diff --git a/crates/oxc_prettier/src/doc.rs b/crates/oxc_prettier/src/doc.rs
index 825d7ba3e..8fd1b5662 100644
--- a/crates/oxc_prettier/src/doc.rs
+++ b/crates/oxc_prettier/src/doc.rs
@@ -6,7 +6,7 @@
 use oxc_allocator::{Allocator, Box, String, Vec};
 use std::fmt;
 
-use crate::{array, line, ss};
+use crate::{array, line, ss, GroupId};
 
 #[derive(Debug)]
 pub enum Doc<'a> {
@@ -37,7 +37,7 @@ pub enum Doc<'a> {
     /// `lineSuffix` buffers docs passed to it and flushes them before any new line.
     LineSuffix(Vec<'a, Doc<'a>>),
     /// Print something if the current `group` or the current element of `fill` breaks and something else if it doesn't.
-    IfBreak(Box<'a, Doc<'a>>),
+    IfBreak(IfBreak<'a>),
     /// This is an alternative type of group which behaves like text layout:
     /// it's going to add a break whenever the next element doesn't fit in the line anymore.
     /// The difference with `group` is that it's not going to break all the separators, just the ones that are at the end of lines.
@@ -50,11 +50,16 @@ pub enum Doc<'a> {
 pub struct Group<'a> {
     pub contents: Vec<'a, Doc<'a>>,
     pub should_break: bool,
+    pub id: Option<u32>,
 }
 
 impl<'a> Group<'a> {
     pub fn new(contents: Vec<'a, Doc<'a>>, should_break: bool) -> Self {
-        Self { contents, should_break }
+        Self { contents, should_break, id: None }
+    }
+    pub fn with_id(mut self, id: u32) -> Self {
+        self.id = Some(id);
+        self
     }
 }
 
@@ -90,6 +95,13 @@ impl<'a> Fill<'a> {
     }
 }
 
+#[derive(Debug)]
+pub struct IfBreak<'a> {
+    pub break_contents: Box<'a, Doc<'a>>,
+    pub flat_content: Box<'a, Doc<'a>>,
+    pub group_id: Option<GroupId>,
+}
+
 #[derive(Clone, Copy)]
 #[allow(unused)]
 pub enum Separator {
@@ -190,6 +202,9 @@ fn print_doc_to_debug(doc: &Doc<'_>) -> std::string::String {
             }
             string.push_str("], { shouldBreak: ");
             string.push_str(&group.should_break.to_string());
+            if let Some(id) = group.id {
+                string.push_str(&format!(", id: {id}"));
+            }
             string.push_str(" })");
         }
         Doc::Line => {
@@ -201,9 +216,15 @@ fn print_doc_to_debug(doc: &Doc<'_>) -> std::string::String {
         Doc::Hardline => {
             string.push_str("hardline");
         }
-        Doc::IfBreak(break_contents) => {
-            string.push_str("ifBreak(");
-            string.push_str(&print_doc_to_debug(break_contents));
+        Doc::IfBreak(if_break) => {
+            string.push_str(&format!(
+                "ifBreak({}, {})",
+                print_doc_to_debug(&if_break.break_contents),
+                print_doc_to_debug(&if_break.flat_content)
+            ));
+            if let Some(group_id) = if_break.group_id {
+                string.push_str(&format!("{{ groupId: {group_id} }}"));
+            }
             string.push(')');
         }
         Doc::Fill(fill) => {
diff --git a/crates/oxc_prettier/src/format/array.rs b/crates/oxc_prettier/src/format/array.rs
index 854558825..fcfac9c61 100644
--- a/crates/oxc_prettier/src/format/array.rs
+++ b/crates/oxc_prettier/src/format/array.rs
@@ -82,6 +82,7 @@ pub(super) fn print_array<'a>(p: &mut Prettier<'a>, array: &Array<'a, '_>) -> Do
             (false, false)
         };
 
+    let id = p.next_id();
     let should_use_concise_formatting = array.is_concisely_printed();
     let trailing_comma_fn = |p: &Prettier<'a>| {
         if !can_have_trailing_comma {
@@ -89,7 +90,7 @@ pub(super) fn print_array<'a>(p: &mut Prettier<'a>, array: &Array<'a, '_>) -> Do
         } else if needs_forced_trailing_comma {
             ss!(",")
         } else if should_use_concise_formatting {
-            if_break!(p, ",")
+            if_break!(p, ",", "", Some(id))
         } else {
             ss!("")
         }
@@ -110,7 +111,7 @@ pub(super) fn print_array<'a>(p: &mut Prettier<'a>, array: &Array<'a, '_>) -> Do
     };
     parts.push(group!(p, ss!("["), parts_inner, softline!(), ss!("]")));
     let should_break = should_break(array);
-    Doc::Group(Group::new(parts, should_break))
+    Doc::Group(Group::new(parts, should_break).with_id(id))
 }
 
 fn print_empty_array_elements<'a>(p: &mut Prettier<'a>, array: &Array<'a, '_>) -> Doc<'a> {
diff --git a/crates/oxc_prettier/src/format/binaryish.rs b/crates/oxc_prettier/src/format/binaryish.rs
index 01612581c..502c29434 100644
--- a/crates/oxc_prettier/src/format/binaryish.rs
+++ b/crates/oxc_prettier/src/format/binaryish.rs
@@ -78,7 +78,7 @@ pub(super) fn print_binaryish_expression<'a>(
 
     if operator.is_binary() {
         parts.push(group!(p, ss!(operator.as_str()), Doc::Line, right.format(p)));
-        Doc::Group(Group { contents: parts, should_break: false })
+        Doc::Group(Group::new(parts, false))
     } else {
         parts.push(ss!(operator.as_str()));
         parts.push(Doc::Line);
diff --git a/crates/oxc_prettier/src/format/call_expression.rs b/crates/oxc_prettier/src/format/call_expression.rs
index 10be9029d..a3bef6101 100644
--- a/crates/oxc_prettier/src/format/call_expression.rs
+++ b/crates/oxc_prettier/src/format/call_expression.rs
@@ -64,7 +64,7 @@ pub(super) fn print_call_expression<'a>(
 
     parts.push(print_call_expression_arguments(p, expression));
 
-    Doc::Group(Group { contents: parts, should_break: false })
+    Doc::Group(Group::new(parts, false))
 }
 
 fn print_call_expression_arguments<'a>(
@@ -100,7 +100,7 @@ fn print_call_expression_arguments<'a>(
     if should_break {
         parts_inner.insert(0, Doc::Softline);
         parts.push(Doc::Indent(parts_inner));
-        parts.push(if_break!(p, ","));
+        parts.push(if_break!(p, ",", "", None));
         parts.push(Doc::Softline);
     } else {
         parts.extend(parts_inner);
diff --git a/crates/oxc_prettier/src/format/mod.rs b/crates/oxc_prettier/src/format/mod.rs
index 8192c83ed..d0af9209e 100644
--- a/crates/oxc_prettier/src/format/mod.rs
+++ b/crates/oxc_prettier/src/format/mod.rs
@@ -471,10 +471,7 @@ impl<'a> Format<'a> for SwitchCase<'a> {
             if is_only_one_block_statement {
                 parts.extend(consequent_parts);
             } else {
-                parts.push(indent!(
-                    p,
-                    Doc::Group(Group { contents: consequent_parts, should_break: false })
-                ));
+                parts.push(indent!(p, Doc::Group(Group::new(consequent_parts, false))));
             }
         }
 
diff --git a/crates/oxc_prettier/src/format/module.rs b/crates/oxc_prettier/src/format/module.rs
index d52a63093..f469d62e7 100644
--- a/crates/oxc_prettier/src/format/module.rs
+++ b/crates/oxc_prettier/src/format/module.rs
@@ -105,7 +105,7 @@ pub fn print_module_specifiers<'a, T: Format<'a>>(
                         if p.options.bracket_spacing { line!() } else { softline!() },
                         Doc::Array(p.join(Separator::CommaLine, docs))
                     ],
-                    if_break!(p, if p.should_print_es5_comma() { "," } else { "" }),
+                    if_break!(p, if p.should_print_es5_comma() { "," } else { "" }, "", None),
                     if p.options.bracket_spacing { line!() } else { softline!() },
                     ss!("}"),
                 ]);
diff --git a/crates/oxc_prettier/src/format/object.rs b/crates/oxc_prettier/src/format/object.rs
index 2464b5fe7..a76f539dd 100644
--- a/crates/oxc_prettier/src/format/object.rs
+++ b/crates/oxc_prettier/src/format/object.rs
@@ -57,7 +57,7 @@ pub(super) fn print_object_properties<'a, F: Format<'a> + GetSpan>(
         }
 
         parts.push(Doc::Indent(indent_parts));
-        parts.push(if_break!(p, ","));
+        parts.push(if_break!(p, ",", "", None));
 
         if p.options.bracket_spacing {
             parts.push(Doc::Line);
diff --git a/crates/oxc_prettier/src/lib.rs b/crates/oxc_prettier/src/lib.rs
index bba555c3f..f5fb29361 100644
--- a/crates/oxc_prettier/src/lib.rs
+++ b/crates/oxc_prettier/src/lib.rs
@@ -23,6 +23,19 @@ use crate::{doc::Doc, format::Format, printer::Printer};
 
 pub use crate::options::{ArrowParens, EndOfLine, PrettierOptions, QuoteProps, TrailingComma};
 
+type GroupId = u32;
+#[derive(Default)]
+struct GroupIdBuilder {
+    id: GroupId,
+}
+
+impl GroupIdBuilder {
+    pub fn next_id(&mut self) -> GroupId {
+        self.id += 1;
+        self.id
+    }
+}
+
 pub struct Prettier<'a> {
     allocator: &'a Allocator,
 
@@ -36,6 +49,8 @@ pub struct Prettier<'a> {
     /// The stack of AST Nodes
     /// See <https://github.com/prettier/prettier/blob/main/src/common/ast-path.js>
     nodes: Vec<AstKind<'a>>,
+
+    group_id_builder: GroupIdBuilder,
 }
 
 impl<'a> DocBuilder<'a> for Prettier<'a> {
@@ -58,6 +73,7 @@ impl<'a> Prettier<'a> {
             options,
             trivias: trivias.into_iter().peekable(),
             nodes: vec![],
+            group_id_builder: GroupIdBuilder::default(),
         }
     }
 
@@ -178,4 +194,8 @@ impl<'a> Prettier<'a> {
         let idx2 = self.skip_newline(idx, true);
         idx != idx2
     }
+
+    fn next_id(&mut self) -> GroupId {
+        self.group_id_builder.next_id()
+    }
 }
diff --git a/crates/oxc_prettier/src/macros.rs b/crates/oxc_prettier/src/macros.rs
index be16ccbb3..abdc3986d 100644
--- a/crates/oxc_prettier/src/macros.rs
+++ b/crates/oxc_prettier/src/macros.rs
@@ -100,9 +100,13 @@ macro_rules! group {
 
 #[macro_export]
 macro_rules! if_break {
-    ($p:ident, $s:expr) => {{
-        use $crate::doc::DocBuilder;
-        Doc::IfBreak($p.boxed(Doc::Str($s)))
+    ($p:ident, $s:expr, $flat:expr, $group_id:expr) => {{
+        use $crate::doc::{DocBuilder, IfBreak};
+        Doc::IfBreak(IfBreak {
+            break_contents: $p.boxed(Doc::Str($s)),
+            flat_content: $p.boxed(Doc::Str($flat)),
+            group_id: $group_id,
+        })
     }};
 }
 
diff --git a/crates/oxc_prettier/src/printer/mod.rs b/crates/oxc_prettier/src/printer/mod.rs
index 800f7b8d5..71f38475e 100644
--- a/crates/oxc_prettier/src/printer/mod.rs
+++ b/crates/oxc_prettier/src/printer/mod.rs
@@ -6,11 +6,11 @@
 mod command;
 
 use oxc_allocator::Allocator;
-use std::collections::VecDeque;
+use std::collections::{HashMap, VecDeque};
 
 use crate::{
-    doc::{Doc, DocBuilder, Fill},
-    PrettierOptions,
+    doc::{Doc, DocBuilder, Fill, IfBreak},
+    GroupId, PrettierOptions,
 };
 
 use self::command::{Command, Indent, Mode};
@@ -27,6 +27,7 @@ pub struct Printer<'a> {
     cmds: Vec<Command<'a>>,
 
     line_suffix: Vec<Command<'a>>,
+    group_mode_map: HashMap<GroupId, Mode>,
 
     // states
     new_line: &'static str,
@@ -58,6 +59,7 @@ impl<'a> Printer<'a> {
             pos: 0,
             cmds,
             line_suffix: vec![],
+            group_mode_map: HashMap::new(),
             new_line: options.end_of_line.as_str(),
             allocator,
         }
@@ -82,7 +84,7 @@ impl<'a> Printer<'a> {
                 }
                 group.should_break
             }
-            Doc::IfBreak(d) => Self::propagate_breaks(d),
+            Doc::IfBreak(d) => Self::propagate_breaks(&mut d.break_contents),
             Doc::Array(arr) | Doc::Indent(arr) | Doc::IndentIfBreak(arr) => {
                 arr.iter_mut().any(|doc| Self::propagate_breaks(doc))
             }
@@ -107,7 +109,7 @@ impl<'a> Printer<'a> {
                 Doc::Softline => self.handle_softline(indent, mode),
                 Doc::Hardline => self.handle_line(indent, Mode::Break),
                 Doc::LineSuffix(docs) => self.handle_line_suffix(indent, mode, docs),
-                Doc::IfBreak(doc) => self.handle_if_break(doc.unbox(), indent, mode),
+                Doc::IfBreak(if_break) => self.handle_if_break(if_break, indent, mode),
                 Doc::Fill(fill) => self.handle_fill(indent, mode, fill),
                 Doc::BreakParent => {} // No op
             }
@@ -152,6 +154,7 @@ impl<'a> Printer<'a> {
                     return;
                 };
                 let should_break = group.should_break;
+                let id = group.id;
                 let cmd = Command::new(indent, Mode::Flat, doc);
                 if !should_break && self.fits(&cmd, remaining_width) {
                     self.cmds.push(Command::new(indent, Mode::Flat, cmd.doc));
@@ -167,6 +170,11 @@ impl<'a> Printer<'a> {
                             .map(|doc| Command::new(indent, Mode::Break, doc)),
                     );
                 }
+
+                if let Some(id) = id {
+                    let Some(mode) = self.cmds.last().map(|cmd| cmd.mode) else { return };
+                    self.group_mode_map.insert(id, mode);
+                }
             }
         }
     }
@@ -226,9 +234,18 @@ impl<'a> Printer<'a> {
         self.line_suffix.push(Command { indent, mode, doc: Doc::Array(docs) });
     }
 
-    fn handle_if_break(&mut self, doc: Doc<'a>, indent: Indent, mode: Mode) {
-        if mode == Mode::Break {
-            self.cmds.push(Command::new(indent, Mode::Break, doc));
+    fn handle_if_break(&mut self, if_break: IfBreak<'a>, indent: Indent, mode: Mode) {
+        let IfBreak { break_contents, flat_content, group_id } = if_break;
+        let group_mode = group_id.map_or(Some(mode), |id| self.group_mode_map.get(&id).copied());
+
+        match group_mode {
+            Some(Mode::Flat) => {
+                self.cmds.push(Command::new(indent, Mode::Flat, flat_content.unbox()));
+            }
+            Some(Mode::Break) => {
+                self.cmds.push(Command::new(indent, Mode::Break, break_contents.unbox()));
+            }
+            None => {}
         }
     }
 
@@ -339,10 +356,18 @@ impl<'a> Printer<'a> {
                         queue.push_front((mode, d));
                     }
                 }
-                Doc::IfBreak(doc) => {
-                    if is_break {
-                        queue.push_front((mode, doc));
-                    }
+                Doc::IfBreak(if_break_doc) => {
+                    let group_mode = if_break_doc
+                        .group_id
+                        .map_or(mode, |id| *self.group_mode_map.get(&id).unwrap_or(&Mode::Flat));
+
+                    let contents = if group_mode.is_break() {
+                        &if_break_doc.break_contents
+                    } else {
+                        &if_break_doc.flat_content
+                    };
+
+                    queue.push_front((mode, contents));
                 }
                 Doc::Line => {
                     if is_break {
diff --git a/tasks/prettier_conformance/prettier.snap.md b/tasks/prettier_conformance/prettier.snap.md
index 3b68b9d2a..4d6ac0821 100644
--- a/tasks/prettier_conformance/prettier.snap.md
+++ b/tasks/prettier_conformance/prettier.snap.md
@@ -1,4 +1,8 @@
+<<<<<<< HEAD
 Compatibility: 173/591 (29.27%)
+=======
+Compatibility: 171/591 (28.93%)
+>>>>>>> 169f7a38 (feat(prettier): add id on `IfBreak` and `Group`)
 
 # Failed
 
@@ -7,14 +11,11 @@ Compatibility: 173/591 (29.27%)
 * arrays/issue-10159.js
 * arrays/nested.js
 * arrays/numbers-in-args.js
-* arrays/numbers-in-assignment.js
 * arrays/numbers-negative-comment-after-minus.js
 * arrays/numbers-negative.js
-* arrays/numbers-trailing-comma.js
 * arrays/numbers-with-holes.js
 * arrays/numbers-with-trailing-comments.js
 * arrays/numbers-with-tricky-comments.js
-* arrays/numbers1.js
 * arrays/numbers2.js
 * arrays/numbers3.js
 * arrays/preserve_empty_lines.js