diff --git a/crates/oxc_prettier/src/comment.rs b/crates/oxc_prettier/src/comment.rs
index 9eda3703a..675b5d0e3 100644
--- a/crates/oxc_prettier/src/comment.rs
+++ b/crates/oxc_prettier/src/comment.rs
@@ -8,6 +8,7 @@ use oxc_ast::CommentKind;
 use oxc_span::Span;
 
 use crate::{
+    array,
     doc::{Doc, DocBuilder, Separator},
     hardline, indent, line, ss, Prettier,
 };
@@ -40,6 +41,30 @@ impl DanglingCommentsPrintOptions {
     }
 }
 
+#[derive(Debug, Clone, Copy)]
+struct Comment {
+    start: u32,
+    end: u32,
+    is_block: bool,
+    has_line_suffix: bool,
+}
+
+impl Comment {
+    fn new(start: u32, end: u32, kind: CommentKind) -> Self {
+        // The comment span is for the comment value
+        // -2 for `//` and `/*`
+        let start = start - 2;
+        // +2 for `/*`
+        let end = if kind.is_multi_line() { end + 2 } else { end };
+        Self { start, end, is_block: kind.is_multi_line(), has_line_suffix: false }
+    }
+
+    fn with_line_suffix(mut self, yes: bool) -> Self {
+        self.has_line_suffix = yes;
+        self
+    }
+}
+
 impl<'a> Prettier<'a> {
     #[must_use]
     pub(crate) fn print_comments(
@@ -71,34 +96,11 @@ impl<'a> Prettier<'a> {
     pub(crate) fn print_leading_comments(&mut self, range: Span) -> Option<Doc<'a>> {
         let mut parts = self.vec();
         while let Some((start, end, kind)) = self.trivias.peek().copied() {
+            let comment = Comment::new(start, end, kind);
             // Comment before the span
             if end <= range.start {
                 self.trivias.next();
-
-                parts.push(self.print_comment(start, end, kind));
-                if kind.is_multi_line() {
-                    let line_break = if self.has_newline(end) {
-                        if self.has_newline(start) {
-                            hardline!()
-                        } else {
-                            line!()
-                        }
-                    } else {
-                        ss!(" ")
-                    };
-                    parts.push(line_break);
-                } else {
-                    parts.push(hardline!());
-                }
-
-                if self
-                    .get_comment_end(kind, end)
-                    .map(|end| self.skip_spaces(end))
-                    .and_then(|idx| self.skip_newline(idx))
-                    .is_some_and(|i| self.has_newline(i))
-                {
-                    parts.push(hardline!());
-                }
+                self.print_leading_comment(&mut parts, comment);
             } else {
                 break;
             }
@@ -109,20 +111,109 @@ impl<'a> Prettier<'a> {
         Some(Doc::Array(parts))
     }
 
+    fn print_leading_comment(&mut self, parts: &mut Vec<'a, Doc<'a>>, comment: Comment) {
+        let printed = self.print_comment(comment);
+        parts.push(printed);
+
+        if comment.is_block {
+            let line_break = if self.has_newline(comment.end, /* backwards */ false) {
+                if self.has_newline(comment.start, /* backwards */ true) {
+                    hardline!()
+                } else {
+                    line!()
+                }
+            } else {
+                ss!(" ")
+            };
+            parts.push(line_break);
+        } else {
+            parts.push(hardline!());
+        }
+
+        if self
+            .skip_spaces(comment.end, false)
+            .and_then(|idx| self.skip_newline(Some(idx), false))
+            .is_some_and(|i| self.has_newline(i, /* backwards */ false))
+        {
+            parts.push(hardline!());
+        }
+    }
+
     #[must_use]
-    #[allow(clippy::unused_self)]
-    pub(crate) fn print_trailing_comments(&mut self, _range: Span) -> Option<Doc<'a>> {
-        None
+    pub(crate) fn print_trailing_comments(&mut self, range: Span) -> Option<Doc<'a>> {
+        let mut parts = self.vec();
+        let mut previous_comment: Option<Comment> = None;
+        while let Some((start, end, kind)) = self.trivias.peek().copied() {
+            let comment = Comment::new(start, end, kind);
+            // Trailing comment if there is nothing in between.
+            if range.end < comment.start
+                && self.source_text[range.end as usize..comment.start as usize]
+                    .chars()
+                    .all(|c| c == ' ')
+            {
+                self.trivias.next();
+                let previous = self.print_trailing_comment(&mut parts, comment, previous_comment);
+                previous_comment = Some(previous);
+            } else {
+                break;
+            }
+        }
+        if parts.is_empty() {
+            return None;
+        }
+        Some(Doc::Array(parts))
+    }
+
+    fn print_trailing_comment(
+        &mut self,
+        parts: &mut Vec<'a, Doc<'a>>,
+        comment: Comment,
+        previous: Option<Comment>,
+    ) -> Comment {
+        let printed = self.print_comment(comment);
+
+        if previous.is_some_and(|c| c.has_line_suffix && !c.is_block)
+            || self.has_newline(comment.start, /* backwards */ true)
+        {
+            parts.push(printed);
+            let suffix = {
+                let mut parts = self.vec();
+                parts.push(hardline!());
+                if self.is_previous_line_empty(comment.start) {
+                    parts.push(hardline!());
+                }
+                parts
+            };
+            parts.push(Doc::LineSuffix(suffix));
+            return comment.with_line_suffix(true);
+        }
+
+        if !comment.is_block || previous.is_some_and(|c| c.has_line_suffix) {
+            let suffix = {
+                let mut parts = self.vec();
+                parts.push(ss!(" "));
+                parts.push(printed);
+                parts
+            };
+            let doc = array![self, Doc::LineSuffix(suffix), Doc::BreakParent];
+            parts.push(doc);
+            return comment.with_line_suffix(true);
+        }
+
+        let doc = array![self, ss!(" "), printed];
+        parts.push(doc);
+        comment.with_line_suffix(false)
     }
 
     #[must_use]
     pub(crate) fn print_inner_comment(&mut self, range: Span) -> Vec<'a, Doc<'a>> {
         let mut parts = self.vec();
         while let Some((start, end, kind)) = self.trivias.peek().copied() {
+            let comment = Comment::new(start, end, kind);
             // Comment within the span
-            if start >= range.start && end <= range.end {
+            if comment.start >= range.start && comment.end <= range.end {
                 self.trivias.next();
-                parts.push(self.print_comment(start, end, kind));
+                parts.push(self.print_comment(comment));
             } else {
                 break;
             }
@@ -139,9 +230,10 @@ impl<'a> Prettier<'a> {
     ) -> Option<Doc<'a>> {
         let mut parts = vec![];
         while let Some((start, end, kind)) = self.trivias.peek().copied() {
+            let comment = Comment::new(start, end, kind);
             // Comment within the span
-            if end <= range.end {
-                parts.push(self.print_comment(start, end, kind));
+            if comment.end <= range.end {
+                parts.push(self.print_comment(comment));
                 self.trivias.next();
             } else {
                 break;
@@ -157,18 +249,7 @@ impl<'a> Prettier<'a> {
     }
 
     #[must_use]
-    fn print_comment(&self, start: u32, end: u32, kind: CommentKind) -> Doc<'a> {
-        let end_offset = if kind.is_multi_line() { 2 } else { 0 };
-        let comment = Span::new(start - 2, end + end_offset).source_text(self.source_text);
-        Doc::Str(comment)
-    }
-
-    #[allow(clippy::cast_possible_truncation)]
-    fn get_comment_end(&self, kind: CommentKind, end: u32) -> Option<u32> {
-        if kind.is_single_line() {
-            self.source_text[end as usize..].chars().next().map(|c| end + c.len_utf8() as u32)
-        } else {
-            Some(end)
-        }
+    fn print_comment(&self, comment: Comment) -> Doc<'a> {
+        Doc::Str(Span::new(comment.start, comment.end).source_text(self.source_text))
     }
 }
diff --git a/crates/oxc_prettier/src/doc.rs b/crates/oxc_prettier/src/doc.rs
index 1e0ae66ea..825d7ba3e 100644
--- a/crates/oxc_prettier/src/doc.rs
+++ b/crates/oxc_prettier/src/doc.rs
@@ -42,6 +42,8 @@ pub enum Doc<'a> {
     /// 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.
     Fill(Fill<'a>),
+    /// Include this anywhere to force all parent groups to break.
+    BreakParent,
 }
 
 #[derive(Debug)]
@@ -225,6 +227,9 @@ fn print_doc_to_debug(doc: &Doc<'_>) -> std::string::String {
             }
             string.push(')');
         }
+        Doc::BreakParent => {
+            string.push_str("BreakParent");
+        }
     }
 
     string
diff --git a/crates/oxc_prettier/src/format/mod.rs b/crates/oxc_prettier/src/format/mod.rs
index d126fd72d..8192c83ed 100644
--- a/crates/oxc_prettier/src/format/mod.rs
+++ b/crates/oxc_prettier/src/format/mod.rs
@@ -26,7 +26,7 @@ use std::borrow::Cow;
 
 use oxc_allocator::{Box, Vec};
 use oxc_ast::{ast::*, AstKind};
-use oxc_span::{GetSpan, Span};
+use oxc_span::GetSpan;
 
 use crate::{
     array,
@@ -150,13 +150,14 @@ impl<'a> Format<'a> for IfStatement<'a> {
         wrap!(p, self, IfStatement, {
             let mut parts = p.vec();
 
+            let test_doc = format!(p, self.test);
             let consequent = format!(p, self.consequent);
             let consequent = misc::adjust_clause(p, &self.consequent, consequent, false);
 
             let opening = group![
                 p,
                 ss!("if ("),
-                group!(p, indent!(p, softline!(), format!(p, self.test)), softline!()),
+                group!(p, indent!(p, softline!(), test_doc), softline!()),
                 ss!(")"),
                 consequent
             ];
@@ -1490,14 +1491,6 @@ impl<'a> Format<'a> for ObjectProperty<'a> {
                     }
                 } else {
                     parts.push(format!(p, self.key));
-                    let comments = p.print_inner_comment(Span::new(
-                        self.key.span().end,
-                        self.value.span().start,
-                    ));
-                    if !comments.is_empty() {
-                        parts.push(ss!(" "));
-                        parts.extend(comments);
-                    }
                     parts.push(ss!(": "));
                     parts.push(format!(p, self.value));
                 }
@@ -1509,25 +1502,26 @@ impl<'a> Format<'a> for ObjectProperty<'a> {
 
 impl<'a> Format<'a> for PropertyKey<'a> {
     fn format(&self, p: &mut Prettier<'a>) -> Doc<'a> {
-        match self {
-            PropertyKey::Identifier(ident) => ident.format(p),
-            PropertyKey::PrivateIdentifier(ident) => ident.format(p),
-            PropertyKey::Expression(expr) => match expr {
-                Expression::StringLiteral(literal) => {
-                    let expr = format!(p, literal);
-                    let value = literal.value.as_bytes();
-                    if !&value[0].is_ascii_digit() && !value.contains(&b'_') {
-                        p.str(&literal.value)
-                    } else {
-                        literal.format(p)
+        wrap!(p, self, PropertyKey, {
+            match self {
+                PropertyKey::Identifier(ident) => ident.format(p),
+                PropertyKey::PrivateIdentifier(ident) => ident.format(p),
+                PropertyKey::Expression(expr) => match expr {
+                    Expression::StringLiteral(literal) => {
+                        let value = literal.value.as_bytes();
+                        if !&value[0].is_ascii_digit() && !value.contains(&b'_') {
+                            p.str(&literal.value)
+                        } else {
+                            literal.format(p)
+                        }
                     }
-                }
-                Expression::Identifier(ident) => {
-                    array!(p, ss!("["), ident.format(p), ss!("]"))
-                }
-                _ => expr.format(p),
-            },
-        }
+                    Expression::Identifier(ident) => {
+                        array!(p, ss!("["), ident.format(p), ss!("]"))
+                    }
+                    _ => expr.format(p),
+                },
+            }
+        })
     }
 }
 
diff --git a/crates/oxc_prettier/src/lib.rs b/crates/oxc_prettier/src/lib.rs
index 2af0de294..67cfff351 100644
--- a/crates/oxc_prettier/src/lib.rs
+++ b/crates/oxc_prettier/src/lib.rs
@@ -124,26 +124,58 @@ impl<'a> Prettier<'a> {
     }
 
     #[allow(clippy::cast_possible_truncation)]
-    fn skip_newline(&self, start_index: u32) -> Option<u32> {
-        let c = self.source_text[start_index as usize..].chars().next()?;
-        is_line_terminator(c).then(|| start_index + c.len_utf8() as u32)
+    fn skip_newline(&self, start_index: Option<u32>, backwards: bool) -> Option<u32> {
+        let start_index = start_index?;
+        let c = if backwards {
+            self.source_text[..=start_index as usize].chars().next_back()
+        } else {
+            self.source_text[start_index as usize..].chars().next()
+        }?;
+        if is_line_terminator(c) {
+            let len = c.len_utf8() as u32;
+            return Some(if backwards { start_index - len } else { start_index + len });
+        }
+        Some(start_index)
     }
 
-    fn skip_spaces(&self, start_index: u32) -> u32 {
+    fn skip_spaces(&self, start_index: u32, backwards: bool) -> Option<u32> {
         let mut index = start_index;
-        for c in self.source_text[start_index as usize..].chars() {
-            if matches!(c, ' ' | '\t') {
-                index += 1;
-            } else {
-                break;
+        if backwards {
+            for c in self.source_text[..=start_index as usize].chars().rev() {
+                if !matches!(c, ' ' | '\t') {
+                    return Some(index);
+                }
+                index -= 1_u32;
+            }
+        } else {
+            for c in self.source_text[start_index as usize..].chars() {
+                if !matches!(c, ' ' | '\t') {
+                    return Some(index);
+                }
+                index += 1_u32;
             }
         }
-        index
+        None
     }
 
-    fn has_newline(&self, start_index: u32) -> bool {
-        let idx = self.skip_spaces(start_index);
-        let idx2 = self.skip_newline(idx);
-        Some(idx) != idx2
+    fn has_newline(&self, start_index: u32, backwards: bool) -> bool {
+        if (backwards && start_index == 0)
+            || (!backwards && start_index as usize == self.source_text.len())
+        {
+            return false;
+        }
+        let start_index = if backwards { start_index - 1 } else { start_index };
+        let idx = self.skip_spaces(start_index, backwards);
+        let idx2 = self.skip_newline(idx, backwards);
+        idx != idx2
+    }
+
+    fn is_previous_line_empty(&self, start_index: u32) -> bool {
+        let idx = start_index - 1;
+        let idx = self.skip_spaces(idx, true);
+        let Some(idx) = self.skip_newline(idx, true) else { return false };
+        let idx = self.skip_spaces(idx, true);
+        let idx2 = self.skip_newline(idx, true);
+        idx != idx2
     }
 }
diff --git a/crates/oxc_prettier/src/printer/mod.rs b/crates/oxc_prettier/src/printer/mod.rs
index 2540dc8f4..800f7b8d5 100644
--- a/crates/oxc_prettier/src/printer/mod.rs
+++ b/crates/oxc_prettier/src/printer/mod.rs
@@ -105,10 +105,11 @@ impl<'a> Printer<'a> {
                 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),
-                Doc::Hardline => self.handle_hardline(indent),
+                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::Fill(fill) => self.handle_fill(indent, mode, fill),
+                Doc::BreakParent => {} // No op
             }
 
             if self.cmds.is_empty() && !self.line_suffix.is_empty() {
@@ -192,6 +193,11 @@ impl<'a> Printer<'a> {
 
     fn handle_line(&mut self, indent: Indent, mode: Mode) {
         if mode.is_break() {
+            if !self.line_suffix.is_empty() {
+                self.cmds.extend(self.line_suffix.drain(..).rev());
+                return;
+            }
+
             self.handle_hardline(indent);
         } else {
             self.out.push(b' ');
@@ -201,7 +207,7 @@ impl<'a> Printer<'a> {
 
     fn handle_softline(&mut self, indent: Indent, mode: Mode) {
         if mode.is_break() {
-            self.handle_hardline(indent);
+            self.handle_line(indent, Mode::Break);
         }
     }
 
@@ -360,6 +366,7 @@ impl<'a> Printer<'a> {
                 Doc::LineSuffix(_) => {
                     break;
                 }
+                Doc::BreakParent => {}
             }
 
             if remaining_width < 0 {
diff --git a/tasks/prettier_conformance/prettier.snap.md b/tasks/prettier_conformance/prettier.snap.md
index b7919df09..b2e311a7d 100644
--- a/tasks/prettier_conformance/prettier.snap.md
+++ b/tasks/prettier_conformance/prettier.snap.md
@@ -1,4 +1,8 @@
+<<<<<<< Updated upstream
+Compatibility: 171/591 (28.93%)
+=======
 Compatibility: 168/591 (28.43%)
+>>>>>>> Stashed changes
 
 # Failed