diff --git a/flytekit/remote/remote.py b/flytekit/remote/remote.py
index 117abf27e3..60ae7bbf3e 100644
--- a/flytekit/remote/remote.py
+++ b/flytekit/remote/remote.py
@@ -235,9 +235,17 @@ def __init__(
         # Not exposing this as a property for now.
         self._entrypoint_settings = entrypoint_settings
 
+        raw_output_data_prefix = auth_config.RAW_OUTPUT_DATA_PREFIX.get() or os.path.join(
+            sdk_config.LOCAL_SANDBOX.get(), "control_plane_raw"
+        )
+        self._file_access = file_access or FileAccessProvider(
+            local_sandbox_dir=os.path.join(sdk_config.LOCAL_SANDBOX.get(), "control_plane_metadata"),
+            raw_output_prefix=raw_output_data_prefix,
+        )
         # Save the file access object locally, but also make it available for use from the context.
-        FlyteContextManager.with_context(FlyteContextManager.current_context().with_file_access(file_access).build())
-        self._file_access = file_access
+        FlyteContextManager.with_context(
+            FlyteContextManager.current_context().with_file_access(self._file_access).build()
+        )
 
         # TODO: Reconsider whether we want this. Probably best to not cache.
         self._serialized_entity_cache = OrderedDict()
diff --git a/flytekit/types/file/file.py b/flytekit/types/file/file.py
index eb64e5943d..9bff3a5dec 100644
--- a/flytekit/types/file/file.py
+++ b/flytekit/types/file/file.py
@@ -10,6 +10,7 @@
 from flytekit.models.core.types import BlobType
 from flytekit.models.literals import Blob, BlobMetadata, Literal, Scalar
 from flytekit.models.types import LiteralType
+from flytekit.types.pickle.pickle import FlytePickleTransformer
 
 
 def noop():
@@ -348,7 +349,11 @@ def _downloader():
         return ff
 
     def guess_python_type(self, literal_type: LiteralType) -> typing.Type[FlyteFile[typing.Any]]:
-        if literal_type.blob is not None and literal_type.blob.dimensionality == BlobType.BlobDimensionality.SINGLE:
+        if (
+            literal_type.blob is not None
+            and literal_type.blob.dimensionality == BlobType.BlobDimensionality.SINGLE
+            and literal_type.blob.format != FlytePickleTransformer.PYTHON_PICKLE_FORMAT
+        ):
             return FlyteFile.__class_getitem__(literal_type.blob.format)
 
         raise ValueError(f"Transformer {self} cannot reverse {literal_type}")
diff --git a/flytekit/types/pickle/pickle.py b/flytekit/types/pickle/pickle.py
index 9219d3a8b4..3472dec7e6 100644
--- a/flytekit/types/pickle/pickle.py
+++ b/flytekit/types/pickle/pickle.py
@@ -78,6 +78,16 @@ def to_literal(self, ctx: FlyteContext, python_val: T, python_type: Type[T], exp
         ctx.file_access.put_data(uri, remote_path, is_multipart=False)
         return Literal(scalar=Scalar(blob=Blob(metadata=meta, uri=remote_path)))
 
+    def guess_python_type(self, literal_type: LiteralType) -> typing.Type[FlytePickle[typing.Any]]:
+        if (
+            literal_type.blob is not None
+            and literal_type.blob.dimensionality == _core_types.BlobType.BlobDimensionality.SINGLE
+            and literal_type.blob.format == FlytePickleTransformer.PYTHON_PICKLE_FORMAT
+        ):
+            return FlytePickle
+
+        raise ValueError(f"Transformer {self} cannot reverse {literal_type}")
+
     def get_literal_type(self, t: Type[T]) -> LiteralType:
         return LiteralType(
             blob=_core_types.BlobType(
diff --git a/tests/flytekit/unit/core/test_type_engine.py b/tests/flytekit/unit/core/test_type_engine.py
index 50a77c43d9..9f88a80fb2 100644
--- a/tests/flytekit/unit/core/test_type_engine.py
+++ b/tests/flytekit/unit/core/test_type_engine.py
@@ -356,6 +356,14 @@ def test_guessing_basic():
     pt = TypeEngine.guess_python_type(lt)
     assert pt is None
 
+    lt = model_types.LiteralType(
+        blob=BlobType(
+            format=FlytePickleTransformer.PYTHON_PICKLE_FORMAT, dimensionality=BlobType.BlobDimensionality.SINGLE
+        )
+    )
+    pt = TypeEngine.guess_python_type(lt)
+    assert pt is FlytePickle
+
 
 def test_guessing_containers():
     b = model_types.LiteralType(simple=model_types.SimpleType.BOOLEAN)
@@ -552,6 +560,25 @@ def test_enum_type():
         TypeEngine.to_literal_type(UnsupportedEnumValues)
 
 
+def test_pickle_type():
+    class Foo(object):
+        def __init__(self, number: int):
+            self.number = number
+
+    lt = TypeEngine.to_literal_type(FlytePickle)
+    assert lt.blob.format == FlytePickleTransformer.PYTHON_PICKLE_FORMAT
+    assert lt.blob.dimensionality == BlobType.BlobDimensionality.SINGLE
+
+    ctx = FlyteContextManager.current_context()
+    lv = TypeEngine.to_literal(ctx, Foo(1), FlytePickle, lt)
+    assert "/tmp/flyte/" in lv.scalar.blob.uri
+
+    transformer = FlytePickleTransformer()
+    gt = transformer.guess_python_type(lt)
+    pv = transformer.to_python_value(ctx, lv, expected_python_type=gt)
+    assert Foo(1).number == pv.number
+
+
 def test_enum_in_dataclass():
     @dataclass_json
     @dataclass