diff --git a/elementary/operations/upload_source_freshness.py b/elementary/operations/upload_source_freshness.py
index df80deaf4..387ed4155 100644
--- a/elementary/operations/upload_source_freshness.py
+++ b/elementary/operations/upload_source_freshness.py
@@ -1,5 +1,7 @@
 import json
 import os
+from itertools import accumulate, groupby
+from operator import itemgetter
 from pathlib import Path
 
 import click
@@ -10,6 +12,8 @@
 from elementary.monitor import dbt_project_utils
 from elementary.utils.ordered_yaml import OrderedYaml
 
+MAX_SERIALISED_CHARACTER_LENGTH = 90_000
+
 
 class UploadSourceFreshnessOperation:
     def __init__(self, config: Config):
@@ -58,20 +62,32 @@ def upload_results(self, results: dict, metadata: dict):
                 f"Source freshness for invocation id {invocation_id} were already uploaded."
             )
 
-        chunk_size = 100
-        chunk_list = list(range(0, len(results), chunk_size))
+        for result in results:
+            result["metadata"] = metadata
+
+        serialised_argument_lengths = [len(json.dumps(record)) for record in results]
+
+        argument_splits = [
+            (running_total // MAX_SERIALISED_CHARACTER_LENGTH, record)
+            for running_total, record in zip(
+                accumulate(serialised_argument_lengths),
+                results,
+            )
+        ]
+
+        chunked_commands = {
+            chunk_id: [i[1] for i in chunk_tuple]
+            for chunk_id, chunk_tuple in groupby(argument_splits, key=itemgetter(0))
+        }
+
         upload_with_progress_bar = alive_it(
-            chunk_list, title="Uploading source freshness results"
+            chunked_commands.values(), title="Uploading source freshness results"
         )
-        for chunk in upload_with_progress_bar:
-            results_segment = results[chunk : chunk + chunk_size]
-
-            for result in results_segment:
-                result["metadata"] = metadata
 
+        for result_chunk in upload_with_progress_bar:
             dbt_runner.run_operation(
                 "elementary_cli.upload_source_freshness",
-                macro_args={"results": json.dumps(results_segment)},
+                macro_args={"results": json.dumps(result_chunk)},
                 quiet=True,
             )