diff --git a/docs/source/command_line.rst b/docs/source/command_line.rst
index b5081f113f91..996ee8c42aeb 100644
--- a/docs/source/command_line.rst
+++ b/docs/source/command_line.rst
@@ -774,6 +774,21 @@ of the above sections.
        f(memoryview(b""))  # Ok
 
 
+.. option:: --disallow-str-iteration
+
+    Disallow iterating over ``str`` values.
+    This also rejects using ``str`` where an ``Iterable[str]`` or ``Sequence[str]`` is expected.
+    To iterate over characters, call ``iter`` on the string explicitly.
+
+    .. code-block:: python
+
+       s = "hello"
+       for ch in s:  # error: Iterating over "str" is disallowed
+           print(ch)
+
+        for ch in iter(s):  # OK
+           print(ch)
+
 .. option:: --extra-checks
 
     This flag enables additional checks that are technically correct but may be
diff --git a/docs/source/config_file.rst b/docs/source/config_file.rst
index 77f952471007..41c15536230d 100644
--- a/docs/source/config_file.rst
+++ b/docs/source/config_file.rst
@@ -852,6 +852,14 @@ section of the command line docs.
    Disable treating ``bytearray`` and ``memoryview`` as subtypes of ``bytes``.
    This will be enabled by default in *mypy 2.0*.
 
+.. confval:: disallow_str_iteration
+
+   :type: boolean
+   :default: False
+
+   Disallow iterating over ``str`` values.
+   This also rejects using ``str`` where an ``Iterable[str]`` or ``Sequence[str]`` is expected.
+
 .. confval:: strict
 
    :type: boolean
diff --git a/misc/typeshed_patches/0001-Add-explicit-overload-for-iter-of-str.patch b/misc/typeshed_patches/0001-Add-explicit-overload-for-iter-of-str.patch
new file mode 100644
index 000000000000..d5a9a7150291
--- /dev/null
+++ b/misc/typeshed_patches/0001-Add-explicit-overload-for-iter-of-str.patch
@@ -0,0 +1,13 @@
+diff --git a/mypy/typeshed/stdlib/builtins.pyi b/mypy/typeshed/stdlib/builtins.pyi
+index bd425ff3c..5dae75dd9 100644
+--- a/mypy/typeshed/stdlib/builtins.pyi
++++ b/mypy/typeshed/stdlib/builtins.pyi
+@@ -1458,6 +1458,8 @@ class _GetItemIterable(Protocol[_T_co]):
+ @overload
+ def iter(object: SupportsIter[_SupportsNextT_co], /) -> _SupportsNextT_co: ...
+ @overload
++def iter(object: str, /) -> Iterator[str]: ...
++@overload
+ def iter(object: _GetItemIterable[_T], /) -> Iterator[_T]: ...
+ @overload
+ def iter(object: Callable[[], _T | None], sentinel: None, /) -> Iterator[_T]: ...
diff --git a/mypy/checker.py b/mypy/checker.py
index 008becdd3483..17b39b22563e 100644
--- a/mypy/checker.py
+++ b/mypy/checker.py
@@ -32,6 +32,7 @@
 )
 from mypy.checkpattern import PatternChecker
 from mypy.constraints import SUPERTYPE_OF
+from mypy.disallow_str_iteration_state import disallow_str_iteration_state
 from mypy.erasetype import erase_type, erase_typevars, remove_instance_last_known_values
 from mypy.errorcodes import TYPE_VAR, UNUSED_AWAITABLE, UNUSED_COROUTINE, ErrorCode
 from mypy.errors import (
@@ -513,7 +514,11 @@ def check_first_pass(self) -> None:
         Deferred functions will be processed by check_second_pass().
         """
         self.recurse_into_functions = True
-        with state.strict_optional_set(self.options.strict_optional), checker_state.set(self):
+        with (
+            state.strict_optional_set(self.options.strict_optional),
+            disallow_str_iteration_state.set(self.options.disallow_str_iteration),
+            checker_state.set(self),
+        ):
             self.errors.set_file(
                 self.path, self.tree.fullname, scope=self.tscope, options=self.options
             )
@@ -558,7 +563,11 @@ def check_second_pass(
         """
         self.allow_constructor_cache = allow_constructor_cache
         self.recurse_into_functions = True
-        with state.strict_optional_set(self.options.strict_optional), checker_state.set(self):
+        with (
+            state.strict_optional_set(self.options.strict_optional),
+            disallow_str_iteration_state.set(self.options.disallow_str_iteration),
+            checker_state.set(self),
+        ):
             if not todo and not self.deferred_nodes:
                 return False
             self.errors.set_file(
@@ -5378,6 +5387,12 @@ def analyze_iterable_item_type_without_expression(
         echk = self.expr_checker
         iterable: Type
         iterable = get_proper_type(type)
+
+        if disallow_str_iteration_state.disallow_str_iteration and self.is_str_iteration_type(
+            iterable
+        ):
+            self.msg.str_iteration_disallowed(context, iterable)
+
         iterator = echk.check_method_call_by_name("__iter__", iterable, [], [], context)[0]
 
         if (
@@ -5390,6 +5405,18 @@ def analyze_iterable_item_type_without_expression(
             iterable = echk.check_method_call_by_name("__next__", iterator, [], [], context)[0]
             return iterator, iterable
 
+    def is_str_iteration_type(self, typ: Type) -> bool:
+        typ = get_proper_type(typ)
+        if isinstance(typ, LiteralType):
+            return isinstance(typ.value, str)
+        if isinstance(typ, Instance):
+            return is_proper_subtype(typ, self.named_type("builtins.str"))
+        if isinstance(typ, UnionType):
+            return any(self.is_str_iteration_type(item) for item in typ.relevant_items())
+        if isinstance(typ, TypeVarType):
+            return self.is_str_iteration_type(typ.upper_bound)
+        return False
+
     def analyze_range_native_int_type(self, expr: Expression) -> Type | None:
         """Try to infer native int item type from arguments to range(...).
 
diff --git a/mypy/disallow_str_iteration_state.py b/mypy/disallow_str_iteration_state.py
new file mode 100644
index 000000000000..930243b00af1
--- /dev/null
+++ b/mypy/disallow_str_iteration_state.py
@@ -0,0 +1,25 @@
+from __future__ import annotations
+
+from collections.abc import Iterator
+from contextlib import contextmanager
+from typing import Final
+
+
+class DisallowStrIterationState:
+    # Wrap this in a class since it's faster that using a module-level attribute.
+
+    def __init__(self, disallow_str_iteration: bool) -> None:
+        # Value varies by file being processed
+        self.disallow_str_iteration = disallow_str_iteration
+
+    @contextmanager
+    def set(self, value: bool) -> Iterator[None]:
+        saved = self.disallow_str_iteration
+        self.disallow_str_iteration = value
+        try:
+            yield
+        finally:
+            self.disallow_str_iteration = saved
+
+
+disallow_str_iteration_state: Final = DisallowStrIterationState(disallow_str_iteration=False)
diff --git a/mypy/main.py b/mypy/main.py
index 926e72515d95..c46ae3d07edb 100644
--- a/mypy/main.py
+++ b/mypy/main.py
@@ -937,6 +937,14 @@ def add_invertible_flag(
         group=strictness_group,
     )
 
+    add_invertible_flag(
+        "--disallow-str-iteration",
+        default=True,
+        strict_flag=False,
+        help="Disallow iterating over str instances",
+        group=strictness_group,
+    )
+
     add_invertible_flag(
         "--extra-checks",
         default=False,
diff --git a/mypy/meet.py b/mypy/meet.py
index 365544d4584f..92f549915678 100644
--- a/mypy/meet.py
+++ b/mypy/meet.py
@@ -3,6 +3,7 @@
 from collections.abc import Callable
 
 from mypy import join
+from mypy.disallow_str_iteration_state import disallow_str_iteration_state
 from mypy.erasetype import erase_type
 from mypy.maptype import map_instance_to_supertype
 from mypy.state import state
@@ -14,6 +15,7 @@
     is_proper_subtype,
     is_same_type,
     is_subtype,
+    is_subtype_relation_ignored_to_disallow_str_iteration,
 )
 from mypy.typeops import is_recursive_pair, make_simplified_union, tuple_fallback
 from mypy.types import (
@@ -596,6 +598,12 @@ def _type_object_overlap(left: Type, right: Type) -> bool:
         if right.type.fullname == "builtins.int" and left.type.fullname in MYPYC_NATIVE_INT_NAMES:
             return True
 
+        if disallow_str_iteration_state.disallow_str_iteration:
+            if is_subtype_relation_ignored_to_disallow_str_iteration(left, right):
+                return False
+            elif is_subtype_relation_ignored_to_disallow_str_iteration(right, left):
+                return False
+
         # Two unrelated types cannot be partially overlapping: they're disjoint.
         if left.type.has_base(right.type.fullname):
             left = map_instance_to_supertype(left, right.type)
diff --git a/mypy/messages.py b/mypy/messages.py
index 5863b8719b95..665ea3259841 100644
--- a/mypy/messages.py
+++ b/mypy/messages.py
@@ -1136,6 +1136,10 @@ def wrong_number_values_to_unpack(
     def unpacking_strings_disallowed(self, context: Context) -> None:
         self.fail("Unpacking a string is disallowed", context, code=codes.STR_UNPACK)
 
+    def str_iteration_disallowed(self, context: Context, str_type: Type) -> None:
+        self.fail(f"Iterating over {format_type(str_type, self.options)} is disallowed", context)
+        self.note("This is because --disallow-str-iteration is enabled", context)
+
     def type_not_iterable(self, type: Type, context: Context) -> None:
         self.fail(f"{format_type(type, self.options)} object is not iterable", context)
 
@@ -2210,6 +2214,15 @@ def report_protocol_problems(
         conflict_types = get_conflict_protocol_types(
             subtype, supertype, class_obj=class_obj, options=self.options
         )
+
+        if subtype.type.has_base("builtins.str") and supertype.type.has_base("typing.Container"):
+            # `str` doesn't properly conform to the `Container` protocol, but we don't want to show that as the reason for the error.
+            conflict_types = [
+                conflict_type
+                for conflict_type in conflict_types
+                if conflict_type[0] != "__contains__"
+            ]
+
         if conflict_types and (
             not is_subtype(subtype, erase_type(supertype), options=self.options)
             or not subtype.type.defn.type_vars
@@ -3122,6 +3135,7 @@ def get_conflict_protocol_types(
     Return them as a list of ('member', 'got', 'expected', 'is_lvalue').
     """
     assert right.type.is_protocol
+
     conflicts: list[tuple[str, Type, Type, bool]] = []
     for member in right.type.protocol_members:
         if member in ("__init__", "__new__"):
diff --git a/mypy/options.py b/mypy/options.py
index cb5088af7e79..044bacea13f3 100644
--- a/mypy/options.py
+++ b/mypy/options.py
@@ -37,6 +37,7 @@ class BuildType:
     "disallow_any_unimported",
     "disallow_incomplete_defs",
     "disallow_subclassing_any",
+    "disallow_str_iteration",
     "disallow_untyped_calls",
     "disallow_untyped_decorators",
     "disallow_untyped_defs",
@@ -238,6 +239,9 @@ def __init__(self) -> None:
         # Disable treating bytearray and memoryview as subtypes of bytes
         self.strict_bytes = False
 
+        # Disallow iterating over str instances or using them as Sequence[T]
+        self.disallow_str_iteration = True
+
         # Deprecated, use extra_checks instead.
         self.strict_concatenate = False
 
diff --git a/mypy/subtypes.py b/mypy/subtypes.py
index 350d57a7e4ad..8b7c357edfbd 100644
--- a/mypy/subtypes.py
+++ b/mypy/subtypes.py
@@ -8,6 +8,7 @@
 import mypy.constraints
 import mypy.typeops
 from mypy.checker_state import checker_state
+from mypy.disallow_str_iteration_state import disallow_str_iteration_state
 from mypy.erasetype import erase_type
 from mypy.expandtype import (
     expand_self_type,
@@ -479,6 +480,13 @@ def visit_instance(self, left: Instance) -> bool:
             # dynamic base classes correctly, see #5456.
             return not isinstance(self.right, NoneType)
         right = self.right
+
+        if (
+            disallow_str_iteration_state.disallow_str_iteration
+            and isinstance(right, Instance)
+            and is_subtype_relation_ignored_to_disallow_str_iteration(left, right)
+        ):
+            return False
         if isinstance(right, TupleType) and right.partial_fallback.type.is_enum:
             return self._is_subtype(left, mypy.typeops.tuple_fallback(right))
         if isinstance(right, TupleType):
@@ -2311,3 +2319,21 @@ def is_erased_instance(t: Instance) -> bool:
         elif not isinstance(get_proper_type(arg), AnyType):
             return False
     return True
+
+
+def is_subtype_relation_ignored_to_disallow_str_iteration(left: Instance, right: Instance) -> bool:
+    return (
+        left.type.has_base("builtins.str")
+        and not right.type.has_base("builtins.str")
+        and any(
+            right.type.has_base(base)
+            for base in (
+                "collections.abc.Collection",
+                "collections.abc.Iterable",
+                "collections.abc.Sequence",
+                "typing.Collection",
+                "typing.Iterable",
+                "typing.Sequence",
+            )
+        )
+    )
diff --git a/mypy/typeshed/stdlib/builtins.pyi b/mypy/typeshed/stdlib/builtins.pyi
index bd425ff3c212..5dae75dd9815 100644
--- a/mypy/typeshed/stdlib/builtins.pyi
+++ b/mypy/typeshed/stdlib/builtins.pyi
@@ -1458,6 +1458,8 @@ class _GetItemIterable(Protocol[_T_co]):
 @overload
 def iter(object: SupportsIter[_SupportsNextT_co], /) -> _SupportsNextT_co: ...
 @overload
+def iter(object: str, /) -> Iterator[str]: ...
+@overload
 def iter(object: _GetItemIterable[_T], /) -> Iterator[_T]: ...
 @overload
 def iter(object: Callable[[], _T | None], sentinel: None, /) -> Iterator[_T]: ...
diff --git a/test-data/unit/check-flags.test b/test-data/unit/check-flags.test
index 8d18c699e628..72999c88a69e 100644
--- a/test-data/unit/check-flags.test
+++ b/test-data/unit/check-flags.test
@@ -2451,6 +2451,80 @@ f(bytearray(b"asdf"))  # E: Argument 1 to "f" has incompatible type "bytearray";
 f(memoryview(b"asdf"))  # E: Argument 1 to "f" has incompatible type "memoryview"; expected "bytes"
 [builtins fixtures/primitives.pyi]
 
+[case testDisallowStrIteration]
+# flags: --disallow-str-iteration
+from abc import abstractmethod
+from typing import Collection, Container, Iterable, Mapping, Protocol, Sequence, TypeVar, Union
+
+def takes_str(x: str):
+    for ch in x:  # E: Iterating over "str" is disallowed  # N: This is because --disallow-str-iteration is enabled
+        reveal_type(ch)  # N: Revealed type is "builtins.str"
+    [ch for ch in x]  # E: Iterating over "str" is disallowed  # N: This is because --disallow-str-iteration is enabled
+
+s = "hello"
+
+def takes_seq_str(x: Sequence[str]) -> None: ...
+takes_seq_str(s)  # E: Argument 1 to "takes_seq_str" has incompatible type "str"; expected "Sequence[str]"
+
+def takes_iter_str(x: Iterable[str]) -> None: ...
+takes_iter_str(s)  # E: Argument 1 to "takes_iter_str" has incompatible type "str"; expected "Iterable[str]"
+
+def takes_collection_str(x: Collection[str]) -> None: ...
+takes_collection_str(s)  # E: Argument 1 to "takes_collection_str" has incompatible type "str"; expected "Collection[str]"
+
+seq: Sequence[str] = s  # E: Incompatible types in assignment (expression has type "str", variable has type "Sequence[str]")
+iterable: Iterable[str] = s  # E: Incompatible types in assignment (expression has type "str", variable has type "Iterable[str]")
+collection: Collection[str] = s  # E: Incompatible types in assignment (expression has type "str", variable has type "Collection[str]")
+
+def takes_maybe_seq(x: "str | Sequence[int]") -> None:
+    for ch in x:  # E: Iterating over "str | Sequence[int]" is disallowed  # N: This is because --disallow-str-iteration is enabled
+        reveal_type(ch)  # N: Revealed type is "builtins.str | builtins.int"
+
+T = TypeVar('T', bound=str)
+_T_co = TypeVar('_T_co', covariant=True)
+
+def takes_str_upper_bound(x: T) -> None:
+    for ch in x:  # E: Iterating over "T" is disallowed  # N: This is because --disallow-str-iteration is enabled
+        reveal_type(ch)  # N: Revealed type is "builtins.str"
+
+class StrSubclass(str):
+    def __contains__(self, x: object) -> bool: ...
+
+def takes_str_subclass(x: StrSubclass):
+    for ch in x:  # E: Iterating over "StrSubclass" is disallowed  # N: This is because --disallow-str-iteration is enabled
+        reveal_type(ch)  # N: Revealed type is "builtins.str"
+
+class CollectionSubclass(Collection[_T_co], Protocol[_T_co]):
+    @abstractmethod
+    def __missing_impl__(self): ...
+
+def takes_collection_subclass(x: CollectionSubclass[str]) -> None: ...
+
+takes_collection_subclass(s)  # E: Argument 1 to "takes_collection_subclass" has incompatible type "str"; expected "CollectionSubclass[str]" \
+                              # N: "str" is missing following "CollectionSubclass" protocol member: \
+                              # N:     __missing_impl__
+
+takes_collection_subclass(StrSubclass())  # E: Argument 1 to "takes_collection_subclass" has incompatible type "StrSubclass"; expected "CollectionSubclass[str]" \
+                                          # N: "StrSubclass" is missing following "CollectionSubclass" protocol member: \
+                                          # N:     __missing_impl__
+
+def dict_unpacking_unaffected_by_union_simplification(x: Mapping[str, Union[str, Sequence[str]]]) -> None:
+    x = {**x}
+
+def narrowing(x: "str | Sequence[str]"):
+    if isinstance(x, str):
+        reveal_type(x)  # N: Revealed type is "builtins.str"
+    else:
+        reveal_type(x)  # N: Revealed type is "typing.Sequence[builtins.str]"
+
+[builtins fixtures/str-iter.pyi]
+[typing fixtures/typing-str-iter.pyi]
+
+[case testIterStrOverload]
+# flags: --disallow-str-iteration
+reveal_type(iter("foo"))  # N: Revealed type is "typing.Iterable[builtins.str]"
+[builtins fixtures/dict.pyi]
+
 [case testNoCrashFollowImportsForStubs]
 # flags: --config-file tmp/mypy.ini
 {**{"x": "y"}}
diff --git a/test-data/unit/fixtures/dict.pyi b/test-data/unit/fixtures/dict.pyi
index ed2287511161..8fde41357a3d 100644
--- a/test-data/unit/fixtures/dict.pyi
+++ b/test-data/unit/fixtures/dict.pyi
@@ -61,4 +61,7 @@ class ellipsis: pass
 class BaseException: pass
 
 def isinstance(x: object, t: Union[type, Tuple[type, ...]]) -> bool: pass
+@overload
+def iter(__iterable: str) -> Iterable[str]: pass
+@overload
 def iter(__iterable: Iterable[T]) -> Iterator[T]: pass
diff --git a/test-data/unit/fixtures/str-iter.pyi b/test-data/unit/fixtures/str-iter.pyi
new file mode 100644
index 000000000000..49c61bad65d2
--- /dev/null
+++ b/test-data/unit/fixtures/str-iter.pyi
@@ -0,0 +1,52 @@
+# Builtins stub used in disallow-str-iteration tests.
+
+
+from typing import Generic, Iterator, Mapping, Sequence, TypeVar, overload
+
+_T = TypeVar("_T")
+_KT = TypeVar("_KT")
+_VT = TypeVar("_VT")
+
+class object:
+    def __init__(self) -> None: pass
+
+class type: pass
+class int: pass
+class bool(int): pass
+class ellipsis: pass
+class slice: pass
+
+class str(Sequence[str]):
+    def __iter__(self) -> Iterator[str]: pass
+    def __len__(self) -> int: pass
+    def __contains__(self, item: object) -> bool: pass
+    @overload
+    def __getitem__(self, i: int, /) -> str: ...
+    @overload
+    def __getitem__(self, s: slice, /) -> Sequence[str]: ...
+
+class list(Sequence[_T], Generic[_T]):
+    def __iter__(self) -> Iterator[_T]: pass
+    def __len__(self) -> int: pass
+    def __contains__(self, item: object) -> bool: pass
+    @overload
+    def __getitem__(self, i: int, /) -> _T: ...
+    @overload
+    def __getitem__(self, s: slice, /) -> list[_T]: ...
+
+class tuple(Sequence[_T], Generic[_T]):
+    def __iter__(self) -> Iterator[_T]: pass
+    def __len__(self) -> int: pass
+    def __contains__(self, item: object) -> bool: pass
+    @overload
+    def __getitem__(self, i: int, /) -> _T: ...
+    @overload
+    def __getitem__(self, s: slice, /) -> list[_T]: ...
+
+class dict(Mapping[_KT, _VT], Generic[_KT, _VT]):
+    def __iter__(self) -> Iterator[_KT]: pass
+    def __len__(self) -> int: pass
+    def __contains__(self, item: object) -> bool: pass
+    def __getitem__(self, key: _KT) -> _VT: pass
+
+def isinstance(x: object, t: type) -> bool: pass
diff --git a/test-data/unit/fixtures/typing-str-iter.pyi b/test-data/unit/fixtures/typing-str-iter.pyi
new file mode 100644
index 000000000000..f0fb8aa57cfb
--- /dev/null
+++ b/test-data/unit/fixtures/typing-str-iter.pyi
@@ -0,0 +1,63 @@
+# Minimal typing fixture for disallow-str-iteration tests.
+
+import _typeshed
+from abc import ABCMeta, abstractmethod
+
+Any = object()
+TypeVar = 0
+Generic = 0
+Protocol = 0
+Union = 0
+overload = 0
+
+_T = TypeVar("_T")
+_KT = TypeVar("_KT")
+_T_co = TypeVar("_T_co", covariant=True)
+_KT_co = TypeVar("_KT_co", covariant=True)  # Key type covariant containers.
+_VT_co = TypeVar("_VT_co", covariant=True)  # Value type covariant containers.
+_TC = TypeVar("_TC", bound=type[object])
+
+@runtime_checkable
+class Iterable(Protocol[_T_co]):
+    @abstractmethod
+    def __iter__(self) -> Iterator[_T_co]: ...
+
+@runtime_checkable
+class Iterator(Iterable[_T_co], Protocol[_T_co]):
+    @abstractmethod
+    def __next__(self) -> _T_co: ...
+    def __iter__(self) -> Iterator[_T_co]: ...
+
+@runtime_checkable
+class Container(Protocol[_T_co]):
+    # This is generic more on vibes than anything else
+    @abstractmethod
+    def __contains__(self, x: object, /) -> bool: ...
+
+@runtime_checkable
+class Collection(Iterable[_T_co], Container[_T_co], Protocol[_T_co]):
+    # Implement Sized (but don't have it as a base class).
+    @abstractmethod
+    def __len__(self) -> int: ...
+
+class Sequence(Collection[_T_co]):
+    @overload
+    @abstractmethod
+    def __getitem__(self, index: int) -> _T_co: ...
+    @overload
+    @abstractmethod
+    def __getitem__(self, index: slice) -> Sequence[_T_co]: ...
+    def __contains__(self, value: object) -> bool: ...
+    def __iter__(self) -> Iterator[_T_co]: ...
+
+class KeysView(Protocol[_KT_co]):
+    def __iter__(self) -> Iterator[_KT_co]: ...
+
+class Mapping(Collection[_KT], Generic[_KT, _VT_co]):
+    @abstractmethod
+    def __getitem__(self, key: _KT, /) -> _VT_co: ...
+    def __contains__(self, key: object, /) -> bool: ...
+    def keys(self) -> KeysView[_KT]: ...
+
+def runtime_checkable(cls: _TC) -> _TC:
+    return cls