diff --git a/pycardano/plutus.py b/pycardano/plutus.py
index b6b2ac3a..5e76658e 100644
--- a/pycardano/plutus.py
+++ b/pycardano/plutus.py
@@ -804,17 +804,43 @@ class RawPlutusData(CBORSerializable):
     data: RawDatum
 
     def to_primitive(self) -> Primitive:
-        def _dfs(obj):
-            if isinstance(obj, list) and obj:
+        def _dfs(obj, preserve=False):
+            # `preserve` tracks decoded structures: a CBOR round trip marks
+            # indefinite lists as IndefiniteList while definite lists stay
+            # plain lists, and re-encoding must keep that distinction or a
+            # restored datum no longer matches its original bytes. Inside an
+            # IndefiniteList, children are therefore visited in preserve
+            # mode; structures built by from_dict or by hand keep the
+            # historical behaviour of wrapping plain lists as indefinite.
+            if isinstance(obj, IndefiniteList) and obj:
+                return IndefiniteList([_dfs(item, True) for item in obj])
+            elif isinstance(obj, list) and obj:
+                if preserve:
+                    return [_dfs(item, True) for item in obj]
                 return IndefiniteList([_dfs(item) for item in obj])
             elif isinstance(obj, dict):
-                return {_dfs(k): _dfs(v) for k, v in obj.items()}
-            elif isinstance(obj, CBORTag) and isinstance(obj.value, list) and obj.value:
+                return {_dfs(k, preserve): _dfs(v, preserve) for k, v in obj.items()}
+            elif (
+                isinstance(obj, CBORTag)
+                and isinstance(obj.value, (list, IndefiniteList))
+                and obj.value
+            ):
+                child_preserve = preserve or isinstance(obj.value, IndefiniteList)
                 if obj.tag != 102:
-                    value = IndefiniteList([_dfs(item) for item in obj.value])
+                    value = IndefiniteList(
+                        [_dfs(item, child_preserve) for item in obj.value]
+                    )
                 else:
-                    value = [_dfs(item) for item in obj.value]
+                    value = [_dfs(item, child_preserve) for item in obj.value]
                 return CBORTag(tag=obj.tag, value=value)
+            elif isinstance(obj, bytes) and len(obj) > 64:
+                # The ledger requires byte strings longer than 64 bytes in
+                # Plutus data to be chunked (indefinite-length encoding).
+                # from_dict wraps such bytes in ByteString, but a round trip
+                # through CBOR (e.g. deepcopy or from_cbor) decodes them back
+                # to plain bytes, so re-wrap them here to keep the chunked
+                # encoding stable across copies.
+                return ByteString(obj)
             return obj
 
         return _dfs(self.data)
diff --git a/test/pycardano/test_plutus.py b/test/pycardano/test_plutus.py
index 49eb1038..4a99902c 100644
--- a/test/pycardano/test_plutus.py
+++ b/test/pycardano/test_plutus.py
@@ -353,6 +353,37 @@ def test_clone_raw_plutus_data():
     assert cloned_tag != tag
 
 
+def test_raw_plutus_data_long_bytes_stay_chunked():
+    # Byte strings longer than 64 bytes must keep their chunked
+    # (indefinite-length) encoding through deepcopy and CBOR round trips,
+    # otherwise the ledger rejects the datum.
+    data = RawPlutusData.from_dict(
+        {"constructor": 0, "fields": [{"bytes": "ab" * 182}]}
+    )
+    assert bytes.fromhex("5f5840") in data.to_cbor()
+    assert copy.deepcopy(data).to_cbor() == data.to_cbor()
+    assert RawPlutusData.from_cbor(data.to_cbor()).to_cbor() == data.to_cbor()
+
+
+def test_raw_plutus_data_long_bytes_nested_stay_chunked():
+    map_data = RawPlutusData.from_dict(
+        {"map": [{"k": {"bytes": "cd" * 100}, "v": {"bytes": "ef" * 100}}]}
+    )
+    list_data = RawPlutusData.from_dict({"list": [{"bytes": "ab" * 65}]})
+    for datum in (map_data, list_data):
+        assert RawPlutusData.from_cbor(datum.to_cbor()).to_cbor() == datum.to_cbor()
+        assert copy.deepcopy(datum).to_cbor() == datum.to_cbor()
+
+
+def test_raw_plutus_data_short_bytes_stay_definite():
+    data = RawPlutusData.from_dict(
+        {"constructor": 1, "fields": [{"bytes": "ab" * 32}, {"int": 42}]}
+    )
+    assert b"\x5f" not in data.to_cbor()
+    assert RawPlutusData.from_cbor(data.to_cbor()).to_cbor() == data.to_cbor()
+    assert copy.deepcopy(data).to_cbor() == data.to_cbor()
+
+
 def test_clone_plutus_data():
     key_hash = bytes.fromhex("c2ff616e11299d9094ce0a7eb5b7284b705147a822f4ffbd471f971a")
     deadline = 1643235300000