diff --git a/sentry_sdk/client.py b/sentry_sdk/client.py
index 3fa4492e10..8ecea608b3 100644
--- a/sentry_sdk/client.py
+++ b/sentry_sdk/client.py
@@ -142,9 +142,9 @@ def _prepare_event(
         # Postprocess the event here so that annotated types do
         # generally not surface in before_send
         if event is not None:
+            event = convert_types(event)
             strip_event_mut(event)
             event = flatten_metadata(event)
-            event = convert_types(event)
 
         before_send = self.options["before_send"]
         if before_send is not None:
diff --git a/sentry_sdk/utils.py b/sentry_sdk/utils.py
index 3e80098169..d8aecd99a8 100644
--- a/sentry_sdk/utils.py
+++ b/sentry_sdk/utils.py
@@ -709,7 +709,7 @@ def inner(obj):
                     del meta[str(i)]
             return list_rv, (meta or None)
         if isinstance(obj, AnnotatedValue):
-            return obj.value, {"": obj.metadata}
+            return (inner(obj.value)[0], {"": obj.metadata})
         return obj, None
 
     obj, meta = inner(obj)
@@ -727,6 +727,7 @@ def strip_event_mut(event):
             strip_stacktrace_mut(exception.get("stacktrace", None))
 
     strip_request_mut(event.get("request", None))
+    strip_breadcrumbs_mut(event.get("breadcrumbs", None))
 
 
 def strip_stacktrace_mut(stacktrace):
@@ -747,6 +748,14 @@ def strip_request_mut(request):
     request["data"] = strip_databag(data)
 
 
+def strip_breadcrumbs_mut(breadcrumbs):
+    if not breadcrumbs:
+        return
+
+    for i in range(len(breadcrumbs)):
+        breadcrumbs[i] = strip_databag(breadcrumbs[i])
+
+
 def strip_frame_mut(frame):
     # type: (Dict[str, Any]) -> None
     if "vars" in frame:
@@ -769,32 +778,56 @@ def unmemoize(self, obj):
 
 def convert_types(obj):
     # type: (Any) -> Any
+    if obj is None:
+        return None
     if obj is CYCLE_MARKER:
         return u"<cyclic>"
     if isinstance(obj, datetime):
-        return obj.strftime("%Y-%m-%dT%H:%M:%SZ")
+        return text_type(obj.strftime("%Y-%m-%dT%H:%M:%SZ"))
     if isinstance(obj, Mapping):
         return {k: convert_types(v) for k, v in obj.items()}
     if isinstance(obj, Sequence) and not isinstance(obj, (text_type, bytes)):
         return [convert_types(v) for v in obj]
+    if isinstance(obj, AnnotatedValue):
+        return AnnotatedValue(convert_types(obj.value), obj.metadata)
+
     if not isinstance(obj, string_types + number_types):
         return safe_repr(obj)
     if isinstance(obj, bytes):
         return obj.decode("utf-8", "replace")
+
     return obj
 
 
-def strip_databag(obj, remaining_depth=20):
-    # type: (Any, int) -> Any
+def strip_databag(obj, remaining_depth=20, max_breadth=20):
+    # type: (Any, int, int) -> Any
     assert not isinstance(obj, bytes), "bytes should have been normalized before"
     if remaining_depth <= 0:
         return AnnotatedValue(None, {"rem": [["!limit", "x"]]})
     if isinstance(obj, text_type):
         return strip_string(obj)
     if isinstance(obj, Mapping):
-        return {k: strip_databag(v, remaining_depth - 1) for k, v in obj.items()}
+        rv_dict = {}  # type: Dict[Any, Any]
+        for i, (k, v) in enumerate(obj.items()):
+            if i >= max_breadth:
+                return AnnotatedValue(rv_dict, {"len": max_breadth})
+            rv_dict[k] = strip_databag(
+                v, remaining_depth=remaining_depth - 1, max_breadth=max_breadth
+            )
+
+        return rv_dict
     if isinstance(obj, Sequence):
-        return [strip_databag(v, remaining_depth - 1) for v in obj]
+        rv_list = []  # type: List[Any]
+        for i, v in enumerate(obj):
+            if i >= max_breadth:
+                return AnnotatedValue(rv_list, {"len": max_breadth})
+            rv_list.append(
+                strip_databag(
+                    v, remaining_depth=remaining_depth - 1, max_breadth=max_breadth
+                )
+            )
+
+        return rv_list
     return obj
 
 
diff --git a/tests/test_client.py b/tests/test_client.py
index 5627019793..81cbd4bcfc 100644
--- a/tests/test_client.py
+++ b/tests/test_client.py
@@ -397,6 +397,21 @@ def test_databag_stripping(sentry_init, capture_events):
     assert len(json.dumps(event)) < 10000
 
 
+def test_databag_breadth_stripping(sentry_init, capture_events):
+    sentry_init()
+    events = capture_events()
+
+    try:
+        a = ["a"] * 16000  # noqa
+        1 / 0
+    except Exception:
+        capture_exception()
+
+    event, = events
+
+    assert len(json.dumps(event)) < 10000
+
+
 @pytest.mark.skipif(not HAS_CHAINED_EXCEPTIONS, reason="Only works on 3.3+")
 def test_chained_exceptions(sentry_init, capture_events):
     sentry_init()