diff --git a/darwin/importer/importer.py b/darwin/importer/importer.py
index aad713e0c..26d9b0a55 100644
--- a/darwin/importer/importer.py
+++ b/darwin/importer/importer.py
@@ -1,5 +1,7 @@
 import concurrent.futures
 import uuid
+import json
+import copy
 from collections import defaultdict
 from functools import partial
 from logging import getLogger
@@ -20,6 +22,7 @@
     Union,
 )
 
+
 from darwin.datatypes import (
     AnnotationFile,
     Property,
@@ -1864,6 +1867,17 @@ def _import_annotations(
 
     try:
         dataset.import_annotation(id, payload=payload)
+    except RequestEntitySizeExceeded:
+        logger.warning(
+            "Annotation payload exceeds request entity size. Splitting payload into smaller chunks for import."
+        )
+        payloads = _split_payloads(payload)
+        for chunked_payload in payloads:
+            try:
+                dataset.import_annotation(id, payload=chunked_payload)
+            except Exception as e:
+                errors.append(e)
+                success = dt.Success.FAILURE
     except Exception as e:
         errors.append(e)
         success = dt.Success.FAILURE
@@ -2185,3 +2199,57 @@ def _warn_for_annotations_with_multiple_instance_ids(
             console.print(
                 f"- File: {file} has {files_with_multi_instance_id_annotations[file]} annotation(s) with multiple instance IDs"
             )
+
+
+def _split_payloads(
+    payload: Dict[str, Any], max_payload_size: int = 32_000_000
+) -> List[Dict[str, Any]]:
+    """
+    Splits a payload into smaller chunks to avoid HTTP 413 errors due to large request entity sizes.
+
+    This function takes an input payload and splits it into smaller payloads, ensuring each chunk does not exceed the specified maximum size. This is particularly useful when importing annotations, as it prevents HTTP 413 errors (`RequestEntitySizeExceeded`) from occurring due to large request entity sizes.
+
+    Parameters
+    ----------
+    payload : Dict[str, Any]
+        The input payload to be split.
+    max_payload_size : int, optional
+        The maximum size of each split payload. Defaults to 32,000,000 bytes.
+
+    Returns
+    -------
+    List[Dict[str, Any]]
+        A list of split payloads, each not exceeding the specified maximum size.
+
+    Raises
+    ------
+    ValueError
+        If any single annotation exceeds the `max_payload_size` limit
+    """
+    payloads = []
+    base_payload = {"annotations": [], "overwrite": payload["overwrite"]}
+    current_payload = copy.deepcopy(base_payload)
+    current_payload_size = 0
+
+    for annotation in payload["annotations"]:
+        annotation_size = len(json.dumps({"annotations": [annotation]}).encode("utf-8"))
+        if current_payload_size + annotation_size < max_payload_size:
+            current_payload["annotations"].append(annotation)
+            current_payload_size += annotation_size
+        else:
+            if annotation_size > max_payload_size:
+                raise ValueError(
+                    f"One or more annotations exceed the maximum allowed size of 32 MiB ({max_payload_size})"
+                )
+            payloads.append(current_payload)
+            current_payload = copy.deepcopy(base_payload)
+            current_payload["overwrite"] = (
+                False  # Required to make sure subsequent payloads don't overwrite previous ones
+            )
+            current_payload["annotations"].append(annotation)
+            current_payload_size = annotation_size
+
+    if current_payload["annotations"]:
+        payloads.append(current_payload)
+
+    return payloads
diff --git a/tests/darwin/importer/importer_test.py b/tests/darwin/importer/importer_test.py
index 74bf7e7ac..09c313106 100644
--- a/tests/darwin/importer/importer_test.py
+++ b/tests/darwin/importer/importer_test.py
@@ -34,6 +34,7 @@
     _import_properties,
     _warn_for_annotations_with_multiple_instance_ids,
     _serialize_item_level_properties,
+    _split_payloads,
 )
 
 
@@ -3473,3 +3474,62 @@ def test_serialize_item_level_properties_multiple_properties():
     ]
 
     assert result == expected
+
+
+def test__split_payloads_returns_multiple_payloads():
+    payload = {
+        "annotations": [
+            {"id": "annotation_1", "data": "data1"},
+            {"id": "annotation_2", "data": "data2"},
+            {"id": "annotation_3", "data": "data3"},
+        ],
+        "overwrite": True,
+    }
+    max_payload_size = 100
+
+    result = _split_payloads(payload, max_payload_size)
+
+    assert len(result) == 3
+    assert result[0]["annotations"] == [payload["annotations"][0]]
+    assert result[1]["annotations"] == [payload["annotations"][1]]
+    assert result[2]["annotations"] == [payload["annotations"][2]]
+
+
+def test__split_payloads_with_annotation_exceeding_size_limit():
+    payload = {
+        "annotations": [
+            {"id": "annotation_1", "data": "a" * 1000},  # Large annotation
+            {"id": "annotation_2", "data": "data2"},
+        ],
+        "overwrite": True,
+    }
+    max_payload_size = 50
+
+    with pytest.raises(
+        ValueError,
+        match="One or more annotations exceed the maximum allowed size",
+    ):
+        _split_payloads(payload, max_payload_size)
+
+
+def test__split_payloads_overwrites_on_first_payload_and_appends_on_the_rest():
+    """
+    When importing annotations, we need to respect the overwrite behaviour defined by the user.
+    However, if we need to split payloads, all payloads after the first will have to be appended
+    """
+    payload = {
+        "annotations": [
+            {"id": "annotation_1", "data": "data1"},
+            {"id": "annotation_2", "data": "data2"},
+            {"id": "annotation_3", "data": "data3"},
+        ],
+        "overwrite": True,
+    }
+    max_payload_size = 100
+
+    result = _split_payloads(payload, max_payload_size)
+
+    assert len(result) == 3
+    assert result[0]["overwrite"]
+    assert not result[1]["overwrite"]
+    assert not result[2]["overwrite"]