diff --git a/tools/debt_split.py b/tools/debt_split.py
index c344192ece..e7341fefe1 100644
--- a/tools/debt_split.py
+++ b/tools/debt_split.py
@@ -163,7 +163,7 @@ def apply_change(root, base, new, index_text):
         _, section, item, name = entry
         entries = load(name).setdefault(section, [])
         moved = relink(item, INDEX, debt_file(name))
-        position = len(entries)
+        position = 0 if anchor is None else len(entries)
         if anchor is not None and anchor[1] == section and anchor[3] == name:
             anchored = relink(anchor[2], INDEX, debt_file(name))
             if anchored in entries:
diff --git a/tools/tests/test_debt_split.py b/tools/tests/test_debt_split.py
index a9bb72e276..9bdceffa98 100644
--- a/tools/tests/test_debt_split.py
+++ b/tools/tests/test_debt_split.py
@@ -157,6 +157,18 @@ class DebtSplitTests(unittest.TestCase):
         self.assertNotEqual(result.returncode, 0)
         self.assertIn("not in a three-way conflict", result.stderr)
 
+    def test_resolve_preserves_entries_inserted_before_the_first_existing_entry(self):
+        first = "- [libSceA](../../core/libs/prx/libSceA/First.cpp) - `sceAFirst` returns 0"
+        second = "- [libSceA](../../core/libs/prx/libSceA/Second.cpp) - `sceASecond` returns 0"
+        result = self.rebase([first, second, A_STUB, B_STUB, C_STUB], [A_FUNCTIONAL, SHADER, SHARED])
+        self.assertEqual(result.returncode, 0, result.stdout + result.stderr)
+        self.git("rebase", "--continue")
+        self.assertEqual(self.read("docs/dev/debt/libSceA.md"),
+                         "# libSceA technical debt\n\n### Silent stubs\n\n" +
+                         "\n".join(entry.replace("../../", "../../../") for entry in (first, second, A_STUB)) +
+                         "\n\n### Functional\n\n" + A_FUNCTIONAL.replace("../../", "../../../") + "\n")
+        self.assertEqual(self.read(INDEX), self.git("show", "main:" + INDEX).stdout)
+
 
 if __name__ == "__main__":
     unittest.main()