diff --git a/changelog.d/7303.misc b/changelog.d/7303.misc
new file mode 100644
index 000000000000..aa89c2b25444
--- /dev/null
+++ b/changelog.d/7303.misc
@@ -0,0 +1 @@
+Fix StreamChangeCache to work with multiple entities changing on the same stream id.
diff --git a/stubs/sortedcontainers/__init__.pyi b/stubs/sortedcontainers/__init__.pyi
new file mode 100644
index 000000000000..073b806d3c98
--- /dev/null
+++ b/stubs/sortedcontainers/__init__.pyi
@@ -0,0 +1,13 @@
+from .sorteddict import (
+    SortedDict,
+    SortedKeysView,
+    SortedItemsView,
+    SortedValuesView,
+)
+
+__all__ = [
+    "SortedDict",
+    "SortedKeysView",
+    "SortedItemsView",
+    "SortedValuesView",
+]
diff --git a/stubs/sortedcontainers/sorteddict.pyi b/stubs/sortedcontainers/sorteddict.pyi
new file mode 100644
index 000000000000..68779f968ed6
--- /dev/null
+++ b/stubs/sortedcontainers/sorteddict.pyi
@@ -0,0 +1,124 @@
+# stub for SortedDict. This is a lightly edited copy of
+# https://github.com/grantjenks/python-sortedcontainers/blob/eea42df1f7bad2792e8da77335ff888f04b9e5ae/sortedcontainers/sorteddict.pyi
+# (from https://github.com/grantjenks/python-sortedcontainers/pull/107)
+
+from typing import (
+    Any,
+    Callable,
+    Dict,
+    Hashable,
+    Iterator,
+    Iterable,
+    ItemsView,
+    KeysView,
+    List,
+    Mapping,
+    Optional,
+    Sequence,
+    Type,
+    TypeVar,
+    Tuple,
+    Union,
+    ValuesView,
+    overload,
+)
+
+_T = TypeVar("_T")
+_S = TypeVar("_S")
+_T_h = TypeVar("_T_h", bound=Hashable)
+_KT = TypeVar("_KT", bound=Hashable)  # Key type.
+_VT = TypeVar("_VT")  # Value type.
+_KT_co = TypeVar("_KT_co", covariant=True, bound=Hashable)
+_VT_co = TypeVar("_VT_co", covariant=True)
+_SD = TypeVar("_SD", bound=SortedDict)
+_Key = Callable[[_T], Any]
+
+class SortedDict(Dict[_KT, _VT]):
+    @overload
+    def __init__(self, **kwargs: _VT) -> None: ...
+    @overload
+    def __init__(self, __map: Mapping[_KT, _VT], **kwargs: _VT) -> None: ...
+    @overload
+    def __init__(
+        self, __iterable: Iterable[Tuple[_KT, _VT]], **kwargs: _VT
+    ) -> None: ...
+    @overload
+    def __init__(self, __key: _Key[_KT], **kwargs: _VT) -> None: ...
+    @overload
+    def __init__(
+        self, __key: _Key[_KT], __map: Mapping[_KT, _VT], **kwargs: _VT
+    ) -> None: ...
+    @overload
+    def __init__(
+        self, __key: _Key[_KT], __iterable: Iterable[Tuple[_KT, _VT]], **kwargs: _VT
+    ) -> None: ...
+    @property
+    def key(self) -> Optional[_Key[_KT]]: ...
+    @property
+    def iloc(self) -> SortedKeysView[_KT]: ...
+    def clear(self) -> None: ...
+    def __delitem__(self, key: _KT) -> None: ...
+    def __iter__(self) -> Iterator[_KT]: ...
+    def __reversed__(self) -> Iterator[_KT]: ...
+    def __setitem__(self, key: _KT, value: _VT) -> None: ...
+    def _setitem(self, key: _KT, value: _VT) -> None: ...
+    def copy(self: _SD) -> _SD: ...
+    def __copy__(self: _SD) -> _SD: ...
+    @classmethod
+    @overload
+    def fromkeys(cls, seq: Iterable[_T_h]) -> SortedDict[_T_h, None]: ...
+    @classmethod
+    @overload
+    def fromkeys(cls, seq: Iterable[_T_h], value: _S) -> SortedDict[_T_h, _S]: ...
+    def keys(self) -> SortedKeysView[_KT]: ...
+    def items(self) -> SortedItemsView[_KT, _VT]: ...
+    def values(self) -> SortedValuesView[_VT]: ...
+    @overload
+    def pop(self, key: _KT) -> _VT: ...
+    @overload
+    def pop(self, key: _KT, default: _T = ...) -> Union[_VT, _T]: ...
+    def popitem(self, index: int = ...) -> Tuple[_KT, _VT]: ...
+    def peekitem(self, index: int = ...) -> Tuple[_KT, _VT]: ...
+    def setdefault(self, key: _KT, default: Optional[_VT] = ...) -> _VT: ...
+    @overload
+    def update(self, __map: Mapping[_KT, _VT], **kwargs: _VT) -> None: ...
+    @overload
+    def update(self, __iterable: Iterable[Tuple[_KT, _VT]], **kwargs: _VT) -> None: ...
+    @overload
+    def update(self, **kwargs: _VT) -> None: ...
+    def __reduce__(
+        self,
+    ) -> Tuple[
+        Type[SortedDict[_KT, _VT]], Tuple[Callable[[_KT], Any], List[Tuple[_KT, _VT]]],
+    ]: ...
+    def __repr__(self) -> str: ...
+    def _check(self) -> None: ...
+    def islice(
+        self, start: Optional[int] = ..., stop: Optional[int] = ..., reverse=bool,
+    ) -> Iterator[_KT]: ...
+    def bisect_left(self, value: _KT) -> int: ...
+    def bisect_right(self, value: _KT) -> int: ...
+
+class SortedKeysView(KeysView[_KT_co], Sequence[_KT_co]):
+    @overload
+    def __getitem__(self, index: int) -> _KT_co: ...
+    @overload
+    def __getitem__(self, index: slice) -> List[_KT_co]: ...
+    def __delitem__(self, index: Union[int, slice]) -> None: ...
+
+class SortedItemsView(  # type: ignore
+    ItemsView[_KT_co, _VT_co], Sequence[Tuple[_KT_co, _VT_co]]
+):
+    def __iter__(self) -> Iterator[Tuple[_KT_co, _VT_co]]: ...
+    @overload
+    def __getitem__(self, index: int) -> Tuple[_KT_co, _VT_co]: ...
+    @overload
+    def __getitem__(self, index: slice) -> List[Tuple[_KT_co, _VT_co]]: ...
+    def __delitem__(self, index: Union[int, slice]) -> None: ...
+
+class SortedValuesView(ValuesView[_VT_co], Sequence[_VT_co]):
+    @overload
+    def __getitem__(self, index: int) -> _VT_co: ...
+    @overload
+    def __getitem__(self, index: slice) -> List[_VT_co]: ...
+    def __delitem__(self, index: Union[int, slice]) -> None: ...
diff --git a/synapse/util/caches/stream_change_cache.py b/synapse/util/caches/stream_change_cache.py
index c61d36a82e3e..38dc3f501e7c 100644
--- a/synapse/util/caches/stream_change_cache.py
+++ b/synapse/util/caches/stream_change_cache.py
@@ -14,6 +14,7 @@
 # limitations under the License.
 
 import logging
+from typing import Dict, Iterable, List, Mapping, Optional, Set
 
 from six import integer_types
 
@@ -23,8 +24,11 @@
 
 logger = logging.getLogger(__name__)
 
+# for now, assume all entities in the cache are strings
+EntityType = str
 
-class StreamChangeCache(object):
+
+class StreamChangeCache:
     """Keeps track of the stream positions of the latest change in a set of entities.
 
     Typically the entity will be a room or user id.
@@ -34,10 +38,23 @@ class StreamChangeCache(object):
     old then the cache will simply return all given entities.
     """
 
-    def __init__(self, name, current_stream_pos, max_size=10000, prefilled_cache=None):
+    def __init__(
+        self,
+        name: str,
+        current_stream_pos: int,
+        max_size=10000,
+        prefilled_cache: Optional[Mapping[EntityType, int]] = None,
+    ):
         self._max_size = int(max_size * caches.CACHE_SIZE_FACTOR)
-        self._entity_to_key = {}
-        self._cache = SortedDict()
+        self._entity_to_key = {}  # type: Dict[EntityType, int]
+
+        # map from stream id to the a set of entities which changed at that stream id.
+        self._cache = SortedDict()  # type: SortedDict[int, Set[EntityType]]
+
+        # the earliest stream_pos for which we can reliably answer
+        # get_all_entities_changed. In other words, one less than the earliest
+        # stream_pos for which we know _cache is valid.
+        #
         self._earliest_known_stream_pos = current_stream_pos
         self.name = name
         self.metrics = caches.register_cache("cache", self.name, self._cache)
@@ -46,7 +63,7 @@ def __init__(self, name, current_stream_pos, max_size=10000, prefilled_cache=Non
             for entity, stream_pos in prefilled_cache.items():
                 self.entity_has_changed(entity, stream_pos)
 
-    def has_entity_changed(self, entity, stream_pos):
+    def has_entity_changed(self, entity: EntityType, stream_pos: int) -> bool:
         """Returns True if the entity may have been updated since stream_pos
         """
         assert type(stream_pos) in integer_types
@@ -67,22 +84,17 @@ def has_entity_changed(self, entity, stream_pos):
         self.metrics.inc_hits()
         return False
 
-    def get_entities_changed(self, entities, stream_pos):
+    def get_entities_changed(
+        self, entities: Iterable[EntityType], stream_pos: int
+    ) -> Set[EntityType]:
         """
         Returns subset of entities that have had new things since the given
         position.  Entities unknown to the cache will be returned.  If the
         position is too old it will just return the given list.
         """
-        assert type(stream_pos) is int
-
-        if stream_pos >= self._earliest_known_stream_pos:
-            changed_entities = {
-                self._cache[k]
-                for k in self._cache.islice(start=self._cache.bisect_right(stream_pos))
-            }
-
-            result = changed_entities.intersection(entities)
-
+        changed_entities = self.get_all_entities_changed(stream_pos)
+        if changed_entities is not None:
+            result = set(changed_entities).intersection(entities)
             self.metrics.inc_hits()
         else:
             result = set(entities)
@@ -90,13 +102,13 @@ def get_entities_changed(self, entities, stream_pos):
 
         return result
 
-    def has_any_entity_changed(self, stream_pos):
+    def has_any_entity_changed(self, stream_pos: int) -> bool:
         """Returns if any entity has changed
         """
         assert type(stream_pos) is int
 
         if not self._cache:
-            # If we have no cache, nothing can have changed.
+            # If the cache is empty, nothing can have changed.
             return False
 
         if stream_pos >= self._earliest_known_stream_pos:
@@ -106,45 +118,58 @@ def has_any_entity_changed(self, stream_pos):
             self.metrics.inc_misses()
             return True
 
-    def get_all_entities_changed(self, stream_pos):
-        """Returns all entites that have had new things since the given
+    def get_all_entities_changed(self, stream_pos: int) -> Optional[List[EntityType]]:
+        """Returns all entities that have had new things since the given
         position. If the position is too old it will return None.
+
+        Returns the entities in the order that they were changed.
         """
         assert type(stream_pos) is int
 
-        if stream_pos >= self._earliest_known_stream_pos:
-            return [
-                self._cache[k]
-                for k in self._cache.islice(start=self._cache.bisect_right(stream_pos))
-            ]
-        else:
+        if stream_pos < self._earliest_known_stream_pos:
             return None
 
-    def entity_has_changed(self, entity, stream_pos):
+        changed_entities = []  # type: List[EntityType]
+
+        for k in self._cache.islice(start=self._cache.bisect_right(stream_pos)):
+            changed_entities.extend(self._cache[k])
+        return changed_entities
+
+    def entity_has_changed(self, entity: EntityType, stream_pos: int) -> None:
         """Informs the cache that the entity has been changed at the given
         position.
         """
         assert type(stream_pos) is int
 
-        # FIXME: add a sanity check here that we are not overwriting existing
-        # data in self._cache
-
-        if stream_pos > self._earliest_known_stream_pos:
-            old_pos = self._entity_to_key.get(entity, None)
-            if old_pos is not None:
-                stream_pos = max(stream_pos, old_pos)
-                self._cache.pop(old_pos, None)
-            self._cache[stream_pos] = entity
-            self._entity_to_key[entity] = stream_pos
-
-            while len(self._cache) > self._max_size:
-                k, r = self._cache.popitem(0)
-                self._earliest_known_stream_pos = max(
-                    k, self._earliest_known_stream_pos
-                )
-                self._entity_to_key.pop(r, None)
-
-    def get_max_pos_of_last_change(self, entity):
+        if stream_pos <= self._earliest_known_stream_pos:
+            return
+
+        old_pos = self._entity_to_key.get(entity, None)
+        if old_pos is not None:
+            if old_pos >= stream_pos:
+                # nothing to do
+                return
+            e = self._cache[old_pos]
+            e.remove(entity)
+            if not e:
+                # cache at this point is now empty
+                del self._cache[old_pos]
+
+        e1 = self._cache.get(stream_pos)
+        if e1 is None:
+            e1 = self._cache[stream_pos] = set()
+        e1.add(entity)
+        self._entity_to_key[entity] = stream_pos
+
+        # if the cache is too big, remove entries
+        while len(self._cache) > self._max_size:
+            k, r = self._cache.popitem(0)
+            self._earliest_known_stream_pos = max(k, self._earliest_known_stream_pos)
+            for entity in r:
+                del self._entity_to_key[entity]
+
+    def get_max_pos_of_last_change(self, entity: EntityType) -> int:
+
         """Returns an upper bound of the stream id of the last change to an
         entity.
         """
diff --git a/tests/util/test_stream_change_cache.py b/tests/util/test_stream_change_cache.py
index 72a9de5370ec..6857933540d6 100644
--- a/tests/util/test_stream_change_cache.py
+++ b/tests/util/test_stream_change_cache.py
@@ -28,18 +28,26 @@ def test_has_entity_changed(self):
         cache.entity_has_changed("user@foo.com", 6)
         cache.entity_has_changed("bar@baz.net", 7)
 
+        # also test multiple things changing on the same stream ID
+        cache.entity_has_changed("user2@foo.com", 8)
+        cache.entity_has_changed("bar2@baz.net", 8)
+
         # If it's been changed after that stream position, return True
         self.assertTrue(cache.has_entity_changed("user@foo.com", 4))
         self.assertTrue(cache.has_entity_changed("bar@baz.net", 4))
+        self.assertTrue(cache.has_entity_changed("bar2@baz.net", 4))
+        self.assertTrue(cache.has_entity_changed("user2@foo.com", 4))
 
         # If it's been changed at that stream position, return False
         self.assertFalse(cache.has_entity_changed("user@foo.com", 6))
+        self.assertFalse(cache.has_entity_changed("user2@foo.com", 8))
 
         # If there's no changes after that stream position, return False
         self.assertFalse(cache.has_entity_changed("user@foo.com", 7))
+        self.assertFalse(cache.has_entity_changed("user2@foo.com", 9))
 
         # If the entity does not exist, return False.
-        self.assertFalse(cache.has_entity_changed("not@here.website", 7))
+        self.assertFalse(cache.has_entity_changed("not@here.website", 9))
 
         # If we request before the stream cache's earliest known position,
         # return True, whether it's a known entity or not.
@@ -47,7 +55,7 @@ def test_has_entity_changed(self):
         self.assertTrue(cache.has_entity_changed("not@here.website", 0))
 
     @patch("synapse.util.caches.CACHE_SIZE_FACTOR", 1.0)
-    def test_has_entity_changed_pops_off_start(self):
+    def test_entity_has_changed_pops_off_start(self):
         """
         StreamChangeCache.entity_has_changed will respect the max size and
         purge the oldest items upon reaching that max size.
@@ -64,11 +72,20 @@ def test_has_entity_changed_pops_off_start(self):
         # The oldest item has been popped off
         self.assertTrue("user@foo.com" not in cache._entity_to_key)
 
+        self.assertEqual(
+            cache.get_all_entities_changed(2), ["bar@baz.net", "user@elsewhere.org"],
+        )
+        self.assertIsNone(cache.get_all_entities_changed(1))
+
         # If we update an existing entity, it keeps the two existing entities
         cache.entity_has_changed("bar@baz.net", 5)
         self.assertEqual(
             {"bar@baz.net", "user@elsewhere.org"}, set(cache._entity_to_key)
         )
+        self.assertEqual(
+            cache.get_all_entities_changed(2), ["user@elsewhere.org", "bar@baz.net"],
+        )
+        self.assertIsNone(cache.get_all_entities_changed(1))
 
     def test_get_all_entities_changed(self):
         """
@@ -80,18 +97,52 @@ def test_get_all_entities_changed(self):
 
         cache.entity_has_changed("user@foo.com", 2)
         cache.entity_has_changed("bar@baz.net", 3)
+        cache.entity_has_changed("anotheruser@foo.com", 3)
         cache.entity_has_changed("user@elsewhere.org", 4)
 
-        self.assertEqual(
-            cache.get_all_entities_changed(1),
-            ["user@foo.com", "bar@baz.net", "user@elsewhere.org"],
-        )
-        self.assertEqual(
-            cache.get_all_entities_changed(2), ["bar@baz.net", "user@elsewhere.org"]
-        )
+        r = cache.get_all_entities_changed(1)
+
+        # either of these are valid
+        ok1 = [
+            "user@foo.com",
+            "bar@baz.net",
+            "anotheruser@foo.com",
+            "user@elsewhere.org",
+        ]
+        ok2 = [
+            "user@foo.com",
+            "anotheruser@foo.com",
+            "bar@baz.net",
+            "user@elsewhere.org",
+        ]
+        self.assertTrue(r == ok1 or r == ok2)
+
+        r = cache.get_all_entities_changed(2)
+        self.assertTrue(r == ok1[1:] or r == ok2[1:])
+
         self.assertEqual(cache.get_all_entities_changed(3), ["user@elsewhere.org"])
         self.assertEqual(cache.get_all_entities_changed(0), None)
 
+        # ... later, things gest more updates
+        cache.entity_has_changed("user@foo.com", 5)
+        cache.entity_has_changed("bar@baz.net", 5)
+        cache.entity_has_changed("anotheruser@foo.com", 6)
+
+        ok1 = [
+            "user@elsewhere.org",
+            "user@foo.com",
+            "bar@baz.net",
+            "anotheruser@foo.com",
+        ]
+        ok2 = [
+            "user@elsewhere.org",
+            "bar@baz.net",
+            "user@foo.com",
+            "anotheruser@foo.com",
+        ]
+        r = cache.get_all_entities_changed(3)
+        self.assertTrue(r == ok1 or r == ok2)
+
     def test_has_any_entity_changed(self):
         """
         StreamChangeCache.has_any_entity_changed will return True if any
diff --git a/tox.ini b/tox.ini
index 42b2d7489132..31011d7436f5 100644
--- a/tox.ini
+++ b/tox.ini
@@ -202,7 +202,9 @@ commands = mypy \
             synapse/spam_checker_api \
             synapse/storage/engines \
             synapse/storage/database.py \
-            synapse/streams
+            synapse/streams \
+            synapse/util/caches/stream_change_cache.py \
+            tests/util/test_stream_change_cache.py
 
 # To find all folders that pass mypy you run:
 #