diff --git a/CHANGELOG.md b/CHANGELOG.md
index aedaa20f..275c55e6 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,13 @@
 # Change Log
 
+## Unreleased
+
+New error codes:
+* Y062: Disallow duplicate elements inside `Literal[]` slices.
+
+Other changes:
+* Y061 is no longer emitted in situations where Y062 would also be emitted.
+
 ## 23.11.0
 
 New error codes:
diff --git a/ERRORCODES.md b/ERRORCODES.md
index a9db5b7b..1e0bd31d 100644
--- a/ERRORCODES.md
+++ b/ERRORCODES.md
@@ -63,7 +63,8 @@ The following warnings are currently emitted by default:
 | Y058 | Use `Iterator` rather than `Generator` as the return value for simple `__iter__` methods, and `AsyncIterator` rather than `AsyncGenerator` as the return value for simple `__aiter__` methods. Using `(Async)Iterator` for these methods is simpler and more elegant, and reflects the fact that the precise kind of iterator returned from an `__iter__` method is usually an implementation detail that could change at any time, and should not be relied upon.
 | Y059 | `Generic[]` should always be the last base class, if it is present in a class's bases tuple. At runtime, if `Generic[]` is not the final class in a the bases tuple, this [can cause the class creation to fail](https://github.com/python/cpython/issues/106102). In a stub file, however, this rule is enforced purely for stylistic consistency.
 | Y060 | Redundant inheritance from `Generic[]`. For example, `class Foo(Iterable[_T], Generic[_T]): ...` can be written more simply as `class Foo(Iterable[_T]): ...`.<br><br>To avoid false-positive errors, and to avoid complexity in the implementation, this check is deliberately conservative: it only flags classes where all subscripted bases have identical code inside their subscript slices.
-| Y061 | Do not use `None` inside a `Literal[]` slice. For example, use `Literal["foo"] \| None` instead of `Literal["foo", None]`. While both are legal according to [PEP 586](https://peps.python.org/pep-0586/), the former is preferred for stylistic consistency.
+| Y061 | Do not use `None` inside a `Literal[]` slice. For example, use `Literal["foo"] \| None` instead of `Literal["foo", None]`. While both are legal according to [PEP 586](https://peps.python.org/pep-0586/), the former is preferred for stylistic consistency. Note that this warning is not emitted if Y062 is emitted for the same `Literal[]` slice. For example, `Literal[None, None, True, True]` only causes Y062 to be emitted.
+| Y062 | `Literal[]` slices shouldn't contain duplicates, e.g. `Literal[True, True]` is not allowed.
 
 ## Warnings disabled by default
 
diff --git a/pyi.py b/pyi.py
index 1164bf5d..971bde3d 100644
--- a/pyi.py
+++ b/pyi.py
@@ -671,6 +671,43 @@ def _analyse_union(members: Sequence[ast.expr]) -> UnionAnalysis:
     )
 
 
+class TypingLiteralAnalysis(NamedTuple):
+    members_by_dump: defaultdict[str, list[_SliceContents]]
+    members_without_none: list[_SliceContents]
+    none_members: list[_SliceContents]
+    contains_only_none: bool
+
+
+def _analyse_typing_Literal(node: ast.Subscript) -> TypingLiteralAnalysis:
+    """Return a tuple providing analysis of a `typing.Literal` slice."""
+
+    members: Sequence[_SliceContents]
+    members_by_dump: defaultdict[str, list[_SliceContents]] = defaultdict(list)
+    members_without_none: list[_SliceContents] = []
+    none_members: list[_SliceContents] = []
+
+    if isinstance(node.slice, ast.Tuple):
+        members = node.slice.elts
+    else:
+        members = [node.slice]
+
+    for member in members:
+        members_by_dump[ast.dump(member)].append(member)
+        # https://github.com/PyCQA/flake8-pyi/pull/449#discussion_r1391804472
+        # TODO: Remove the `type: ignore` when we drop support for py38
+        if _is_None(member):  # type: ignore[arg-type,unused-ignore]
+            none_members.append(member)
+        else:
+            members_without_none.append(member)
+
+    return TypingLiteralAnalysis(
+        members_by_dump=members_by_dump,
+        members_without_none=members_without_none,
+        none_members=none_members,
+        contains_only_none=bool(none_members and not members_without_none),
+    )
+
+
 _ALLOWED_MATH_ATTRIBUTES_IN_DEFAULTS = frozenset(
     {"math.inf", "math.nan", "math.e", "math.pi", "math.tau"}
 )
@@ -1425,24 +1462,28 @@ def visit_Subscript(self, node: ast.Subscript) -> None:
                 self._Y090_error(node)
 
     def _visit_typing_Literal(self, node: ast.Subscript) -> None:
-        if isinstance(node.slice, ast.Constant) and _is_None(node.slice):
-            # Special case for `Literal[None]`
-            self.error(node.slice, Y061.format(suggestion="None"))
-        elif isinstance(node.slice, ast.Tuple):
-            elts = node.slice.elts
-            for i, elt in enumerate(elts):
-                if _is_None(elt):
-                    elts_without_none = elts[:i] + [
-                        elt for elt in elts[i + 1 :] if not _is_None(elt)
-                    ]
-                    if len(elts_without_none) == 1:
-                        new_literal_slice = unparse(elts_without_none[0])
-                    else:
-                        new_slice_node = ast.Tuple(elts=elts_without_none)
-                        new_literal_slice = unparse(new_slice_node).strip("()")
-                    suggestion = f"Literal[{new_literal_slice}] | None"
-                    self.error(elt, Y061.format(suggestion=suggestion))
-                    break  # Only report the first `None`
+        analysis = _analyse_typing_Literal(node)
+
+        Y062_encountered = False
+        for member_list in analysis.members_by_dump.values():
+            # https://github.com/PyCQA/flake8-pyi/pull/449#discussion_r1391804472
+            # TODO: Remove the `type: ignore` when we drop support for py38
+            if len(member_list) > 1 and not _is_None(member_list[0]):  # type: ignore[arg-type,unused-ignore]
+                Y062_encountered = True
+                self.error(member_list[1], Y062.format(unparse(member_list[1])))
+
+        if not Y062_encountered:
+            if analysis.contains_only_none:
+                self.error(node.slice, Y061.format(suggestion="None"))
+            elif analysis.none_members:
+                if len(analysis.members_without_none) == 1:
+                    new_literal_slice = unparse(analysis.members_without_none[0])
+                else:
+                    new_slice_node = ast.Tuple(elts=analysis.members_without_none)
+                    new_literal_slice = unparse(new_slice_node).strip("()")
+                suggestion = f"Literal[{new_literal_slice}] | None"
+                self.error(analysis.none_members[0], Y061.format(suggestion=suggestion))
+
         self.visit(node.slice)
 
     def _visit_slice_tuple(self, node: ast.Tuple, parent: str | None) -> None:
@@ -2258,6 +2299,7 @@ def parse_options(options: argparse.Namespace) -> None:
     "class would be inferred as generic anyway"
 )
 Y061 = 'Y061 None inside "Literal[]" expression. Replace with "{suggestion}"'
+Y062 = 'Y062 Duplicate "Literal[]" member "{}"'
 Y090 = (
     'Y090 "{original}" means '
     '"a tuple of length 1, in which the sole element is of type {typ!r}". '
diff --git a/tests/literals.pyi b/tests/literals.pyi
index a619881f..57124c07 100644
--- a/tests/literals.pyi
+++ b/tests/literals.pyi
@@ -2,4 +2,22 @@ from typing import Literal
 
 Literal[None]  # Y061 None inside "Literal[]" expression. Replace with "None"
 Literal[True, None]  # Y061 None inside "Literal[]" expression. Replace with "Literal[True] | None"
+
+Literal[True, True]  # Y062 Duplicate "Literal[]" member "True"
+Literal[True, True, True]  # Y062 Duplicate "Literal[]" member "True"
+Literal[True, False, True, False]  # Y062 Duplicate "Literal[]" member "True" # Y062 Duplicate "Literal[]" member "False"
+
+###
+# The following rules here are slightly subtle,
+# but make sense when it comes to giving the best suggestions to users of flake8-pyi.
+###
+
+# If Y061 and Y062 both apply, but all the duplicate members are None,
+# only emit Y061...
+Literal[None, None]  # Y061 None inside "Literal[]" expression. Replace with "None"
 Literal[1, None, "foo", None]  # Y061 None inside "Literal[]" expression. Replace with "Literal[1, 'foo'] | None"
+
+# ... but if Y061 and Y062 both apply
+# and there are no None members in the Literal[] slice,
+# only emit Y062:
+Literal[None, True, None, True]  # Y062 Duplicate "Literal[]" member "True"