From 7360dfccd271864ccf012c3cb29f7e5baea4e2b9 Mon Sep 17 00:00:00 2001
From: Vasilios Syrakis <vsyrakis@atlassian.com>
Date: Fri, 13 Oct 2023 19:35:42 +1100
Subject: [PATCH 1/6] Implementing pickle methods

Continuing work from #484 by @kevinaud to fix #419
---
 src/betterproto/__init__.py |  6 ++++++
 tests/test_features.py      | 38 +++++++++++++++++++++++++++++++++++++
 2 files changed, 44 insertions(+)

diff --git a/src/betterproto/__init__.py b/src/betterproto/__init__.py
index 35acd788f..562d59aa1 100644
--- a/src/betterproto/__init__.py
+++ b/src/betterproto/__init__.py
@@ -1113,6 +1113,12 @@ def SerializeToString(self: T) -> bytes:
         """
         return bytes(self)
 
+    def __getstate__(self) -> bytes:
+        return bytes(self)
+
+    def __setstate__(self: T, pickled_bytes: bytes) -> T:
+        return self.parse(pickled_bytes)
+
     @classmethod
     def _type_hint(cls, field_name: str) -> Type:
         return cls._type_hints()[field_name]
diff --git a/tests/test_features.py b/tests/test_features.py
index 630ca6b6e..4c0de09f3 100644
--- a/tests/test_features.py
+++ b/tests/test_features.py
@@ -1,4 +1,5 @@
 import json
+import pickle
 import sys
 from copy import (
     copy,
@@ -740,3 +741,40 @@ def test_equality_comparison():
     assert msg == TestMessage(value=True)
     assert msg != 1
     assert msg != TestMessage(value=False)
+
+
+
+@dataclass
+class PickleMessage(betterproto.Message):
+    foo: bool = betterproto.bool_field(1)
+    bar: Optional[int] = betterproto.int32_field(2, optional=True)
+
+
+def test_default_pickle():
+    deserialized = pickle.loads(pickle.dumps(PickleMessage()))
+
+    assert deserialized.foo is False
+    assert deserialized.bar is None
+
+
+def test_pickle_with_set_values():
+    msg = PickleMessage(foo=True, bar=42)
+    deserialized = pickle.loads(pickle.dumps(msg))
+
+    assert deserialized.foo is True
+    assert deserialized.bar == 42
+
+
+def test_pickling_recursive_message():
+    from tests.output_betterproto.recursivemessage import Test as RecursiveMessage
+
+    msg = RecursiveMessage()
+    deserialized = pickle.loads(pickle.dumps(msg))
+
+    assert deserialized.child == RecursiveMessage()
+
+    # Lazily-created zero-value children must not affect equality.
+    assert deserialized == RecursiveMessage()
+
+    # Lazily-created zero-value children must not affect serialization.
+    assert bytes(deserialized) == b""

From b8bf8708fd4a164c83fc075f1ccb124642ed9cef Mon Sep 17 00:00:00 2001
From: Vasilios Syrakis <vsyrakis@atlassian.com>
Date: Fri, 13 Oct 2023 19:42:54 +1100
Subject: [PATCH 2/6] Implement __copy__, __reduce__, and fix __setstate__

---
 src/betterproto/__init__.py | 17 +++++++++++++++--
 1 file changed, 15 insertions(+), 2 deletions(-)

diff --git a/src/betterproto/__init__.py b/src/betterproto/__init__.py
index 562d59aa1..af1dfd6ee 100644
--- a/src/betterproto/__init__.py
+++ b/src/betterproto/__init__.py
@@ -11,7 +11,7 @@
     b64decode,
     b64encode,
 )
-from copy import deepcopy
+from copy import deepcopy, copy
 from datetime import (
     datetime,
     timedelta,
@@ -874,6 +874,14 @@ def __deepcopy__(self: T, _: Any = {}) -> T:
                 kwargs[name] = deepcopy(value)
         return self.__class__(**kwargs)  # type: ignore
 
+    def __copy__(self: T, _: Any = {}) -> T:
+        kwargs = {}
+        for name in self._betterproto.sorted_field_names:
+            value = self.__raw_get(name)
+            if value is not PLACEHOLDER:
+                kwargs[name] = copy(value)
+        return self.__class__(**kwargs)  # type: ignore
+
     @property
     def _betterproto(self) -> ProtoClassMetadata:
         """
@@ -1117,7 +1125,12 @@ def __getstate__(self) -> bytes:
         return bytes(self)
 
     def __setstate__(self: T, pickled_bytes: bytes) -> T:
-        return self.parse(pickled_bytes)
+        new = self.parse(pickled_bytes)
+        new.__post_init__()
+        return new
+
+    def __reduce__(self) -> str | tuple[Any, ...]:
+        return (self.__class__, (self.to_dict(),))
 
     @classmethod
     def _type_hint(cls, field_name: str) -> Type:

From 5914cdc31dc0c667aaf72d4b9b5796dddcf2981a Mon Sep 17 00:00:00 2001
From: Vasilios Syrakis <vsyrakis@atlassian.com>
Date: Fri, 13 Oct 2023 19:47:09 +1100
Subject: [PATCH 3/6] Fix __reduce__ signature

---
 src/betterproto/__init__.py | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/src/betterproto/__init__.py b/src/betterproto/__init__.py
index af1dfd6ee..e485c6aad 100644
--- a/src/betterproto/__init__.py
+++ b/src/betterproto/__init__.py
@@ -1129,7 +1129,7 @@ def __setstate__(self: T, pickled_bytes: bytes) -> T:
         new.__post_init__()
         return new
 
-    def __reduce__(self) -> str | tuple[Any, ...]:
+    def __reduce__(self) -> Union[str, Tuple[Any, ...]]:
         return (self.__class__, (self.to_dict(),))
 
     @classmethod

From 7a283eea90613f941661d0b179af7a81a04bf106 Mon Sep 17 00:00:00 2001
From: Vasilios Syrakis <vsyrakis@atlassian.com>
Date: Fri, 13 Oct 2023 20:28:17 +1100
Subject: [PATCH 4/6] Attempting to fix tests

---
 src/betterproto/__init__.py | 10 ++++------
 tests/test_features.py      |  1 -
 2 files changed, 4 insertions(+), 7 deletions(-)

diff --git a/src/betterproto/__init__.py b/src/betterproto/__init__.py
index e485c6aad..50d3f103f 100644
--- a/src/betterproto/__init__.py
+++ b/src/betterproto/__init__.py
@@ -11,7 +11,7 @@
     b64decode,
     b64encode,
 )
-from copy import deepcopy, copy
+from copy import deepcopy
 from datetime import (
     datetime,
     timedelta,
@@ -879,7 +879,7 @@ def __copy__(self: T, _: Any = {}) -> T:
         for name in self._betterproto.sorted_field_names:
             value = self.__raw_get(name)
             if value is not PLACEHOLDER:
-                kwargs[name] = copy(value)
+                kwargs[name] = value
         return self.__class__(**kwargs)  # type: ignore
 
     @property
@@ -1125,12 +1125,10 @@ def __getstate__(self) -> bytes:
         return bytes(self)
 
     def __setstate__(self: T, pickled_bytes: bytes) -> T:
-        new = self.parse(pickled_bytes)
-        new.__post_init__()
-        return new
+        return self.parse(pickled_bytes)
 
     def __reduce__(self) -> Union[str, Tuple[Any, ...]]:
-        return (self.__class__, (self.to_dict(),))
+        return (self.__class__.FromString, (bytes(self),))
 
     @classmethod
     def _type_hint(cls, field_name: str) -> Type:
diff --git a/tests/test_features.py b/tests/test_features.py
index 4c0de09f3..d2151ee61 100644
--- a/tests/test_features.py
+++ b/tests/test_features.py
@@ -743,7 +743,6 @@ def test_equality_comparison():
     assert msg != TestMessage(value=False)
 
 
-
 @dataclass
 class PickleMessage(betterproto.Message):
     foo: bool = betterproto.bool_field(1)

From ce20edfc24d27caf53aaa9e8dd712ad6988263a5 Mon Sep 17 00:00:00 2001
From: Vasilios Syrakis <vsyrakis@atlassian.com>
Date: Fri, 13 Oct 2023 23:53:37 +1100
Subject: [PATCH 5/6] Moved pickling tests into their own file

---
 src/betterproto/__init__.py |   2 +-
 tests/test_features.py      |  37 --------
 tests/test_pickling.py      | 172 ++++++++++++++++++++++++++++++++++++
 3 files changed, 173 insertions(+), 38 deletions(-)
 create mode 100644 tests/test_pickling.py

diff --git a/src/betterproto/__init__.py b/src/betterproto/__init__.py
index 50d3f103f..665ebbc42 100644
--- a/src/betterproto/__init__.py
+++ b/src/betterproto/__init__.py
@@ -1127,7 +1127,7 @@ def __getstate__(self) -> bytes:
     def __setstate__(self: T, pickled_bytes: bytes) -> T:
         return self.parse(pickled_bytes)
 
-    def __reduce__(self) -> Union[str, Tuple[Any, ...]]:
+    def __reduce__(self) -> Tuple[Any, ...]:
         return (self.__class__.FromString, (bytes(self),))
 
     @classmethod
diff --git a/tests/test_features.py b/tests/test_features.py
index d2151ee61..630ca6b6e 100644
--- a/tests/test_features.py
+++ b/tests/test_features.py
@@ -1,5 +1,4 @@
 import json
-import pickle
 import sys
 from copy import (
     copy,
@@ -741,39 +740,3 @@ def test_equality_comparison():
     assert msg == TestMessage(value=True)
     assert msg != 1
     assert msg != TestMessage(value=False)
-
-
-@dataclass
-class PickleMessage(betterproto.Message):
-    foo: bool = betterproto.bool_field(1)
-    bar: Optional[int] = betterproto.int32_field(2, optional=True)
-
-
-def test_default_pickle():
-    deserialized = pickle.loads(pickle.dumps(PickleMessage()))
-
-    assert deserialized.foo is False
-    assert deserialized.bar is None
-
-
-def test_pickle_with_set_values():
-    msg = PickleMessage(foo=True, bar=42)
-    deserialized = pickle.loads(pickle.dumps(msg))
-
-    assert deserialized.foo is True
-    assert deserialized.bar == 42
-
-
-def test_pickling_recursive_message():
-    from tests.output_betterproto.recursivemessage import Test as RecursiveMessage
-
-    msg = RecursiveMessage()
-    deserialized = pickle.loads(pickle.dumps(msg))
-
-    assert deserialized.child == RecursiveMessage()
-
-    # Lazily-created zero-value children must not affect equality.
-    assert deserialized == RecursiveMessage()
-
-    # Lazily-created zero-value children must not affect serialization.
-    assert bytes(deserialized) == b""
diff --git a/tests/test_pickling.py b/tests/test_pickling.py
new file mode 100644
index 000000000..beba093f8
--- /dev/null
+++ b/tests/test_pickling.py
@@ -0,0 +1,172 @@
+import pickle
+from copy import (
+    copy,
+    deepcopy,
+)
+from dataclasses import dataclass
+from typing import (
+    Dict,
+    List,
+)
+from unittest.mock import ANY
+
+import betterproto
+from betterproto.lib.google import protobuf as google
+
+
+def unpickled(message):
+    return pickle.loads(pickle.dumps(message))
+
+
+@dataclass(eq=False, repr=False)
+class Fe(betterproto.Message):
+    abc: str = betterproto.string_field(1)
+
+
+@dataclass(eq=False, repr=False)
+class Fi(betterproto.Message):
+    abc: str = betterproto.string_field(1)
+
+
+@dataclass(eq=False, repr=False)
+class Fo(betterproto.Message):
+    abc: str = betterproto.string_field(1)
+
+
+@dataclass(eq=False, repr=False)
+class NestedData(betterproto.Message):
+    struct_foo: Dict[str, "google.Struct"] = betterproto.map_field(
+        1, betterproto.TYPE_STRING, betterproto.TYPE_MESSAGE
+    )
+    map_str_any_bar: Dict[str, "google.Any"] = betterproto.map_field(
+        2, betterproto.TYPE_STRING, betterproto.TYPE_MESSAGE
+    )
+
+
+@dataclass(eq=False, repr=False)
+class Complex(betterproto.Message):
+    foo_str: str = betterproto.string_field(1)
+    fe: "Fe" = betterproto.message_field(3, group="grp")
+    fi: "Fi" = betterproto.message_field(4, group="grp")
+    fo: "Fo" = betterproto.message_field(5, group="grp")
+    nested_data: "NestedData" = betterproto.message_field(6)
+    mapping: Dict[str, "google.Any"] = betterproto.map_field(
+        7, betterproto.TYPE_STRING, betterproto.TYPE_MESSAGE
+    )
+
+
+def test_pickling_complex_message():
+    msg = Complex(
+        foo_str="yep",
+        fe=Fe(abc="1"),
+        nested_data=NestedData(
+            struct_foo={
+                "foo": google.Struct(
+                    fields={
+                        "hello": google.Value(
+                            list_value=google.ListValue(
+                                values=[google.Value(string_value="world")]
+                            )
+                        )
+                    }
+                ),
+            },
+            map_str_any_bar={
+                "key": google.Any(value=b"value"),
+            },
+        ),
+        mapping={
+            "message": google.Any(value=bytes(Fi(abc="hi"))),
+            "string": google.Any(value=b"howdy"),
+        },
+    )
+    deser = unpickled(msg)
+    assert msg == deser
+    assert msg.fe.abc == "1"
+    assert msg.is_set("fi") is not True
+    assert msg.mapping["message"] == google.Any(value=bytes(Fi(abc="hi")))
+    assert msg.mapping["string"].value.decode() == "howdy"
+    assert (
+        msg.nested_data.struct_foo["foo"]
+        .fields["hello"]
+        .list_value.values[0]
+        .string_value
+        == "world"
+    )
+
+
+def test_recursive_message():
+    from tests.output_betterproto.recursivemessage import Test as RecursiveMessage
+
+    msg = RecursiveMessage()
+    msg = unpickled(msg)
+
+    assert msg.child == RecursiveMessage()
+
+    # Lazily-created zero-value children must not affect equality.
+    assert msg == RecursiveMessage()
+
+    # Lazily-created zero-value children must not affect serialization.
+    assert bytes(msg) == b""
+
+
+def test_recursive_message_defaults():
+    from tests.output_betterproto.recursivemessage import (
+        Intermediate,
+        Test as RecursiveMessage,
+    )
+
+    msg = RecursiveMessage(name="bob", intermediate=Intermediate(42))
+    msg = unpickled(msg)
+
+    # set values are as expected
+    assert msg == RecursiveMessage(name="bob", intermediate=Intermediate(42))
+
+    # lazy initialized works modifies the message
+    assert msg != RecursiveMessage(
+        name="bob", intermediate=Intermediate(42), child=RecursiveMessage(name="jude")
+    )
+    msg.child.child.name = "jude"
+    assert msg == RecursiveMessage(
+        name="bob",
+        intermediate=Intermediate(42),
+        child=RecursiveMessage(child=RecursiveMessage(name="jude")),
+    )
+
+    # lazily initialization recurses as needed
+    assert msg.child.child.child.child.child.child.child == RecursiveMessage()
+    assert msg.intermediate.child.intermediate == Intermediate()
+
+
+@dataclass
+class Spam(betterproto.Message):
+    foo: bool = betterproto.bool_field(1)
+    bar: int = betterproto.int32_field(2)
+    baz: List[str] = betterproto.string_field(3)
+
+
+def test_copyability():
+    msg = Spam(bar=12, baz=["hello"])
+    msg = unpickled(msg)
+
+    copied = copy(msg)
+    assert msg == copied
+    assert msg is not copied
+    assert msg.baz is copied.baz
+
+    deepcopied = deepcopy(msg)
+    assert msg == deepcopied
+    assert msg is not deepcopied
+    assert msg.baz is not deepcopied.baz
+
+
+def test_equality_comparison():
+    from tests.output_betterproto.bool import Test as TestMessage
+
+    msg = TestMessage(value=True)
+    msg = unpickled(msg)
+    assert msg == msg
+    assert msg == ANY
+    assert msg == TestMessage(value=True)
+    assert msg != 1
+    assert msg != TestMessage(value=False)

From fa25d17acb9c0f9defdfa666ce49eb29b7423934 Mon Sep 17 00:00:00 2001
From: Vasilios Syrakis <vsyrakis@atlassian.com>
Date: Mon, 16 Oct 2023 19:30:40 +1100
Subject: [PATCH 6/6] Add test for caching

---
 poetry.lock            | 699 ++++++++++++++++++++++-------------------
 pyproject.toml         |   4 +-
 tests/test_features.py |  60 ----
 tests/test_pickling.py |  59 +++-
 4 files changed, 431 insertions(+), 391 deletions(-)

diff --git a/poetry.lock b/poetry.lock
index 5096de9dc..0d1eeee97 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -1,4 +1,4 @@
-# This file is automatically @generated by Poetry 1.5.1 and should not be changed by hand.
+# This file is automatically @generated by Poetry 1.6.1 and should not be changed by hand.
 
 [[package]]
 name = "alabaster"
@@ -71,18 +71,21 @@ tests-no-zope = ["cloudpickle", "hypothesis", "mypy (>=1.1.1)", "pympler", "pyte
 
 [[package]]
 name = "babel"
-version = "2.12.1"
+version = "2.13.0"
 description = "Internationalization utilities"
 optional = false
 python-versions = ">=3.7"
 files = [
-    {file = "Babel-2.12.1-py3-none-any.whl", hash = "sha256:b4246fb7677d3b98f501a39d43396d3cafdc8eadb045f4a31be01863f655c610"},
-    {file = "Babel-2.12.1.tar.gz", hash = "sha256:cc2d99999cd01d44420ae725a21c9e3711b3aadc7976d6147f622d8581963455"},
+    {file = "Babel-2.13.0-py3-none-any.whl", hash = "sha256:fbfcae1575ff78e26c7449136f1abbefc3c13ce542eeb13d43d50d8b047216ec"},
+    {file = "Babel-2.13.0.tar.gz", hash = "sha256:04c3e2d28d2b7681644508f836be388ae49e0cfe91465095340395b60d00f210"},
 ]
 
 [package.dependencies]
 pytz = {version = ">=2015.7", markers = "python_version < \"3.9\""}
 
+[package.extras]
+dev = ["freezegun (>=1.0,<2.0)", "pytest (>=6.0)", "pytest-cov"]
+
 [[package]]
 name = "backports-cached-property"
 version = "1.0.2"
@@ -183,6 +186,17 @@ jedi = ["jedi"]
 urwid = ["urwid"]
 watch = ["watchdog"]
 
+[[package]]
+name = "cachelib"
+version = "0.10.2"
+description = "A collection of cache libraries in the same API interface."
+optional = false
+python-versions = ">=3.7"
+files = [
+    {file = "cachelib-0.10.2-py3-none-any.whl", hash = "sha256:42d49f2fad9310dd946d7be73d46776bcd4d5fde4f49ad210cfdd447fbdfc346"},
+    {file = "cachelib-0.10.2.tar.gz", hash = "sha256:593faeee62a7c037d50fc835617a01b887503f972fb52b188ae7e50e9cb69740"},
+]
+
 [[package]]
 name = "certifi"
 version = "2023.7.22"
@@ -207,97 +221,112 @@ files = [
 
 [[package]]
 name = "charset-normalizer"
-version = "3.2.0"
+version = "3.3.0"
 description = "The Real First Universal Charset Detector. Open, modern and actively maintained alternative to Chardet."
 optional = false
 python-versions = ">=3.7.0"
 files = [
-    {file = "charset-normalizer-3.2.0.tar.gz", hash = "sha256:3bb3d25a8e6c0aedd251753a79ae98a093c7e7b471faa3aa9a93a81431987ace"},
-    {file = "charset_normalizer-3.2.0-cp310-cp310-macosx_10_9_universal2.whl", hash = "sha256:0b87549028f680ca955556e3bd57013ab47474c3124dc069faa0b6545b6c9710"},
-    {file = "charset_normalizer-3.2.0-cp310-cp310-macosx_10_9_x86_64.whl", hash = "sha256:7c70087bfee18a42b4040bb9ec1ca15a08242cf5867c58726530bdf3945672ed"},
-    {file = "charset_normalizer-3.2.0-cp310-cp310-macosx_11_0_arm64.whl", hash = "sha256:a103b3a7069b62f5d4890ae1b8f0597618f628b286b03d4bc9195230b154bfa9"},
-    {file = "charset_normalizer-3.2.0-cp310-cp310-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:94aea8eff76ee6d1cdacb07dd2123a68283cb5569e0250feab1240058f53b623"},
-    {file = "charset_normalizer-3.2.0-cp310-cp310-manylinux_2_17_ppc64le.manylinux2014_ppc64le.whl", hash = "sha256:db901e2ac34c931d73054d9797383d0f8009991e723dab15109740a63e7f902a"},
-    {file = "charset_normalizer-3.2.0-cp310-cp310-manylinux_2_17_s390x.manylinux2014_s390x.whl", hash = "sha256:b0dac0ff919ba34d4df1b6131f59ce95b08b9065233446be7e459f95554c0dc8"},
-    {file = "charset_normalizer-3.2.0-cp310-cp310-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:193cbc708ea3aca45e7221ae58f0fd63f933753a9bfb498a3b474878f12caaad"},
-    {file = "charset_normalizer-3.2.0-cp310-cp310-manylinux_2_5_i686.manylinux1_i686.manylinux_2_17_i686.manylinux2014_i686.whl", hash = "sha256:09393e1b2a9461950b1c9a45d5fd251dc7c6f228acab64da1c9c0165d9c7765c"},
-    {file = "charset_normalizer-3.2.0-cp310-cp310-musllinux_1_1_aarch64.whl", hash = "sha256:baacc6aee0b2ef6f3d308e197b5d7a81c0e70b06beae1f1fcacffdbd124fe0e3"},
-    {file = "charset_normalizer-3.2.0-cp310-cp310-musllinux_1_1_i686.whl", hash = "sha256:bf420121d4c8dce6b889f0e8e4ec0ca34b7f40186203f06a946fa0276ba54029"},
-    {file = "charset_normalizer-3.2.0-cp310-cp310-musllinux_1_1_ppc64le.whl", hash = "sha256:c04a46716adde8d927adb9457bbe39cf473e1e2c2f5d0a16ceb837e5d841ad4f"},
-    {file = "charset_normalizer-3.2.0-cp310-cp310-musllinux_1_1_s390x.whl", hash = "sha256:aaf63899c94de41fe3cf934601b0f7ccb6b428c6e4eeb80da72c58eab077b19a"},
-    {file = "charset_normalizer-3.2.0-cp310-cp310-musllinux_1_1_x86_64.whl", hash = "sha256:d62e51710986674142526ab9f78663ca2b0726066ae26b78b22e0f5e571238dd"},
-    {file = "charset_normalizer-3.2.0-cp310-cp310-win32.whl", hash = "sha256:04e57ab9fbf9607b77f7d057974694b4f6b142da9ed4a199859d9d4d5c63fe96"},
-    {file = "charset_normalizer-3.2.0-cp310-cp310-win_amd64.whl", hash = "sha256:48021783bdf96e3d6de03a6e39a1171ed5bd7e8bb93fc84cc649d11490f87cea"},
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 [package.dependencies]
@@ -487,201 +516,221 @@ testing = ["covdefaults (>=2.3)", "coverage (>=7.2.7)", "diff-cover (>=7.5)", "p
 
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 [package.extras]
-docs = ["Sphinx", "docutils (<0.18)"]
+docs = ["Sphinx"]
 test = ["objgraph", "psutil"]
 
 [[package]]
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 protobuf = ">=4.21.6,<5.0dev"
 setuptools = "*"
 
 [[package]]
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 multidict = "*"
 
 [package.extras]
-protobuf = ["protobuf (>=3.15.0)"]
+protobuf = ["protobuf (>=3.20.0)"]
 
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-version = "2.0.4"
+version = "2.0.6"
 description = "HTTP library with thread-safe connection pooling, file post, and more."
 optional = false
 python-versions = ">=3.7"
 files = [
-    {file = "urllib3-2.0.4-py3-none-any.whl", hash = "sha256:de7df1803967d2c2a98e4b11bb7d6bd9210474c46e8a0401514e3a42a75ebde4"},
-    {file = "urllib3-2.0.4.tar.gz", hash = "sha256:8d22f86aae8ef5e410d4f539fde9ce6b2113a001bb4d189e0aed70642d602b11"},
+    {file = "urllib3-2.0.6-py3-none-any.whl", hash = "sha256:7a7c7003b000adf9e7ca2a377c9688bbc54ed41b985789ed576570342a375cd2"},
+    {file = "urllib3-2.0.6.tar.gz", hash = "sha256:b19e1a85d206b56d7df1d5e683df4a7725252a964e3993648dd0fb5a1c157564"},
 ]
 
 [package.extras]
@@ -1744,13 +1813,13 @@ zstd = ["zstandard (>=0.18.0)"]
 
 [[package]]
 name = "virtualenv"
-version = "20.24.3"
+version = "20.24.5"
 description = "Virtual Python Environment builder"
 optional = false
 python-versions = ">=3.7"
 files = [
-    {file = "virtualenv-20.24.3-py3-none-any.whl", hash = "sha256:95a6e9398b4967fbcb5fef2acec5efaf9aa4972049d9ae41f95e0972a683fd02"},
-    {file = "virtualenv-20.24.3.tar.gz", hash = "sha256:e5c3b4ce817b0b328af041506a2a299418c98747c4b1e68cb7527e74ced23efc"},
+    {file = "virtualenv-20.24.5-py3-none-any.whl", hash = "sha256:b80039f280f4919c77b30f1c23294ae357c4c8701042086e3fc005963e4e537b"},
+    {file = "virtualenv-20.24.5.tar.gz", hash = "sha256:e8361967f6da6fbdf1426483bfe9fca8287c242ac0bc30429905721cefbff752"},
 ]
 
 [package.dependencies]
@@ -1760,18 +1829,18 @@ importlib-metadata = {version = ">=6.6", markers = "python_version < \"3.8\""}
 platformdirs = ">=3.9.1,<4"
 
 [package.extras]
-docs = ["furo (>=2023.5.20)", "proselint (>=0.13)", "sphinx (>=7.0.1)", "sphinx-argparse (>=0.4)", "sphinxcontrib-towncrier (>=0.2.1a0)", "towncrier (>=23.6)"]
+docs = ["furo (>=2023.7.26)", "proselint (>=0.13)", "sphinx (>=7.1.2)", "sphinx-argparse (>=0.4)", "sphinxcontrib-towncrier (>=0.2.1a0)", "towncrier (>=23.6)"]
 test = ["covdefaults (>=2.3)", "coverage (>=7.2.7)", "coverage-enable-subprocess (>=1)", "flaky (>=3.7)", "packaging (>=23.1)", "pytest (>=7.4)", "pytest-env (>=0.8.2)", "pytest-freezer (>=0.4.8)", "pytest-mock (>=3.11.1)", "pytest-randomly (>=3.12)", "pytest-timeout (>=2.1)", "setuptools (>=68)", "time-machine (>=2.10)"]
 
 [[package]]
 name = "wcwidth"
-version = "0.2.6"
+version = "0.2.8"
 description = "Measures the displayed width of unicode strings in a terminal"
 optional = false
 python-versions = "*"
 files = [
-    {file = "wcwidth-0.2.6-py2.py3-none-any.whl", hash = "sha256:795b138f6875577cd91bba52baf9e445cd5118fd32723b460e30a0af30ea230e"},
-    {file = "wcwidth-0.2.6.tar.gz", hash = "sha256:a5220780a404dbe3353789870978e472cfe477761f06ee55077256e509b156d0"},
+    {file = "wcwidth-0.2.8-py2.py3-none-any.whl", hash = "sha256:77f719e01648ed600dfa5402c347481c0992263b81a027344f3e1ba25493a704"},
+    {file = "wcwidth-0.2.8.tar.gz", hash = "sha256:8705c569999ffbb4f6a87c6d1b80f324bd6db952f5eb0b95bc07517f4c1813d4"},
 ]
 
 [[package]]
@@ -1795,4 +1864,4 @@ compiler = ["black", "isort", "jinja2"]
 [metadata]
 lock-version = "2.0"
 python-versions = "^3.7"
-content-hash = "a60f4140db2d1edf5b7c08f54894405d4a0f0f3a6fefcdaaef00049cdec63121"
+content-hash = "1b58712beae70053ef9187c5635909a548abb7c05776b09f37416ab122167ade"
diff --git a/pyproject.toml b/pyproject.toml
index 383b6233c..5b8c5a395 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -21,7 +21,7 @@ python-dateutil = "^2.8"
 isort = {version = "^5.11.5", optional = true}
 typing-extensions = "^4.7.1"
 
-[tool.poetry.dev-dependencies]
+[tool.poetry.group.dev.dependencies]
 asv = "^0.4.2"
 bpython = "^0.19"
 grpcio-tools = "^1.54.2"
@@ -39,7 +39,7 @@ tomlkit = "^0.7.0"
 tox = "^3.15.1"
 pre-commit = "^2.17.0"
 pydantic = ">=1.8.0,<2"
-
+cachelib = "^0.10.2"
 
 [tool.poetry.scripts]
 protoc-gen-python_betterproto = "betterproto.plugin:main"
diff --git a/tests/test_features.py b/tests/test_features.py
index 630ca6b6e..193e6b250 100644
--- a/tests/test_features.py
+++ b/tests/test_features.py
@@ -545,47 +545,6 @@ def _round_trip_serialization(foo: Foo) -> Foo:
     )
 
 
-def test_recursive_message():
-    from tests.output_betterproto.recursivemessage import Test as RecursiveMessage
-
-    msg = RecursiveMessage()
-
-    assert msg.child == RecursiveMessage()
-
-    # Lazily-created zero-value children must not affect equality.
-    assert msg == RecursiveMessage()
-
-    # Lazily-created zero-value children must not affect serialization.
-    assert bytes(msg) == b""
-
-
-def test_recursive_message_defaults():
-    from tests.output_betterproto.recursivemessage import (
-        Intermediate,
-        Test as RecursiveMessage,
-    )
-
-    msg = RecursiveMessage(name="bob", intermediate=Intermediate(42))
-
-    # set values are as expected
-    assert msg == RecursiveMessage(name="bob", intermediate=Intermediate(42))
-
-    # lazy initialized works modifies the message
-    assert msg != RecursiveMessage(
-        name="bob", intermediate=Intermediate(42), child=RecursiveMessage(name="jude")
-    )
-    msg.child.child.name = "jude"
-    assert msg == RecursiveMessage(
-        name="bob",
-        intermediate=Intermediate(42),
-        child=RecursiveMessage(child=RecursiveMessage(name="jude")),
-    )
-
-    # lazily initialization recurses as needed
-    assert msg.child.child.child.child.child.child.child == RecursiveMessage()
-    assert msg.intermediate.child.intermediate == Intermediate()
-
-
 def test_message_repr():
     from tests.output_betterproto.recursivemessage import Test
 
@@ -699,25 +658,6 @@ def test_service_argument__expected_parameter():
     assert do_thing_request_parameter.annotation == "DoThingRequest"
 
 
-def test_copyability():
-    @dataclass
-    class Spam(betterproto.Message):
-        foo: bool = betterproto.bool_field(1)
-        bar: int = betterproto.int32_field(2)
-        baz: List[str] = betterproto.string_field(3)
-
-    spam = Spam(bar=12, baz=["hello"])
-    copied = copy(spam)
-    assert spam == copied
-    assert spam is not copied
-    assert spam.baz is copied.baz
-
-    deepcopied = deepcopy(spam)
-    assert spam == deepcopied
-    assert spam is not deepcopied
-    assert spam.baz is not deepcopied.baz
-
-
 def test_is_set():
     @dataclass
     class Spam(betterproto.Message):
diff --git a/tests/test_pickling.py b/tests/test_pickling.py
index beba093f8..5650f7501 100644
--- a/tests/test_pickling.py
+++ b/tests/test_pickling.py
@@ -10,6 +10,8 @@
 )
 from unittest.mock import ANY
 
+import cachelib
+
 import betterproto
 from betterproto.lib.google import protobuf as google
 
@@ -55,8 +57,8 @@ class Complex(betterproto.Message):
     )
 
 
-def test_pickling_complex_message():
-    msg = Complex(
+def complex_msg():
+    return Complex(
         foo_str="yep",
         fe=Fe(abc="1"),
         nested_data=NestedData(
@@ -80,6 +82,10 @@ def test_pickling_complex_message():
             "string": google.Any(value=b"howdy"),
         },
     )
+
+
+def test_pickling_complex_message():
+    msg = complex_msg()
     deser = unpickled(msg)
     assert msg == deser
     assert msg.fe.abc == "1"
@@ -139,14 +145,14 @@ def test_recursive_message_defaults():
 
 
 @dataclass
-class Spam(betterproto.Message):
+class PickledMessage(betterproto.Message):
     foo: bool = betterproto.bool_field(1)
     bar: int = betterproto.int32_field(2)
     baz: List[str] = betterproto.string_field(3)
 
 
 def test_copyability():
-    msg = Spam(bar=12, baz=["hello"])
+    msg = PickledMessage(bar=12, baz=["hello"])
     msg = unpickled(msg)
 
     copied = copy(msg)
@@ -160,13 +166,38 @@ def test_copyability():
     assert msg.baz is not deepcopied.baz
 
 
-def test_equality_comparison():
-    from tests.output_betterproto.bool import Test as TestMessage
-
-    msg = TestMessage(value=True)
-    msg = unpickled(msg)
-    assert msg == msg
-    assert msg == ANY
-    assert msg == TestMessage(value=True)
-    assert msg != 1
-    assert msg != TestMessage(value=False)
+def test_message_can_be_cached():
+    """Cachelib uses pickling to cache values"""
+
+    cache = cachelib.SimpleCache()
+
+    def use_cache():
+        calls = getattr(use_cache, "calls", 0)
+        result = cache.get("message")
+        if result is not None:
+            return result
+        else:
+            setattr(use_cache, "calls", calls + 1)
+            result = complex_msg()
+            cache.set("message", result)
+            return result
+
+    for n in range(10):
+        if n == 0:
+            assert not cache.has("message")
+        else:
+            assert cache.has("message")
+
+        msg = use_cache()
+        assert use_cache.calls == 1  # The message is only ever built once
+        assert msg.fe.abc == "1"
+        assert msg.is_set("fi") is not True
+        assert msg.mapping["message"] == google.Any(value=bytes(Fi(abc="hi")))
+        assert msg.mapping["string"].value.decode() == "howdy"
+        assert (
+            msg.nested_data.struct_foo["foo"]
+            .fields["hello"]
+            .list_value.values[0]
+            .string_value
+            == "world"
+        )