diff --git a/main.py b/main.py
index e3fc768..b9a4fb2 100644
--- a/main.py
+++ b/main.py
@@ -7,6 +7,7 @@ from pathlib import Path
 from typing import Any
 
 import ynab
+from dateutil.relativedelta import relativedelta
 
 from category_suggester import CategoryHistory
 from wf_credit_extractor import WellsFargoPayloadExtractor as CreditExtractor
@@ -601,27 +602,48 @@ def _execute_import(
     # --- Create new + duplicates ---
     to_create = classification.new + classification.duplicates
     if to_create:
-        new_txns = [
-            ynab.NewTransaction(
-                account_id=t["account_id"],
-                date=date.fromisoformat(t["date"]),
-                amount=t["amount"],
-                payee_name=t["payee_name"],
-                category_id=t.get("category_id"),
-                cleared=ynab.TransactionClearedStatus(t["cleared"]),
-                flag_color=ynab.TransactionFlagColor(t["flag_color"]),
-                import_id=t["import_id"],
-                approved=t.get("approved", False),
+        today = date.today()
+        earliest_ynab_date = today - relativedelta(years=5)
+        eligible_to_create = []
+        skipped_for_date = []
+        for transaction in to_create:
+            transaction_date = date.fromisoformat(transaction["date"])
+            if earliest_ynab_date <= transaction_date <= today:
+                eligible_to_create.append(transaction)
+            else:
+                skipped_for_date.append(transaction)
+
+        if skipped_for_date:
+            print(
+                f"  [ynab] Skipped {len(skipped_for_date)} transaction(s) outside "
+                f"the supported date range ({earliest_ynab_date} through {today}):"
+            )
+            for transaction in skipped_for_date:
+                payee = transaction.get("payee_name") or "(no payee)"
+                print(f"    {transaction['date']} | {payee}")
+
+        if eligible_to_create:
+            new_txns = [
+                ynab.NewTransaction(
+                    account_id=t["account_id"],
+                    date=date.fromisoformat(t["date"]),
+                    amount=t["amount"],
+                    payee_name=t["payee_name"],
+                    category_id=t.get("category_id"),
+                    cleared=ynab.TransactionClearedStatus(t["cleared"]),
+                    flag_color=ynab.TransactionFlagColor(t["flag_color"]),
+                    import_id=t["import_id"],
+                    approved=t.get("approved", False),
+                )
+                for t in eligible_to_create
+            ]
+            resp = ynab_client.create_transactions(new_txns)
+            created_ids = resp.transaction_ids or []
+            dup_ids = resp.duplicate_import_ids or []
+            print(
+                f"  [ynab] Created {len(created_ids)} transaction(s)"
+                + (f", {len(dup_ids)} server-side duplicate(s) skipped" if dup_ids else "")
             )
-            for t in to_create
-        ]
-        resp = ynab_client.create_transactions(new_txns)
-        created_ids = resp.transaction_ids or []
-        dup_ids = resp.duplicate_import_ids or []
-        print(
-            f"  [ynab] Created {len(created_ids)} transaction(s)"
-            + (f", {len(dup_ids)} server-side duplicate(s) skipped" if dup_ids else "")
-        )
 
     # --- Update pending→posted ---
     if classification.pending_to_posted: