diff --git a/tools/debt_split.py b/tools/debt_split.py
index 6f8bfc054c..d6b0ef0793 100644
--- a/tools/debt_split.py
+++ b/tools/debt_split.py
@@ -197,7 +197,7 @@ def apply_change(root, base, new, index_text):
         for offset, fresh in enumerate(added):
             if offset in kept_new:
                 continue
-            anchor = after[j1 + offset - 1] if j1 + offset > 0 else None
+            anchor = next((entry for entry in reversed(after[:j1 + offset]) if entry[1] == fresh[1] and entry[3] == fresh[3]), None)
             insert(fresh, anchor)
     for name, sections in files.items():
         write_debt(root, name, sections, order)
diff --git a/tools/tests/test_debt_split.py b/tools/tests/test_debt_split.py
index 14eb2bac77..3596e47a76 100644
--- a/tools/tests/test_debt_split.py
+++ b/tools/tests/test_debt_split.py
@@ -198,6 +198,16 @@ class DebtSplitTests(unittest.TestCase):
                          "\n\n### Functional\n\n" + A_FUNCTIONAL.replace("../../", "../../../") + "\n")
         self.assertEqual(self.read(INDEX), self.git("show", "main:" + INDEX).stdout)
 
+    def test_resolve_places_an_entry_inserted_at_the_top_of_a_later_section(self):
+        added = "- [libSceA](../../core/libs/prx/libSceA/Added.cpp) - `sceAAdded` returns 0"
+        result = self.rebase([A_STUB, B_STUB, C_STUB], [added, 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" + A_STUB.replace("../../", "../../../") +
+                         "\n\n### Functional\n\n" +
+                         "\n".join(entry.replace("../../", "../../../") for entry in (added, A_FUNCTIONAL)) + "\n")
+
     def test_indented_continuation_after_a_blank_line_moves_with_its_entry(self):
         note = "  - sub note about sceAOne"
         self.write(INDEX, "# Project technical debt\n\n### Silent stubs\n\n" + A_STUB + "\n\n" + note + "\n")