diff --git a/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI016.py b/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI016.py
index 6b11efb181e2d..967f056a92345 100644
--- a/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI016.py
+++ b/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI016.py
@@ -84,3 +84,27 @@ def func2() -> str | str:  # PYI016: Duplicate union member `str`
 # duplicates of the outer `int`), but not three times (which would indicate that
 # we incorrectly re-checked the nested union).
 field25: typing.Union[int, int | int]  # PYI016: Duplicate union member `int`
+
+# Should emit in cases with nested `typing.Union`
+field26: typing.Union[typing.Union[int, int]]  # PYI016: Duplicate union member `int`
+
+# Should emit in cases with nested `typing.Union`
+field27: typing.Union[typing.Union[typing.Union[int, int]]]  # PYI016: Duplicate union member `int`
+
+# Should emit in cases with mixed `typing.Union` and `|`
+field28: typing.Union[int | int]  # Error
+
+# Should emit twice in cases with multiple nested `typing.Union`
+field29: typing.Union[int, typing.Union[typing.Union[int, int]]]  # Error
+
+# Should emit once in cases with multiple nested `typing.Union`
+field30: typing.Union[int, typing.Union[typing.Union[int, str]]]  # Error
+
+# Should emit once, and fix to `typing.Union[float, int]`
+field31: typing.Union[float, typing.Union[int | int]]  # Error
+
+# Should emit once, and fix to `typing.Union[float, int]`
+field32: typing.Union[float, typing.Union[int | int | int]]  # Error
+
+# Test case for mixed union type fix
+field33: typing.Union[typing.Union[int | int] | typing.Union[int | int]] # Error
diff --git a/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI016.pyi b/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI016.pyi
index 6b11efb181e2d..7fc398be26408 100644
--- a/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI016.pyi
+++ b/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI016.pyi
@@ -84,3 +84,27 @@ field24: typing.Union[int, typing.Union[int, int]]  # PYI016: Duplicate union me
 # duplicates of the outer `int`), but not three times (which would indicate that
 # we incorrectly re-checked the nested union).
 field25: typing.Union[int, int | int]  # PYI016: Duplicate union member `int`
+
+# Should emit in cases with nested `typing.Union`
+field26: typing.Union[typing.Union[int, int]]  # PYI016: Duplicate union member `int`
+
+# Should emit in cases with nested `typing.Union`
+field27: typing.Union[typing.Union[typing.Union[int, int]]]  # PYI016: Duplicate union member `int`
+
+# Should emit in cases with mixed `typing.Union` and `|`
+field28: typing.Union[int | int]  # Error
+
+# Should emit twice in cases with multiple nested `typing.Union`
+field29: typing.Union[int, typing.Union[typing.Union[int, int]]]  # Error
+
+# Should emit once in cases with multiple nested `typing.Union`
+field30: typing.Union[int, typing.Union[typing.Union[int, str]]]  # Error
+
+# Should emit once, and fix to `typing.Union[float, int]`
+field31: typing.Union[float, typing.Union[int | int]]  # Error
+
+# Should emit once, and fix to `typing.Union[float, int]`
+field32: typing.Union[float, typing.Union[int | int | int]]  # Error
+
+# Test case for mixed union type fix
+field33: typing.Union[typing.Union[int | int] | typing.Union[int | int]] # Error
\ No newline at end of file
diff --git a/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI041.py b/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI041.py
index d1349b3ee3a0f..ba0b1f0c1bee9 100644
--- a/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI041.py
+++ b/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI041.py
@@ -39,6 +39,22 @@ async def f4(**kwargs: int | int | float) -> None:
     ...
 
 
+def f5(arg1: int, *args: Union[int, int, float]) -> None: 
+    ...
+
+
+def f6(arg1: int, *args: Union[Union[int, int, float]]) -> None: 
+    ...
+
+
+def f7(arg1: int, *args: Union[Union[Union[int, int, float]]]) -> None: 
+    ...
+
+
+def f8(arg1: int, *args: Union[Union[Union[int | int | float]]]) -> None: 
+    ...
+
+
 class Foo:
     def good(self, arg: int) -> None:
         ...
diff --git a/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI041.pyi b/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI041.pyi
index 07c2bd3fd67a3..8d95a56a58b12 100644
--- a/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI041.pyi
+++ b/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI041.pyi
@@ -33,6 +33,18 @@ def f3(arg1: int, *args: Union[int | int | float]) -> None: ...  # PYI041
 async def f4(**kwargs: int | int | float) -> None: ...  # PYI041
 
 
+def f5(arg1: int, *args: Union[int, int, float]) -> None: ...  # PYI041
+
+
+def f6(arg1: int, *args: Union[Union[int, int, float]]) -> None: ...  # PYI041
+
+
+def f7(arg1: int, *args: Union[Union[Union[int, int, float]]]) -> None: ...  # PYI041
+
+
+def f8(arg1: int, *args: Union[Union[Union[int | int | float]]]) -> None: ...  # PYI041
+
+
 class Foo:
     def good(self, arg: int) -> None: ...
 
diff --git a/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI051.py b/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI051.py
index 543c12974c36e..85e867f84e489 100644
--- a/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI051.py
+++ b/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI051.py
@@ -5,6 +5,9 @@
 B: TypeAlias = typing.Union[Literal[b"bar", b"foo"], bytes, str]
 C: TypeAlias = typing.Union[Literal[5], int, typing.Union[Literal["foo"], str]]
 D: TypeAlias = typing.Union[Literal[b"str_bytes", 42], bytes, int]
+E: TypeAlias = typing.Union[typing.Union[typing.Union[typing.Union[Literal["foo"], str]]]]
+F: TypeAlias = typing.Union[str, typing.Union[typing.Union[typing.Union[Literal["foo"], int]]]]
+G: typing.Union[str, typing.Union[typing.Union[typing.Union[Literal["foo"], int]]]]
 
 def func(x: complex | Literal[1J], y: Union[Literal[3.14], float]): ...
 
diff --git a/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI051.pyi b/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI051.pyi
index 543c12974c36e..85e867f84e489 100644
--- a/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI051.pyi
+++ b/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI051.pyi
@@ -5,6 +5,9 @@ A: str | Literal["foo"]
 B: TypeAlias = typing.Union[Literal[b"bar", b"foo"], bytes, str]
 C: TypeAlias = typing.Union[Literal[5], int, typing.Union[Literal["foo"], str]]
 D: TypeAlias = typing.Union[Literal[b"str_bytes", 42], bytes, int]
+E: TypeAlias = typing.Union[typing.Union[typing.Union[typing.Union[Literal["foo"], str]]]]
+F: TypeAlias = typing.Union[str, typing.Union[typing.Union[typing.Union[Literal["foo"], int]]]]
+G: typing.Union[str, typing.Union[typing.Union[typing.Union[Literal["foo"], int]]]]
 
 def func(x: complex | Literal[1J], y: Union[Literal[3.14], float]): ...
 
diff --git a/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI055.py b/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI055.py
index 2a9c2d77871cc..f039340e4a4cf 100644
--- a/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI055.py
+++ b/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI055.py
@@ -1,11 +1,14 @@
 import builtins
 from typing import Union
 
-w: builtins.type[int] | builtins.type[str] | builtins.type[complex]
-x: type[int] | type[str] | type[float]
-y: builtins.type[int] | type[str] | builtins.type[complex]
-z: Union[type[float], type[complex]]
-z: Union[type[float, int], type[complex]]
+s: builtins.type[int] | builtins.type[str] | builtins.type[complex]
+t: type[int] | type[str] | type[float]
+u: builtins.type[int] | type[str] | builtins.type[complex]
+v: Union[type[float], type[complex]]
+w: Union[type[float, int], type[complex]]
+x: Union[Union[type[float, int], type[complex]]]
+y: Union[Union[Union[type[float, int], type[complex]]]]
+z: Union[type[complex], Union[Union[type[float, int]]]]
 
 
 def func(arg: type[int] | str | type[float]) -> None:
diff --git a/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI055.pyi b/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI055.pyi
index 530f395dfa359..403fc40459580 100644
--- a/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI055.pyi
+++ b/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI055.pyi
@@ -1,11 +1,14 @@
 import builtins
 from typing import Union
 
-w: builtins.type[int] | builtins.type[str] | builtins.type[complex]
-x: type[int] | type[str] | type[float]
-y: builtins.type[int] | type[str] | builtins.type[complex]
-z: Union[type[float], type[complex]]
-z: Union[type[float, int], type[complex]]
+s: builtins.type[int] | builtins.type[str] | builtins.type[complex]
+t: type[int] | type[str] | type[float]
+u: builtins.type[int] | type[str] | builtins.type[complex]
+v: Union[type[float], type[complex]]
+w: Union[type[float, int], type[complex]]
+x: Union[Union[type[float, int], type[complex]]]
+y: Union[Union[Union[type[float, int], type[complex]]]]
+z: Union[type[complex], Union[Union[type[float, int]]]]
 
 def func(arg: type[int] | str | type[float]) -> None: ...
 
diff --git a/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI062.py b/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI062.py
index 9e3b46c1f80c0..7fbb70ce6a71f 100644
--- a/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI062.py
+++ b/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI062.py
@@ -14,8 +14,20 @@
 Literal[1, Literal[2], Literal[2]]  # once
 t.Literal[1, t.Literal[2, t.Literal[1]]]  # once
 typing_extensions.Literal[1, 1, 1]  # twice
+Literal[
+    1, # comment
+    Literal[ # another comment
+        1
+    ]
+]  # once
 
 # Ensure issue is only raised once, even on nested literals
 MyType = Literal["foo", Literal[True, False, True], "bar"]  # PYI062
 
 n: Literal["No", "duplicates", "here", 1, "1"]
+
+
+# nested literals, all equivalent to `Literal[1]`
+Literal[Literal[1]]  # no duplicate
+Literal[Literal[Literal[1], Literal[1]]]  # once
+Literal[Literal[1], Literal[Literal[Literal[1]]]]  # once
diff --git a/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI062.pyi b/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI062.pyi
index 38d04bcd9df68..7fbb70ce6a71f 100644
--- a/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI062.pyi
+++ b/crates/ruff_linter/resources/test/fixtures/flake8_pyi/PYI062.pyi
@@ -2,11 +2,11 @@ from typing import Literal
 import typing as t
 import typing_extensions
 
-x: Literal[True, False, True, False]  # PY062 twice here
+x: Literal[True, False, True, False]  # PYI062 twice here
 
-y: Literal[1, print("hello"), 3, Literal[4, 1]]  # PY062 on the last 1
+y: Literal[1, print("hello"), 3, Literal[4, 1]]  # PYI062 on the last 1
 
-z: Literal[{1, 3, 5}, "foobar", {1,3,5}]  # PY062 on the set literal
+z: Literal[{1, 3, 5}, "foobar", {1,3,5}]  # PYI062 on the set literal
 
 Literal[1, Literal[1]]  # once
 Literal[1, 2, Literal[1, 2]]  # twice
@@ -14,8 +14,20 @@ Literal[1, Literal[1], Literal[1]]  # twice
 Literal[1, Literal[2], Literal[2]]  # once
 t.Literal[1, t.Literal[2, t.Literal[1]]]  # once
 typing_extensions.Literal[1, 1, 1]  # twice
+Literal[
+    1, # comment
+    Literal[ # another comment
+        1
+    ]
+]  # once
 
 # Ensure issue is only raised once, even on nested literals
 MyType = Literal["foo", Literal[True, False, True], "bar"]  # PYI062
 
 n: Literal["No", "duplicates", "here", 1, "1"]
+
+
+# nested literals, all equivalent to `Literal[1]`
+Literal[Literal[1]]  # no duplicate
+Literal[Literal[Literal[1], Literal[1]]]  # once
+Literal[Literal[1], Literal[Literal[Literal[1]]]]  # once
diff --git a/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI016_PYI016.py.snap b/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI016_PYI016.py.snap
index d3ba1b4f1334b..4ffb35d5fd343 100644
--- a/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI016_PYI016.py.snap
+++ b/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI016_PYI016.py.snap
@@ -514,6 +514,8 @@ PYI016.py:86:28: PYI016 [*] Duplicate union member `int`
 85 | # we incorrectly re-checked the nested union).
 86 | field25: typing.Union[int, int | int]  # PYI016: Duplicate union member `int`
    |                            ^^^ PYI016
+87 | 
+88 | # Should emit in cases with nested `typing.Union`
    |
    = help: Remove duplicate union member `int`
 
@@ -523,6 +525,9 @@ PYI016.py:86:28: PYI016 [*] Duplicate union member `int`
 85 85 | # we incorrectly re-checked the nested union).
 86    |-field25: typing.Union[int, int | int]  # PYI016: Duplicate union member `int`
    86 |+field25: typing.Union[int, int]  # PYI016: Duplicate union member `int`
+87 87 | 
+88 88 | # Should emit in cases with nested `typing.Union`
+89 89 | field26: typing.Union[typing.Union[int, int]]  # PYI016: Duplicate union member `int`
 
 PYI016.py:86:34: PYI016 [*] Duplicate union member `int`
    |
@@ -530,6 +535,8 @@ PYI016.py:86:34: PYI016 [*] Duplicate union member `int`
 85 | # we incorrectly re-checked the nested union).
 86 | field25: typing.Union[int, int | int]  # PYI016: Duplicate union member `int`
    |                                  ^^^ PYI016
+87 | 
+88 | # Should emit in cases with nested `typing.Union`
    |
    = help: Remove duplicate union member `int`
 
@@ -539,5 +546,151 @@ PYI016.py:86:34: PYI016 [*] Duplicate union member `int`
 85 85 | # we incorrectly re-checked the nested union).
 86    |-field25: typing.Union[int, int | int]  # PYI016: Duplicate union member `int`
    86 |+field25: typing.Union[int, int]  # PYI016: Duplicate union member `int`
+87 87 | 
+88 88 | # Should emit in cases with nested `typing.Union`
+89 89 | field26: typing.Union[typing.Union[int, int]]  # PYI016: Duplicate union member `int`
 
+PYI016.py:89:41: PYI016 Duplicate union member `int`
+   |
+88 | # Should emit in cases with nested `typing.Union`
+89 | field26: typing.Union[typing.Union[int, int]]  # PYI016: Duplicate union member `int`
+   |                                         ^^^ PYI016
+90 | 
+91 | # Should emit in cases with nested `typing.Union`
+   |
+   = help: Remove duplicate union member `int`
 
+PYI016.py:95:29: PYI016 [*] Duplicate union member `int`
+   |
+94 | # Should emit in cases with mixed `typing.Union` and `|`
+95 | field28: typing.Union[int | int]  # Error
+   |                             ^^^ PYI016
+96 | 
+97 | # Should emit twice in cases with multiple nested `typing.Union`
+   |
+   = help: Remove duplicate union member `int`
+
+ℹ Safe fix
+92 92 | field27: typing.Union[typing.Union[typing.Union[int, int]]]  # PYI016: Duplicate union member `int`
+93 93 | 
+94 94 | # Should emit in cases with mixed `typing.Union` and `|`
+95    |-field28: typing.Union[int | int]  # Error
+   95 |+field28: typing.Union[int]  # Error
+96 96 | 
+97 97 | # Should emit twice in cases with multiple nested `typing.Union`
+98 98 | field29: typing.Union[int, typing.Union[typing.Union[int, int]]]  # Error
+
+PYI016.py:98:59: PYI016 Duplicate union member `int`
+    |
+ 97 | # Should emit twice in cases with multiple nested `typing.Union`
+ 98 | field29: typing.Union[int, typing.Union[typing.Union[int, int]]]  # Error
+    |                                                           ^^^ PYI016
+ 99 | 
+100 | # Should emit once in cases with multiple nested `typing.Union`
+    |
+    = help: Remove duplicate union member `int`
+
+PYI016.py:104:49: PYI016 [*] Duplicate union member `int`
+    |
+103 | # Should emit once, and fix to `typing.Union[float, int]`
+104 | field31: typing.Union[float, typing.Union[int | int]]  # Error
+    |                                                 ^^^ PYI016
+105 | 
+106 | # Should emit once, and fix to `typing.Union[float, int]`
+    |
+    = help: Remove duplicate union member `int`
+
+ℹ Safe fix
+101 101 | field30: typing.Union[int, typing.Union[typing.Union[int, str]]]  # Error
+102 102 | 
+103 103 | # Should emit once, and fix to `typing.Union[float, int]`
+104     |-field31: typing.Union[float, typing.Union[int | int]]  # Error
+    104 |+field31: typing.Union[float, typing.Union[int]]  # Error
+105 105 | 
+106 106 | # Should emit once, and fix to `typing.Union[float, int]`
+107 107 | field32: typing.Union[float, typing.Union[int | int | int]]  # Error
+
+PYI016.py:107:49: PYI016 [*] Duplicate union member `int`
+    |
+106 | # Should emit once, and fix to `typing.Union[float, int]`
+107 | field32: typing.Union[float, typing.Union[int | int | int]]  # Error
+    |                                                 ^^^ PYI016
+108 | 
+109 | # Test case for mixed union type fix
+    |
+    = help: Remove duplicate union member `int`
+
+ℹ Safe fix
+104 104 | field31: typing.Union[float, typing.Union[int | int]]  # Error
+105 105 | 
+106 106 | # Should emit once, and fix to `typing.Union[float, int]`
+107     |-field32: typing.Union[float, typing.Union[int | int | int]]  # Error
+    107 |+field32: typing.Union[float, typing.Union[int | int]]  # Error
+108 108 | 
+109 109 | # Test case for mixed union type fix
+110 110 | field33: typing.Union[typing.Union[int | int] | typing.Union[int | int]] # Error
+
+PYI016.py:107:55: PYI016 [*] Duplicate union member `int`
+    |
+106 | # Should emit once, and fix to `typing.Union[float, int]`
+107 | field32: typing.Union[float, typing.Union[int | int | int]]  # Error
+    |                                                       ^^^ PYI016
+108 | 
+109 | # Test case for mixed union type fix
+    |
+    = help: Remove duplicate union member `int`
+
+ℹ Safe fix
+104 104 | field31: typing.Union[float, typing.Union[int | int]]  # Error
+105 105 | 
+106 106 | # Should emit once, and fix to `typing.Union[float, int]`
+107     |-field32: typing.Union[float, typing.Union[int | int | int]]  # Error
+    107 |+field32: typing.Union[float, typing.Union[int | int]]  # Error
+108 108 | 
+109 109 | # Test case for mixed union type fix
+110 110 | field33: typing.Union[typing.Union[int | int] | typing.Union[int | int]] # Error
+
+PYI016.py:110:42: PYI016 [*] Duplicate union member `int`
+    |
+109 | # Test case for mixed union type fix
+110 | field33: typing.Union[typing.Union[int | int] | typing.Union[int | int]] # Error
+    |                                          ^^^ PYI016
+    |
+    = help: Remove duplicate union member `int`
+
+ℹ Safe fix
+107 107 | field32: typing.Union[float, typing.Union[int | int | int]]  # Error
+108 108 | 
+109 109 | # Test case for mixed union type fix
+110     |-field33: typing.Union[typing.Union[int | int] | typing.Union[int | int]] # Error
+    110 |+field33: typing.Union[typing.Union[int] | typing.Union[int | int]] # Error
+
+PYI016.py:110:49: PYI016 [*] Duplicate union member `typing.Union[int | int]`
+    |
+109 | # Test case for mixed union type fix
+110 | field33: typing.Union[typing.Union[int | int] | typing.Union[int | int]] # Error
+    |                                                 ^^^^^^^^^^^^^^^^^^^^^^^ PYI016
+    |
+    = help: Remove duplicate union member `typing.Union[int | int]`
+
+ℹ Safe fix
+107 107 | field32: typing.Union[float, typing.Union[int | int | int]]  # Error
+108 108 | 
+109 109 | # Test case for mixed union type fix
+110     |-field33: typing.Union[typing.Union[int | int] | typing.Union[int | int]] # Error
+    110 |+field33: typing.Union[typing.Union[int | int]] # Error
+
+PYI016.py:110:68: PYI016 [*] Duplicate union member `int`
+    |
+109 | # Test case for mixed union type fix
+110 | field33: typing.Union[typing.Union[int | int] | typing.Union[int | int]] # Error
+    |                                                                    ^^^ PYI016
+    |
+    = help: Remove duplicate union member `int`
+
+ℹ Safe fix
+107 107 | field32: typing.Union[float, typing.Union[int | int | int]]  # Error
+108 108 | 
+109 109 | # Test case for mixed union type fix
+110     |-field33: typing.Union[typing.Union[int | int] | typing.Union[int | int]] # Error
+    110 |+field33: typing.Union[typing.Union[int | int] | typing.Union[int]] # Error
diff --git a/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI016_PYI016.pyi.snap b/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI016_PYI016.pyi.snap
index 647791e92b21e..59159d245cfea 100644
--- a/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI016_PYI016.pyi.snap
+++ b/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI016_PYI016.pyi.snap
@@ -514,6 +514,8 @@ PYI016.pyi:86:28: PYI016 [*] Duplicate union member `int`
 85 | # we incorrectly re-checked the nested union).
 86 | field25: typing.Union[int, int | int]  # PYI016: Duplicate union member `int`
    |                            ^^^ PYI016
+87 | 
+88 | # Should emit in cases with nested `typing.Union`
    |
    = help: Remove duplicate union member `int`
 
@@ -523,6 +525,9 @@ PYI016.pyi:86:28: PYI016 [*] Duplicate union member `int`
 85 85 | # we incorrectly re-checked the nested union).
 86    |-field25: typing.Union[int, int | int]  # PYI016: Duplicate union member `int`
    86 |+field25: typing.Union[int, int]  # PYI016: Duplicate union member `int`
+87 87 | 
+88 88 | # Should emit in cases with nested `typing.Union`
+89 89 | field26: typing.Union[typing.Union[int, int]]  # PYI016: Duplicate union member `int`
 
 PYI016.pyi:86:34: PYI016 [*] Duplicate union member `int`
    |
@@ -530,6 +535,8 @@ PYI016.pyi:86:34: PYI016 [*] Duplicate union member `int`
 85 | # we incorrectly re-checked the nested union).
 86 | field25: typing.Union[int, int | int]  # PYI016: Duplicate union member `int`
    |                                  ^^^ PYI016
+87 | 
+88 | # Should emit in cases with nested `typing.Union`
    |
    = help: Remove duplicate union member `int`
 
@@ -539,5 +546,151 @@ PYI016.pyi:86:34: PYI016 [*] Duplicate union member `int`
 85 85 | # we incorrectly re-checked the nested union).
 86    |-field25: typing.Union[int, int | int]  # PYI016: Duplicate union member `int`
    86 |+field25: typing.Union[int, int]  # PYI016: Duplicate union member `int`
+87 87 | 
+88 88 | # Should emit in cases with nested `typing.Union`
+89 89 | field26: typing.Union[typing.Union[int, int]]  # PYI016: Duplicate union member `int`
 
+PYI016.pyi:89:41: PYI016 Duplicate union member `int`
+   |
+88 | # Should emit in cases with nested `typing.Union`
+89 | field26: typing.Union[typing.Union[int, int]]  # PYI016: Duplicate union member `int`
+   |                                         ^^^ PYI016
+90 | 
+91 | # Should emit in cases with nested `typing.Union`
+   |
+   = help: Remove duplicate union member `int`
 
+PYI016.pyi:95:29: PYI016 [*] Duplicate union member `int`
+   |
+94 | # Should emit in cases with mixed `typing.Union` and `|`
+95 | field28: typing.Union[int | int]  # Error
+   |                             ^^^ PYI016
+96 | 
+97 | # Should emit twice in cases with multiple nested `typing.Union`
+   |
+   = help: Remove duplicate union member `int`
+
+ℹ Safe fix
+92 92 | field27: typing.Union[typing.Union[typing.Union[int, int]]]  # PYI016: Duplicate union member `int`
+93 93 | 
+94 94 | # Should emit in cases with mixed `typing.Union` and `|`
+95    |-field28: typing.Union[int | int]  # Error
+   95 |+field28: typing.Union[int]  # Error
+96 96 | 
+97 97 | # Should emit twice in cases with multiple nested `typing.Union`
+98 98 | field29: typing.Union[int, typing.Union[typing.Union[int, int]]]  # Error
+
+PYI016.pyi:98:59: PYI016 Duplicate union member `int`
+    |
+ 97 | # Should emit twice in cases with multiple nested `typing.Union`
+ 98 | field29: typing.Union[int, typing.Union[typing.Union[int, int]]]  # Error
+    |                                                           ^^^ PYI016
+ 99 | 
+100 | # Should emit once in cases with multiple nested `typing.Union`
+    |
+    = help: Remove duplicate union member `int`
+
+PYI016.pyi:104:49: PYI016 [*] Duplicate union member `int`
+    |
+103 | # Should emit once, and fix to `typing.Union[float, int]`
+104 | field31: typing.Union[float, typing.Union[int | int]]  # Error
+    |                                                 ^^^ PYI016
+105 | 
+106 | # Should emit once, and fix to `typing.Union[float, int]`
+    |
+    = help: Remove duplicate union member `int`
+
+ℹ Safe fix
+101 101 | field30: typing.Union[int, typing.Union[typing.Union[int, str]]]  # Error
+102 102 | 
+103 103 | # Should emit once, and fix to `typing.Union[float, int]`
+104     |-field31: typing.Union[float, typing.Union[int | int]]  # Error
+    104 |+field31: typing.Union[float, typing.Union[int]]  # Error
+105 105 | 
+106 106 | # Should emit once, and fix to `typing.Union[float, int]`
+107 107 | field32: typing.Union[float, typing.Union[int | int | int]]  # Error
+
+PYI016.pyi:107:49: PYI016 [*] Duplicate union member `int`
+    |
+106 | # Should emit once, and fix to `typing.Union[float, int]`
+107 | field32: typing.Union[float, typing.Union[int | int | int]]  # Error
+    |                                                 ^^^ PYI016
+108 | 
+109 | # Test case for mixed union type fix
+    |
+    = help: Remove duplicate union member `int`
+
+ℹ Safe fix
+104 104 | field31: typing.Union[float, typing.Union[int | int]]  # Error
+105 105 | 
+106 106 | # Should emit once, and fix to `typing.Union[float, int]`
+107     |-field32: typing.Union[float, typing.Union[int | int | int]]  # Error
+    107 |+field32: typing.Union[float, typing.Union[int | int]]  # Error
+108 108 | 
+109 109 | # Test case for mixed union type fix
+110 110 | field33: typing.Union[typing.Union[int | int] | typing.Union[int | int]] # Error
+
+PYI016.pyi:107:55: PYI016 [*] Duplicate union member `int`
+    |
+106 | # Should emit once, and fix to `typing.Union[float, int]`
+107 | field32: typing.Union[float, typing.Union[int | int | int]]  # Error
+    |                                                       ^^^ PYI016
+108 | 
+109 | # Test case for mixed union type fix
+    |
+    = help: Remove duplicate union member `int`
+
+ℹ Safe fix
+104 104 | field31: typing.Union[float, typing.Union[int | int]]  # Error
+105 105 | 
+106 106 | # Should emit once, and fix to `typing.Union[float, int]`
+107     |-field32: typing.Union[float, typing.Union[int | int | int]]  # Error
+    107 |+field32: typing.Union[float, typing.Union[int | int]]  # Error
+108 108 | 
+109 109 | # Test case for mixed union type fix
+110 110 | field33: typing.Union[typing.Union[int | int] | typing.Union[int | int]] # Error
+
+PYI016.pyi:110:42: PYI016 [*] Duplicate union member `int`
+    |
+109 | # Test case for mixed union type fix
+110 | field33: typing.Union[typing.Union[int | int] | typing.Union[int | int]] # Error
+    |                                          ^^^ PYI016
+    |
+    = help: Remove duplicate union member `int`
+
+ℹ Safe fix
+107 107 | field32: typing.Union[float, typing.Union[int | int | int]]  # Error
+108 108 | 
+109 109 | # Test case for mixed union type fix
+110     |-field33: typing.Union[typing.Union[int | int] | typing.Union[int | int]] # Error
+    110 |+field33: typing.Union[typing.Union[int] | typing.Union[int | int]] # Error
+
+PYI016.pyi:110:49: PYI016 [*] Duplicate union member `typing.Union[int | int]`
+    |
+109 | # Test case for mixed union type fix
+110 | field33: typing.Union[typing.Union[int | int] | typing.Union[int | int]] # Error
+    |                                                 ^^^^^^^^^^^^^^^^^^^^^^^ PYI016
+    |
+    = help: Remove duplicate union member `typing.Union[int | int]`
+
+ℹ Safe fix
+107 107 | field32: typing.Union[float, typing.Union[int | int | int]]  # Error
+108 108 | 
+109 109 | # Test case for mixed union type fix
+110     |-field33: typing.Union[typing.Union[int | int] | typing.Union[int | int]] # Error
+    110 |+field33: typing.Union[typing.Union[int | int]] # Error
+
+PYI016.pyi:110:68: PYI016 [*] Duplicate union member `int`
+    |
+109 | # Test case for mixed union type fix
+110 | field33: typing.Union[typing.Union[int | int] | typing.Union[int | int]] # Error
+    |                                                                    ^^^ PYI016
+    |
+    = help: Remove duplicate union member `int`
+
+ℹ Safe fix
+107 107 | field32: typing.Union[float, typing.Union[int | int | int]]  # Error
+108 108 | 
+109 109 | # Test case for mixed union type fix
+110     |-field33: typing.Union[typing.Union[int | int] | typing.Union[int | int]] # Error
+    110 |+field33: typing.Union[typing.Union[int | int] | typing.Union[int]] # Error
diff --git a/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI041_PYI041.py.snap b/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI041_PYI041.py.snap
index e1721adde5913..d477fa4e5481d 100644
--- a/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI041_PYI041.py.snap
+++ b/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI041_PYI041.py.snap
@@ -29,22 +29,27 @@ PYI041.py:38:24: PYI041 Use `float` instead of `int | float`
 39 |     ...
    |
 
-PYI041.py:46:24: PYI041 Use `complex` instead of `float | complex`
+PYI041.py:42:26: PYI041 Use `float` instead of `int | float`
    |
-44 |         ...
-45 | 
-46 |     def bad(self, arg: int | float | complex) -> None:
-   |                        ^^^^^^^^^^^^^^^^^^^^^ PYI041
-47 |         ...
+42 | def f5(arg1: int, *args: Union[int, int, float]) -> None: 
+   |                          ^^^^^^^^^^^^^^^^^^^^^^ PYI041
+43 |     ...
    |
 
-PYI041.py:46:24: PYI041 Use `complex` instead of `int | complex`
+PYI041.py:62:24: PYI041 Use `complex` instead of `float | complex`
    |
-44 |         ...
-45 | 
-46 |     def bad(self, arg: int | float | complex) -> None:
+60 |         ...
+61 | 
+62 |     def bad(self, arg: int | float | complex) -> None:
    |                        ^^^^^^^^^^^^^^^^^^^^^ PYI041
-47 |         ...
+63 |         ...
    |
 
-
+PYI041.py:62:24: PYI041 Use `complex` instead of `int | complex`
+   |
+60 |         ...
+61 | 
+62 |     def bad(self, arg: int | float | complex) -> None:
+   |                        ^^^^^^^^^^^^^^^^^^^^^ PYI041
+63 |         ...
+   |
diff --git a/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI041_PYI041.pyi.snap b/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI041_PYI041.pyi.snap
index 914faa51566ad..1eb0532519ffe 100644
--- a/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI041_PYI041.pyi.snap
+++ b/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI041_PYI041.pyi.snap
@@ -25,20 +25,24 @@ PYI041.pyi:33:24: PYI041 Use `float` instead of `int | float`
    |                        ^^^^^^^^^^^^^^^^^ PYI041
    |
 
-PYI041.pyi:39:24: PYI041 Use `complex` instead of `float | complex`
+PYI041.pyi:36:26: PYI041 Use `float` instead of `int | float`
    |
-37 |     def good(self, arg: int) -> None: ...
-38 | 
-39 |     def bad(self, arg: int | float | complex) -> None: ...  # PYI041
-   |                        ^^^^^^^^^^^^^^^^^^^^^ PYI041
+36 | def f5(arg1: int, *args: Union[int, int, float]) -> None: ...  # PYI041
+   |                          ^^^^^^^^^^^^^^^^^^^^^^ PYI041
    |
 
-PYI041.pyi:39:24: PYI041 Use `complex` instead of `int | complex`
+PYI041.pyi:51:24: PYI041 Use `complex` instead of `float | complex`
    |
-37 |     def good(self, arg: int) -> None: ...
-38 | 
-39 |     def bad(self, arg: int | float | complex) -> None: ...  # PYI041
+49 |     def good(self, arg: int) -> None: ...
+50 | 
+51 |     def bad(self, arg: int | float | complex) -> None: ...  # PYI041
    |                        ^^^^^^^^^^^^^^^^^^^^^ PYI041
    |
 
-
+PYI041.pyi:51:24: PYI041 Use `complex` instead of `int | complex`
+   |
+49 |     def good(self, arg: int) -> None: ...
+50 | 
+51 |     def bad(self, arg: int | float | complex) -> None: ...  # PYI041
+   |                        ^^^^^^^^^^^^^^^^^^^^^ PYI041
+   |
diff --git a/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI051_PYI051.py.snap b/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI051_PYI051.py.snap
index 1e67d47c63e82..5bbbb9809aadc 100644
--- a/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI051_PYI051.py.snap
+++ b/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI051_PYI051.py.snap
@@ -36,6 +36,7 @@ PYI051.py:6:37: PYI051 `Literal[5]` is redundant in a union with `int`
 6 | C: TypeAlias = typing.Union[Literal[5], int, typing.Union[Literal["foo"], str]]
   |                                     ^ PYI051
 7 | D: TypeAlias = typing.Union[Literal[b"str_bytes", 42], bytes, int]
+8 | E: TypeAlias = typing.Union[typing.Union[typing.Union[typing.Union[Literal["foo"], str]]]]
   |
 
 PYI051.py:6:67: PYI051 `Literal["foo"]` is redundant in a union with `str`
@@ -45,6 +46,7 @@ PYI051.py:6:67: PYI051 `Literal["foo"]` is redundant in a union with `str`
 6 | C: TypeAlias = typing.Union[Literal[5], int, typing.Union[Literal["foo"], str]]
   |                                                                   ^^^^^ PYI051
 7 | D: TypeAlias = typing.Union[Literal[b"str_bytes", 42], bytes, int]
+8 | E: TypeAlias = typing.Union[typing.Union[typing.Union[typing.Union[Literal["foo"], str]]]]
   |
 
 PYI051.py:7:37: PYI051 `Literal[b"str_bytes"]` is redundant in a union with `bytes`
@@ -53,8 +55,8 @@ PYI051.py:7:37: PYI051 `Literal[b"str_bytes"]` is redundant in a union with `byt
 6 | C: TypeAlias = typing.Union[Literal[5], int, typing.Union[Literal["foo"], str]]
 7 | D: TypeAlias = typing.Union[Literal[b"str_bytes", 42], bytes, int]
   |                                     ^^^^^^^^^^^^ PYI051
-8 | 
-9 | def func(x: complex | Literal[1J], y: Union[Literal[3.14], float]): ...
+8 | E: TypeAlias = typing.Union[typing.Union[typing.Union[typing.Union[Literal["foo"], str]]]]
+9 | F: TypeAlias = typing.Union[str, typing.Union[typing.Union[typing.Union[Literal["foo"], int]]]]
   |
 
 PYI051.py:7:51: PYI051 `Literal[42]` is redundant in a union with `int`
@@ -63,28 +65,26 @@ PYI051.py:7:51: PYI051 `Literal[42]` is redundant in a union with `int`
 6 | C: TypeAlias = typing.Union[Literal[5], int, typing.Union[Literal["foo"], str]]
 7 | D: TypeAlias = typing.Union[Literal[b"str_bytes", 42], bytes, int]
   |                                                   ^^ PYI051
-8 | 
-9 | def func(x: complex | Literal[1J], y: Union[Literal[3.14], float]): ...
+8 | E: TypeAlias = typing.Union[typing.Union[typing.Union[typing.Union[Literal["foo"], str]]]]
+9 | F: TypeAlias = typing.Union[str, typing.Union[typing.Union[typing.Union[Literal["foo"], int]]]]
   |
 
-PYI051.py:9:31: PYI051 `Literal[1J]` is redundant in a union with `complex`
+PYI051.py:12:31: PYI051 `Literal[1J]` is redundant in a union with `complex`
    |
- 7 | D: TypeAlias = typing.Union[Literal[b"str_bytes", 42], bytes, int]
- 8 | 
- 9 | def func(x: complex | Literal[1J], y: Union[Literal[3.14], float]): ...
+10 | G: typing.Union[str, typing.Union[typing.Union[typing.Union[Literal["foo"], int]]]]
+11 | 
+12 | def func(x: complex | Literal[1J], y: Union[Literal[3.14], float]): ...
    |                               ^^ PYI051
-10 | 
-11 | # OK
+13 | 
+14 | # OK
    |
 
-PYI051.py:9:53: PYI051 `Literal[3.14]` is redundant in a union with `float`
+PYI051.py:12:53: PYI051 `Literal[3.14]` is redundant in a union with `float`
    |
- 7 | D: TypeAlias = typing.Union[Literal[b"str_bytes", 42], bytes, int]
- 8 | 
- 9 | def func(x: complex | Literal[1J], y: Union[Literal[3.14], float]): ...
+10 | G: typing.Union[str, typing.Union[typing.Union[typing.Union[Literal["foo"], int]]]]
+11 | 
+12 | def func(x: complex | Literal[1J], y: Union[Literal[3.14], float]): ...
    |                                                     ^^^^ PYI051
-10 | 
-11 | # OK
+13 | 
+14 | # OK
    |
-
-
diff --git a/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI051_PYI051.pyi.snap b/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI051_PYI051.pyi.snap
index b5da422a00a7f..bdf063c455cea 100644
--- a/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI051_PYI051.pyi.snap
+++ b/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI051_PYI051.pyi.snap
@@ -36,6 +36,7 @@ PYI051.pyi:6:37: PYI051 `Literal[5]` is redundant in a union with `int`
 6 | C: TypeAlias = typing.Union[Literal[5], int, typing.Union[Literal["foo"], str]]
   |                                     ^ PYI051
 7 | D: TypeAlias = typing.Union[Literal[b"str_bytes", 42], bytes, int]
+8 | E: TypeAlias = typing.Union[typing.Union[typing.Union[typing.Union[Literal["foo"], str]]]]
   |
 
 PYI051.pyi:6:67: PYI051 `Literal["foo"]` is redundant in a union with `str`
@@ -45,6 +46,7 @@ PYI051.pyi:6:67: PYI051 `Literal["foo"]` is redundant in a union with `str`
 6 | C: TypeAlias = typing.Union[Literal[5], int, typing.Union[Literal["foo"], str]]
   |                                                                   ^^^^^ PYI051
 7 | D: TypeAlias = typing.Union[Literal[b"str_bytes", 42], bytes, int]
+8 | E: TypeAlias = typing.Union[typing.Union[typing.Union[typing.Union[Literal["foo"], str]]]]
   |
 
 PYI051.pyi:7:37: PYI051 `Literal[b"str_bytes"]` is redundant in a union with `bytes`
@@ -53,8 +55,8 @@ PYI051.pyi:7:37: PYI051 `Literal[b"str_bytes"]` is redundant in a union with `by
 6 | C: TypeAlias = typing.Union[Literal[5], int, typing.Union[Literal["foo"], str]]
 7 | D: TypeAlias = typing.Union[Literal[b"str_bytes", 42], bytes, int]
   |                                     ^^^^^^^^^^^^ PYI051
-8 | 
-9 | def func(x: complex | Literal[1J], y: Union[Literal[3.14], float]): ...
+8 | E: TypeAlias = typing.Union[typing.Union[typing.Union[typing.Union[Literal["foo"], str]]]]
+9 | F: TypeAlias = typing.Union[str, typing.Union[typing.Union[typing.Union[Literal["foo"], int]]]]
   |
 
 PYI051.pyi:7:51: PYI051 `Literal[42]` is redundant in a union with `int`
@@ -63,28 +65,26 @@ PYI051.pyi:7:51: PYI051 `Literal[42]` is redundant in a union with `int`
 6 | C: TypeAlias = typing.Union[Literal[5], int, typing.Union[Literal["foo"], str]]
 7 | D: TypeAlias = typing.Union[Literal[b"str_bytes", 42], bytes, int]
   |                                                   ^^ PYI051
-8 | 
-9 | def func(x: complex | Literal[1J], y: Union[Literal[3.14], float]): ...
+8 | E: TypeAlias = typing.Union[typing.Union[typing.Union[typing.Union[Literal["foo"], str]]]]
+9 | F: TypeAlias = typing.Union[str, typing.Union[typing.Union[typing.Union[Literal["foo"], int]]]]
   |
 
-PYI051.pyi:9:31: PYI051 `Literal[1J]` is redundant in a union with `complex`
+PYI051.pyi:12:31: PYI051 `Literal[1J]` is redundant in a union with `complex`
    |
- 7 | D: TypeAlias = typing.Union[Literal[b"str_bytes", 42], bytes, int]
- 8 | 
- 9 | def func(x: complex | Literal[1J], y: Union[Literal[3.14], float]): ...
+10 | G: typing.Union[str, typing.Union[typing.Union[typing.Union[Literal["foo"], int]]]]
+11 | 
+12 | def func(x: complex | Literal[1J], y: Union[Literal[3.14], float]): ...
    |                               ^^ PYI051
-10 | 
-11 | # OK
+13 | 
+14 | # OK
    |
 
-PYI051.pyi:9:53: PYI051 `Literal[3.14]` is redundant in a union with `float`
+PYI051.pyi:12:53: PYI051 `Literal[3.14]` is redundant in a union with `float`
    |
- 7 | D: TypeAlias = typing.Union[Literal[b"str_bytes", 42], bytes, int]
- 8 | 
- 9 | def func(x: complex | Literal[1J], y: Union[Literal[3.14], float]): ...
+10 | G: typing.Union[str, typing.Union[typing.Union[typing.Union[Literal["foo"], int]]]]
+11 | 
+12 | def func(x: complex | Literal[1J], y: Union[Literal[3.14], float]): ...
    |                                                     ^^^^ PYI051
-10 | 
-11 | # OK
+13 | 
+14 | # OK
    |
-
-
diff --git a/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI055_PYI055.py.snap b/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI055_PYI055.py.snap
index e93e79a12d48a..2b03a0e9dc3ae 100644
--- a/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI055_PYI055.py.snap
+++ b/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI055_PYI055.py.snap
@@ -1,144 +1,142 @@
 ---
 source: crates/ruff_linter/src/rules/flake8_pyi/mod.rs
 ---
-PYI055.py:31:8: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[requests_mock.Mocker | httpretty | str]`.
+PYI055.py:34:8: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[requests_mock.Mocker | httpretty | str]`.
    |
-29 | def func():
-30 |     # PYI055
-31 |     x: type[requests_mock.Mocker] | type[httpretty] | type[str] = requests_mock.Mocker
+32 | def func():
+33 |     # PYI055
+34 |     x: type[requests_mock.Mocker] | type[httpretty] | type[str] = requests_mock.Mocker
    |        ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ PYI055
-32 |     y: Union[type[requests_mock.Mocker], type[httpretty], type[str]] = requests_mock.Mocker
+35 |     y: Union[type[requests_mock.Mocker], type[httpretty], type[str]] = requests_mock.Mocker
    |
    = help: Combine multiple `type` members
 
 ℹ Safe fix
-28 28 | 
-29 29 | def func():
-30 30 |     # PYI055
-31    |-    x: type[requests_mock.Mocker] | type[httpretty] | type[str] = requests_mock.Mocker
-   31 |+    x: type[requests_mock.Mocker | httpretty | str] = requests_mock.Mocker
-32 32 |     y: Union[type[requests_mock.Mocker], type[httpretty], type[str]] = requests_mock.Mocker
-33 33 | 
-34 34 | 
+31 31 | 
+32 32 | def func():
+33 33 |     # PYI055
+34    |-    x: type[requests_mock.Mocker] | type[httpretty] | type[str] = requests_mock.Mocker
+   34 |+    x: type[requests_mock.Mocker | httpretty | str] = requests_mock.Mocker
+35 35 |     y: Union[type[requests_mock.Mocker], type[httpretty], type[str]] = requests_mock.Mocker
+36 36 | 
+37 37 | 
 
-PYI055.py:32:8: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[Union[requests_mock.Mocker, httpretty, str]]`.
+PYI055.py:35:8: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[Union[requests_mock.Mocker, httpretty, str]]`.
    |
-30 |     # PYI055
-31 |     x: type[requests_mock.Mocker] | type[httpretty] | type[str] = requests_mock.Mocker
-32 |     y: Union[type[requests_mock.Mocker], type[httpretty], type[str]] = requests_mock.Mocker
+33 |     # PYI055
+34 |     x: type[requests_mock.Mocker] | type[httpretty] | type[str] = requests_mock.Mocker
+35 |     y: Union[type[requests_mock.Mocker], type[httpretty], type[str]] = requests_mock.Mocker
    |        ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ PYI055
    |
    = help: Combine multiple `type` members
 
 ℹ Safe fix
-29 29 | def func():
-30 30 |     # PYI055
-31 31 |     x: type[requests_mock.Mocker] | type[httpretty] | type[str] = requests_mock.Mocker
-32    |-    y: Union[type[requests_mock.Mocker], type[httpretty], type[str]] = requests_mock.Mocker
-   32 |+    y: type[Union[requests_mock.Mocker, httpretty, str]] = requests_mock.Mocker
-33 33 | 
-34 34 | 
-35 35 | def func():
+32 32 | def func():
+33 33 |     # PYI055
+34 34 |     x: type[requests_mock.Mocker] | type[httpretty] | type[str] = requests_mock.Mocker
+35    |-    y: Union[type[requests_mock.Mocker], type[httpretty], type[str]] = requests_mock.Mocker
+   35 |+    y: type[Union[requests_mock.Mocker, httpretty, str]] = requests_mock.Mocker
+36 36 | 
+37 37 | 
+38 38 | def func():
 
-PYI055.py:39:8: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[Union[requests_mock.Mocker, httpretty, str]]`.
+PYI055.py:42:8: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[Union[requests_mock.Mocker, httpretty, str]]`.
    |
-38 |     # PYI055
-39 |     x: Union[type[requests_mock.Mocker], type[httpretty], type[str]] = requests_mock.Mocker
+41 |     # PYI055
+42 |     x: Union[type[requests_mock.Mocker], type[httpretty], type[str]] = requests_mock.Mocker
    |        ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ PYI055
    |
    = help: Combine multiple `type` members
 
 ℹ Safe fix
-36 36 |     from typing import Union as U
-37 37 | 
-38 38 |     # PYI055
-39    |-    x: Union[type[requests_mock.Mocker], type[httpretty], type[str]] = requests_mock.Mocker
-   39 |+    x: type[Union[requests_mock.Mocker, httpretty, str]] = requests_mock.Mocker
+39 39 |     from typing import Union as U
 40 40 | 
-41 41 | 
-42 42 | def convert_union(union: UnionType) -> _T | None:
+41 41 |     # PYI055
+42    |-    x: Union[type[requests_mock.Mocker], type[httpretty], type[str]] = requests_mock.Mocker
+   42 |+    x: type[Union[requests_mock.Mocker, httpretty, str]] = requests_mock.Mocker
+43 43 | 
+44 44 | 
+45 45 | def convert_union(union: UnionType) -> _T | None:
 
-PYI055.py:44:9: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[_T | Converter[_T]]`.
+PYI055.py:47:9: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[_T | Converter[_T]]`.
    |
-42 | def convert_union(union: UnionType) -> _T | None:
-43 |     converters: tuple[
-44 |         type[_T] | type[Converter[_T]] | Converter[_T] | Callable[[str], _T], ...  # PYI055
+45 | def convert_union(union: UnionType) -> _T | None:
+46 |     converters: tuple[
+47 |         type[_T] | type[Converter[_T]] | Converter[_T] | Callable[[str], _T], ...  # PYI055
    |         ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ PYI055
-45 |     ] = union.__args__
-46 |     ...
+48 |     ] = union.__args__
+49 |     ...
    |
    = help: Combine multiple `type` members
 
 ℹ Safe fix
-41 41 | 
-42 42 | def convert_union(union: UnionType) -> _T | None:
-43 43 |     converters: tuple[
-44    |-        type[_T] | type[Converter[_T]] | Converter[_T] | Callable[[str], _T], ...  # PYI055
-   44 |+        type[_T | Converter[_T]] | Converter[_T] | Callable[[str], _T], ...  # PYI055
-45 45 |     ] = union.__args__
-46 46 |     ...
-47 47 | 
+44 44 | 
+45 45 | def convert_union(union: UnionType) -> _T | None:
+46 46 |     converters: tuple[
+47    |-        type[_T] | type[Converter[_T]] | Converter[_T] | Callable[[str], _T], ...  # PYI055
+   47 |+        type[_T | Converter[_T]] | Converter[_T] | Callable[[str], _T], ...  # PYI055
+48 48 |     ] = union.__args__
+49 49 |     ...
+50 50 | 
 
-PYI055.py:50:15: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[_T | Converter[_T]]`.
+PYI055.py:53:15: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[_T | Converter[_T]]`.
    |
-48 | def convert_union(union: UnionType) -> _T | None:
-49 |     converters: tuple[
-50 |         Union[type[_T] | type[Converter[_T]] | Converter[_T] | Callable[[str], _T]], ...  # PYI055
+51 | def convert_union(union: UnionType) -> _T | None:
+52 |     converters: tuple[
+53 |         Union[type[_T] | type[Converter[_T]] | Converter[_T] | Callable[[str], _T]], ...  # PYI055
    |               ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ PYI055
-51 |     ] = union.__args__
-52 |     ...
+54 |     ] = union.__args__
+55 |     ...
    |
    = help: Combine multiple `type` members
 
 ℹ Safe fix
-47 47 | 
-48 48 | def convert_union(union: UnionType) -> _T | None:
-49 49 |     converters: tuple[
-50    |-        Union[type[_T] | type[Converter[_T]] | Converter[_T] | Callable[[str], _T]], ...  # PYI055
-   50 |+        Union[type[_T | Converter[_T]] | Converter[_T] | Callable[[str], _T]], ...  # PYI055
-51 51 |     ] = union.__args__
-52 52 |     ...
-53 53 | 
+50 50 | 
+51 51 | def convert_union(union: UnionType) -> _T | None:
+52 52 |     converters: tuple[
+53    |-        Union[type[_T] | type[Converter[_T]] | Converter[_T] | Callable[[str], _T]], ...  # PYI055
+   53 |+        Union[type[_T | Converter[_T]] | Converter[_T] | Callable[[str], _T]], ...  # PYI055
+54 54 |     ] = union.__args__
+55 55 |     ...
+56 56 | 
 
-PYI055.py:56:15: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[_T | Converter[_T]]`.
+PYI055.py:59:15: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[_T | Converter[_T]]`.
    |
-54 | def convert_union(union: UnionType) -> _T | None:
-55 |     converters: tuple[
-56 |         Union[type[_T] | type[Converter[_T]]] | Converter[_T] | Callable[[str], _T], ...  # PYI055
+57 | def convert_union(union: UnionType) -> _T | None:
+58 |     converters: tuple[
+59 |         Union[type[_T] | type[Converter[_T]]] | Converter[_T] | Callable[[str], _T], ...  # PYI055
    |               ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ PYI055
-57 |     ] = union.__args__
-58 |     ...
+60 |     ] = union.__args__
+61 |     ...
    |
    = help: Combine multiple `type` members
 
 ℹ Safe fix
-53 53 | 
-54 54 | def convert_union(union: UnionType) -> _T | None:
-55 55 |     converters: tuple[
-56    |-        Union[type[_T] | type[Converter[_T]]] | Converter[_T] | Callable[[str], _T], ...  # PYI055
-   56 |+        Union[type[_T | Converter[_T]]] | Converter[_T] | Callable[[str], _T], ...  # PYI055
-57 57 |     ] = union.__args__
-58 58 |     ...
-59 59 | 
+56 56 | 
+57 57 | def convert_union(union: UnionType) -> _T | None:
+58 58 |     converters: tuple[
+59    |-        Union[type[_T] | type[Converter[_T]]] | Converter[_T] | Callable[[str], _T], ...  # PYI055
+   59 |+        Union[type[_T | Converter[_T]]] | Converter[_T] | Callable[[str], _T], ...  # PYI055
+60 60 |     ] = union.__args__
+61 61 |     ...
+62 62 | 
 
-PYI055.py:62:15: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[_T | Converter[_T]]`.
+PYI055.py:65:15: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[_T | Converter[_T]]`.
    |
-60 | def convert_union(union: UnionType) -> _T | None:
-61 |     converters: tuple[
-62 |         Union[type[_T] | type[Converter[_T]] | str] | Converter[_T] | Callable[[str], _T], ...  # PYI055
+63 | def convert_union(union: UnionType) -> _T | None:
+64 |     converters: tuple[
+65 |         Union[type[_T] | type[Converter[_T]] | str] | Converter[_T] | Callable[[str], _T], ...  # PYI055
    |               ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ PYI055
-63 |     ] = union.__args__
-64 |     ...
+66 |     ] = union.__args__
+67 |     ...
    |
    = help: Combine multiple `type` members
 
 ℹ Safe fix
-59 59 | 
-60 60 | def convert_union(union: UnionType) -> _T | None:
-61 61 |     converters: tuple[
-62    |-        Union[type[_T] | type[Converter[_T]] | str] | Converter[_T] | Callable[[str], _T], ...  # PYI055
-   62 |+        Union[type[_T | Converter[_T]] | str] | Converter[_T] | Callable[[str], _T], ...  # PYI055
-63 63 |     ] = union.__args__
-64 64 |     ...
-
-
+62 62 | 
+63 63 | def convert_union(union: UnionType) -> _T | None:
+64 64 |     converters: tuple[
+65    |-        Union[type[_T] | type[Converter[_T]] | str] | Converter[_T] | Callable[[str], _T], ...  # PYI055
+   65 |+        Union[type[_T | Converter[_T]] | str] | Converter[_T] | Callable[[str], _T], ...  # PYI055
+66 66 |     ] = union.__args__
+67 67 |     ...
diff --git a/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI055_PYI055.pyi.snap b/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI055_PYI055.pyi.snap
index 0e41288be5073..764d5c519dc2a 100644
--- a/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI055_PYI055.pyi.snap
+++ b/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI055_PYI055.pyi.snap
@@ -5,10 +5,10 @@ PYI055.pyi:4:4: PYI055 [*] Multiple `type` members in a union. Combine them into
   |
 2 | from typing import Union
 3 | 
-4 | w: builtins.type[int] | builtins.type[str] | builtins.type[complex]
+4 | s: builtins.type[int] | builtins.type[str] | builtins.type[complex]
   |    ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ PYI055
-5 | x: type[int] | type[str] | type[float]
-6 | y: builtins.type[int] | type[str] | builtins.type[complex]
+5 | t: type[int] | type[str] | type[float]
+6 | u: builtins.type[int] | type[str] | builtins.type[complex]
   |
   = help: Combine multiple `type` members
 
@@ -16,167 +16,187 @@ PYI055.pyi:4:4: PYI055 [*] Multiple `type` members in a union. Combine them into
 1 1 | import builtins
 2 2 | from typing import Union
 3 3 | 
-4   |-w: builtins.type[int] | builtins.type[str] | builtins.type[complex]
-  4 |+w: type[int | str | complex]
-5 5 | x: type[int] | type[str] | type[float]
-6 6 | y: builtins.type[int] | type[str] | builtins.type[complex]
-7 7 | z: Union[type[float], type[complex]]
+4   |-s: builtins.type[int] | builtins.type[str] | builtins.type[complex]
+  4 |+s: type[int | str | complex]
+5 5 | t: type[int] | type[str] | type[float]
+6 6 | u: builtins.type[int] | type[str] | builtins.type[complex]
+7 7 | v: Union[type[float], type[complex]]
 
 PYI055.pyi:5:4: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[int | str | float]`.
   |
-4 | w: builtins.type[int] | builtins.type[str] | builtins.type[complex]
-5 | x: type[int] | type[str] | type[float]
+4 | s: builtins.type[int] | builtins.type[str] | builtins.type[complex]
+5 | t: type[int] | type[str] | type[float]
   |    ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ PYI055
-6 | y: builtins.type[int] | type[str] | builtins.type[complex]
-7 | z: Union[type[float], type[complex]]
+6 | u: builtins.type[int] | type[str] | builtins.type[complex]
+7 | v: Union[type[float], type[complex]]
   |
   = help: Combine multiple `type` members
 
 ℹ Safe fix
 2 2 | from typing import Union
 3 3 | 
-4 4 | w: builtins.type[int] | builtins.type[str] | builtins.type[complex]
-5   |-x: type[int] | type[str] | type[float]
-  5 |+x: type[int | str | float]
-6 6 | y: builtins.type[int] | type[str] | builtins.type[complex]
-7 7 | z: Union[type[float], type[complex]]
-8 8 | z: Union[type[float, int], type[complex]]
+4 4 | s: builtins.type[int] | builtins.type[str] | builtins.type[complex]
+5   |-t: type[int] | type[str] | type[float]
+  5 |+t: type[int | str | float]
+6 6 | u: builtins.type[int] | type[str] | builtins.type[complex]
+7 7 | v: Union[type[float], type[complex]]
+8 8 | w: Union[type[float, int], type[complex]]
 
 PYI055.pyi:6:4: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[int | str | complex]`.
   |
-4 | w: builtins.type[int] | builtins.type[str] | builtins.type[complex]
-5 | x: type[int] | type[str] | type[float]
-6 | y: builtins.type[int] | type[str] | builtins.type[complex]
+4 | s: builtins.type[int] | builtins.type[str] | builtins.type[complex]
+5 | t: type[int] | type[str] | type[float]
+6 | u: builtins.type[int] | type[str] | builtins.type[complex]
   |    ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ PYI055
-7 | z: Union[type[float], type[complex]]
-8 | z: Union[type[float, int], type[complex]]
+7 | v: Union[type[float], type[complex]]
+8 | w: Union[type[float, int], type[complex]]
   |
   = help: Combine multiple `type` members
 
 ℹ Safe fix
 3 3 | 
-4 4 | w: builtins.type[int] | builtins.type[str] | builtins.type[complex]
-5 5 | x: type[int] | type[str] | type[float]
-6   |-y: builtins.type[int] | type[str] | builtins.type[complex]
-  6 |+y: type[int | str | complex]
-7 7 | z: Union[type[float], type[complex]]
-8 8 | z: Union[type[float, int], type[complex]]
-9 9 | 
+4 4 | s: builtins.type[int] | builtins.type[str] | builtins.type[complex]
+5 5 | t: type[int] | type[str] | type[float]
+6   |-u: builtins.type[int] | type[str] | builtins.type[complex]
+  6 |+u: type[int | str | complex]
+7 7 | v: Union[type[float], type[complex]]
+8 8 | w: Union[type[float, int], type[complex]]
+9 9 | x: Union[Union[type[float, int], type[complex]]]
 
 PYI055.pyi:7:4: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[Union[float, complex]]`.
   |
-5 | x: type[int] | type[str] | type[float]
-6 | y: builtins.type[int] | type[str] | builtins.type[complex]
-7 | z: Union[type[float], type[complex]]
+5 | t: type[int] | type[str] | type[float]
+6 | u: builtins.type[int] | type[str] | builtins.type[complex]
+7 | v: Union[type[float], type[complex]]
   |    ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ PYI055
-8 | z: Union[type[float, int], type[complex]]
+8 | w: Union[type[float, int], type[complex]]
+9 | x: Union[Union[type[float, int], type[complex]]]
   |
   = help: Combine multiple `type` members
 
 ℹ Safe fix
-4 4 | w: builtins.type[int] | builtins.type[str] | builtins.type[complex]
-5 5 | x: type[int] | type[str] | type[float]
-6 6 | y: builtins.type[int] | type[str] | builtins.type[complex]
-7   |-z: Union[type[float], type[complex]]
-  7 |+z: type[Union[float, complex]]
-8 8 | z: Union[type[float, int], type[complex]]
-9 9 | 
-10 10 | def func(arg: type[int] | str | type[float]) -> None: ...
+4 4 | s: builtins.type[int] | builtins.type[str] | builtins.type[complex]
+5 5 | t: type[int] | type[str] | type[float]
+6 6 | u: builtins.type[int] | type[str] | builtins.type[complex]
+7   |-v: Union[type[float], type[complex]]
+  7 |+v: type[Union[float, complex]]
+8 8 | w: Union[type[float, int], type[complex]]
+9 9 | x: Union[Union[type[float, int], type[complex]]]
+10 10 | y: Union[Union[Union[type[float, int], type[complex]]]]
 
 PYI055.pyi:8:4: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[Union[float, int, complex]]`.
    |
- 6 | y: builtins.type[int] | type[str] | builtins.type[complex]
- 7 | z: Union[type[float], type[complex]]
- 8 | z: Union[type[float, int], type[complex]]
+ 6 | u: builtins.type[int] | type[str] | builtins.type[complex]
+ 7 | v: Union[type[float], type[complex]]
+ 8 | w: Union[type[float, int], type[complex]]
    |    ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ PYI055
- 9 | 
-10 | def func(arg: type[int] | str | type[float]) -> None: ...
+ 9 | x: Union[Union[type[float, int], type[complex]]]
+10 | y: Union[Union[Union[type[float, int], type[complex]]]]
    |
    = help: Combine multiple `type` members
 
 ℹ Safe fix
-5 5 | x: type[int] | type[str] | type[float]
-6 6 | y: builtins.type[int] | type[str] | builtins.type[complex]
-7 7 | z: Union[type[float], type[complex]]
-8   |-z: Union[type[float, int], type[complex]]
-  8 |+z: type[Union[float, int, complex]]
-9 9 | 
-10 10 | def func(arg: type[int] | str | type[float]) -> None: ...
-11 11 | 
-
-PYI055.pyi:10:15: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[int | float]`.
+5 5 | t: type[int] | type[str] | type[float]
+6 6 | u: builtins.type[int] | type[str] | builtins.type[complex]
+7 7 | v: Union[type[float], type[complex]]
+8   |-w: Union[type[float, int], type[complex]]
+  8 |+w: type[Union[float, int, complex]]
+9 9 | x: Union[Union[type[float, int], type[complex]]]
+10 10 | y: Union[Union[Union[type[float, int], type[complex]]]]
+11 11 | z: Union[type[complex], Union[Union[type[float, int]]]]
+
+PYI055.pyi:9:10: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[Union[float, int, complex]]`.
    |
- 8 | z: Union[type[float, int], type[complex]]
- 9 | 
-10 | def func(arg: type[int] | str | type[float]) -> None: ...
+ 7 | v: Union[type[float], type[complex]]
+ 8 | w: Union[type[float, int], type[complex]]
+ 9 | x: Union[Union[type[float, int], type[complex]]]
+   |          ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ PYI055
+10 | y: Union[Union[Union[type[float, int], type[complex]]]]
+11 | z: Union[type[complex], Union[Union[type[float, int]]]]
+   |
+   = help: Combine multiple `type` members
+
+ℹ Safe fix
+6  6  | u: builtins.type[int] | type[str] | builtins.type[complex]
+7  7  | v: Union[type[float], type[complex]]
+8  8  | w: Union[type[float, int], type[complex]]
+9     |-x: Union[Union[type[float, int], type[complex]]]
+   9  |+x: Union[type[Union[float, int, complex]]]
+10 10 | y: Union[Union[Union[type[float, int], type[complex]]]]
+11 11 | z: Union[type[complex], Union[Union[type[float, int]]]]
+12 12 | 
+
+PYI055.pyi:13:15: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[int | float]`.
+   |
+11 | z: Union[type[complex], Union[Union[type[float, int]]]]
+12 | 
+13 | def func(arg: type[int] | str | type[float]) -> None: ...
    |               ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ PYI055
-11 | 
-12 | # OK
+14 | 
+15 | # OK
    |
    = help: Combine multiple `type` members
 
 ℹ Safe fix
-7  7  | z: Union[type[float], type[complex]]
-8  8  | z: Union[type[float, int], type[complex]]
-9  9  | 
-10    |-def func(arg: type[int] | str | type[float]) -> None: ...
-   10 |+def func(arg: type[int | float] | str) -> None: ...
-11 11 | 
-12 12 | # OK
-13 13 | x: type[int, str, float]
-
-PYI055.pyi:20:7: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[requests_mock.Mocker | httpretty]`.
+10 10 | y: Union[Union[Union[type[float, int], type[complex]]]]
+11 11 | z: Union[type[complex], Union[Union[type[float, int]]]]
+12 12 | 
+13    |-def func(arg: type[int] | str | type[float]) -> None: ...
+   13 |+def func(arg: type[int | float] | str) -> None: ...
+14 14 | 
+15 15 | # OK
+16 16 | x: type[int, str, float]
+
+PYI055.pyi:23:7: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[requests_mock.Mocker | httpretty]`.
    |
-19 | # OK
-20 | item: type[requests_mock.Mocker] | type[httpretty] = requests_mock.Mocker
+22 | # OK
+23 | item: type[requests_mock.Mocker] | type[httpretty] = requests_mock.Mocker
    |       ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ PYI055
-21 | 
-22 | def func():
+24 | 
+25 | def func():
    |
    = help: Combine multiple `type` members
 
 ℹ Safe fix
-17 17 | def func(arg: type[int, float] | str) -> None: ...
-18 18 | 
-19 19 | # OK
-20    |-item: type[requests_mock.Mocker] | type[httpretty] = requests_mock.Mocker
-   20 |+item: type[requests_mock.Mocker | httpretty] = requests_mock.Mocker
+20 20 | def func(arg: type[int, float] | str) -> None: ...
 21 21 | 
-22 22 | def func():
-23 23 |     # PYI055
-
-PYI055.pyi:24:11: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[requests_mock.Mocker | httpretty | str]`.
+22 22 | # OK
+23    |-item: type[requests_mock.Mocker] | type[httpretty] = requests_mock.Mocker
+   23 |+item: type[requests_mock.Mocker | httpretty] = requests_mock.Mocker
+24 24 | 
+25 25 | def func():
+26 26 |     # PYI055
+
+PYI055.pyi:27:11: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[requests_mock.Mocker | httpretty | str]`.
    |
-22 | def func():
-23 |     # PYI055
-24 |     item: type[requests_mock.Mocker] | type[httpretty] | type[str] = requests_mock.Mocker
+25 | def func():
+26 |     # PYI055
+27 |     item: type[requests_mock.Mocker] | type[httpretty] | type[str] = requests_mock.Mocker
    |           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ PYI055
-25 |     item2: Union[type[requests_mock.Mocker], type[httpretty], type[str]] = requests_mock.Mocker
+28 |     item2: Union[type[requests_mock.Mocker], type[httpretty], type[str]] = requests_mock.Mocker
    |
    = help: Combine multiple `type` members
 
 ℹ Safe fix
-21 21 | 
-22 22 | def func():
-23 23 |     # PYI055
-24    |-    item: type[requests_mock.Mocker] | type[httpretty] | type[str] = requests_mock.Mocker
-   24 |+    item: type[requests_mock.Mocker | httpretty | str] = requests_mock.Mocker
-25 25 |     item2: Union[type[requests_mock.Mocker], type[httpretty], type[str]] = requests_mock.Mocker
-
-PYI055.pyi:25:12: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[Union[requests_mock.Mocker, httpretty, str]]`.
+24 24 | 
+25 25 | def func():
+26 26 |     # PYI055
+27    |-    item: type[requests_mock.Mocker] | type[httpretty] | type[str] = requests_mock.Mocker
+   27 |+    item: type[requests_mock.Mocker | httpretty | str] = requests_mock.Mocker
+28 28 |     item2: Union[type[requests_mock.Mocker], type[httpretty], type[str]] = requests_mock.Mocker
+
+PYI055.pyi:28:12: PYI055 [*] Multiple `type` members in a union. Combine them into one, e.g., `type[Union[requests_mock.Mocker, httpretty, str]]`.
    |
-23 |     # PYI055
-24 |     item: type[requests_mock.Mocker] | type[httpretty] | type[str] = requests_mock.Mocker
-25 |     item2: Union[type[requests_mock.Mocker], type[httpretty], type[str]] = requests_mock.Mocker
+26 |     # PYI055
+27 |     item: type[requests_mock.Mocker] | type[httpretty] | type[str] = requests_mock.Mocker
+28 |     item2: Union[type[requests_mock.Mocker], type[httpretty], type[str]] = requests_mock.Mocker
    |            ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ PYI055
    |
    = help: Combine multiple `type` members
 
 ℹ Safe fix
-22 22 | def func():
-23 23 |     # PYI055
-24 24 |     item: type[requests_mock.Mocker] | type[httpretty] | type[str] = requests_mock.Mocker
-25    |-    item2: Union[type[requests_mock.Mocker], type[httpretty], type[str]] = requests_mock.Mocker
-   25 |+    item2: type[Union[requests_mock.Mocker, httpretty, str]] = requests_mock.Mocker
-
-
+25 25 | def func():
+26 26 |     # PYI055
+27 27 |     item: type[requests_mock.Mocker] | type[httpretty] | type[str] = requests_mock.Mocker
+28    |-    item2: Union[type[requests_mock.Mocker], type[httpretty], type[str]] = requests_mock.Mocker
+   28 |+    item2: type[Union[requests_mock.Mocker, httpretty, str]] = requests_mock.Mocker
diff --git a/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI062_PYI062.py.snap b/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI062_PYI062.py.snap
index c73ae4f46e55b..224e48cbc7ab8 100644
--- a/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI062_PYI062.py.snap
+++ b/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI062_PYI062.py.snap
@@ -207,7 +207,7 @@ PYI062.py:14:32: PYI062 [*] Duplicate literal member `2`
    14 |+Literal[1, 2]  # once
 15 15 | t.Literal[1, t.Literal[2, t.Literal[1]]]  # once
 16 16 | typing_extensions.Literal[1, 1, 1]  # twice
-17 17 | 
+17 17 | Literal[
 
 PYI062.py:15:37: PYI062 [*] Duplicate literal member `1`
    |
@@ -216,6 +216,7 @@ PYI062.py:15:37: PYI062 [*] Duplicate literal member `1`
 15 | t.Literal[1, t.Literal[2, t.Literal[1]]]  # once
    |                                     ^ PYI062
 16 | typing_extensions.Literal[1, 1, 1]  # twice
+17 | Literal[
    |
    = help: Remove duplicates
 
@@ -226,8 +227,8 @@ PYI062.py:15:37: PYI062 [*] Duplicate literal member `1`
 15    |-t.Literal[1, t.Literal[2, t.Literal[1]]]  # once
    15 |+t.Literal[1, 2]  # once
 16 16 | typing_extensions.Literal[1, 1, 1]  # twice
-17 17 | 
-18 18 | # Ensure issue is only raised once, even on nested literals
+17 17 | Literal[
+18 18 |     1, # comment
 
 PYI062.py:16:30: PYI062 [*] Duplicate literal member `1`
    |
@@ -235,8 +236,8 @@ PYI062.py:16:30: PYI062 [*] Duplicate literal member `1`
 15 | t.Literal[1, t.Literal[2, t.Literal[1]]]  # once
 16 | typing_extensions.Literal[1, 1, 1]  # twice
    |                              ^ PYI062
-17 | 
-18 | # Ensure issue is only raised once, even on nested literals
+17 | Literal[
+18 |     1, # comment
    |
    = help: Remove duplicates
 
@@ -246,9 +247,9 @@ PYI062.py:16:30: PYI062 [*] Duplicate literal member `1`
 15 15 | t.Literal[1, t.Literal[2, t.Literal[1]]]  # once
 16    |-typing_extensions.Literal[1, 1, 1]  # twice
    16 |+typing_extensions.Literal[1]  # twice
-17 17 | 
-18 18 | # Ensure issue is only raised once, even on nested literals
-19 19 | MyType = Literal["foo", Literal[True, False, True], "bar"]  # PYI062
+17 17 | Literal[
+18 18 |     1, # comment
+19 19 |     Literal[ # another comment
 
 PYI062.py:16:33: PYI062 [*] Duplicate literal member `1`
    |
@@ -256,8 +257,8 @@ PYI062.py:16:33: PYI062 [*] Duplicate literal member `1`
 15 | t.Literal[1, t.Literal[2, t.Literal[1]]]  # once
 16 | typing_extensions.Literal[1, 1, 1]  # twice
    |                                 ^ PYI062
-17 | 
-18 | # Ensure issue is only raised once, even on nested literals
+17 | Literal[
+18 |     1, # comment
    |
    = help: Remove duplicates
 
@@ -267,25 +268,104 @@ PYI062.py:16:33: PYI062 [*] Duplicate literal member `1`
 15 15 | t.Literal[1, t.Literal[2, t.Literal[1]]]  # once
 16    |-typing_extensions.Literal[1, 1, 1]  # twice
    16 |+typing_extensions.Literal[1]  # twice
-17 17 | 
-18 18 | # Ensure issue is only raised once, even on nested literals
-19 19 | MyType = Literal["foo", Literal[True, False, True], "bar"]  # PYI062
+17 17 | Literal[
+18 18 |     1, # comment
+19 19 |     Literal[ # another comment
 
-PYI062.py:19:46: PYI062 [*] Duplicate literal member `True`
+PYI062.py:20:9: PYI062 [*] Duplicate literal member `1`
    |
-18 | # Ensure issue is only raised once, even on nested literals
-19 | MyType = Literal["foo", Literal[True, False, True], "bar"]  # PYI062
-   |                                              ^^^^ PYI062
-20 | 
-21 | n: Literal["No", "duplicates", "here", 1, "1"]
+18 |     1, # comment
+19 |     Literal[ # another comment
+20 |         1
+   |         ^ PYI062
+21 |     ]
+22 | ]  # once
    |
    = help: Remove duplicates
 
 ℹ Safe fix
+14 14 | Literal[1, Literal[2], Literal[2]]  # once
+15 15 | t.Literal[1, t.Literal[2, t.Literal[1]]]  # once
 16 16 | typing_extensions.Literal[1, 1, 1]  # twice
-17 17 | 
-18 18 | # Ensure issue is only raised once, even on nested literals
-19    |-MyType = Literal["foo", Literal[True, False, True], "bar"]  # PYI062
-   19 |+MyType = Literal["foo", True, False, "bar"]  # PYI062
-20 20 | 
-21 21 | n: Literal["No", "duplicates", "here", 1, "1"]
+17    |-Literal[
+18    |-    1, # comment
+19    |-    Literal[ # another comment
+20    |-        1
+21    |-    ]
+22    |-]  # once
+   17 |+Literal[1]  # once
+23 18 | 
+24 19 | # Ensure issue is only raised once, even on nested literals
+25 20 | MyType = Literal["foo", Literal[True, False, True], "bar"]  # PYI062
+
+PYI062.py:25:46: PYI062 [*] Duplicate literal member `True`
+   |
+24 | # Ensure issue is only raised once, even on nested literals
+25 | MyType = Literal["foo", Literal[True, False, True], "bar"]  # PYI062
+   |                                              ^^^^ PYI062
+26 | 
+27 | n: Literal["No", "duplicates", "here", 1, "1"]
+   |
+   = help: Remove duplicates
+
+ℹ Safe fix
+22 22 | ]  # once
+23 23 | 
+24 24 | # Ensure issue is only raised once, even on nested literals
+25    |-MyType = Literal["foo", Literal[True, False, True], "bar"]  # PYI062
+   25 |+MyType = Literal["foo", True, False, "bar"]  # PYI062
+26 26 | 
+27 27 | n: Literal["No", "duplicates", "here", 1, "1"]
+28 28 | 
+
+PYI062.py:32:37: PYI062 [*] Duplicate literal member `1`
+   |
+30 | # nested literals, all equivalent to `Literal[1]`
+31 | Literal[Literal[1]]  # no duplicate
+32 | Literal[Literal[Literal[1], Literal[1]]]  # once
+   |                                     ^ PYI062
+33 | Literal[Literal[1], Literal[Literal[Literal[1]]]]  # once
+   |
+   = help: Remove duplicates
+
+ℹ Safe fix
+29 29 | 
+30 30 | # nested literals, all equivalent to `Literal[1]`
+31 31 | Literal[Literal[1]]  # no duplicate
+32    |-Literal[Literal[Literal[1], Literal[1]]]  # once
+   32 |+Literal[Literal[1]]  # once
+33 33 | Literal[Literal[1], Literal[Literal[Literal[1]]]]  # once
+
+PYI062.py:32:37: PYI062 [*] Duplicate literal member `1`
+   |
+30 | # nested literals, all equivalent to `Literal[1]`
+31 | Literal[Literal[1]]  # no duplicate
+32 | Literal[Literal[Literal[1], Literal[1]]]  # once
+   |                                     ^ PYI062
+33 | Literal[Literal[1], Literal[Literal[Literal[1]]]]  # once
+   |
+   = help: Remove duplicates
+
+ℹ Safe fix
+29 29 | 
+30 30 | # nested literals, all equivalent to `Literal[1]`
+31 31 | Literal[Literal[1]]  # no duplicate
+32    |-Literal[Literal[Literal[1], Literal[1]]]  # once
+   32 |+Literal[1]  # once
+33 33 | Literal[Literal[1], Literal[Literal[Literal[1]]]]  # once
+
+PYI062.py:33:45: PYI062 [*] Duplicate literal member `1`
+   |
+31 | Literal[Literal[1]]  # no duplicate
+32 | Literal[Literal[Literal[1], Literal[1]]]  # once
+33 | Literal[Literal[1], Literal[Literal[Literal[1]]]]  # once
+   |                                             ^ PYI062
+   |
+   = help: Remove duplicates
+
+ℹ Safe fix
+30 30 | # nested literals, all equivalent to `Literal[1]`
+31 31 | Literal[Literal[1]]  # no duplicate
+32 32 | Literal[Literal[Literal[1], Literal[1]]]  # once
+33    |-Literal[Literal[1], Literal[Literal[Literal[1]]]]  # once
+   33 |+Literal[1]  # once
diff --git a/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI062_PYI062.pyi.snap b/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI062_PYI062.pyi.snap
index 0a96dea0cec1e..c5ab4f3f20370 100644
--- a/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI062_PYI062.pyi.snap
+++ b/crates/ruff_linter/src/rules/flake8_pyi/snapshots/ruff_linter__rules__flake8_pyi__tests__PYI062_PYI062.pyi.snap
@@ -5,10 +5,10 @@ PYI062.pyi:5:25: PYI062 [*] Duplicate literal member `True`
   |
 3 | import typing_extensions
 4 | 
-5 | x: Literal[True, False, True, False]  # PY062 twice here
+5 | x: Literal[True, False, True, False]  # PYI062 twice here
   |                         ^^^^ PYI062
 6 | 
-7 | y: Literal[1, print("hello"), 3, Literal[4, 1]]  # PY062 on the last 1
+7 | y: Literal[1, print("hello"), 3, Literal[4, 1]]  # PYI062 on the last 1
   |
   = help: Remove duplicates
 
@@ -16,20 +16,20 @@ PYI062.pyi:5:25: PYI062 [*] Duplicate literal member `True`
 2 2 | import typing as t
 3 3 | import typing_extensions
 4 4 | 
-5   |-x: Literal[True, False, True, False]  # PY062 twice here
-  5 |+x: Literal[True, False]  # PY062 twice here
+5   |-x: Literal[True, False, True, False]  # PYI062 twice here
+  5 |+x: Literal[True, False]  # PYI062 twice here
 6 6 | 
-7 7 | y: Literal[1, print("hello"), 3, Literal[4, 1]]  # PY062 on the last 1
+7 7 | y: Literal[1, print("hello"), 3, Literal[4, 1]]  # PYI062 on the last 1
 8 8 | 
 
 PYI062.pyi:5:31: PYI062 [*] Duplicate literal member `False`
   |
 3 | import typing_extensions
 4 | 
-5 | x: Literal[True, False, True, False]  # PY062 twice here
+5 | x: Literal[True, False, True, False]  # PYI062 twice here
   |                               ^^^^^ PYI062
 6 | 
-7 | y: Literal[1, print("hello"), 3, Literal[4, 1]]  # PY062 on the last 1
+7 | y: Literal[1, print("hello"), 3, Literal[4, 1]]  # PYI062 on the last 1
   |
   = help: Remove duplicates
 
@@ -37,38 +37,38 @@ PYI062.pyi:5:31: PYI062 [*] Duplicate literal member `False`
 2 2 | import typing as t
 3 3 | import typing_extensions
 4 4 | 
-5   |-x: Literal[True, False, True, False]  # PY062 twice here
-  5 |+x: Literal[True, False]  # PY062 twice here
+5   |-x: Literal[True, False, True, False]  # PYI062 twice here
+  5 |+x: Literal[True, False]  # PYI062 twice here
 6 6 | 
-7 7 | y: Literal[1, print("hello"), 3, Literal[4, 1]]  # PY062 on the last 1
+7 7 | y: Literal[1, print("hello"), 3, Literal[4, 1]]  # PYI062 on the last 1
 8 8 | 
 
 PYI062.pyi:7:45: PYI062 [*] Duplicate literal member `1`
   |
-5 | x: Literal[True, False, True, False]  # PY062 twice here
+5 | x: Literal[True, False, True, False]  # PYI062 twice here
 6 | 
-7 | y: Literal[1, print("hello"), 3, Literal[4, 1]]  # PY062 on the last 1
+7 | y: Literal[1, print("hello"), 3, Literal[4, 1]]  # PYI062 on the last 1
   |                                             ^ PYI062
 8 | 
-9 | z: Literal[{1, 3, 5}, "foobar", {1,3,5}]  # PY062 on the set literal
+9 | z: Literal[{1, 3, 5}, "foobar", {1,3,5}]  # PYI062 on the set literal
   |
   = help: Remove duplicates
 
 ℹ Safe fix
 4 4 | 
-5 5 | x: Literal[True, False, True, False]  # PY062 twice here
+5 5 | x: Literal[True, False, True, False]  # PYI062 twice here
 6 6 | 
-7   |-y: Literal[1, print("hello"), 3, Literal[4, 1]]  # PY062 on the last 1
-  7 |+y: Literal[1, print("hello"), 3, 4]  # PY062 on the last 1
+7   |-y: Literal[1, print("hello"), 3, Literal[4, 1]]  # PYI062 on the last 1
+  7 |+y: Literal[1, print("hello"), 3, 4]  # PYI062 on the last 1
 8 8 | 
-9 9 | z: Literal[{1, 3, 5}, "foobar", {1,3,5}]  # PY062 on the set literal
+9 9 | z: Literal[{1, 3, 5}, "foobar", {1,3,5}]  # PYI062 on the set literal
 10 10 | 
 
 PYI062.pyi:9:33: PYI062 [*] Duplicate literal member `{1, 3, 5}`
    |
- 7 | y: Literal[1, print("hello"), 3, Literal[4, 1]]  # PY062 on the last 1
+ 7 | y: Literal[1, print("hello"), 3, Literal[4, 1]]  # PYI062 on the last 1
  8 | 
- 9 | z: Literal[{1, 3, 5}, "foobar", {1,3,5}]  # PY062 on the set literal
+ 9 | z: Literal[{1, 3, 5}, "foobar", {1,3,5}]  # PYI062 on the set literal
    |                                 ^^^^^^^ PYI062
 10 | 
 11 | Literal[1, Literal[1]]  # once
@@ -77,17 +77,17 @@ PYI062.pyi:9:33: PYI062 [*] Duplicate literal member `{1, 3, 5}`
 
 ℹ Safe fix
 6  6  | 
-7  7  | y: Literal[1, print("hello"), 3, Literal[4, 1]]  # PY062 on the last 1
+7  7  | y: Literal[1, print("hello"), 3, Literal[4, 1]]  # PYI062 on the last 1
 8  8  | 
-9     |-z: Literal[{1, 3, 5}, "foobar", {1,3,5}]  # PY062 on the set literal
-   9  |+z: Literal[{1, 3, 5}, "foobar"]  # PY062 on the set literal
+9     |-z: Literal[{1, 3, 5}, "foobar", {1,3,5}]  # PYI062 on the set literal
+   9  |+z: Literal[{1, 3, 5}, "foobar"]  # PYI062 on the set literal
 10 10 | 
 11 11 | Literal[1, Literal[1]]  # once
 12 12 | Literal[1, 2, Literal[1, 2]]  # twice
 
 PYI062.pyi:11:20: PYI062 [*] Duplicate literal member `1`
    |
- 9 | z: Literal[{1, 3, 5}, "foobar", {1,3,5}]  # PY062 on the set literal
+ 9 | z: Literal[{1, 3, 5}, "foobar", {1,3,5}]  # PYI062 on the set literal
 10 | 
 11 | Literal[1, Literal[1]]  # once
    |                    ^ PYI062
@@ -98,7 +98,7 @@ PYI062.pyi:11:20: PYI062 [*] Duplicate literal member `1`
 
 ℹ Safe fix
 8  8  | 
-9  9  | z: Literal[{1, 3, 5}, "foobar", {1,3,5}]  # PY062 on the set literal
+9  9  | z: Literal[{1, 3, 5}, "foobar", {1,3,5}]  # PYI062 on the set literal
 10 10 | 
 11    |-Literal[1, Literal[1]]  # once
    11 |+Literal[1]  # once
@@ -117,7 +117,7 @@ PYI062.pyi:12:23: PYI062 [*] Duplicate literal member `1`
    = help: Remove duplicates
 
 ℹ Safe fix
-9  9  | z: Literal[{1, 3, 5}, "foobar", {1,3,5}]  # PY062 on the set literal
+9  9  | z: Literal[{1, 3, 5}, "foobar", {1,3,5}]  # PYI062 on the set literal
 10 10 | 
 11 11 | Literal[1, Literal[1]]  # once
 12    |-Literal[1, 2, Literal[1, 2]]  # twice
@@ -137,7 +137,7 @@ PYI062.pyi:12:26: PYI062 [*] Duplicate literal member `2`
    = help: Remove duplicates
 
 ℹ Safe fix
-9  9  | z: Literal[{1, 3, 5}, "foobar", {1,3,5}]  # PY062 on the set literal
+9  9  | z: Literal[{1, 3, 5}, "foobar", {1,3,5}]  # PYI062 on the set literal
 10 10 | 
 11 11 | Literal[1, Literal[1]]  # once
 12    |-Literal[1, 2, Literal[1, 2]]  # twice
@@ -207,7 +207,7 @@ PYI062.pyi:14:32: PYI062 [*] Duplicate literal member `2`
    14 |+Literal[1, 2]  # once
 15 15 | t.Literal[1, t.Literal[2, t.Literal[1]]]  # once
 16 16 | typing_extensions.Literal[1, 1, 1]  # twice
-17 17 | 
+17 17 | Literal[
 
 PYI062.pyi:15:37: PYI062 [*] Duplicate literal member `1`
    |
@@ -216,6 +216,7 @@ PYI062.pyi:15:37: PYI062 [*] Duplicate literal member `1`
 15 | t.Literal[1, t.Literal[2, t.Literal[1]]]  # once
    |                                     ^ PYI062
 16 | typing_extensions.Literal[1, 1, 1]  # twice
+17 | Literal[
    |
    = help: Remove duplicates
 
@@ -226,8 +227,8 @@ PYI062.pyi:15:37: PYI062 [*] Duplicate literal member `1`
 15    |-t.Literal[1, t.Literal[2, t.Literal[1]]]  # once
    15 |+t.Literal[1, 2]  # once
 16 16 | typing_extensions.Literal[1, 1, 1]  # twice
-17 17 | 
-18 18 | # Ensure issue is only raised once, even on nested literals
+17 17 | Literal[
+18 18 |     1, # comment
 
 PYI062.pyi:16:30: PYI062 [*] Duplicate literal member `1`
    |
@@ -235,8 +236,8 @@ PYI062.pyi:16:30: PYI062 [*] Duplicate literal member `1`
 15 | t.Literal[1, t.Literal[2, t.Literal[1]]]  # once
 16 | typing_extensions.Literal[1, 1, 1]  # twice
    |                              ^ PYI062
-17 | 
-18 | # Ensure issue is only raised once, even on nested literals
+17 | Literal[
+18 |     1, # comment
    |
    = help: Remove duplicates
 
@@ -246,9 +247,9 @@ PYI062.pyi:16:30: PYI062 [*] Duplicate literal member `1`
 15 15 | t.Literal[1, t.Literal[2, t.Literal[1]]]  # once
 16    |-typing_extensions.Literal[1, 1, 1]  # twice
    16 |+typing_extensions.Literal[1]  # twice
-17 17 | 
-18 18 | # Ensure issue is only raised once, even on nested literals
-19 19 | MyType = Literal["foo", Literal[True, False, True], "bar"]  # PYI062
+17 17 | Literal[
+18 18 |     1, # comment
+19 19 |     Literal[ # another comment
 
 PYI062.pyi:16:33: PYI062 [*] Duplicate literal member `1`
    |
@@ -256,8 +257,8 @@ PYI062.pyi:16:33: PYI062 [*] Duplicate literal member `1`
 15 | t.Literal[1, t.Literal[2, t.Literal[1]]]  # once
 16 | typing_extensions.Literal[1, 1, 1]  # twice
    |                                 ^ PYI062
-17 | 
-18 | # Ensure issue is only raised once, even on nested literals
+17 | Literal[
+18 |     1, # comment
    |
    = help: Remove duplicates
 
@@ -267,25 +268,104 @@ PYI062.pyi:16:33: PYI062 [*] Duplicate literal member `1`
 15 15 | t.Literal[1, t.Literal[2, t.Literal[1]]]  # once
 16    |-typing_extensions.Literal[1, 1, 1]  # twice
    16 |+typing_extensions.Literal[1]  # twice
-17 17 | 
-18 18 | # Ensure issue is only raised once, even on nested literals
-19 19 | MyType = Literal["foo", Literal[True, False, True], "bar"]  # PYI062
+17 17 | Literal[
+18 18 |     1, # comment
+19 19 |     Literal[ # another comment
 
-PYI062.pyi:19:46: PYI062 [*] Duplicate literal member `True`
+PYI062.pyi:20:9: PYI062 [*] Duplicate literal member `1`
    |
-18 | # Ensure issue is only raised once, even on nested literals
-19 | MyType = Literal["foo", Literal[True, False, True], "bar"]  # PYI062
-   |                                              ^^^^ PYI062
-20 | 
-21 | n: Literal["No", "duplicates", "here", 1, "1"]
+18 |     1, # comment
+19 |     Literal[ # another comment
+20 |         1
+   |         ^ PYI062
+21 |     ]
+22 | ]  # once
    |
    = help: Remove duplicates
 
 ℹ Safe fix
+14 14 | Literal[1, Literal[2], Literal[2]]  # once
+15 15 | t.Literal[1, t.Literal[2, t.Literal[1]]]  # once
 16 16 | typing_extensions.Literal[1, 1, 1]  # twice
-17 17 | 
-18 18 | # Ensure issue is only raised once, even on nested literals
-19    |-MyType = Literal["foo", Literal[True, False, True], "bar"]  # PYI062
-   19 |+MyType = Literal["foo", True, False, "bar"]  # PYI062
-20 20 | 
-21 21 | n: Literal["No", "duplicates", "here", 1, "1"]
+17    |-Literal[
+18    |-    1, # comment
+19    |-    Literal[ # another comment
+20    |-        1
+21    |-    ]
+22    |-]  # once
+   17 |+Literal[1]  # once
+23 18 | 
+24 19 | # Ensure issue is only raised once, even on nested literals
+25 20 | MyType = Literal["foo", Literal[True, False, True], "bar"]  # PYI062
+
+PYI062.pyi:25:46: PYI062 [*] Duplicate literal member `True`
+   |
+24 | # Ensure issue is only raised once, even on nested literals
+25 | MyType = Literal["foo", Literal[True, False, True], "bar"]  # PYI062
+   |                                              ^^^^ PYI062
+26 | 
+27 | n: Literal["No", "duplicates", "here", 1, "1"]
+   |
+   = help: Remove duplicates
+
+ℹ Safe fix
+22 22 | ]  # once
+23 23 | 
+24 24 | # Ensure issue is only raised once, even on nested literals
+25    |-MyType = Literal["foo", Literal[True, False, True], "bar"]  # PYI062
+   25 |+MyType = Literal["foo", True, False, "bar"]  # PYI062
+26 26 | 
+27 27 | n: Literal["No", "duplicates", "here", 1, "1"]
+28 28 | 
+
+PYI062.pyi:32:37: PYI062 [*] Duplicate literal member `1`
+   |
+30 | # nested literals, all equivalent to `Literal[1]`
+31 | Literal[Literal[1]]  # no duplicate
+32 | Literal[Literal[Literal[1], Literal[1]]]  # once
+   |                                     ^ PYI062
+33 | Literal[Literal[1], Literal[Literal[Literal[1]]]]  # once
+   |
+   = help: Remove duplicates
+
+ℹ Safe fix
+29 29 | 
+30 30 | # nested literals, all equivalent to `Literal[1]`
+31 31 | Literal[Literal[1]]  # no duplicate
+32    |-Literal[Literal[Literal[1], Literal[1]]]  # once
+   32 |+Literal[Literal[1]]  # once
+33 33 | Literal[Literal[1], Literal[Literal[Literal[1]]]]  # once
+
+PYI062.pyi:32:37: PYI062 [*] Duplicate literal member `1`
+   |
+30 | # nested literals, all equivalent to `Literal[1]`
+31 | Literal[Literal[1]]  # no duplicate
+32 | Literal[Literal[Literal[1], Literal[1]]]  # once
+   |                                     ^ PYI062
+33 | Literal[Literal[1], Literal[Literal[Literal[1]]]]  # once
+   |
+   = help: Remove duplicates
+
+ℹ Safe fix
+29 29 | 
+30 30 | # nested literals, all equivalent to `Literal[1]`
+31 31 | Literal[Literal[1]]  # no duplicate
+32    |-Literal[Literal[Literal[1], Literal[1]]]  # once
+   32 |+Literal[1]  # once
+33 33 | Literal[Literal[1], Literal[Literal[Literal[1]]]]  # once
+
+PYI062.pyi:33:45: PYI062 [*] Duplicate literal member `1`
+   |
+31 | Literal[Literal[1]]  # no duplicate
+32 | Literal[Literal[Literal[1], Literal[1]]]  # once
+33 | Literal[Literal[1], Literal[Literal[Literal[1]]]]  # once
+   |                                             ^ PYI062
+   |
+   = help: Remove duplicates
+
+ℹ Safe fix
+30 30 | # nested literals, all equivalent to `Literal[1]`
+31 31 | Literal[Literal[1]]  # no duplicate
+32 32 | Literal[Literal[Literal[1], Literal[1]]]  # once
+33    |-Literal[Literal[1], Literal[Literal[Literal[1]]]]  # once
+   33 |+Literal[1]  # once