IfBreak(Box<'a, Doc<'a>>),
 }
 
+#[derive(Debug)]
+pub struct Group<'a> {
+    pub contents: Vec<'a, Doc<'a>>,
+    pub should_break: bool,
+}
+
+impl<'a> Group<'a> {
+    pub fn new(contents: Vec<'a, Doc<'a>>, should_break: bool) -> Self {
+        Self { contents, should_break }
+    }
+}
+
 #[derive(Clone, Copy)]
 #[allow(unused)]
 pub enum Separator {
@@ -129,15 +141,17 @@ fn print_do_to_debug(doc: &Doc<'_>) -> std::string::String {
             }
             string.push_str("]) \n");
         }
-        Doc::Group(contents) => {
+        Doc::Group(group) => {
             string.push_str("group([\n");
-            for (idx, doc) in contents.iter().enumerate() {
+            for (idx, doc) in group.contents.iter().enumerate() {
                 string.push_str(&print_do_to_debug(doc));
-                if idx != contents.len() - 1 {
+                if idx != group.contents.len() - 1 {
                     string.push_str(", ");
                 }
             }
-            string.push_str("])\n");
+            string.push_str("], { shouldBreak: ");
+            string.push_str(&group.should_break.to_string());
+            string.push_str(" })");
         }
         Doc::Line => {
             string.push_str("line");
diff --git a/crates/oxc_prettier/src/format/array.rs b/crates/oxc_prettier/src/format/array.rs
index fb6dc5a34..54bd5afec 100644
--- a/crates/oxc_prettier/src/format/array.rs
+++ b/crates/oxc_prettier/src/format/array.rs
@@ -2,7 +2,10 @@ use oxc_ast::ast::*;
 use oxc_span::Span;
 
 use crate::{
-    array, comment::DanglingCommentsPrintOptions, doc::Doc, group, indent, softline, ss, Prettier,
+    array,
+    comment::DanglingCommentsPrintOptions,
+    doc::{Doc, Group},
+    group, indent, softline, ss, Prettier,
 };
 
 use super::Format;
@@ -68,7 +71,7 @@ pub(super) fn print_array<'a>(p: &mut Prettier<'a>, array: &Array<'a, '_>) -> Do
         indent!(p, softline!(), elements)
     };
     parts.push(group!(p, ss!("["), parts_inner, softline!(), ss!("]")));
-    Doc::Group(parts)
+    Doc::Group(Group::new(parts, false))
 }
 
 fn print_empty_array_elements<'a>(p: &mut Prettier<'a>, array: &Array<'a, '_>) -> Doc<'a> {
diff --git a/crates/oxc_prettier/src/format/call_expression.rs b/crates/oxc_prettier/src/format/call_expression.rs
index a1cc9db34..ed1799e90 100644
--- a/crates/oxc_prettier/src/format/call_expression.rs
+++ b/crates/oxc_prettier/src/format/call_expression.rs
@@ -1,7 +1,10 @@
 use oxc_allocator::{Box, Vec};
 use oxc_ast::ast::*;
 
-use crate::{doc::Doc, if_break, ss, Format, Prettier};
+use crate::{
+    doc::{Doc, Group},
+    if_break, ss, Format, Prettier,
+};
 
 pub(super) fn print_call_expression<'a>(
     p: &mut Prettier<'a>,
@@ -42,5 +45,5 @@ fn print_call_expression_arguments<'a>(
     parts.push(if_break!(p, ","));
     parts.push(Doc::Softline);
     parts.push(ss!(")"));
-    Doc::Group(parts)
+    Doc::Group(Group::new(parts, false))
 }
diff --git a/crates/oxc_prettier/src/format/mod.rs b/crates/oxc_prettier/src/format/mod.rs
index b5106f81a..8b0cb526f 100644
--- a/crates/oxc_prettier/src/format/mod.rs
+++ b/crates/oxc_prettier/src/format/mod.rs
@@ -29,7 +29,7 @@ use oxc_span::GetSpan;
 
 use crate::{
     array,
-    doc::{Doc, Separator},
+    doc::{Doc, Group, Separator},
     format, group, hardline, indent, line, softline, ss, string, wrap, Prettier,
 };
 
@@ -229,7 +229,7 @@ impl<'a> Format<'a> for ForInStatement<'a> {
             parts.push(ss!(")"));
             let body = format!(p, self.body);
             parts.push(misc::adjust_clause(p, &self.body, body, false));
-            Doc::Group(parts)
+            Doc::Group(Group::new(parts, false))
         })
     }
 }
@@ -287,7 +287,7 @@ impl<'a> Format<'a> for ForOfStatement<'a> {
             parts.push(ss!(")"));
             let body = format!(p, self.body);
             parts.push(misc::adjust_clause(p, &self.body, body, false));
-            Doc::Group(parts)
+            Doc::Group(Group::new(parts, false))
         })
     }
 }
@@ -314,7 +314,7 @@ impl<'a> Format<'a> for WhileStatement<'a> {
             let body = format!(p, self.body);
             parts.push(misc::adjust_clause(p, &self.body, body, false));
 
-            Doc::Group(parts)
+            Doc::Group(Group::new(parts, false))
         })
     }
 }
@@ -573,7 +573,7 @@ impl<'a> Format<'a> for VariableDeclaration<'a> {
                 parts.push(ss!(";"));
             }
 
-            Doc::Group(parts)
+            Doc::Group(Group::new(parts, false))
         })
     }
 }
@@ -1408,7 +1408,7 @@ impl<'a> Format<'a> for ObjectProperty<'a> {
                 parts.push(ss!(": "));
                 parts.push(format!(p, self.value));
             }
-            Doc::Group(parts)
+            Doc::Group(Group::new(parts, false))
         }
     }
 }
@@ -1660,7 +1660,7 @@ impl<'a> Format<'a> for ImportExpression<'a> {
         }
         parts.push(ss!(")"));
 
-        Doc::Group(parts)
+        Doc::Group(Group::new(parts, false))
     }
 }
 
diff --git a/crates/oxc_prettier/src/format/object.rs b/crates/oxc_prettier/src/format/object.rs
index 74476fcb1..972961c12 100644
--- a/crates/oxc_prettier/src/format/object.rs
+++ b/crates/oxc_prettier/src/format/object.rs
@@ -1,6 +1,9 @@
 use oxc_allocator::Vec;
 
-use crate::{doc::Doc, group, if_break, line, softline, ss, Prettier};
+use crate::{
+    doc::{Doc, Group},
+    group, if_break, line, softline, ss, Prettier,
+};
 
 use super::Format;
 
@@ -36,7 +39,7 @@ pub(super) fn print_object_properties<'a, F: Format<'a>>(
         }
 
         parts.push(ss!("}"));
-        Doc::Group(parts)
+        Doc::Group(Group::new(parts, false))
     };
 
     content
diff --git a/crates/oxc_prettier/src/format/statement.rs b/crates/oxc_prettier/src/format/statement.rs
index 0607e4865..18fd502ae 100644
--- a/crates/oxc_prettier/src/format/statement.rs
+++ b/crates/oxc_prettier/src/format/statement.rs
@@ -1,6 +1,9 @@
 use oxc_allocator::Vec;
 
-use crate::{doc::Doc, hardline, Prettier};
+use crate::{
+    doc::{Doc, Group},
+    hardline, Prettier,
+};
 use oxc_span::GetSpan;
 
 use super::Format;
@@ -17,7 +20,7 @@ pub(super) fn print_statement_sequence<'a, F: Format<'a> + GetSpan>(
 
         if remove_last_statement_hardline && i == stmts.len() - 1 {
             match docs {
-                Doc::Array(ref mut docs) | Doc::Group(ref mut docs) => {
+                Doc::Array(ref mut docs) | Doc::Group(Group { contents: ref mut docs, .. }) => {
                     if matches!(docs.last(), Some(Doc::Hardline)) {
                         docs.pop();
                     }
diff --git a/crates/oxc_prettier/src/macros.rs b/crates/oxc_prettier/src/macros.rs
index 3a1f9aecf..a5c07dd63 100644
--- a/crates/oxc_prettier/src/macros.rs
+++ b/crates/oxc_prettier/src/macros.rs
@@ -90,7 +90,7 @@ macro_rules! group {
             $(
                 temp_vec.push($x);
             )*
-            Doc::Group(temp_vec)
+            Doc::Group($crate::doc::Group::new(temp_vec, false))
         }
     };
 }
diff --git a/crates/oxc_prettier/src/printer/mod.rs b/crates/oxc_prettier/src/printer/mod.rs
index 8210e1620..a285dbb4d 100644
--- a/crates/oxc_prettier/src/printer/mod.rs
+++ b/crates/oxc_prettier/src/printer/mod.rs
@@ -7,7 +7,10 @@ mod command;
 
 use std::collections::VecDeque;
 
-use crate::{doc::Doc, PrettierOptions};
+use crate::{
+    doc::{Doc, Group},
+    PrettierOptions,
+};
 
 use self::command::{Command, Indent, Mode};
 
@@ -51,7 +54,7 @@ impl<'a> Printer<'a> {
                 Doc::Str(s) => self.handle_str(s),
                 Doc::Array(docs) => self.handle_array(indent, mode, docs),
                 Doc::Indent(docs) => self.handle_indent(indent, mode, docs),
-                Doc::Group(docs) => self.handle_group(indent, mode, docs),
+                Doc::Group(group) => self.handle_group(indent, mode, group),
                 Doc::IndentIfBreak(docs) => self.handle_indent_if_break(indent, mode, docs),
                 Doc::Line => self.handle_line(indent, mode),
                 Doc::Softline => self.handle_softline(indent, mode),
@@ -78,25 +81,37 @@ impl<'a> Printer<'a> {
         );
     }
 
-    fn handle_group(&mut self, indent: Indent, mode: Mode, docs: oxc_allocator::Vec<'a, Doc<'a>>) {
+    fn handle_group(&mut self, indent: Indent, mode: Mode, group: Group<'a>) {
         match mode {
             Mode::Flat => {
                 // TODO: consider supporting `group mode` e.g. Break/Flat
-                self.cmds.extend(
-                    docs.into_iter().rev().map(|doc| Command::new(indent, Mode::Flat, doc)),
-                );
+                self.cmds.extend(group.contents.into_iter().rev().map(|doc| {
+                    Command::new(
+                        indent,
+                        if group.should_break { Mode::Break } else { Mode::Flat },
+                        doc,
+                    )
+                }));
             }
             Mode::Break => {
                 #[allow(clippy::cast_possible_wrap)]
                 let remaining_width = (self.options.print_width as isize) - (self.pos as isize);
 
-                if self.fits(&docs, indent, remaining_width) {
+                if !group.should_break && self.fits(&group.contents, indent, remaining_width) {
                     self.cmds.extend(
-                        docs.into_iter().rev().map(|doc| Command::new(indent, Mode::Flat, doc)),
+                        group
+                            .contents
+                            .into_iter()
+                            .rev()
+                            .map(|doc| Command::new(indent, Mode::Flat, doc)),
                     );
                 } else {
                     self.cmds.extend(
-                        docs.into_iter().rev().map(|doc| Command::new(indent, Mode::Break, doc)),
+                        group
+                            .contents
+                            .into_iter()
+                            .rev()
+                            .map(|doc| Command::new(indent, Mode::Break, doc)),
                     );
                 }
             }
@@ -167,10 +182,7 @@ impl<'a> Printer<'a> {
                 Doc::Str(string) => {
                     remaining_width -= string.len() as isize;
                 }
-                Doc::IndentIfBreak(docs)
-                | Doc::Array(docs)
-                | Doc::Indent(docs)
-                | Doc::Group(docs) => {
+                Doc::IndentIfBreak(docs) | Doc::Array(docs) | Doc::Indent(docs) => {
                     // Prepend docs to the queue
                     for d in docs.iter().rev() {
                         queue.push_front(d);
@@ -180,6 +192,14 @@ impl<'a> Printer<'a> {
                         remaining_width -= (self.options.tab_width * indent.length) as isize;
                     }
                 }
+                Doc::Group(group) => {
+                    if group.should_break {
+                        return false;
+                    }
+                    for d in group.contents.iter().rev() {
+                        queue.push_front(d);
+                    }
+                }
                 // trying to fit on a single line, so we don't need to consider line breaks
                 Doc::IfBreak { .. } | Doc::Softline => {}
                 Doc::Line => remaining_width -= 1,