diff --git a/.gitignore b/.gitignore
index ec56a0f239..73c81d2a6a 100644
--- a/.gitignore
+++ b/.gitignore
@@ -3,7 +3,7 @@
 *.pyt
 *.pytc
 *.egg-info
-.*.swp
+.*.sw*
 .DS_Store
 venv/
 .venv/
diff --git a/dev-requirements.txt b/dev-requirements.txt
index 28c22afa15..6e17840325 100644
--- a/dev-requirements.txt
+++ b/dev-requirements.txt
@@ -32,7 +32,6 @@ certifi==2021.10.8
     #   requests
 cffi==1.15.0
     # via
-    #   -c requirements.txt
     #   bcrypt
     #   cryptography
     #   pynacl
diff --git a/flytekit/core/annotation.py b/flytekit/core/annotation.py
new file mode 100644
index 0000000000..b4a70a6469
--- /dev/null
+++ b/flytekit/core/annotation.py
@@ -0,0 +1,30 @@
+from typing import Any, Dict
+
+
+class FlyteAnnotation:
+    """A core object to add arbitrary annotations to flyte types.
+
+    This metadata is ingested as a python dictionary and will be serialized
+    into fields on the flyteidl type literals. This data is not accessible at
+    runtime but rather can be retrieved from flyteadmin for custom presentation
+    of typed parameters.
+
+    Flytekit expects to receive a maximum of one `FlyteAnnotation` object
+    within each typehint.
+
+    For a task definition:
+
+    .. code-block:: python
+
+        @task
+        def x(a: typing.Annotated[int, FlyteAnnotation({"foo": {"bar": 1}})]):
+            return
+
+    """
+
+    def __init__(self, data: Dict[str, Any]):
+        self._data = data
+
+    @property
+    def data(self):
+        return self._data
diff --git a/flytekit/core/type_engine.py b/flytekit/core/type_engine.py
index 07faf178ce..62f2daadc0 100644
--- a/flytekit/core/type_engine.py
+++ b/flytekit/core/type_engine.py
@@ -25,12 +25,14 @@
 from marshmallow_enum import EnumField, LoadDumpOptions
 from marshmallow_jsonschema import JSONSchema
 
+from flytekit.core.annotation import FlyteAnnotation
 from flytekit.core.context_manager import FlyteContext
 from flytekit.core.type_helpers import load_type_from_tag
 from flytekit.exceptions import user as user_exceptions
 from flytekit.loggers import logger
 from flytekit.models import interface as _interface_models
 from flytekit.models import types as _type_models
+from flytekit.models.annotation import TypeAnnotation as TypeAnnotationModel
 from flytekit.models.core import types as _core_types
 from flytekit.models.literals import (
     Blob,
@@ -235,6 +237,12 @@ def get_literal_type(self, t: Type[T]) -> LiteralType:
         Extracts the Literal type definition for a Dataclass and returns a type Struct.
         If possible also extracts the JSONSchema for the dataclass.
         """
+        if get_origin(t) is Annotated:
+            raise ValueError(
+                "Flytekit does not currently have support for FlyteAnnotations applied to Dataclass."
+                f"Type {t} cannot be parsed."
+            )
+
         if not issubclass(t, DataClassJsonMixin):
             raise AssertionError(
                 f"Dataclass {t} should be decorated with @dataclass_json to be " f"serialized correctly"
@@ -551,6 +559,7 @@ def get_transformer(cls, python_type: Type) -> TypeTransformer[T]:
             TODO lets make this deterministic by using an ordered dict
 
         """
+
         # Step 1
         if get_origin(python_type) is Annotated:
             python_type = get_args(python_type)[0]
@@ -560,8 +569,14 @@ def get_transformer(cls, python_type: Type) -> TypeTransformer[T]:
 
         # Step 2
         if hasattr(python_type, "__origin__"):
+            # Handling of annotated generics, eg:
+            # Annotated[typing.List[int], 'foo']
+            if get_origin(python_type) is Annotated:
+                return cls.get_transformer(get_args(python_type)[0])
+
             if python_type.__origin__ in cls._REGISTRY:
                 return cls._REGISTRY[python_type.__origin__]
+
             raise ValueError(f"Generic Type {python_type.__origin__} not supported currently in Flytekit.")
 
         # Step 3
@@ -590,7 +605,30 @@ def to_literal_type(cls, python_type: Type) -> LiteralType:
         Converts a python type into a flyte specific ``LiteralType``
         """
         transformer = cls.get_transformer(python_type)
-        return transformer.get_literal_type(python_type)
+        res = transformer.get_literal_type(python_type)
+        data = None
+        if get_origin(python_type) is Annotated:
+            for x in get_args(python_type)[1:]:
+                if not isinstance(x, FlyteAnnotation):
+                    continue
+                if data is not None:
+                    raise ValueError(
+                        f"More than one FlyteAnnotation used within {python_type} typehint. Flytekit requires a max of one."
+                    )
+                data = x.data
+        if data is not None:
+            idl_type_annotation = TypeAnnotationModel(annotations=data)
+            return LiteralType(
+                simple=res.simple,
+                schema=res.schema,
+                collection_type=res.collection_type,
+                map_value_type=res.map_value_type,
+                blob=res.blob,
+                enum_type=res.enum_type,
+                metadata=res.metadata,
+                annotation=idl_type_annotation,
+            )
+        return res
 
     @classmethod
     def to_literal(cls, ctx: FlyteContext, python_val: typing.Any, python_type: Type, expected: LiteralType) -> Literal:
@@ -718,9 +756,16 @@ def get_sub_type(t: Type[T]) -> Type[T]:
         """
         Return the generic Type T of the List
         """
-        if hasattr(t, "__origin__") and t.__origin__ is list:  # type: ignore
-            if hasattr(t, "__args__"):
-                return t.__args__[0]  # type: ignore
+
+        if hasattr(t, "__origin__"):
+            # Handle annotation on list generic, eg:
+            # Annotated[typing.List[int], 'foo']
+            if get_origin(t) is Annotated:
+                return ListTransformer.get_sub_type(get_args(t)[0])
+
+            if t.__origin__ is list and hasattr(t, "__args__"):
+                return t.__args__[0]
+
         raise ValueError("Only generic univariate typing.List[T] type is supported.")
 
     def get_literal_type(self, t: Type[T]) -> Optional[LiteralType]:
@@ -763,9 +808,17 @@ def get_dict_types(t: Optional[Type[dict]]) -> typing.Tuple[Optional[type], Opti
         """
         Return the generic Type T of the Dict
         """
-        if hasattr(t, "__origin__") and t.__origin__ is dict:  # type: ignore
-            if hasattr(t, "__args__"):
-                return t.__args__  # type: ignore
+        _origin = get_origin(t)
+        _args = get_args(t)
+        if _origin is not None:
+            if _origin is Annotated:
+                raise ValueError(
+                    f"Flytekit does not currently have support \
+                        for FlyteAnnotations applied to dicts. {t} cannot be \
+                        parsed."
+                )
+            if _origin is dict and _args is not None:
+                return _args
         return None, None
 
     @staticmethod
@@ -913,6 +966,13 @@ def __init__(self):
         super().__init__(name="DefaultEnumTransformer", t=enum.Enum)
 
     def get_literal_type(self, t: Type[T]) -> LiteralType:
+        if get_origin(t) is Annotated:
+            raise ValueError(
+                f"Flytekit does not currently have support \
+                    for FlyteAnnotations applied to enums. {t} cannot be \
+                    parsed."
+            )
+
         values = [v.value for v in t]  # type: ignore
         if not isinstance(values[0], str):
             raise AssertionError("Only EnumTypes with value of string are supported")
diff --git a/flytekit/models/annotation.py b/flytekit/models/annotation.py
new file mode 100644
index 0000000000..ced935c57e
--- /dev/null
+++ b/flytekit/models/annotation.py
@@ -0,0 +1,43 @@
+import json as _json
+from typing import Any, Dict
+
+from flyteidl.core import types_pb2 as _types_pb2
+from google.protobuf import json_format as _json_format
+from google.protobuf import struct_pb2 as _struct
+
+
+class TypeAnnotation:
+    """Python class representation of the flyteidl TypeAnnotation message."""
+
+    def __init__(self, annotations: Dict[str, Any]):
+        self._annotations = annotations
+
+    @property
+    def annotations(self) -> Dict[str, Any]:
+        """
+        :rtype: dict[str, Any]
+        """
+        return self._annotations
+
+    def to_flyte_idl(self) -> _types_pb2.TypeAnnotation:
+        """
+        :rtype: flyteidl.core.types_pb2.TypeAnnotation
+        """
+
+        if self._annotations is not None:
+            annotations = _json_format.Parse(_json.dumps(self.annotations), _struct.Struct())
+        else:
+            annotations = None
+
+        return _types_pb2.TypeAnnotation(
+            annotations=annotations,
+        )
+
+    @classmethod
+    def from_flyte_idl(cls, proto):
+        """
+        :param flyteidl.core.types_pb2.TypeAnnotation proto:
+        :rtype: TypeAnnotation
+        """
+
+        return cls(annotations=_json_format.MessageToDict(proto.annotations))
diff --git a/flytekit/models/types.py b/flytekit/models/types.py
index 09ed947642..0a0a2f8ced 100644
--- a/flytekit/models/types.py
+++ b/flytekit/models/types.py
@@ -6,6 +6,7 @@
 from google.protobuf import struct_pb2 as _struct
 
 from flytekit.models import common as _common
+from flytekit.models.annotation import TypeAnnotation as TypeAnnotationModel
 from flytekit.models.core import types as _core_types
 
 
@@ -195,6 +196,7 @@ def __init__(
         enum_type=None,
         structured_dataset_type=None,
         metadata=None,
+        annotation=None,
     ):
         """
         This is a oneof message, only one of the kwargs may be set, representing one of the Flyte types.
@@ -208,6 +210,8 @@ def __init__(
         :param flytekit.models.core.types.EnumType enum_type: For enum objects, describes an enum
         :param flytekit.models.core.types.StructuredDatasetType structured_dataset_type: structured dataset
         :param dict[Text, T] metadata: Additional data describing the type
+        :param flytekit.models.annotation.FlyteAnnotation annotation: Additional data
+            describing the type _intended to be saturated by the client_
         """
         self._simple = simple
         self._schema = schema
@@ -217,6 +221,7 @@ def __init__(
         self._enum_type = enum_type
         self._structured_dataset_type = structured_dataset_type
         self._metadata = metadata
+        self._annotation = annotation
 
     @property
     def simple(self) -> SimpleType:
@@ -259,18 +264,31 @@ def metadata(self):
         """
         return self._metadata
 
+    @property
+    def annotation(self) -> TypeAnnotationModel:
+        """
+        :rtype: flytekit.models.annotation.TypeAnnotation
+        """
+        return self._annotation
+
     @metadata.setter
     def metadata(self, value):
         self._metadata = value
 
+    @annotation.setter
+    def annotation(self, value):
+        self.annotation = value
+
     def to_flyte_idl(self):
         """
         :rtype: flyteidl.core.types_pb2.LiteralType
         """
+
         if self.metadata is not None:
             metadata = _json_format.Parse(_json.dumps(self.metadata), _struct.Struct())
         else:
             metadata = None
+
         t = _types_pb2.LiteralType(
             simple=self.simple if self.simple is not None else None,
             schema=self.schema.to_flyte_idl() if self.schema is not None else None,
@@ -282,6 +300,7 @@ def to_flyte_idl(self):
             if self.structured_dataset_type
             else None,
             metadata=metadata,
+            annotation=self.annotation.to_flyte_idl() if self.annotation else None,
         )
         return t
 
@@ -308,6 +327,7 @@ def from_flyte_idl(cls, proto):
             if proto.HasField("structured_dataset_type")
             else None,
             metadata=_json_format.MessageToDict(proto.metadata) or None,
+            annotation=TypeAnnotationModel.from_flyte_idl(proto.annotation) if proto.HasField("annotation") else None,
         )
 
 
diff --git a/plugins/flytekit-aws-athena/requirements.txt b/plugins/flytekit-aws-athena/requirements.txt
index 6fe91c53c8..a1acae494f 100644
--- a/plugins/flytekit-aws-athena/requirements.txt
+++ b/plugins/flytekit-aws-athena/requirements.txt
@@ -12,8 +12,6 @@ binaryornot==0.4.4
     # via cookiecutter
 certifi==2021.10.8
     # via requests
-cffi==1.15.0
-    # via cryptography
 chardet==4.0.0
     # via binaryornot
 charset-normalizer==2.0.11
@@ -54,10 +52,6 @@ idna==3.3
     # via requests
 importlib-metadata==4.10.1
     # via keyring
-jeepney==0.7.1
-    # via
-    #   keyring
-    #   secretstorage
 jinja2==3.0.3
     # via
     #   cookiecutter
@@ -126,8 +120,6 @@ responses==0.18.0
     # via flytekit
 retry==0.9.2
     # via flytekit
-secretstorage==3.3.1
-    # via keyring
 six==1.16.0
     # via
     #   cookiecutter
diff --git a/plugins/flytekit-aws-sagemaker/requirements.txt b/plugins/flytekit-aws-sagemaker/requirements.txt
index 2624f28a98..11396f213e 100644
--- a/plugins/flytekit-aws-sagemaker/requirements.txt
+++ b/plugins/flytekit-aws-sagemaker/requirements.txt
@@ -73,10 +73,6 @@ importlib-metadata==4.10.1
     # via keyring
 inotify-simple==1.2.1
     # via sagemaker-training
-jeepney==0.7.1
-    # via
-    #   keyring
-    #   secretstorage
 jinja2==3.0.3
     # via
     #   cookiecutter
@@ -167,8 +163,6 @@ sagemaker-training==3.9.2
     # via flytekitplugins-awssagemaker
 scipy==1.8.0
     # via sagemaker-training
-secretstorage==3.3.1
-    # via keyring
 six==1.16.0
     # via
     #   bcrypt
diff --git a/plugins/flytekit-data-fsspec/requirements.txt b/plugins/flytekit-data-fsspec/requirements.txt
index a14a5bf6cf..c644ac98e7 100644
--- a/plugins/flytekit-data-fsspec/requirements.txt
+++ b/plugins/flytekit-data-fsspec/requirements.txt
@@ -12,8 +12,6 @@ binaryornot==0.4.4
     # via cookiecutter
 certifi==2021.10.8
     # via requests
-cffi==1.15.0
-    # via cryptography
 chardet==4.0.0
     # via binaryornot
 charset-normalizer==2.0.11
@@ -56,10 +54,6 @@ idna==3.3
     # via requests
 importlib-metadata==4.10.1
     # via keyring
-jeepney==0.7.1
-    # via
-    #   keyring
-    #   secretstorage
 jinja2==3.0.3
     # via
     #   cookiecutter
@@ -128,8 +122,6 @@ responses==0.18.0
     # via flytekit
 retry==0.9.2
     # via flytekit
-secretstorage==3.3.1
-    # via keyring
 six==1.16.0
     # via
     #   cookiecutter
diff --git a/plugins/flytekit-dolt/requirements.txt b/plugins/flytekit-dolt/requirements.txt
index 559d5b2085..01dfe2cb6b 100644
--- a/plugins/flytekit-dolt/requirements.txt
+++ b/plugins/flytekit-dolt/requirements.txt
@@ -12,8 +12,6 @@ binaryornot==0.4.4
     # via cookiecutter
 certifi==2021.10.8
     # via requests
-cffi==1.15.0
-    # via cryptography
 chardet==4.0.0
     # via binaryornot
 charset-normalizer==2.0.11
@@ -60,10 +58,6 @@ idna==3.3
     # via requests
 importlib-metadata==4.10.1
     # via keyring
-jeepney==0.7.1
-    # via
-    #   keyring
-    #   secretstorage
 jinja2==3.0.3
     # via
     #   cookiecutter
@@ -134,8 +128,6 @@ responses==0.18.0
     # via flytekit
 retry==0.9.2
     # via flytekit
-secretstorage==3.3.1
-    # via keyring
 six==1.16.0
     # via
     #   cookiecutter
diff --git a/plugins/flytekit-greatexpectations/requirements.txt b/plugins/flytekit-greatexpectations/requirements.txt
index fdbb857264..624f3dc633 100644
--- a/plugins/flytekit-greatexpectations/requirements.txt
+++ b/plugins/flytekit-greatexpectations/requirements.txt
@@ -110,10 +110,6 @@ ipywidgets==7.6.5
     # via great-expectations
 jedi==0.18.1
     # via ipython
-jeepney==0.7.1
-    # via
-    #   keyring
-    #   secretstorage
 jinja2==3.0.3
     # via
     #   altair
@@ -295,8 +291,6 @@ ruamel.yaml.clib==0.2.6
     # via ruamel.yaml
 scipy==1.7.3
     # via great-expectations
-secretstorage==3.3.1
-    # via keyring
 send2trash==1.8.0
     # via notebook
 six==1.16.0
diff --git a/plugins/flytekit-hive/requirements.txt b/plugins/flytekit-hive/requirements.txt
index 269d52fceb..3ae057f9a0 100644
--- a/plugins/flytekit-hive/requirements.txt
+++ b/plugins/flytekit-hive/requirements.txt
@@ -12,8 +12,6 @@ binaryornot==0.4.4
     # via cookiecutter
 certifi==2021.10.8
     # via requests
-cffi==1.15.0
-    # via cryptography
 chardet==4.0.0
     # via binaryornot
 charset-normalizer==2.0.11
@@ -54,10 +52,6 @@ idna==3.3
     # via requests
 importlib-metadata==4.10.1
     # via keyring
-jeepney==0.7.1
-    # via
-    #   keyring
-    #   secretstorage
 jinja2==3.0.3
     # via
     #   cookiecutter
@@ -126,8 +120,6 @@ responses==0.18.0
     # via flytekit
 retry==0.9.2
     # via flytekit
-secretstorage==3.3.1
-    # via keyring
 six==1.16.0
     # via
     #   cookiecutter
diff --git a/plugins/flytekit-k8s-pod/requirements.txt b/plugins/flytekit-k8s-pod/requirements.txt
index 6574f4ab66..d60d9c46b6 100644
--- a/plugins/flytekit-k8s-pod/requirements.txt
+++ b/plugins/flytekit-k8s-pod/requirements.txt
@@ -16,8 +16,6 @@ certifi==2021.10.8
     # via
     #   kubernetes
     #   requests
-cffi==1.15.0
-    # via cryptography
 chardet==4.0.0
     # via binaryornot
 charset-normalizer==2.0.11
@@ -60,10 +58,6 @@ idna==3.3
     # via requests
 importlib-metadata==4.10.1
     # via keyring
-jeepney==0.7.1
-    # via
-    #   keyring
-    #   secretstorage
 jinja2==3.0.3
     # via
     #   cookiecutter
@@ -151,8 +145,6 @@ retry==0.9.2
     # via flytekit
 rsa==4.8
     # via google-auth
-secretstorage==3.3.1
-    # via keyring
 six==1.16.0
     # via
     #   cookiecutter
diff --git a/plugins/flytekit-kf-mpi/requirements.txt b/plugins/flytekit-kf-mpi/requirements.txt
index ef91243daf..c13f9f3b74 100644
--- a/plugins/flytekit-kf-mpi/requirements.txt
+++ b/plugins/flytekit-kf-mpi/requirements.txt
@@ -12,8 +12,6 @@ binaryornot==0.4.4
     # via cookiecutter
 certifi==2021.10.8
     # via requests
-cffi==1.15.0
-    # via cryptography
 chardet==4.0.0
     # via binaryornot
 charset-normalizer==2.0.11
@@ -56,10 +54,6 @@ idna==3.3
     # via requests
 importlib-metadata==4.10.1
     # via keyring
-jeepney==0.7.1
-    # via
-    #   keyring
-    #   secretstorage
 jinja2==3.0.3
     # via
     #   cookiecutter
@@ -128,8 +122,6 @@ responses==0.18.0
     # via flytekit
 retry==0.9.2
     # via flytekit
-secretstorage==3.3.1
-    # via keyring
 six==1.16.0
     # via
     #   cookiecutter
diff --git a/plugins/flytekit-kf-pytorch/requirements.txt b/plugins/flytekit-kf-pytorch/requirements.txt
index 9fc8665f43..1696646c87 100644
--- a/plugins/flytekit-kf-pytorch/requirements.txt
+++ b/plugins/flytekit-kf-pytorch/requirements.txt
@@ -12,8 +12,6 @@ binaryornot==0.4.4
     # via cookiecutter
 certifi==2021.10.8
     # via requests
-cffi==1.15.0
-    # via cryptography
 chardet==4.0.0
     # via binaryornot
 charset-normalizer==2.0.11
@@ -54,10 +52,6 @@ idna==3.3
     # via requests
 importlib-metadata==4.10.1
     # via keyring
-jeepney==0.7.1
-    # via
-    #   keyring
-    #   secretstorage
 jinja2==3.0.3
     # via
     #   cookiecutter
@@ -126,8 +120,6 @@ responses==0.18.0
     # via flytekit
 retry==0.9.2
     # via flytekit
-secretstorage==3.3.1
-    # via keyring
 six==1.16.0
     # via
     #   cookiecutter
diff --git a/plugins/flytekit-kf-tensorflow/requirements.txt b/plugins/flytekit-kf-tensorflow/requirements.txt
index ae428e9215..d3b6253664 100644
--- a/plugins/flytekit-kf-tensorflow/requirements.txt
+++ b/plugins/flytekit-kf-tensorflow/requirements.txt
@@ -12,8 +12,6 @@ binaryornot==0.4.4
     # via cookiecutter
 certifi==2021.10.8
     # via requests
-cffi==1.15.0
-    # via cryptography
 chardet==4.0.0
     # via binaryornot
 charset-normalizer==2.0.11
@@ -54,10 +52,6 @@ idna==3.3
     # via requests
 importlib-metadata==4.10.1
     # via keyring
-jeepney==0.7.1
-    # via
-    #   keyring
-    #   secretstorage
 jinja2==3.0.3
     # via
     #   cookiecutter
@@ -126,8 +120,6 @@ responses==0.18.0
     # via flytekit
 retry==0.9.2
     # via flytekit
-secretstorage==3.3.1
-    # via keyring
 six==1.16.0
     # via
     #   cookiecutter
diff --git a/plugins/flytekit-modin/requirements.txt b/plugins/flytekit-modin/requirements.txt
index adaa0b7307..4f3b01e5e4 100644
--- a/plugins/flytekit-modin/requirements.txt
+++ b/plugins/flytekit-modin/requirements.txt
@@ -16,8 +16,6 @@ binaryornot==0.4.4
     # via cookiecutter
 certifi==2021.10.8
     # via requests
-cffi==1.15.0
-    # via cryptography
 chardet==4.0.0
     # via binaryornot
 charset-normalizer==2.0.11
@@ -69,10 +67,6 @@ idna==3.3
     # via requests
 importlib-metadata==4.10.1
     # via keyring
-jeepney==0.7.1
-    # via
-    #   keyring
-    #   secretstorage
 jinja2==3.0.3
     # via
     #   cookiecutter
@@ -166,8 +160,6 @@ responses==0.18.0
     # via flytekit
 retry==0.9.2
     # via flytekit
-secretstorage==3.3.1
-    # via keyring
 six==1.16.0
     # via
     #   cookiecutter
diff --git a/plugins/flytekit-pandera/requirements.txt b/plugins/flytekit-pandera/requirements.txt
index 82df51d30e..f0b65cec17 100644
--- a/plugins/flytekit-pandera/requirements.txt
+++ b/plugins/flytekit-pandera/requirements.txt
@@ -12,8 +12,6 @@ binaryornot==0.4.4
     # via cookiecutter
 certifi==2021.10.8
     # via requests
-cffi==1.15.0
-    # via cryptography
 chardet==4.0.0
     # via binaryornot
 charset-normalizer==2.0.11
@@ -54,10 +52,6 @@ idna==3.3
     # via requests
 importlib-metadata==4.10.1
     # via keyring
-jeepney==0.7.1
-    # via
-    #   keyring
-    #   secretstorage
 jinja2==3.0.3
     # via
     #   cookiecutter
@@ -137,8 +131,6 @@ responses==0.18.0
     # via flytekit
 retry==0.9.2
     # via flytekit
-secretstorage==3.3.1
-    # via keyring
 six==1.16.0
     # via
     #   cookiecutter
diff --git a/plugins/flytekit-papermill/dev-requirements.txt b/plugins/flytekit-papermill/dev-requirements.txt
index 849cef4c9f..d647708f20 100644
--- a/plugins/flytekit-papermill/dev-requirements.txt
+++ b/plugins/flytekit-papermill/dev-requirements.txt
@@ -38,7 +38,7 @@ docker-image-py==0.1.12
     # via flytekit
 docstring-parser==0.13
     # via flytekit
-flyteidl==0.21.23
+flyteidl==0.22.0
     # via flytekit
 flytekit==0.26.0
     # via flytekitplugins-spark
diff --git a/plugins/flytekit-papermill/requirements.txt b/plugins/flytekit-papermill/requirements.txt
index b06adde647..8c3e4570e9 100644
--- a/plugins/flytekit-papermill/requirements.txt
+++ b/plugins/flytekit-papermill/requirements.txt
@@ -71,7 +71,7 @@ entrypoints==0.3
     #   papermill
 executing==0.8.2
     # via stack-data
-flyteidl==0.21.24
+flyteidl==0.22.0
     # via flytekit
 flytekit==0.26.1
     # via flytekitplugins-papermill
diff --git a/plugins/flytekit-snowflake/requirements.txt b/plugins/flytekit-snowflake/requirements.txt
index b563e54814..53951100b5 100644
--- a/plugins/flytekit-snowflake/requirements.txt
+++ b/plugins/flytekit-snowflake/requirements.txt
@@ -12,8 +12,6 @@ binaryornot==0.4.4
     # via cookiecutter
 certifi==2021.10.8
     # via requests
-cffi==1.15.0
-    # via cryptography
 chardet==4.0.0
     # via binaryornot
 charset-normalizer==2.0.11
@@ -54,10 +52,6 @@ idna==3.3
     # via requests
 importlib-metadata==4.10.1
     # via keyring
-jeepney==0.7.1
-    # via
-    #   keyring
-    #   secretstorage
 jinja2==3.0.3
     # via
     #   cookiecutter
@@ -126,8 +120,6 @@ responses==0.18.0
     # via flytekit
 retry==0.9.2
     # via flytekit
-secretstorage==3.3.1
-    # via keyring
 six==1.16.0
     # via
     #   cookiecutter
diff --git a/plugins/flytekit-spark/requirements.txt b/plugins/flytekit-spark/requirements.txt
index fed298d4b4..75d1e32d53 100644
--- a/plugins/flytekit-spark/requirements.txt
+++ b/plugins/flytekit-spark/requirements.txt
@@ -12,8 +12,6 @@ binaryornot==0.4.4
     # via cookiecutter
 certifi==2021.10.8
     # via requests
-cffi==1.15.0
-    # via cryptography
 chardet==4.0.0
     # via binaryornot
 charset-normalizer==2.0.11
@@ -54,10 +52,6 @@ idna==3.3
     # via requests
 importlib-metadata==4.10.1
     # via keyring
-jeepney==0.7.1
-    # via
-    #   keyring
-    #   secretstorage
 jinja2==3.0.3
     # via
     #   cookiecutter
@@ -130,8 +124,6 @@ responses==0.18.0
     # via flytekit
 retry==0.9.2
     # via flytekit
-secretstorage==3.3.1
-    # via keyring
 six==1.16.0
     # via
     #   cookiecutter
diff --git a/plugins/flytekit-sqlalchemy/requirements.txt b/plugins/flytekit-sqlalchemy/requirements.txt
index 134f8960e8..93dcc2790c 100644
--- a/plugins/flytekit-sqlalchemy/requirements.txt
+++ b/plugins/flytekit-sqlalchemy/requirements.txt
@@ -12,8 +12,6 @@ binaryornot==0.4.4
     # via cookiecutter
 certifi==2021.10.8
     # via requests
-cffi==1.15.0
-    # via cryptography
 chardet==4.0.0
     # via binaryornot
 charset-normalizer==2.0.11
@@ -56,10 +54,6 @@ idna==3.3
     # via requests
 importlib-metadata==4.10.1
     # via keyring
-jeepney==0.7.1
-    # via
-    #   keyring
-    #   secretstorage
 jinja2==3.0.3
     # via
     #   cookiecutter
@@ -128,8 +122,6 @@ responses==0.18.0
     # via flytekit
 retry==0.9.2
     # via flytekit
-secretstorage==3.3.1
-    # via keyring
 six==1.16.0
     # via
     #   cookiecutter
diff --git a/setup.py b/setup.py
index 48250dac6b..885f32b897 100644
--- a/setup.py
+++ b/setup.py
@@ -35,7 +35,7 @@
         ]
     },
     install_requires=[
-        "flyteidl>=0.21.17",
+        "flyteidl>=0.22.0",
         "wheel>=0.30.0,<1.0.0",
         "pandas>=1.0.0,<2.0.0",
         "pyarrow>=4.0.0,<7.0.0",
@@ -67,6 +67,7 @@
         "checksumdir>=1.2.0",
         "cloudpickle>=2.0.0",
         "cookiecutter>=1.7.3",
+        "numpy<=1.22.1; python_version < '3.8.0'",
     ],
     extras_require=extras_require,
     scripts=[
diff --git a/tests/flytekit/integration/remote/mock_flyte_repo/workflows/requirements.txt b/tests/flytekit/integration/remote/mock_flyte_repo/workflows/requirements.txt
index dc2ddebe81..93514898b2 100644
--- a/tests/flytekit/integration/remote/mock_flyte_repo/workflows/requirements.txt
+++ b/tests/flytekit/integration/remote/mock_flyte_repo/workflows/requirements.txt
@@ -10,8 +10,6 @@ binaryornot==0.4.4
     # via cookiecutter
 certifi==2021.10.8
     # via requests
-cffi==1.15.0
-    # via cryptography
 chardet==4.0.0
     # via binaryornot
 charset-normalizer==2.0.11
@@ -28,8 +26,6 @@ cookiecutter==1.7.3
     # via flytekit
 croniter==1.2.0
     # via flytekit
-cryptography==36.0.1
-    # via secretstorage
 cycler==0.11.0
     # via matplotlib
 dataclasses-json==0.5.6
@@ -56,10 +52,6 @@ idna==3.3
     # via requests
 importlib-metadata==4.10.1
     # via keyring
-jeepney==0.7.1
-    # via
-    #   keyring
-    #   secretstorage
 jinja2==3.0.3
     # via
     #   cookiecutter
@@ -121,7 +113,6 @@ pyparsing==3.0.7
     #   packaging
 python-dateutil==2.8.2
     # via
-    #   arrow
     #   croniter
     #   flytekit
     #   matplotlib
@@ -147,8 +138,6 @@ responses==0.18.0
     # via flytekit
 retry==0.9.2
     # via flytekit
-secretstorage==3.3.1
-    # via keyring
 six==1.16.0
     # via
     #   cookiecutter
diff --git a/tests/flytekit/unit/core/test_type_engine.py b/tests/flytekit/unit/core/test_type_engine.py
index d738d12ea5..df1ae3e11f 100644
--- a/tests/flytekit/unit/core/test_type_engine.py
+++ b/tests/flytekit/unit/core/test_type_engine.py
@@ -9,6 +9,7 @@
 import pandas as pd
 import pyarrow as pa
 import pytest
+import typing_extensions
 from dataclasses_json import DataClassJsonMixin, dataclass_json
 from flyteidl.core import errors_pb2
 from google.protobuf import json_format as _json_format
@@ -18,6 +19,7 @@
 from pandas._testing import assert_frame_equal
 
 from flytekit import kwtypes
+from flytekit.core.annotation import FlyteAnnotation
 from flytekit.core.context_manager import FlyteContext, FlyteContextManager
 from flytekit.core.type_engine import (
     DataclassTransformer,
@@ -31,6 +33,7 @@
 )
 from flytekit.exceptions import user as user_exceptions
 from flytekit.models import types as model_types
+from flytekit.models.annotation import TypeAnnotation
 from flytekit.models.core.types import BlobType
 from flytekit.models.literals import Blob, BlobMetadata, Literal, LiteralCollection, LiteralMap, Primitive, Scalar
 from flytekit.models.types import LiteralType, SimpleType
@@ -840,6 +843,65 @@ def test_dict_to_literal_map_with_wrong_input_type():
         TypeEngine.dict_to_literal_map(ctx, input, guessed_python_types)
 
 
+def test_annotated_simple_types():
+    def _check_annotation(t, annotation):
+        lt = TypeEngine.to_literal_type(t)
+        assert isinstance(lt.annotation, TypeAnnotation)
+        assert lt.annotation.annotations == annotation
+
+    _check_annotation(typing_extensions.Annotated[int, FlyteAnnotation({"foo": "bar"})], {"foo": "bar"})
+    _check_annotation(typing_extensions.Annotated[int, FlyteAnnotation(["foo", "bar"])], ["foo", "bar"])
+    _check_annotation(
+        typing_extensions.Annotated[int, FlyteAnnotation({"d": {"test": "data"}, "l": ["nested", ["list"]]})],
+        {"d": {"test": "data"}, "l": ["nested", ["list"]]},
+    )
+    _check_annotation(
+        typing_extensions.Annotated[int, FlyteAnnotation(InnerStruct(a=1, b="fizz", c=[1]))],
+        InnerStruct(a=1, b="fizz", c=[1]),
+    )
+
+
+def test_annotated_list():
+    t = typing_extensions.Annotated[typing.List[int], FlyteAnnotation({"foo": "bar"})]
+    lt = TypeEngine.to_literal_type(t)
+    assert isinstance(lt.annotation, TypeAnnotation)
+    assert lt.annotation.annotations == {"foo": "bar"}
+
+    t = typing.List[typing_extensions.Annotated[int, FlyteAnnotation({"foo": "bar"})]]
+    lt = TypeEngine.to_literal_type(t)
+    assert isinstance(lt.collection_type.annotation, TypeAnnotation)
+    assert lt.collection_type.annotation.annotations == {"foo": "bar"}
+
+
+def test_type_alias():
+    inner_t = typing_extensions.Annotated[int, FlyteAnnotation("foo")]
+    t = typing_extensions.Annotated[inner_t, FlyteAnnotation("bar")]
+    with pytest.raises(ValueError):
+        TypeEngine.to_literal_type(t)
+
+
+def test_unsupported_complex_literals():
+    t = typing_extensions.Annotated[typing.Dict[int, str], FlyteAnnotation({"foo": "bar"})]
+    with pytest.raises(ValueError):
+        TypeEngine.to_literal_type(t)
+
+    # Enum.
+    t = typing_extensions.Annotated[Color, FlyteAnnotation({"foo": "bar"})]
+    with pytest.raises(ValueError):
+        TypeEngine.to_literal_type(t)
+
+    # Dataclass.
+    t = typing_extensions.Annotated[Result, FlyteAnnotation({"foo": "bar"})]
+    with pytest.raises(ValueError):
+        TypeEngine.to_literal_type(t)
+
+
+def test_multiple_annotations():
+    t = typing_extensions.Annotated[int, FlyteAnnotation({"foo": "bar"}), FlyteAnnotation({"anotha": "one"})]
+    with pytest.raises(Exception):
+        TypeEngine.to_literal_type(t)
+
+
 TestSchema = FlyteSchema[kwtypes(some_str=str)]
 
 
diff --git a/tests/flytekit/unit/core/test_typing_annotation.py b/tests/flytekit/unit/core/test_typing_annotation.py
new file mode 100644
index 0000000000..f999c62612
--- /dev/null
+++ b/tests/flytekit/unit/core/test_typing_annotation.py
@@ -0,0 +1,62 @@
+import typing
+from collections import OrderedDict
+
+import typing_extensions
+
+from flytekit.core import context_manager
+from flytekit.core.annotation import FlyteAnnotation
+from flytekit.core.context_manager import Image, ImageConfig
+from flytekit.core.task import task
+from flytekit.models.annotation import TypeAnnotation
+from flytekit.tools.translator import get_serializable
+
+default_img = Image(name="default", fqn="test", tag="tag")
+serialization_settings = context_manager.SerializationSettings(
+    project="project",
+    domain="domain",
+    version="version",
+    env=None,
+    image_config=ImageConfig(default_image=default_img, images=[default_img]),
+)
+entity_mapping = OrderedDict()
+
+
+@task
+def x(a: typing_extensions.Annotated[int, FlyteAnnotation({"foo": {"bar": 1}})], b: str):
+    ...
+
+
+@task
+def y0(a: typing.List[typing_extensions.Annotated[int, FlyteAnnotation({"foo": {"bar": 1}})]]):
+    ...
+
+
+@task
+def y1(a: typing_extensions.Annotated[typing.List[int], FlyteAnnotation({"foo": {"bar": 1}})]):
+    ...
+
+
+def test_get_variable_descriptions():
+    x_tsk = get_serializable(entity_mapping, serialization_settings, x)
+    x_input_vars = x_tsk.template.interface.inputs
+
+    a_ann = x_input_vars["a"].type.annotation
+    assert isinstance(a_ann, TypeAnnotation)
+    assert a_ann.annotations["foo"] == {"bar": 1}
+
+    b_ann = x_input_vars["b"].type.annotation
+    assert b_ann is None
+
+    # Annotated simple type within list generic
+    y0_tsk = get_serializable(entity_mapping, serialization_settings, y0)
+    y0_input_vars = y0_tsk.template.interface.inputs
+    y0_a_ann = y0_input_vars["a"].type.collection_type.annotation
+    assert isinstance(y0_a_ann, TypeAnnotation)
+    assert y0_a_ann.annotations["foo"] == {"bar": 1}
+
+    # Annotated list generic
+    y1_tsk = get_serializable(entity_mapping, serialization_settings, y1)
+    y1_input_vars = y1_tsk.template.interface.inputs
+    y1_a_ann = y1_input_vars["a"].type.annotation
+    assert isinstance(y1_a_ann, TypeAnnotation)
+    assert y1_a_ann.annotations["foo"] == {"bar": 1}
diff --git a/tests/flytekit/unit/models/test_types.py b/tests/flytekit/unit/models/test_types.py
index 27b5ddf595..82f0b9b519 100644
--- a/tests/flytekit/unit/models/test_types.py
+++ b/tests/flytekit/unit/models/test_types.py
@@ -2,6 +2,7 @@
 from flyteidl.core import types_pb2
 
 from flytekit.models import types as _types
+from flytekit.models.annotation import TypeAnnotation
 from tests.flytekit.common import parameterizers
 
 
@@ -81,6 +82,16 @@ def test_literal_types():
     assert obj == _types.LiteralType.from_flyte_idl(obj.to_flyte_idl())
 
 
+def test_annotated_literal_types():
+    obj = _types.LiteralType(simple=_types.SimpleType.INTEGER, annotation=TypeAnnotation(annotations={"foo": "bar"}))
+    assert obj.simple == _types.SimpleType.INTEGER
+    assert obj.schema is None
+    assert obj.collection_type is None
+    assert obj.map_value_type is None
+    assert obj.annotation.annotations == {"foo": "bar"}
+    assert obj == _types.LiteralType.from_flyte_idl(obj.to_flyte_idl())
+
+
 @pytest.mark.parametrize("literal_type", parameterizers.LIST_OF_ALL_LITERAL_TYPES)
 def test_literal_collections(literal_type):
     obj = _types.LiteralType(collection_type=literal_type)