diff --git a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/binary.py b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/binary.py
index 30cf4c4465f47..572518635ea86 100644
--- a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/binary.py
+++ b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/binary.py
@@ -211,3 +211,14 @@
     log(self.price / self.strike)
     + (self.risk_free - self.div_cont + 0.5 * (self.sigma**2)) * self.exp_time
 ) / self.sigmaT
+
+# Stability with end-of-line comments between empty tuples and bin op
+x = () - (#
+)
+x = (
+    ()
+    - ()  #
+)
+x = (
+    () - ()  #
+)
diff --git a/crates/ruff_python_formatter/resources/test/fixtures/ruff/statement/delete.py b/crates/ruff_python_formatter/resources/test/fixtures/ruff/statement/delete.py
index c8ca7da9d70e1..a86c65dde8f04 100644
--- a/crates/ruff_python_formatter/resources/test/fixtures/ruff/statement/delete.py
+++ b/crates/ruff_python_formatter/resources/test/fixtures/ruff/statement/delete.py
@@ -73,3 +73,7 @@
 
 del (  # dangling end of line comment
 )
+
+del (  # dangling end of line comment
+    # dangling own line comment
+)  # trailing statement comment
diff --git a/crates/ruff_python_formatter/src/builders.rs b/crates/ruff_python_formatter/src/builders.rs
index 8acf77004400b..5d7e0c2c3f98f 100644
--- a/crates/ruff_python_formatter/src/builders.rs
+++ b/crates/ruff_python_formatter/src/builders.rs
@@ -253,6 +253,16 @@ impl<'ast> Format<PyFormatContext<'ast>> for EmptyWithDanglingComments<'_> {
                 self.opening,
                 // end-of-line comments
                 trailing_comments(&self.comments[..end_of_line_split]),
+                // Avoid unstable formatting with
+                // ```python
+                // x = () - (#
+                // )
+                // ```
+                // Without this the comment would go after the empty tuple first, but still expand
+                // the bin op. In the second formatting pass they are trailing bin op comments
+                // so the bin op collapse. Suboptimally we keep parentheses around the bin op in
+                // either case.
+                (!self.comments[..end_of_line_split].is_empty()).then_some(hard_line_break()),
                 // own line comments, which need to be indented
                 soft_block_indent(&dangling_comments(&self.comments[end_of_line_split..])),
                 self.closing
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@expression__binary.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@expression__binary.py.snap
index 61499e20e362e..172b318812e4c 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@expression__binary.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@expression__binary.py.snap
@@ -217,6 +217,17 @@ for user_id in set(target_user_ids) - {u.user_id for u in updates}:
     log(self.price / self.strike)
     + (self.risk_free - self.div_cont + 0.5 * (self.sigma**2)) * self.exp_time
 ) / self.sigmaT
+
+# Stability with end-of-line comments between empty tuples and bin op
+x = () - (#
+)
+x = (
+    ()
+    - ()  #
+)
+x = (
+    () - ()  #
+)
 ```
 
 ## Output
@@ -488,6 +499,19 @@ for user_id in set(target_user_ids) - {u.user_id for u in updates}:
     log(self.price / self.strike)
     + (self.risk_free - self.div_cont + 0.5 * (self.sigma**2)) * self.exp_time
 ) / self.sigmaT
+
+# Stability with end-of-line comments between empty tuples and bin op
+x = (
+    ()
+    - (  #
+    )
+)
+x = (
+    () - ()  #
+)
+x = (
+    () - ()  #
+)
 ```
 
 
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@expression__call.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@expression__call.py.snap
index 45bcc8a76ab86..86880bd396c5e 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@expression__call.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@expression__call.py.snap
@@ -213,7 +213,8 @@ f(
     a.very_long_function_function_that_is_so_long_that_it_expands_the_parent_but_its_only_a_single_argument()
 )
 
-f()  # abc
+f(  # abc
+)
 
 f(  # abc
     # abc
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@expression__dict.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@expression__dict.py.snap
index e27a63126d6f1..a5b6c5e896034 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@expression__dict.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@expression__dict.py.snap
@@ -129,7 +129,8 @@ a = {
     3: True,
 }
 
-x = {}  # dangling end of line comment
+x = {  # dangling end of line comment
+}
 ```
 
 
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@expression__lambda.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@expression__lambda.py.snap
index 6937a6e5e160c..2d126b34084a2 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@expression__lambda.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@expression__lambda.py.snap
@@ -165,7 +165,8 @@ a = (
 # Regression test: lambda empty arguments ranges were too long, leading to unstable
 # formatting
 (
-    lambda: (),  #
+    lambda: (  #
+    ),
 )
 
 
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@expression__list.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@expression__list.py.snap
index 04f9c816e3229..ff883a8f45d2b 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@expression__list.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@expression__list.py.snap
@@ -62,7 +62,8 @@ c1 = [ # trailing open bracket
 ```py
 # Dangling comment placement in empty lists
 # Regression test for https://github.com/python/cpython/blob/03160630319ca26dcbbad65225da4248e54c45ec/Tools/c-analyzer/c_analyzer/datafiles.py#L14-L16
-a1 = []  # a
+a1 = [  # a
+]
 a2 = [  # a
     # b
 ]
@@ -93,7 +94,8 @@ c1 = [  # trailing open bracket
 ]  # trailing close bracket
 
 
-[]  # end-of-line comment
+[  # end-of-line comment
+]
 
 [  # end-of-line comment
     # own-line comment
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@statement__delete.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@statement__delete.py.snap
index 39a4afbc07410..ce4add0b9462c 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@statement__delete.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@statement__delete.py.snap
@@ -79,6 +79,10 @@ del (
 
 del (  # dangling end of line comment
 )
+
+del (  # dangling end of line comment
+    # dangling own line comment
+)  # trailing statement comment
 ```
 
 ## Output
@@ -215,7 +219,12 @@ del (
 )  # Completed
 # Done
 
-del ()  # dangling end of line comment
+del (  # dangling end of line comment
+)
+
+del (  # dangling end of line comment
+    # dangling own line comment
+)  # trailing statement comment
 ```
 
 
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@statement__function.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@statement__function.py.snap
index 8a7676fce96f6..7f77fc37abe04 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@statement__function.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@statement__function.py.snap
@@ -845,7 +845,8 @@ def f(  # first
     ...
 
 
-def f():  # first  # second
+def f(  # first
+):  # second
     ...
 
 
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@statement__raise.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@statement__raise.py.snap
index db7ed62b7382d..1c9746b12aa5d 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@statement__raise.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@statement__raise.py.snap
@@ -192,7 +192,8 @@ raise aksjdhflsakhdflkjsadlfajkslhfdkjsaldajlahflashdfljahlfk < (
 )  # the other end
 # sneaky comment
 
-raise ()  # another comment
+raise (  # another comment
+)
 
 raise ()  # what now