diff --git a/crates/oxc_prettier/src/binaryish.rs b/crates/oxc_prettier/src/binaryish.rs
index 260a507157ee0..f3213ee31287e 100644
--- a/crates/oxc_prettier/src/binaryish.rs
+++ b/crates/oxc_prettier/src/binaryish.rs
@@ -1,4 +1,5 @@
 use oxc_ast::ast::*;
+use oxc_span::{GetSpan, Span};
 use oxc_syntax::{
     operator::{BinaryOperator, LogicalOperator},
     precedence::{GetPrecedence, Precedence},
@@ -36,6 +37,12 @@ impl<'a, 'b> BinaryishLeft<'a, 'b> {
             _ => None,
         }
     }
+    pub fn span(&self) -> Span {
+        match self {
+            Self::Expression(e) => e.span(),
+            Self::PrivateIdentifier(e) => e.span,
+        }
+    }
 }
 
 impl<'a, 'b> Format<'a> for BinaryishLeft<'a, 'b> {
diff --git a/crates/oxc_prettier/src/format/binaryish.rs b/crates/oxc_prettier/src/format/binaryish.rs
index b9307409e4d46..460fec7add21d 100644
--- a/crates/oxc_prettier/src/format/binaryish.rs
+++ b/crates/oxc_prettier/src/format/binaryish.rs
@@ -2,6 +2,7 @@ use oxc_ast::ast::*;
 
 use crate::{
     binaryish::{BinaryishLeft, BinaryishOperator},
+    comments::CommentFlags,
     doc::{Doc, DocBuilder, Group},
     group, line, ss, Format, Prettier,
 };
@@ -11,31 +12,50 @@ pub(super) fn print_binaryish_expression<'a>(
     left: BinaryishLeft<'a, '_>,
     operator: BinaryishOperator,
     right: &Expression<'a>,
+) -> Doc<'a> {
+    print_binaryish_expressions(p, left, operator, right)
+}
+
+fn print_binaryish_expressions<'a>(
+    p: &mut Prettier<'a>,
+    left: BinaryishLeft<'a, '_>,
+    operator: BinaryishOperator,
+    right: &Expression<'a>,
 ) -> Doc<'a> {
     let mut parts = p.vec();
 
     if left.operator().is_some_and(|left_operator| operator.should_flatten(left_operator)) {
         parts.push(match left {
             BinaryishLeft::Expression(Expression::BinaryExpression(e)) => {
-                print_binaryish_expression(p, (&e.left).into(), e.operator.into(), &e.right)
+                print_binaryish_expressions(p, (&e.left).into(), e.operator.into(), &e.right)
             }
             BinaryishLeft::Expression(Expression::LogicalExpression(e)) => {
-                print_binaryish_expression(p, (&e.left).into(), e.operator.into(), &e.right)
+                print_binaryish_expressions(p, (&e.left).into(), e.operator.into(), &e.right)
             }
             _ => unreachable!(),
         });
     } else {
         parts.push(group!(p, left.format(p)));
     }
+    let should_inline = should_inline_logical_expression(right);
+    let mut right_parts = p.vec();
+    right_parts.push(ss!(operator.as_str()));
+    right_parts.push(if should_inline { ss!(" ") } else { line!() });
+    right_parts.push(right.format(p));
+
+    let should_break = p.has_comment(left.span(), CommentFlags::Trailing | CommentFlags::Line);
+
     parts.push(ss!(" "));
+    if should_break {
+        let group = Doc::Group(Group::new(right_parts, should_break));
+        parts.push(group);
+    } else {
+        parts.push(Doc::Array(right_parts));
+    }
 
     if operator.is_binary() {
-        parts.push(group!(p, ss!(operator.as_str()), line!(), right.format(p)));
         Doc::Group(Group::new(parts, false))
     } else {
-        parts.push(ss!(operator.as_str()));
-        parts.push(line!());
-        parts.push(right.format(p));
         Doc::Array(parts)
     }
 }
diff --git a/tasks/prettier_conformance/prettier.snap.md b/tasks/prettier_conformance/prettier.snap.md
index 1da39942c449f..1ca1bde9d09f3 100644
--- a/tasks/prettier_conformance/prettier.snap.md
+++ b/tasks/prettier_conformance/prettier.snap.md
@@ -1,4 +1,4 @@
-Compatibility: 231/550 (42.00%)
+Compatibility: 232/550 (42.18%)
 
 # Failed
 
@@ -91,7 +91,6 @@ Compatibility: 231/550 (42.00%)
 * chain-expression/test.js
 
 ### class-comment
-* class-comment/class-property.js
 * class-comment/misc.js
 * class-comment/superclass.js