diff --git a/mypy/checker.py b/mypy/checker.py
index 0ae499916ec6..59de599006a8 100644
--- a/mypy/checker.py
+++ b/mypy/checker.py
@@ -6011,11 +6011,16 @@ def has_no_custom_eq_checks(t: Type) -> bool:
                     if_map, else_map = {}, {}
 
                     if left_index in narrowable_operand_index_to_hash:
-                        # We only try and narrow away 'None' for now
-                        if is_overlapping_none(item_type):
-                            collection_item_type = get_proper_type(
-                                builtin_item_type(iterable_type)
-                            )
+                        collection_item_type = get_proper_type(builtin_item_type(iterable_type))
+                        # Narrow if the collection is a subtype
+                        if (
+                            collection_item_type is not None
+                            and collection_item_type != item_type
+                            and is_subtype(collection_item_type, item_type)
+                        ):
+                            if_map[operands[left_index]] = collection_item_type
+                        # Try and narrow away 'None'
+                        elif is_overlapping_none(item_type):
                             if (
                                 collection_item_type is not None
                                 and not is_overlapping_none(collection_item_type)
diff --git a/test-data/unit/check-narrowing.test b/test-data/unit/check-narrowing.test
index 8612df9bc663..e142fdd5d060 100644
--- a/test-data/unit/check-narrowing.test
+++ b/test-data/unit/check-narrowing.test
@@ -1376,13 +1376,13 @@ else:
     reveal_type(val)  # N: Revealed type is "Union[__main__.A, None]"
 
 if val in (None,):
-    reveal_type(val)  # N: Revealed type is "Union[__main__.A, None]"
+    reveal_type(val)  # N: Revealed type is "None"
 else:
     reveal_type(val)  # N: Revealed type is "Union[__main__.A, None]"
 if val not in (None,):
     reveal_type(val)  # N: Revealed type is "Union[__main__.A, None]"
 else:
-    reveal_type(val)  # N: Revealed type is "Union[__main__.A, None]"
+    reveal_type(val)  # N: Revealed type is "None"
 [builtins fixtures/primitives.pyi]
 
 [case testNarrowingWithTupleOfTypes]
@@ -2114,3 +2114,111 @@ else:
 
 [typing fixtures/typing-medium.pyi]
 [builtins fixtures/ops.pyi]
+
+
+[case testTypeNarrowingStringInLiteralUnion]
+from typing import Literal, Tuple
+typ: Tuple[Literal['a', 'b'], ...] = ('a', 'b')
+x: str = "hi!"
+if x in typ:
+    reveal_type(x)  # N: Revealed type is "Union[Literal['a'], Literal['b']]"
+else:
+    reveal_type(x)  # N: Revealed type is "builtins.str"
+[builtins fixtures/tuple.pyi]
+[typing fixtures/typing-medium.pyi]
+
+[case testTypeNarrowingStringInLiteralUnionSubset]
+from typing import Literal, Tuple
+typeAlpha: Tuple[Literal['a', 'b', 'c'], ...] = ('a', 'b')
+strIn: str = "b"
+strOut: str = "c"
+if strIn in typeAlpha:
+    reveal_type(strIn)  # N: Revealed type is "Union[Literal['a'], Literal['b'], Literal['c']]"
+else:
+    reveal_type(strIn)  # N: Revealed type is "builtins.str"
+if strOut in typeAlpha:
+    reveal_type(strOut)  # N: Revealed type is "Union[Literal['a'], Literal['b'], Literal['c']]"
+else:
+    reveal_type(strOut)  # N: Revealed type is "builtins.str"
+[builtins fixtures/primitives.pyi]
+[typing fixtures/typing-medium.pyi]
+
+[case testNarrowingStringNotInLiteralUnion]
+from typing import Literal, Tuple
+typeAlpha: Tuple[Literal['a', 'b', 'c'],...] = ('a', 'b', 'c')
+strIn: str = "c"
+strOut: str = "d"
+if strIn not in typeAlpha:
+    reveal_type(strIn)  # N: Revealed type is "builtins.str"
+else:
+    reveal_type(strIn)  # N: Revealed type is "Union[Literal['a'], Literal['b'], Literal['c']]"
+if strOut in typeAlpha:
+    reveal_type(strOut)  # N: Revealed type is "Union[Literal['a'], Literal['b'], Literal['c']]"
+else:
+    reveal_type(strOut)  # N: Revealed type is "builtins.str"
+[builtins fixtures/primitives.pyi]
+[typing fixtures/typing-medium.pyi]
+
+[case testNarrowingStringInLiteralUnionDontExpand]
+from typing import Literal, Tuple
+typeAlpha: Tuple[Literal['a', 'b', 'c'], ...] = ('a', 'b', 'c')
+strIn: Literal['c'] = "c"
+reveal_type(strIn)  # N: Revealed type is "Literal['c']"
+#Check we don't expand a Literal into the Union type
+if strIn not in typeAlpha:
+    reveal_type(strIn)  # N: Revealed type is "Literal['c']"
+else:
+    reveal_type(strIn)  # N: Revealed type is "Literal['c']"
+[builtins fixtures/primitives.pyi]
+[typing fixtures/typing-medium.pyi]
+
+[case testTypeNarrowingStringInMixedUnion]
+from typing import Literal, Tuple
+typ: Tuple[Literal['a', 'b'], ...] = ('a', 'b')
+x: str = "hi!"
+if x in typ:
+    reveal_type(x)  # N: Revealed type is "Union[Literal['a'], Literal['b']]"
+else:
+    reveal_type(x)  # N: Revealed type is "builtins.str"
+[builtins fixtures/tuple.pyi]
+[typing fixtures/typing-medium.pyi]
+
+[case testTypeNarrowingStringInSet]
+from typing import Literal, Set
+typ: Set[Literal['a', 'b']] = {'a', 'b'}
+x: str = "hi!"
+if x in typ:
+    reveal_type(x)  # N: Revealed type is "Union[Literal['a'], Literal['b']]"
+else:
+    reveal_type(x)  # N: Revealed type is "builtins.str"
+if x not in typ:
+    reveal_type(x)  # N: Revealed type is "builtins.str"
+else:
+    reveal_type(x)  # N: Revealed type is "Union[Literal['a'], Literal['b']]"
+[builtins fixtures/narrowing.pyi]
+[typing fixtures/typing-medium.pyi]
+
+[case testTypeNarrowingStringInList]
+from typing import Literal, List
+typ: List[Literal['a', 'b']] = ['a', 'b']
+x: str = "hi!"
+if x in typ:
+    reveal_type(x)  # N: Revealed type is "Union[Literal['a'], Literal['b']]"
+else:
+    reveal_type(x)  # N: Revealed type is "builtins.str"
+if x not in typ:
+    reveal_type(x)  # N: Revealed type is "builtins.str"
+else:
+    reveal_type(x)  # N: Revealed type is "Union[Literal['a'], Literal['b']]"
+[builtins fixtures/narrowing.pyi]
+[typing fixtures/typing-medium.pyi]
+
+[case testTypeNarrowingUnionStringFloat]
+from typing import Union
+def foobar(foo: Union[str, float]):
+    if foo in ['a', 'b']:
+        reveal_type(foo)  # N: Revealed type is "builtins.str"
+    else:
+        reveal_type(foo)  # N: Revealed type is "Union[builtins.str, builtins.float]"
+[builtins fixtures/primitives.pyi]
+[typing fixtures/typing-medium.pyi]
diff --git a/test-data/unit/fixtures/narrowing.pyi b/test-data/unit/fixtures/narrowing.pyi
index 89ee011c1c80..a36ac7f29bd2 100644
--- a/test-data/unit/fixtures/narrowing.pyi
+++ b/test-data/unit/fixtures/narrowing.pyi
@@ -1,5 +1,5 @@
 # Builtins stub used in check-narrowing test cases.
-from typing import Generic, Sequence, Tuple, Type, TypeVar, Union
+from typing import Generic, Sequence, Tuple, Type, TypeVar, Union, Iterable
 
 
 Tco = TypeVar('Tco', covariant=True)
@@ -15,6 +15,13 @@ class function: pass
 class ellipsis: pass
 class int: pass
 class str: pass
+class float: pass
 class dict(Generic[KT, VT]): pass
 
 def isinstance(x: object, t: Union[Type[object], Tuple[Type[object], ...]]) -> bool: pass
+
+class list(Sequence[Tco]):
+    def __contains__(self, other: object) -> bool: pass
+class set(Iterable[Tco], Generic[Tco]):
+    def __init__(self, iterable: Iterable[Tco] = ...) -> None: ...
+    def __contains__(self, item: object) -> bool: pass