diff --git a/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI061.py b/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI061.py
index aa7d8d3734..51baabe892 100644
--- a/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI061.py
+++ b/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI061.py
@@ -1,4 +1,4 @@
-from typing import Literal
+from typing import Literal, Union
 
 
 def func1(arg1: Literal[None]):
@@ -17,7 +17,7 @@ def func4(arg1: Literal[int, None, float]):
     ...
 
 
-def func5(arg1: Literal[None, None]): 
+def func5(arg1: Literal[None, None]):
     ...
 
 
@@ -25,13 +25,21 @@ def func6(arg1: Literal[
     "hello",
     None  # Comment 1
     , "world"
-    ]): 
+    ]):
     ...
 
 
 def func7(arg1: Literal[
     None  # Comment 1
-    ]): 
+    ]):
+    ...
+
+
+def func8(arg1: Literal[None] | None):
+    ...
+
+
+def func9(arg1: Union[Literal[None], None]):
     ...
 
 
@@ -58,3 +66,16 @@ Literal[1, None, "foo", None]  # Y061 None inside "Literal[]" expression. Replac
 # and there are no None members in the Literal[] slice,
 # only emit Y062:
 Literal[None, True, None, True]  # Y062 Duplicate "Literal[]" member "True"
+
+
+# Regression tests for https://github.com/astral-sh/ruff/issues/14567
+x: Literal[None] | None
+y: None | Literal[None]
+z: Union[Literal[None], None]
+
+a: int | Literal[None] | None
+b: None | Literal[None] | None
+c: (None | Literal[None]) | None
+d: None | (Literal[None] | None)
+e: None | ((None | Literal[None]) | None) | None
+f: Literal[None] | Literal[None]
diff --git a/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI061.pyi b/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI061.pyi
index a43ab1460d..ed879dd646 100644
--- a/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI061.pyi
+++ b/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI061.pyi
@@ -1,4 +1,4 @@
-from typing import Literal
+from typing import Literal, Union
 
 
 def func1(arg1: Literal[None]): ...
@@ -28,6 +28,12 @@ def func7(arg1: Literal[
 ]): ...
 
 
+def func8(arg1: Literal[None] | None):...
+
+
+def func9(arg1: Union[Literal[None], None]): ...
+
+
 # OK
 def good_func(arg1: Literal[int] | None): ...
 
@@ -35,3 +41,16 @@ def good_func(arg1: Literal[int] | None): ...
 # From flake8-pyi
 Literal[None]  # PYI061 None inside "Literal[]" expression. Replace with "None"
 Literal[True, None]  # PYI061 None inside "Literal[]" expression. Replace with "Literal[True] | None"
+
+
+# Regression tests for https://github.com/astral-sh/ruff/issues/14567
+x: Literal[None] | None
+y: None | Literal[None]
+z: Union[Literal[None], None]
+
+a: int | Literal[None] | None
+b: None | Literal[None] | None
+c: (None | Literal[None]) | None
+d: None | (Literal[None] | None)
+e: None | ((None | Literal[None]) | None) | None
+f: Literal[None] | Literal[None]
diff --git a/crates/ruff_linter/src/rules/flake8_pyi/rules/redundant_none_literal.rs b/crates/ruff_linter/src/rules/flake8_pyi/rules/redundant_none_literal.rs
index da8066943f..9a23fff1b8 100644
--- a/crates/ruff_linter/src/rules/flake8_pyi/rules/redundant_none_literal.rs
+++ b/crates/ruff_linter/src/rules/flake8_pyi/rules/redundant_none_literal.rs
@@ -1,7 +1,10 @@
 use ruff_diagnostics::{Applicability, Diagnostic, Edit, Fix, FixAvailability, Violation};
 use ruff_macros::{derive_message_formats, violation};
-use ruff_python_ast::{Expr, ExprNoneLiteral};
-use ruff_python_semantic::analyze::typing::traverse_literal;
+use ruff_python_ast::{Expr, ExprBinOp, ExprNoneLiteral, ExprSubscript, Operator};
+use ruff_python_semantic::{
+    analyze::typing::{traverse_literal, traverse_union},
+    SemanticModel,
+};
 use ruff_text_size::Ranged;
 
 use smallvec::SmallVec;
@@ -31,6 +34,9 @@ use crate::checkers::ast::Checker;
 /// Literal[1, 2, 3, "foo", 5] | None
 /// ```
 ///
+/// ## Fix safety
+/// This rule's fix is marked as safe unless the literal contains comments.
+///
 /// ## References
 /// - [Typing documentation: Legal parameters for `Literal` at type check time](https://typing.readthedocs.io/en/latest/spec/literal.html#legal-parameters-for-literal-at-type-check-time)
 #[violation]
@@ -87,14 +93,16 @@ pub(crate) fn redundant_none_literal<'a>(checker: &mut Checker, literal_expr: &'
     let fix = if other_literal_elements_seen {
         None
     } else {
-        Some(Fix::applicable_edit(
-            Edit::range_replacement("None".to_string(), literal_expr.range()),
-            if checker.comment_ranges().intersects(literal_expr.range()) {
-                Applicability::Unsafe
-            } else {
-                Applicability::Safe
-            },
-        ))
+        create_fix_edit(checker.semantic(), literal_expr).map(|edit| {
+            Fix::applicable_edit(
+                edit,
+                if checker.comment_ranges().intersects(literal_expr.range()) {
+                    Applicability::Unsafe
+                } else {
+                    Applicability::Safe
+                },
+            )
+        })
     };
 
     for none_expr in none_exprs {
@@ -110,3 +118,47 @@ pub(crate) fn redundant_none_literal<'a>(checker: &mut Checker, literal_expr: &'
         checker.diagnostics.push(diagnostic);
     }
 }
+
+fn create_fix_edit(semantic: &SemanticModel, literal_expr: &Expr) -> Option<Edit> {
+    let mut enclosing_union = None;
+    for expr in semantic.current_expressions().skip(1).take_while(|expr| {
+        matches!(
+            expr,
+            Expr::BinOp(ExprBinOp {
+                op: Operator::BitOr,
+                ..
+            })
+        )
+    }) {
+        enclosing_union = Some(expr);
+    }
+
+    let mut is_fixable = true;
+    if let Some(enclosing_union) = enclosing_union {
+        traverse_union(
+            &mut |expr, _| {
+                if matches!(expr, Expr::NoneLiteral(_)) {
+                    is_fixable = false;
+                }
+                if expr != literal_expr {
+                    if let Expr::Subscript(ExprSubscript { value, slice, .. }) = expr {
+                        if semantic.match_typing_expr(value, "Literal")
+                            && matches!(**slice, Expr::NoneLiteral(_))
+                        {
+                            is_fixable = false;
+                        }
+                    }
+                }
+            },
+            semantic,
+            enclosing_union,
+        );
+    }
+
+    // Avoid producing code that would raise an exception when
+    // `Literal[None] | None` would be fixed to `None | None`.
+    // Instead do not provide a fix. No action needed for `typing.Union`,
+    // as `Union[None, None]` is valid Python.
+    // See https://github.com/astral-sh/ruff/issues/14567.
+    is_fixable.then(|| Edit::range_replacement("None".to_string(), literal_expr.range()))
+}
diff --git a/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI061_PYI061.py.snap b/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI061_PYI061.py.snap
index 41a074e440..380b81d37b 100644
--- a/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI061_PYI061.py.snap
+++ b/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI061_PYI061.py.snap
@@ -10,7 +10,7 @@ PYI061.py:4:25: PYI061 [*] `Literal[None]` can be replaced with `None`
   = help: Replace with `None`
 
 ℹ Safe fix
-1 1 | from typing import Literal
+1 1 | from typing import Literal, Union
 2 2 | 
 3 3 | 
 4   |-def func1(arg1: Literal[None]):
@@ -65,7 +65,7 @@ PYI061.py:16:30: PYI061 `Literal[None, ...]` can be replaced with `Literal[...]
 
 PYI061.py:20:25: PYI061 [*] `Literal[None]` can be replaced with `None`
    |
-20 | def func5(arg1: Literal[None, None]): 
+20 | def func5(arg1: Literal[None, None]):
    |                         ^^^^ PYI061
 21 |     ...
    |
@@ -75,15 +75,15 @@ PYI061.py:20:25: PYI061 [*] `Literal[None]` can be replaced with `None`
 17 17 |     ...
 18 18 | 
 19 19 | 
-20    |-def func5(arg1: Literal[None, None]): 
-   20 |+def func5(arg1: None): 
+20    |-def func5(arg1: Literal[None, None]):
+   20 |+def func5(arg1: None):
 21 21 |     ...
 22 22 | 
 23 23 | 
 
 PYI061.py:20:31: PYI061 [*] `Literal[None]` can be replaced with `None`
    |
-20 | def func5(arg1: Literal[None, None]): 
+20 | def func5(arg1: Literal[None, None]):
    |                               ^^^^ PYI061
 21 |     ...
    |
@@ -93,8 +93,8 @@ PYI061.py:20:31: PYI061 [*] `Literal[None]` can be replaced with `None`
 17 17 |     ...
 18 18 | 
 19 19 | 
-20    |-def func5(arg1: Literal[None, None]): 
-   20 |+def func5(arg1: None): 
+20    |-def func5(arg1: Literal[None, None]):
+   20 |+def func5(arg1: None):
 21 21 |     ...
 22 22 | 
 23 23 | 
@@ -106,7 +106,7 @@ PYI061.py:26:5: PYI061 `Literal[None, ...]` can be replaced with `Literal[...] |
 26 |     None  # Comment 1
    |     ^^^^ PYI061
 27 |     , "world"
-28 |     ]): 
+28 |     ]):
    |
    = help: Replace with `Literal[...] | None`
 
@@ -115,7 +115,7 @@ PYI061.py:33:5: PYI061 [*] `Literal[None]` can be replaced with `None`
 32 | def func7(arg1: Literal[
 33 |     None  # Comment 1
    |     ^^^^ PYI061
-34 |     ]): 
+34 |     ]):
 35 |     ...
    |
    = help: Replace with `None`
@@ -126,118 +126,256 @@ PYI061.py:33:5: PYI061 [*] `Literal[None]` can be replaced with `None`
 31 31 | 
 32    |-def func7(arg1: Literal[
 33    |-    None  # Comment 1
-34    |-    ]): 
-   32 |+def func7(arg1: None): 
+34    |-    ]):
+   32 |+def func7(arg1: None):
 35 33 |     ...
 36 34 | 
 37 35 | 
 
-PYI061.py:44:9: PYI061 [*] `Literal[None]` can be replaced with `None`
+PYI061.py:38:25: PYI061 `Literal[None]` can be replaced with `None`
    |
-43 | # From flake8-pyi
-44 | Literal[None]  # Y061 None inside "Literal[]" expression. Replace with "None"
-   |         ^^^^ PYI061
-45 | Literal[True, None]  # Y061 None inside "Literal[]" expression. Replace with "Literal[True] | None"
-   |
-   = help: Replace with `None`
-
-ℹ Safe fix
-41 41 | 
-42 42 | 
-43 43 | # From flake8-pyi
-44    |-Literal[None]  # Y061 None inside "Literal[]" expression. Replace with "None"
-   44 |+None  # Y061 None inside "Literal[]" expression. Replace with "None"
-45 45 | Literal[True, None]  # Y061 None inside "Literal[]" expression. Replace with "Literal[True] | None"
-46 46 | 
-47 47 | ###
-
-PYI061.py:45:15: PYI061 `Literal[None, ...]` can be replaced with `Literal[...] | None`
-   |
-43 | # From flake8-pyi
-44 | Literal[None]  # Y061 None inside "Literal[]" expression. Replace with "None"
-45 | Literal[True, None]  # Y061 None inside "Literal[]" expression. Replace with "Literal[True] | None"
-   |               ^^^^ PYI061
-46 | 
-47 | ###
-   |
-   = help: Replace with `Literal[...] | None`
-
-PYI061.py:54:9: PYI061 [*] `Literal[None]` can be replaced with `None`
-   |
-52 | # If Y061 and Y062 both apply, but all the duplicate members are None,
-53 | # only emit Y061...
-54 | Literal[None, None]  # Y061 None inside "Literal[]" expression. Replace with "None"
-   |         ^^^^ PYI061
-55 | Literal[1, None, "foo", None]  # Y061 None inside "Literal[]" expression. Replace with "Literal[1, 'foo'] | None"
-   |
-   = help: Replace with `None`
-
-ℹ Safe fix
-51 51 | 
-52 52 | # If Y061 and Y062 both apply, but all the duplicate members are None,
-53 53 | # only emit Y061...
-54    |-Literal[None, None]  # Y061 None inside "Literal[]" expression. Replace with "None"
-   54 |+None  # Y061 None inside "Literal[]" expression. Replace with "None"
-55 55 | Literal[1, None, "foo", None]  # Y061 None inside "Literal[]" expression. Replace with "Literal[1, 'foo'] | None"
-56 56 | 
-57 57 | # ... but if Y061 and Y062 both apply
-
-PYI061.py:54:15: PYI061 [*] `Literal[None]` can be replaced with `None`
-   |
-52 | # If Y061 and Y062 both apply, but all the duplicate members are None,
-53 | # only emit Y061...
-54 | Literal[None, None]  # Y061 None inside "Literal[]" expression. Replace with "None"
-   |               ^^^^ PYI061
-55 | Literal[1, None, "foo", None]  # Y061 None inside "Literal[]" expression. Replace with "Literal[1, 'foo'] | None"
-   |
-   = help: Replace with `None`
-
-ℹ Safe fix
-51 51 | 
-52 52 | # If Y061 and Y062 both apply, but all the duplicate members are None,
-53 53 | # only emit Y061...
-54    |-Literal[None, None]  # Y061 None inside "Literal[]" expression. Replace with "None"
-   54 |+None  # Y061 None inside "Literal[]" expression. Replace with "None"
-55 55 | Literal[1, None, "foo", None]  # Y061 None inside "Literal[]" expression. Replace with "Literal[1, 'foo'] | None"
-56 56 | 
-57 57 | # ... but if Y061 and Y062 both apply
-
-PYI061.py:55:12: PYI061 `Literal[None, ...]` can be replaced with `Literal[...] | None`
-   |
-53 | # only emit Y061...
-54 | Literal[None, None]  # Y061 None inside "Literal[]" expression. Replace with "None"
-55 | Literal[1, None, "foo", None]  # Y061 None inside "Literal[]" expression. Replace with "Literal[1, 'foo'] | None"
-   |            ^^^^ PYI061
-56 | 
-57 | # ... but if Y061 and Y062 both apply
-   |
-   = help: Replace with `Literal[...] | None`
-
-PYI061.py:55:25: PYI061 `Literal[None, ...]` can be replaced with `Literal[...] | None`
-   |
-53 | # only emit Y061...
-54 | Literal[None, None]  # Y061 None inside "Literal[]" expression. Replace with "None"
-55 | Literal[1, None, "foo", None]  # Y061 None inside "Literal[]" expression. Replace with "Literal[1, 'foo'] | None"
+38 | def func8(arg1: Literal[None] | None):
    |                         ^^^^ PYI061
-56 | 
-57 | # ... but if Y061 and Y062 both apply
+39 |     ...
+   |
+   = help: Replace with `None`
+
+PYI061.py:42:31: PYI061 [*] `Literal[None]` can be replaced with `None`
+   |
+42 | def func9(arg1: Union[Literal[None], None]):
+   |                               ^^^^ PYI061
+43 |     ...
+   |
+   = help: Replace with `None`
+
+ℹ Safe fix
+39 39 |     ...
+40 40 | 
+41 41 | 
+42    |-def func9(arg1: Union[Literal[None], None]):
+   42 |+def func9(arg1: Union[None, None]):
+43 43 |     ...
+44 44 | 
+45 45 | 
+
+PYI061.py:52:9: PYI061 [*] `Literal[None]` can be replaced with `None`
+   |
+51 | # From flake8-pyi
+52 | Literal[None]  # Y061 None inside "Literal[]" expression. Replace with "None"
+   |         ^^^^ PYI061
+53 | Literal[True, None]  # Y061 None inside "Literal[]" expression. Replace with "Literal[True] | None"
+   |
+   = help: Replace with `None`
+
+ℹ Safe fix
+49 49 | 
+50 50 | 
+51 51 | # From flake8-pyi
+52    |-Literal[None]  # Y061 None inside "Literal[]" expression. Replace with "None"
+   52 |+None  # Y061 None inside "Literal[]" expression. Replace with "None"
+53 53 | Literal[True, None]  # Y061 None inside "Literal[]" expression. Replace with "Literal[True] | None"
+54 54 | 
+55 55 | ###
+
+PYI061.py:53:15: PYI061 `Literal[None, ...]` can be replaced with `Literal[...] | None`
+   |
+51 | # From flake8-pyi
+52 | Literal[None]  # Y061 None inside "Literal[]" expression. Replace with "None"
+53 | Literal[True, None]  # Y061 None inside "Literal[]" expression. Replace with "Literal[True] | None"
+   |               ^^^^ PYI061
+54 | 
+55 | ###
    |
    = help: Replace with `Literal[...] | None`
 
-PYI061.py:60:9: PYI061 `Literal[None, ...]` can be replaced with `Literal[...] | None`
+PYI061.py:62:9: PYI061 [*] `Literal[None]` can be replaced with `None`
    |
-58 | # and there are no None members in the Literal[] slice,
-59 | # only emit Y062:
-60 | Literal[None, True, None, True]  # Y062 Duplicate "Literal[]" member "True"
+60 | # If Y061 and Y062 both apply, but all the duplicate members are None,
+61 | # only emit Y061...
+62 | Literal[None, None]  # Y061 None inside "Literal[]" expression. Replace with "None"
+   |         ^^^^ PYI061
+63 | Literal[1, None, "foo", None]  # Y061 None inside "Literal[]" expression. Replace with "Literal[1, 'foo'] | None"
+   |
+   = help: Replace with `None`
+
+ℹ Safe fix
+59 59 | 
+60 60 | # If Y061 and Y062 both apply, but all the duplicate members are None,
+61 61 | # only emit Y061...
+62    |-Literal[None, None]  # Y061 None inside "Literal[]" expression. Replace with "None"
+   62 |+None  # Y061 None inside "Literal[]" expression. Replace with "None"
+63 63 | Literal[1, None, "foo", None]  # Y061 None inside "Literal[]" expression. Replace with "Literal[1, 'foo'] | None"
+64 64 | 
+65 65 | # ... but if Y061 and Y062 both apply
+
+PYI061.py:62:15: PYI061 [*] `Literal[None]` can be replaced with `None`
+   |
+60 | # If Y061 and Y062 both apply, but all the duplicate members are None,
+61 | # only emit Y061...
+62 | Literal[None, None]  # Y061 None inside "Literal[]" expression. Replace with "None"
+   |               ^^^^ PYI061
+63 | Literal[1, None, "foo", None]  # Y061 None inside "Literal[]" expression. Replace with "Literal[1, 'foo'] | None"
+   |
+   = help: Replace with `None`
+
+ℹ Safe fix
+59 59 | 
+60 60 | # If Y061 and Y062 both apply, but all the duplicate members are None,
+61 61 | # only emit Y061...
+62    |-Literal[None, None]  # Y061 None inside "Literal[]" expression. Replace with "None"
+   62 |+None  # Y061 None inside "Literal[]" expression. Replace with "None"
+63 63 | Literal[1, None, "foo", None]  # Y061 None inside "Literal[]" expression. Replace with "Literal[1, 'foo'] | None"
+64 64 | 
+65 65 | # ... but if Y061 and Y062 both apply
+
+PYI061.py:63:12: PYI061 `Literal[None, ...]` can be replaced with `Literal[...] | None`
+   |
+61 | # only emit Y061...
+62 | Literal[None, None]  # Y061 None inside "Literal[]" expression. Replace with "None"
+63 | Literal[1, None, "foo", None]  # Y061 None inside "Literal[]" expression. Replace with "Literal[1, 'foo'] | None"
+   |            ^^^^ PYI061
+64 | 
+65 | # ... but if Y061 and Y062 both apply
+   |
+   = help: Replace with `Literal[...] | None`
+
+PYI061.py:63:25: PYI061 `Literal[None, ...]` can be replaced with `Literal[...] | None`
+   |
+61 | # only emit Y061...
+62 | Literal[None, None]  # Y061 None inside "Literal[]" expression. Replace with "None"
+63 | Literal[1, None, "foo", None]  # Y061 None inside "Literal[]" expression. Replace with "Literal[1, 'foo'] | None"
+   |                         ^^^^ PYI061
+64 | 
+65 | # ... but if Y061 and Y062 both apply
+   |
+   = help: Replace with `Literal[...] | None`
+
+PYI061.py:68:9: PYI061 `Literal[None, ...]` can be replaced with `Literal[...] | None`
+   |
+66 | # and there are no None members in the Literal[] slice,
+67 | # only emit Y062:
+68 | Literal[None, True, None, True]  # Y062 Duplicate "Literal[]" member "True"
    |         ^^^^ PYI061
    |
    = help: Replace with `Literal[...] | None`
 
-PYI061.py:60:21: PYI061 `Literal[None, ...]` can be replaced with `Literal[...] | None`
+PYI061.py:68:21: PYI061 `Literal[None, ...]` can be replaced with `Literal[...] | None`
    |
-58 | # and there are no None members in the Literal[] slice,
-59 | # only emit Y062:
-60 | Literal[None, True, None, True]  # Y062 Duplicate "Literal[]" member "True"
+66 | # and there are no None members in the Literal[] slice,
+67 | # only emit Y062:
+68 | Literal[None, True, None, True]  # Y062 Duplicate "Literal[]" member "True"
    |                     ^^^^ PYI061
    |
    = help: Replace with `Literal[...] | None`
+
+PYI061.py:72:12: PYI061 `Literal[None]` can be replaced with `None`
+   |
+71 | # Regression tests for https://github.com/astral-sh/ruff/issues/14567
+72 | x: Literal[None] | None
+   |            ^^^^ PYI061
+73 | y: None | Literal[None]
+74 | z: Union[Literal[None], None]
+   |
+   = help: Replace with `None`
+
+PYI061.py:73:19: PYI061 `Literal[None]` can be replaced with `None`
+   |
+71 | # Regression tests for https://github.com/astral-sh/ruff/issues/14567
+72 | x: Literal[None] | None
+73 | y: None | Literal[None]
+   |                   ^^^^ PYI061
+74 | z: Union[Literal[None], None]
+   |
+   = help: Replace with `None`
+
+PYI061.py:74:18: PYI061 [*] `Literal[None]` can be replaced with `None`
+   |
+72 | x: Literal[None] | None
+73 | y: None | Literal[None]
+74 | z: Union[Literal[None], None]
+   |                  ^^^^ PYI061
+75 | 
+76 | a: int | Literal[None] | None
+   |
+   = help: Replace with `None`
+
+ℹ Safe fix
+71 71 | # Regression tests for https://github.com/astral-sh/ruff/issues/14567
+72 72 | x: Literal[None] | None
+73 73 | y: None | Literal[None]
+74    |-z: Union[Literal[None], None]
+   74 |+z: Union[None, None]
+75 75 | 
+76 76 | a: int | Literal[None] | None
+77 77 | b: None | Literal[None] | None
+
+PYI061.py:76:18: PYI061 `Literal[None]` can be replaced with `None`
+   |
+74 | z: Union[Literal[None], None]
+75 | 
+76 | a: int | Literal[None] | None
+   |                  ^^^^ PYI061
+77 | b: None | Literal[None] | None
+78 | c: (None | Literal[None]) | None
+   |
+   = help: Replace with `None`
+
+PYI061.py:77:19: PYI061 `Literal[None]` can be replaced with `None`
+   |
+76 | a: int | Literal[None] | None
+77 | b: None | Literal[None] | None
+   |                   ^^^^ PYI061
+78 | c: (None | Literal[None]) | None
+79 | d: None | (Literal[None] | None)
+   |
+   = help: Replace with `None`
+
+PYI061.py:78:20: PYI061 `Literal[None]` can be replaced with `None`
+   |
+76 | a: int | Literal[None] | None
+77 | b: None | Literal[None] | None
+78 | c: (None | Literal[None]) | None
+   |                    ^^^^ PYI061
+79 | d: None | (Literal[None] | None)
+80 | e: None | ((None | Literal[None]) | None) | None
+   |
+   = help: Replace with `None`
+
+PYI061.py:79:20: PYI061 `Literal[None]` can be replaced with `None`
+   |
+77 | b: None | Literal[None] | None
+78 | c: (None | Literal[None]) | None
+79 | d: None | (Literal[None] | None)
+   |                    ^^^^ PYI061
+80 | e: None | ((None | Literal[None]) | None) | None
+81 | f: Literal[None] | Literal[None]
+   |
+   = help: Replace with `None`
+
+PYI061.py:80:28: PYI061 `Literal[None]` can be replaced with `None`
+   |
+78 | c: (None | Literal[None]) | None
+79 | d: None | (Literal[None] | None)
+80 | e: None | ((None | Literal[None]) | None) | None
+   |                            ^^^^ PYI061
+81 | f: Literal[None] | Literal[None]
+   |
+   = help: Replace with `None`
+
+PYI061.py:81:12: PYI061 `Literal[None]` can be replaced with `None`
+   |
+79 | d: None | (Literal[None] | None)
+80 | e: None | ((None | Literal[None]) | None) | None
+81 | f: Literal[None] | Literal[None]
+   |            ^^^^ PYI061
+   |
+   = help: Replace with `None`
+
+PYI061.py:81:28: PYI061 `Literal[None]` can be replaced with `None`
+   |
+79 | d: None | (Literal[None] | None)
+80 | e: None | ((None | Literal[None]) | None) | None
+81 | f: Literal[None] | Literal[None]
+   |                            ^^^^ PYI061
+   |
+   = help: Replace with `None`
diff --git a/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI061_PYI061.pyi.snap b/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI061_PYI061.pyi.snap
index e7ca825f64..d1b695f73d 100644
--- a/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI061_PYI061.pyi.snap
+++ b/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI061_PYI061.pyi.snap
@@ -9,7 +9,7 @@ PYI061.pyi:4:25: PYI061 [*] `Literal[None]` can be replaced with `None`
   = help: Replace with `None`
 
 ℹ Safe fix
-1 1 | from typing import Literal
+1 1 | from typing import Literal, Union
 2 2 | 
 3 3 | 
 4   |-def func1(arg1: Literal[None]): ...
@@ -123,30 +123,168 @@ PYI061.pyi:27:5: PYI061 [*] `Literal[None]` can be replaced with `None`
    26 |+def func7(arg1: None): ...
 29 27 | 
 30 28 | 
-31 29 | # OK
+31 29 | def func8(arg1: Literal[None] | None):...
 
-PYI061.pyi:36:9: PYI061 [*] `Literal[None]` can be replaced with `None`
+PYI061.pyi:31:25: PYI061 `Literal[None]` can be replaced with `None`
    |
-35 | # From flake8-pyi
-36 | Literal[None]  # PYI061 None inside "Literal[]" expression. Replace with "None"
-   |         ^^^^ PYI061
-37 | Literal[True, None]  # PYI061 None inside "Literal[]" expression. Replace with "Literal[True] | None"
+31 | def func8(arg1: Literal[None] | None):...
+   |                         ^^^^ PYI061
+   |
+   = help: Replace with `None`
+
+PYI061.pyi:34:31: PYI061 [*] `Literal[None]` can be replaced with `None`
+   |
+34 | def func9(arg1: Union[Literal[None], None]): ...
+   |                               ^^^^ PYI061
    |
    = help: Replace with `None`
 
 ℹ Safe fix
+31 31 | def func8(arg1: Literal[None] | None):...
+32 32 | 
 33 33 | 
-34 34 | 
-35 35 | # From flake8-pyi
-36    |-Literal[None]  # PYI061 None inside "Literal[]" expression. Replace with "None"
-   36 |+None  # PYI061 None inside "Literal[]" expression. Replace with "None"
-37 37 | Literal[True, None]  # PYI061 None inside "Literal[]" expression. Replace with "Literal[True] | None"
+34    |-def func9(arg1: Union[Literal[None], None]): ...
+   34 |+def func9(arg1: Union[None, None]): ...
+35 35 | 
+36 36 | 
+37 37 | # OK
 
-PYI061.pyi:37:15: PYI061 `Literal[None, ...]` can be replaced with `Literal[...] | None`
+PYI061.pyi:42:9: PYI061 [*] `Literal[None]` can be replaced with `None`
    |
-35 | # From flake8-pyi
-36 | Literal[None]  # PYI061 None inside "Literal[]" expression. Replace with "None"
-37 | Literal[True, None]  # PYI061 None inside "Literal[]" expression. Replace with "Literal[True] | None"
+41 | # From flake8-pyi
+42 | Literal[None]  # PYI061 None inside "Literal[]" expression. Replace with "None"
+   |         ^^^^ PYI061
+43 | Literal[True, None]  # PYI061 None inside "Literal[]" expression. Replace with "Literal[True] | None"
+   |
+   = help: Replace with `None`
+
+ℹ Safe fix
+39 39 | 
+40 40 | 
+41 41 | # From flake8-pyi
+42    |-Literal[None]  # PYI061 None inside "Literal[]" expression. Replace with "None"
+   42 |+None  # PYI061 None inside "Literal[]" expression. Replace with "None"
+43 43 | Literal[True, None]  # PYI061 None inside "Literal[]" expression. Replace with "Literal[True] | None"
+44 44 | 
+45 45 | 
+
+PYI061.pyi:43:15: PYI061 `Literal[None, ...]` can be replaced with `Literal[...] | None`
+   |
+41 | # From flake8-pyi
+42 | Literal[None]  # PYI061 None inside "Literal[]" expression. Replace with "None"
+43 | Literal[True, None]  # PYI061 None inside "Literal[]" expression. Replace with "Literal[True] | None"
    |               ^^^^ PYI061
    |
    = help: Replace with `Literal[...] | None`
+
+PYI061.pyi:47:12: PYI061 `Literal[None]` can be replaced with `None`
+   |
+46 | # Regression tests for https://github.com/astral-sh/ruff/issues/14567
+47 | x: Literal[None] | None
+   |            ^^^^ PYI061
+48 | y: None | Literal[None]
+49 | z: Union[Literal[None], None]
+   |
+   = help: Replace with `None`
+
+PYI061.pyi:48:19: PYI061 `Literal[None]` can be replaced with `None`
+   |
+46 | # Regression tests for https://github.com/astral-sh/ruff/issues/14567
+47 | x: Literal[None] | None
+48 | y: None | Literal[None]
+   |                   ^^^^ PYI061
+49 | z: Union[Literal[None], None]
+   |
+   = help: Replace with `None`
+
+PYI061.pyi:49:18: PYI061 [*] `Literal[None]` can be replaced with `None`
+   |
+47 | x: Literal[None] | None
+48 | y: None | Literal[None]
+49 | z: Union[Literal[None], None]
+   |                  ^^^^ PYI061
+50 | 
+51 | a: int | Literal[None] | None
+   |
+   = help: Replace with `None`
+
+ℹ Safe fix
+46 46 | # Regression tests for https://github.com/astral-sh/ruff/issues/14567
+47 47 | x: Literal[None] | None
+48 48 | y: None | Literal[None]
+49    |-z: Union[Literal[None], None]
+   49 |+z: Union[None, None]
+50 50 | 
+51 51 | a: int | Literal[None] | None
+52 52 | b: None | Literal[None] | None
+
+PYI061.pyi:51:18: PYI061 `Literal[None]` can be replaced with `None`
+   |
+49 | z: Union[Literal[None], None]
+50 | 
+51 | a: int | Literal[None] | None
+   |                  ^^^^ PYI061
+52 | b: None | Literal[None] | None
+53 | c: (None | Literal[None]) | None
+   |
+   = help: Replace with `None`
+
+PYI061.pyi:52:19: PYI061 `Literal[None]` can be replaced with `None`
+   |
+51 | a: int | Literal[None] | None
+52 | b: None | Literal[None] | None
+   |                   ^^^^ PYI061
+53 | c: (None | Literal[None]) | None
+54 | d: None | (Literal[None] | None)
+   |
+   = help: Replace with `None`
+
+PYI061.pyi:53:20: PYI061 `Literal[None]` can be replaced with `None`
+   |
+51 | a: int | Literal[None] | None
+52 | b: None | Literal[None] | None
+53 | c: (None | Literal[None]) | None
+   |                    ^^^^ PYI061
+54 | d: None | (Literal[None] | None)
+55 | e: None | ((None | Literal[None]) | None) | None
+   |
+   = help: Replace with `None`
+
+PYI061.pyi:54:20: PYI061 `Literal[None]` can be replaced with `None`
+   |
+52 | b: None | Literal[None] | None
+53 | c: (None | Literal[None]) | None
+54 | d: None | (Literal[None] | None)
+   |                    ^^^^ PYI061
+55 | e: None | ((None | Literal[None]) | None) | None
+56 | f: Literal[None] | Literal[None]
+   |
+   = help: Replace with `None`
+
+PYI061.pyi:55:28: PYI061 `Literal[None]` can be replaced with `None`
+   |
+53 | c: (None | Literal[None]) | None
+54 | d: None | (Literal[None] | None)
+55 | e: None | ((None | Literal[None]) | None) | None
+   |                            ^^^^ PYI061
+56 | f: Literal[None] | Literal[None]
+   |
+   = help: Replace with `None`
+
+PYI061.pyi:56:12: PYI061 `Literal[None]` can be replaced with `None`
+   |
+54 | d: None | (Literal[None] | None)
+55 | e: None | ((None | Literal[None]) | None) | None
+56 | f: Literal[None] | Literal[None]
+   |            ^^^^ PYI061
+   |
+   = help: Replace with `None`
+
+PYI061.pyi:56:28: PYI061 `Literal[None]` can be replaced with `None`
+   |
+54 | d: None | (Literal[None] | None)
+55 | e: None | ((None | Literal[None]) | None) | None
+56 | f: Literal[None] | Literal[None]
+   |                            ^^^^ PYI061
+   |
+   = help: Replace with `None`