diff --git a/sentry_sdk/_types.py b/sentry_sdk/_types.py
index baf5f6a2fd..e071ff07ff 100644
--- a/sentry_sdk/_types.py
+++ b/sentry_sdk/_types.py
@@ -13,6 +13,10 @@
 
 SENSITIVE_DATA_SUBSTITUTE = "[Filtered]"
 BLOB_DATA_SUBSTITUTE = "[Blob substitute]"
+OVER_SIZE_LIMIT_SUBSTITUTE = (
+    "[Value removed due to size of field exceeding configured maximum size.]"
+)
+UNPARSABLE_RAW_DATA_SUBSTITUTE = "[Value removed due to being unparsable.]"
 
 
 class AnnotatedValue:
@@ -47,6 +51,8 @@ def __len__(self: "AnnotatedValue") -> int:
     @classmethod
     def removed_because_raw_data(cls) -> "AnnotatedValue":
         """The value was removed because it could not be parsed. This is done for request body values that are not json nor a form."""
+        # This is the legacy approach - we want to transition over to `substituted_because_raw_data` after we completely transition
+        # to span-first
         return AnnotatedValue(
             value="",
             metadata={
@@ -59,12 +65,29 @@ def removed_because_raw_data(cls) -> "AnnotatedValue":
             },
         )
 
+    @classmethod
+    def substituted_because_raw_data(cls) -> "AnnotatedValue":
+        """The value was replaced because it could not be parsed. This is done for request body values that are not json nor a form."""
+        return AnnotatedValue(
+            value=UNPARSABLE_RAW_DATA_SUBSTITUTE,
+            metadata={
+                "rem": [  # Remark
+                    [
+                        "!raw",  # Unparsable raw data
+                        "s",  # The fields original value was substituted
+                    ]
+                ]
+            },
+        )
+
     @classmethod
     def removed_because_over_size_limit(cls, value: "Any" = "") -> "AnnotatedValue":
         """
         The actual value was removed because the size of the field exceeded the configured maximum size,
         for example specified with the max_request_body_size sdk option.
         """
+        # This is the legacy approach - we want to transition over to `substituted_because_over_size_limit` after we completely transition
+        # to span-first
         return AnnotatedValue(
             value=value,
             metadata={
@@ -77,6 +100,26 @@ def removed_because_over_size_limit(cls, value: "Any" = "") -> "AnnotatedValue":
             },
         )
 
+    @classmethod
+    def substituted_because_over_size_limit(
+        cls, value: "Any" = OVER_SIZE_LIMIT_SUBSTITUTE
+    ) -> "AnnotatedValue":
+        """
+        The actual value was replaced because the size of the field exceeded the configured maximum size,
+        for example specified with the max_request_body_size sdk option.
+        """
+        return AnnotatedValue(
+            value=value,
+            metadata={
+                "rem": [  # Remark
+                    [
+                        "!config",  # Because of configured maximum size
+                        "s",  # The fields original value was substituted
+                    ]
+                ]
+            },
+        )
+
     @classmethod
     def substituted_because_contains_sensitive_data(cls) -> "AnnotatedValue":
         """The actual value was removed because it contained sensitive information."""
diff --git a/sentry_sdk/integrations/_asgi_common.py b/sentry_sdk/integrations/_asgi_common.py
index 525ca4b5b5..82edc6ce99 100644
--- a/sentry_sdk/integrations/_asgi_common.py
+++ b/sentry_sdk/integrations/_asgi_common.py
@@ -93,7 +93,9 @@ def _get_request_data(asgi_scope: "Any") -> "Dict[str, Any]":
     if ty in ("http", "websocket"):
         request_data["method"] = asgi_scope.get("method")
 
-        request_data["headers"] = headers = _filter_headers(_get_headers(asgi_scope))
+        request_data["headers"] = headers = _filter_headers(
+            _get_headers(asgi_scope),
+        )
         request_data["query_string"] = _get_query(asgi_scope)
 
         request_data["url"] = _get_url(
diff --git a/sentry_sdk/integrations/_wsgi_common.py b/sentry_sdk/integrations/_wsgi_common.py
index bcac1eb2d4..4208955620 100644
--- a/sentry_sdk/integrations/_wsgi_common.py
+++ b/sentry_sdk/integrations/_wsgi_common.py
@@ -218,11 +218,11 @@ def _filter_headers(
     if should_send_default_pii():
         return headers
 
-    substitute: "Union[AnnotatedValue, str]"
-    if use_annotated_value:
-        substitute = AnnotatedValue.removed_because_over_size_limit()
-    else:
-        substitute = SENSITIVE_DATA_SUBSTITUTE
+    substitute: "Union[AnnotatedValue, str]" = (
+        SENSITIVE_DATA_SUBSTITUTE
+        if not use_annotated_value
+        else AnnotatedValue.removed_because_over_size_limit()
+    )
 
     return {
         k: (v if k.upper().replace("-", "_") not in SENSITIVE_HEADERS else substitute)