diff --git a/.github/workflows/check-license.yml b/.github/workflows/check-license.yml
index 133817b2a..e5e885c89 100644
--- a/.github/workflows/check-license.yml
+++ b/.github/workflows/check-license.yml
@@ -2,19 +2,20 @@ name: License Header Check
 
 on:
   pull_request:
-    branches:
-      - develop
   push:
     branches:
       - develop
 
+permissions:
+  contents: read
+
 jobs:
   check-license-header: 
     name: Check License Header
     runs-on: ubuntu-latest
     steps:
-      - uses: actions/checkout@v5
+      - uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8
 
-      - uses: apache/skywalking-eyes/header@main
+      - uses: apache/skywalking-eyes/header@55373684d1b70e5f8fd9fc8ec114a89ad11a56a3
         with:
           mode: check 
diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 1d594bf6e..5b523cb62 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -1,14 +1,14 @@
 name: CI
 
 on:
+    pull_request:
     push:
         branches:
           - develop
           - main
 
-    pull_request:
-        branches:
-          - develop
+permissions:
+  contents: read
 
 jobs:
   ci:
@@ -20,19 +20,19 @@ jobs:
 
     steps:
       - name: Checkout Repository
-        uses: actions/checkout@v5
+        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8
 
       - name: Set up JDK 17
-        uses: actions/setup-java@v5
+        uses: actions/setup-java@f2beeb24e141e01a676f977032f5a29d81c9e27e
         with:
           java-version: 17
           distribution: 'corretto'
 
       - name: Setup Gradle
-        uses: gradle/actions/setup-gradle@v5
+        uses: gradle/actions/setup-gradle@4d9f0ba0025fe599b4ebab900eb7f3a1d93ef4c2
 
       - name: Install uv and set the Python version
-        uses: astral-sh/setup-uv@v7
+        uses: astral-sh/setup-uv@681c641aba71e4a1c380be3ab5e12ad51f415867
         with:
           python-version: ${{ matrix.python-version }}
           activate-environment: true
diff --git a/.github/workflows/update-gradle-wrapper.yml b/.github/workflows/update-gradle-wrapper.yml
index 7c1c34ab1..d3c6ffedf 100644
--- a/.github/workflows/update-gradle-wrapper.yml
+++ b/.github/workflows/update-gradle-wrapper.yml
@@ -7,14 +7,21 @@ on:
     # Run at midnight (UTC) every wednesday
     - cron: "0 0 * * 3"
 
+permissions:
+  contents: read
+
 jobs:
   update-gradle-wrapper:
     runs-on: ubuntu-latest
 
+    permissions:
+        # allow job to open a pull request with changes
+        pull-requests: write
+
     steps:
-      - uses: actions/checkout@v5
+      - uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8
 
       - name: Update Gradle Wrapper
-        uses: gradle-update/update-gradle-wrapper-action@v2
+        uses: gradle-update/update-gradle-wrapper-action@512b1875f3b6270828abfe77b247d5895a2da1e5
         with:
           paths: codegen/**
diff --git a/codegen/aws/core/src/main/java/software/amazon/smithy/python/aws/codegen/AwsPythonDependency.java b/codegen/aws/core/src/main/java/software/amazon/smithy/python/aws/codegen/AwsPythonDependency.java
index 90aa2e0fe..1e7b67ac1 100644
--- a/codegen/aws/core/src/main/java/software/amazon/smithy/python/aws/codegen/AwsPythonDependency.java
+++ b/codegen/aws/core/src/main/java/software/amazon/smithy/python/aws/codegen/AwsPythonDependency.java
@@ -22,7 +22,7 @@ private AwsPythonDependency() {}
      */
     public static final PythonDependency SMITHY_AWS_CORE = new PythonDependency(
             "smithy_aws_core",
-            "~=0.2.0",
+            "~=0.3.0",
             PythonDependency.Type.DEPENDENCY,
             false);
 }
diff --git a/codegen/build.gradle.kts b/codegen/build.gradle.kts
index c8f736a5d..cec136127 100644
--- a/codegen/build.gradle.kts
+++ b/codegen/build.gradle.kts
@@ -15,5 +15,5 @@
 
 allprojects {
     group = "software.amazon.smithy.python"
-    version = "0.1.0"
+    version = "0.2.0"
 }
diff --git a/codegen/core/src/main/java/software/amazon/smithy/python/codegen/ClientGenerator.java b/codegen/core/src/main/java/software/amazon/smithy/python/codegen/ClientGenerator.java
index 95c6e0d5a..a189712bf 100644
--- a/codegen/core/src/main/java/software/amazon/smithy/python/codegen/ClientGenerator.java
+++ b/codegen/core/src/main/java/software/amazon/smithy/python/codegen/ClientGenerator.java
@@ -207,22 +207,9 @@ private void writeSharedOperationInit(PythonWriter writer, OperationShape operat
                 if config.protocol is None or config.transport is None:
                     raise ExpectationNotMetError("protocol and transport MUST be set on the config to make calls.")
 
-                # Resolve retry strategy from config
-                if isinstance(config.retry_strategy, RetryStrategy):
-                    retry_strategy = config.retry_strategy
-                elif isinstance(config.retry_strategy, RetryStrategyOptions):
-                    retry_strategy = await self._retry_strategy_resolver.resolve_retry_strategy(
-                        options=config.retry_strategy
-                    )
-                elif config.retry_strategy is None:
-                    retry_strategy = await self._retry_strategy_resolver.resolve_retry_strategy(
-                        options=RetryStrategyOptions()
-                    )
-                else:
-                    raise TypeError(
-                        f"retry_strategy must be RetryStrategy, RetryStrategyOptions, or None, "
-                        f"got {type(config.retry_strategy).__name__}"
-                    )
+                retry_strategy = await self._retry_strategy_resolver.resolve_retry_strategy(
+                    retry_strategy=config.retry_strategy
+                )
 
                 pipeline = RequestPipeline(
                     protocol=config.protocol,
diff --git a/codegen/core/src/main/java/software/amazon/smithy/python/codegen/SmithyPythonDependency.java b/codegen/core/src/main/java/software/amazon/smithy/python/codegen/SmithyPythonDependency.java
index 71fde8b10..220c80df2 100644
--- a/codegen/core/src/main/java/software/amazon/smithy/python/codegen/SmithyPythonDependency.java
+++ b/codegen/core/src/main/java/software/amazon/smithy/python/codegen/SmithyPythonDependency.java
@@ -22,7 +22,7 @@ public final class SmithyPythonDependency {
      */
     public static final PythonDependency SMITHY_CORE = new PythonDependency(
             "smithy_core",
-            "~=0.2.0",
+            "~=0.3.0",
             Type.DEPENDENCY,
             false);
 
@@ -78,7 +78,7 @@ public final class SmithyPythonDependency {
      */
     public static final PythonDependency SMITHY_AWS_CORE = new PythonDependency(
             "smithy_aws_core",
-            "~=0.2.0",
+            "~=0.3.0",
             Type.DEPENDENCY,
             false);
 
@@ -87,7 +87,7 @@ public final class SmithyPythonDependency {
      */
     public static final PythonDependency PYTEST = new PythonDependency(
             "pytest",
-            ">=7.2.0,<8.0.0",
+            ">=9.0.1,<10.0.0",
             Type.TEST_DEPENDENCY,
             false);
 
@@ -96,7 +96,7 @@ public final class SmithyPythonDependency {
      */
     public static final PythonDependency PYTEST_ASYNCIO = new PythonDependency(
             "pytest-asyncio",
-            ">=0.20.3,<0.21.0",
+            ">=1.3.0,<1.4.0",
             Type.TEST_DEPENDENCY,
             false);
 
diff --git a/codegen/gradle/libs.versions.toml b/codegen/gradle/libs.versions.toml
index 4ccc1b007..0eebde41c 100644
--- a/codegen/gradle/libs.versions.toml
+++ b/codegen/gradle/libs.versions.toml
@@ -1,11 +1,11 @@
 [versions]
 junit5 = "6.0.1"
-smithy = "1.64.0"
+smithy = "1.65.0"
 test-logger-plugin = "4.0.0"
 spotbugs = "6.0.22"
 spotless = "8.1.0"
 smithy-gradle-plugins = "1.3.0"
-dep-analysis = "3.4.1"
+dep-analysis = "3.5.1"
 jsoup = "1.21.2"
 commonmark = "0.17.0"
 
diff --git a/packages/aws-sdk-signers/src/aws_sdk_signers/_io.py b/packages/aws-sdk-signers/src/aws_sdk_signers/_io.py
index ba50f3c4d..9a88ea756 100644
--- a/packages/aws-sdk-signers/src/aws_sdk_signers/_io.py
+++ b/packages/aws-sdk-signers/src/aws_sdk_signers/_io.py
@@ -1,8 +1,8 @@
 # Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
 # SPDX-License-Identifier: Apache-2.0
 
-from asyncio import iscoroutinefunction
 from collections.abc import AsyncIterable, AsyncIterator, Awaitable, Callable
+from inspect import iscoroutinefunction
 from io import BytesIO
 from typing import (
     Self,
diff --git a/packages/aws-sdk-signers/src/aws_sdk_signers/signers.py b/packages/aws-sdk-signers/src/aws_sdk_signers/signers.py
index 29ba02894..f74179be5 100644
--- a/packages/aws-sdk-signers/src/aws_sdk_signers/signers.py
+++ b/packages/aws-sdk-signers/src/aws_sdk_signers/signers.py
@@ -6,11 +6,11 @@
 import hmac
 import io
 import warnings
-from asyncio import iscoroutinefunction
 from binascii import hexlify
 from collections.abc import AsyncIterable, Iterable
 from copy import deepcopy
 from hashlib import sha256
+from inspect import iscoroutinefunction
 from typing import TYPE_CHECKING, Required, TypedDict, TypeGuard
 from urllib.parse import parse_qsl, quote
 
diff --git a/packages/smithy-aws-core/.changes/0.3.0.json b/packages/smithy-aws-core/.changes/0.3.0.json
new file mode 100644
index 000000000..8a075baeb
--- /dev/null
+++ b/packages/smithy-aws-core/.changes/0.3.0.json
@@ -0,0 +1,8 @@
+{
+  "changes": [
+    {
+      "type": "dependency",
+      "description": "Bump `smithy-core` from `~=0.2.0` to `~=0.3.0`."
+    }
+  ]
+}
diff --git a/packages/smithy-aws-core/CHANGELOG.md b/packages/smithy-aws-core/CHANGELOG.md
index 90a18a3d5..5727dae72 100644
--- a/packages/smithy-aws-core/CHANGELOG.md
+++ b/packages/smithy-aws-core/CHANGELOG.md
@@ -1,5 +1,10 @@
 # Changelog
 
+## v0.3.0
+
+### Dependencies
+* Bump `smithy-core` from `~=0.2.0` to `~=0.3.0`.
+
 ## v0.2.0
 
 ### Dependencies
diff --git a/packages/smithy-aws-core/pyproject.toml b/packages/smithy-aws-core/pyproject.toml
index c9c2defe5..7dbd5ffbc 100644
--- a/packages/smithy-aws-core/pyproject.toml
+++ b/packages/smithy-aws-core/pyproject.toml
@@ -26,7 +26,7 @@ classifiers = [
   "Topic :: Software Development :: Libraries"
 ]
 dependencies = [
-    "smithy-core~=0.2.0",
+    "smithy-core~=0.3.0",
     "smithy-http~=0.3.0",
     "aws-sdk-signers~=0.1.0"
 ]
diff --git a/packages/smithy-aws-core/src/smithy_aws_core/__init__.py b/packages/smithy-aws-core/src/smithy_aws_core/__init__.py
index d4291a169..fa1387347 100644
--- a/packages/smithy-aws-core/src/smithy_aws_core/__init__.py
+++ b/packages/smithy-aws-core/src/smithy_aws_core/__init__.py
@@ -1,4 +1,4 @@
 #  Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
 #  SPDX-License-Identifier: Apache-2.0
 
-__version__ = "0.2.0"
+__version__ = "0.3.0"
diff --git a/packages/smithy-aws-event-stream/.changes/0.2.1.json b/packages/smithy-aws-event-stream/.changes/0.2.1.json
new file mode 100644
index 000000000..cfaba4aa1
--- /dev/null
+++ b/packages/smithy-aws-event-stream/.changes/0.2.1.json
@@ -0,0 +1,8 @@
+{
+  "changes": [
+    {
+      "type": "dependency",
+      "description": "Removed strict pinning on `smithy-core` in favor of client managed versions."
+    }
+  ]
+}
\ No newline at end of file
diff --git a/packages/smithy-aws-event-stream/CHANGELOG.md b/packages/smithy-aws-event-stream/CHANGELOG.md
index 50724dc71..25709de38 100644
--- a/packages/smithy-aws-event-stream/CHANGELOG.md
+++ b/packages/smithy-aws-event-stream/CHANGELOG.md
@@ -1,5 +1,10 @@
 # Changelog
 
+## v0.2.1
+
+### Dependencies
+* Removed strict pinning on `smithy-core` in favor of client managed versions.
+
 ## v0.2.0
 
 ### Dependencies
diff --git a/packages/smithy-aws-event-stream/pyproject.toml b/packages/smithy-aws-event-stream/pyproject.toml
index 081b7761b..25a219268 100644
--- a/packages/smithy-aws-event-stream/pyproject.toml
+++ b/packages/smithy-aws-event-stream/pyproject.toml
@@ -26,7 +26,7 @@ classifiers = [
   "Topic :: Software Development :: Libraries"
 ]
 dependencies = [
-    "smithy-core~=0.2.0",
+    "smithy-core",
 ]
 
 [project.urls]
diff --git a/packages/smithy-aws-event-stream/src/smithy_aws_event_stream/__init__.py b/packages/smithy-aws-event-stream/src/smithy_aws_event_stream/__init__.py
index c392c786c..068e5f449 100644
--- a/packages/smithy-aws-event-stream/src/smithy_aws_event_stream/__init__.py
+++ b/packages/smithy-aws-event-stream/src/smithy_aws_event_stream/__init__.py
@@ -1,4 +1,4 @@
 # Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
 # SPDX-License-Identifier: Apache-2.0
 
-__version__ = "0.2.0"
+__version__ = "0.2.1"
diff --git a/packages/smithy-core/.changes/0.3.0.json b/packages/smithy-core/.changes/0.3.0.json
new file mode 100644
index 000000000..06eb6613d
--- /dev/null
+++ b/packages/smithy-core/.changes/0.3.0.json
@@ -0,0 +1,12 @@
+{
+  "changes": [
+    {
+      "type": "enhancement",
+      "description": "Improved default error message for instances of ClientTimeoutError."
+    },
+    {
+      "type": "breaking",
+      "description": "Refactored `resolve_retry_strategy` to avoid code duplication per operation."
+    }
+  ]
+}
diff --git a/packages/smithy-core/CHANGELOG.md b/packages/smithy-core/CHANGELOG.md
index 29d49d545..5af0e57f0 100644
--- a/packages/smithy-core/CHANGELOG.md
+++ b/packages/smithy-core/CHANGELOG.md
@@ -1,5 +1,13 @@
 # Changelog
 
+## v0.3.0
+
+### Breaking Changes
+* Refactored `resolve_retry_strategy` to avoid code duplication per operation.
+
+### Enhancements
+* Improved default error message for instances of ClientTimeoutError.
+
 ## v0.2.0
 
 ### Features
diff --git a/packages/smithy-core/src/smithy_core/__init__.py b/packages/smithy-core/src/smithy_core/__init__.py
index f6c4e1583..860e7402f 100644
--- a/packages/smithy-core/src/smithy_core/__init__.py
+++ b/packages/smithy-core/src/smithy_core/__init__.py
@@ -8,7 +8,7 @@
 from . import interfaces, rfc3986
 from .exceptions import SmithyError
 
-__version__ = "0.2.0"
+__version__ = "0.3.0"
 
 
 class HostType(Enum):
diff --git a/packages/smithy-core/src/smithy_core/aio/client.py b/packages/smithy-core/src/smithy_core/aio/client.py
index 01f18097b..6060727b4 100644
--- a/packages/smithy-core/src/smithy_core/aio/client.py
+++ b/packages/smithy-core/src/smithy_core/aio/client.py
@@ -469,9 +469,7 @@ async def _handle_attempt[I: SerializeableShape, O: DeserializeableShape](
                     )
             except Exception as e:
                 if isinstance(e, self.transport.TIMEOUT_EXCEPTIONS):
-                    raise ClientTimeoutError(
-                        message=f"Client timeout occurred: {e}"
-                    ) from e
+                    raise ClientTimeoutError(message="A timeout error occurred.") from e
                 raise
 
             _LOGGER.debug("Received response: %s", transport_response)
diff --git a/packages/smithy-core/src/smithy_core/aio/types.py b/packages/smithy-core/src/smithy_core/aio/types.py
index d175e7e25..3b84317cd 100644
--- a/packages/smithy-core/src/smithy_core/aio/types.py
+++ b/packages/smithy-core/src/smithy_core/aio/types.py
@@ -1,9 +1,9 @@
 #  Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
 #  SPDX-License-Identifier: Apache-2.0
 import asyncio
-from asyncio import iscoroutinefunction
 from collections import deque
 from collections.abc import AsyncIterable, AsyncIterator, Awaitable, Callable
+from inspect import iscoroutinefunction
 from io import BytesIO
 from typing import Any, Self, cast
 
diff --git a/packages/smithy-core/src/smithy_core/interfaces/__init__.py b/packages/smithy-core/src/smithy_core/interfaces/__init__.py
index 39be88d23..558c4c15e 100644
--- a/packages/smithy-core/src/smithy_core/interfaces/__init__.py
+++ b/packages/smithy-core/src/smithy_core/interfaces/__init__.py
@@ -1,7 +1,7 @@
 # Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
 # SPDX-License-Identifier: Apache-2.0
-from asyncio import iscoroutinefunction
 from collections.abc import ItemsView, Iterator, KeysView, ValuesView
+from inspect import iscoroutinefunction
 from typing import TYPE_CHECKING, Any, Protocol, TypeGuard, overload, runtime_checkable
 
 if TYPE_CHECKING:
diff --git a/packages/smithy-core/src/smithy_core/retries.py b/packages/smithy-core/src/smithy_core/retries.py
index ce990e6b4..67c63c1a3 100644
--- a/packages/smithy-core/src/smithy_core/retries.py
+++ b/packages/smithy-core/src/smithy_core/retries.py
@@ -34,13 +34,24 @@ class RetryStrategyResolver:
     """
 
     async def resolve_retry_strategy(
-        self, *, options: RetryStrategyOptions
+        self, *, retry_strategy: RetryStrategy | RetryStrategyOptions | None
     ) -> RetryStrategy:
         """Resolve a retry strategy from the provided options, using cache when possible.
 
-        :param options: The retry strategy options to use for creating the strategy.
+        :param retry_strategy: An explicitly configured retry strategy or options for creating one.
         """
-        return self._create_retry_strategy(options.retry_mode, options.max_attempts)
+        if isinstance(retry_strategy, RetryStrategy):
+            return retry_strategy
+        elif retry_strategy is None:
+            retry_strategy = RetryStrategyOptions()
+        elif not isinstance(retry_strategy, RetryStrategyOptions):  # type: ignore[reportUnnecessaryIsInstance]
+            raise TypeError(
+                f"retry_strategy must be RetryStrategy, RetryStrategyOptions, or None, "
+                f"got {type(retry_strategy).__name__}"
+            )
+        return self._create_retry_strategy(
+            retry_strategy.retry_mode, retry_strategy.max_attempts
+        )
 
     @lru_cache
     def _create_retry_strategy(
diff --git a/packages/smithy-core/tests/functional/__init__.py b/packages/smithy-core/tests/functional/__init__.py
new file mode 100644
index 000000000..04f8b7b76
--- /dev/null
+++ b/packages/smithy-core/tests/functional/__init__.py
@@ -0,0 +1,2 @@
+# Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
+# SPDX-License-Identifier: Apache-2.0
diff --git a/packages/smithy-core/tests/functional/test_retries.py b/packages/smithy-core/tests/functional/test_retries.py
new file mode 100644
index 000000000..9a72b491b
--- /dev/null
+++ b/packages/smithy-core/tests/functional/test_retries.py
@@ -0,0 +1,153 @@
+# Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
+# SPDX-License-Identifier: Apache-2.0
+
+from asyncio import gather, sleep
+
+import pytest
+from smithy_core.exceptions import CallError, ClientTimeoutError, RetryError
+from smithy_core.interfaces import retries as retries_interface
+from smithy_core.retries import (
+    ExponentialBackoffJitterType,
+    ExponentialRetryBackoffStrategy,
+    StandardRetryQuota,
+    StandardRetryStrategy,
+)
+
+
+# TODO: Refactor this to use a smithy-testing generated client
+async def retry_operation(
+    strategy: retries_interface.RetryStrategy,
+    responses: list[int | Exception],
+) -> tuple[str, int]:
+    token = strategy.acquire_initial_retry_token()
+    response_iter = iter(responses)
+
+    while True:
+        if token.retry_delay:
+            await sleep(token.retry_delay)
+
+        response = next(response_iter)
+        attempt = token.retry_count + 1
+
+        # Success case
+        if response == 200:
+            strategy.record_success(token=token)
+            return "success", attempt
+
+        # Error case - either status code or exception
+        if isinstance(response, Exception):
+            error = response
+        else:
+            error = CallError(
+                fault="server" if response >= 500 else "client",
+                message=f"HTTP {response}",
+                is_retry_safe=response >= 500,
+            )
+
+        try:
+            token = strategy.refresh_retry_token_for_retry(
+                token_to_renew=token, error=error
+            )
+        except RetryError:
+            raise error
+
+
+async def test_standard_retry_eventually_succeeds():
+    quota = StandardRetryQuota(initial_capacity=500)
+    strategy = StandardRetryStrategy(max_attempts=3, retry_quota=quota)
+
+    result, attempts = await retry_operation(strategy, [500, 500, 200])
+
+    assert result == "success"
+    assert attempts == 3
+    assert quota.available_capacity == 495
+
+
+async def test_standard_retry_fails_due_to_max_attempts():
+    quota = StandardRetryQuota(initial_capacity=500)
+    strategy = StandardRetryStrategy(max_attempts=3, retry_quota=quota)
+
+    with pytest.raises(CallError, match="502"):
+        await retry_operation(strategy, [502, 502, 502])
+
+    assert quota.available_capacity == 490
+
+
+async def test_retry_quota_exhausted_after_single_retry():
+    quota = StandardRetryQuota(initial_capacity=5)
+    strategy = StandardRetryStrategy(max_attempts=3, retry_quota=quota)
+
+    with pytest.raises(CallError, match="502"):
+        await retry_operation(strategy, [500, 502])
+
+    assert quota.available_capacity == 0
+
+
+async def test_retry_quota_prevents_retries_when_quota_zero():
+    quota = StandardRetryQuota(initial_capacity=0)
+    strategy = StandardRetryStrategy(max_attempts=3, retry_quota=quota)
+
+    with pytest.raises(CallError, match="500"):
+        await retry_operation(strategy, [500])
+
+    assert quota.available_capacity == 0
+
+
+async def test_retry_quota_stops_retries_when_exhausted():
+    quota = StandardRetryQuota(initial_capacity=10)
+    strategy = StandardRetryStrategy(max_attempts=5, retry_quota=quota)
+
+    with pytest.raises(CallError, match="503"):
+        await retry_operation(strategy, [500, 502, 503])
+
+    assert quota.available_capacity == 0
+
+
+async def test_retry_quota_recovers_after_successful_responses():
+    quota = StandardRetryQuota(initial_capacity=15)
+    strategy = StandardRetryStrategy(max_attempts=5, retry_quota=quota)
+
+    # First operation: 2 retries then success
+    await retry_operation(strategy, [500, 502, 200])
+    assert quota.available_capacity == 10
+
+    # Second operation: 1 retry then success
+    await retry_operation(strategy, [500, 200])
+    assert quota.available_capacity == 10
+
+
+async def test_retry_quota_shared_across_concurrent_operations():
+    quota = StandardRetryQuota(initial_capacity=500)
+    backoff = ExponentialRetryBackoffStrategy(
+        backoff_scale_value=1,
+        max_backoff=10,
+        jitter_type=ExponentialBackoffJitterType.FULL,
+    )
+    strategy = StandardRetryStrategy(
+        max_attempts=5,
+        retry_quota=quota,
+        backoff_strategy=backoff,
+    )
+
+    result1, result2 = await gather(
+        retry_operation(strategy, [500, 500, 200]),
+        retry_operation(strategy, [500, 200]),
+    )
+
+    assert result1 == ("success", 3)
+    assert result2 == ("success", 2)
+    assert quota.available_capacity == 495
+
+
+async def test_retry_quota_handles_timeout_errors():
+    quota = StandardRetryQuota(initial_capacity=500)
+    strategy = StandardRetryStrategy(max_attempts=3, retry_quota=quota)
+
+    timeout1 = ClientTimeoutError()
+    timeout2 = ClientTimeoutError()
+
+    result, attempts = await retry_operation(strategy, [timeout1, timeout2, 200])
+
+    assert result == "success"
+    assert attempts == 3
+    assert quota.available_capacity == 490
diff --git a/packages/smithy-core/tests/unit/test_retries.py b/packages/smithy-core/tests/unit/test_retries.py
index 18f9e380c..c36c5b758 100644
--- a/packages/smithy-core/tests/unit/test_retries.py
+++ b/packages/smithy-core/tests/unit/test_retries.py
@@ -220,34 +220,58 @@ def test_retry_quota_acquire_timeout_error(
     assert retry_quota.available_capacity == 0
 
 
-async def test_caching_retry_strategy_default_resolution() -> None:
+async def test_retry_strategy_resolver_none_returns_default() -> None:
     resolver = RetryStrategyResolver()
-    options = RetryStrategyOptions()
 
-    strategy = await resolver.resolve_retry_strategy(options=options)
+    strategy = await resolver.resolve_retry_strategy(retry_strategy=None)
 
     assert isinstance(strategy, StandardRetryStrategy)
     assert strategy.max_attempts == 3
 
 
-async def test_caching_retry_strategy_resolver_creates_strategies_by_options() -> None:
+async def test_retry_strategy_resolver_creates_different_strategies() -> None:
     resolver = RetryStrategyResolver()
 
     options1 = RetryStrategyOptions(max_attempts=3)
     options2 = RetryStrategyOptions(max_attempts=5)
 
-    strategy1 = await resolver.resolve_retry_strategy(options=options1)
-    strategy2 = await resolver.resolve_retry_strategy(options=options2)
+    strategy1 = await resolver.resolve_retry_strategy(retry_strategy=options1)
+    strategy2 = await resolver.resolve_retry_strategy(retry_strategy=options2)
 
     assert strategy1.max_attempts == 3
     assert strategy2.max_attempts == 5
+    assert strategy1 is not strategy2
 
 
-async def test_caching_retry_strategy_resolver_caches_strategies() -> None:
+async def test_retry_strategy_resolver_caches_strategies() -> None:
     resolver = RetryStrategyResolver()
 
+    strategy1 = await resolver.resolve_retry_strategy(retry_strategy=None)
+    strategy2 = await resolver.resolve_retry_strategy(retry_strategy=None)
     options = RetryStrategyOptions(max_attempts=5)
-    strategy1 = await resolver.resolve_retry_strategy(options=options)
-    strategy2 = await resolver.resolve_retry_strategy(options=options)
+    strategy3 = await resolver.resolve_retry_strategy(retry_strategy=options)
+    strategy4 = await resolver.resolve_retry_strategy(retry_strategy=options)
 
     assert strategy1 is strategy2
+    assert strategy3 is strategy4
+    assert strategy1 is not strategy3
+
+
+async def test_retry_strategy_resolver_returns_existing_strategy() -> None:
+    resolver = RetryStrategyResolver()
+    provided_strategy = SimpleRetryStrategy(max_attempts=7)
+
+    strategy = await resolver.resolve_retry_strategy(retry_strategy=provided_strategy)
+
+    assert strategy is provided_strategy
+    assert strategy.max_attempts == 7
+
+
+async def test_retry_strategy_resolver_rejects_invalid_type() -> None:
+    resolver = RetryStrategyResolver()
+
+    with pytest.raises(
+        TypeError,
+        match="retry_strategy must be RetryStrategy, RetryStrategyOptions, or None",
+    ):
+        await resolver.resolve_retry_strategy(retry_strategy="invalid")  # type: ignore
diff --git a/packages/smithy-http/.changes/0.3.1.json b/packages/smithy-http/.changes/0.3.1.json
new file mode 100644
index 000000000..a5b6c090b
--- /dev/null
+++ b/packages/smithy-http/.changes/0.3.1.json
@@ -0,0 +1,12 @@
+{
+  "changes": [
+    {
+      "type": "bugfix",
+      "description": "Fixed empty error messaging for CRT-based timeout errors."
+    },
+    {
+      "type": "dependency",
+      "description": "Removed strict pinning on `smithy-core` in favor of client managed versions."
+    }
+  ]
+}
diff --git a/packages/smithy-http/CHANGELOG.md b/packages/smithy-http/CHANGELOG.md
index e999a0232..bc0e08daf 100644
--- a/packages/smithy-http/CHANGELOG.md
+++ b/packages/smithy-http/CHANGELOG.md
@@ -1,5 +1,13 @@
 # Changelog
 
+## v0.3.1
+
+### Bug fixes
+* Fixed empty error messaging for CRT-based timeout errors.
+
+### Dependencies
+* Removed strict pinning on `smithy-core` in favor of client managed versions.
+
 ## v0.3.0
 
 ### Features
diff --git a/packages/smithy-http/pyproject.toml b/packages/smithy-http/pyproject.toml
index 18a5ce0a7..f9b609a60 100644
--- a/packages/smithy-http/pyproject.toml
+++ b/packages/smithy-http/pyproject.toml
@@ -26,7 +26,7 @@ classifiers = [
   "Topic :: Software Development :: Libraries"
 ]
 dependencies = [
-    "smithy-core~=0.2.0",
+    "smithy-core",
 ]
 
 [project.urls]
diff --git a/packages/smithy-http/src/smithy_http/__init__.py b/packages/smithy-http/src/smithy_http/__init__.py
index f877b9f44..5f6aea018 100644
--- a/packages/smithy-http/src/smithy_http/__init__.py
+++ b/packages/smithy-http/src/smithy_http/__init__.py
@@ -6,7 +6,7 @@
 from . import interfaces
 from .interfaces import FieldPosition
 
-__version__ = "0.3.0"
+__version__ = "0.3.1"
 
 
 class Field(interfaces.Field):
diff --git a/packages/smithy-http/src/smithy_http/aio/crt.py b/packages/smithy-http/src/smithy_http/aio/crt.py
index db13162e1..5e5cc861c 100644
--- a/packages/smithy-http/src/smithy_http/aio/crt.py
+++ b/packages/smithy-http/src/smithy_http/aio/crt.py
@@ -187,7 +187,7 @@ async def send(
             return await self._await_response(crt_stream)
         except AwsCrtError as e:
             if e.name in self._TIMEOUT_ERROR_NAMES:
-                raise _CRTTimeoutError() from e
+                raise _CRTTimeoutError(f"CRT {e.name}: {e.message}") from e
             raise
 
     async def _await_response(
diff --git a/packages/smithy-http/src/smithy_http/serializers.py b/packages/smithy-http/src/smithy_http/serializers.py
index acac7ac75..11a5f18ea 100644
--- a/packages/smithy-http/src/smithy_http/serializers.py
+++ b/packages/smithy-http/src/smithy_http/serializers.py
@@ -1,11 +1,11 @@
 # Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
 # SPDX-License-Identifier: Apache-2.0
-from asyncio import iscoroutinefunction
 from base64 import b64encode
 from collections.abc import Callable, Iterator, Sized
 from contextlib import contextmanager
 from datetime import datetime
 from decimal import Decimal
+from inspect import iscoroutinefunction
 from io import BytesIO
 from typing import TYPE_CHECKING
 from urllib.parse import quote as urlquote
diff --git a/packages/smithy-http/tests/unit/test_serializers.py b/packages/smithy-http/tests/unit/test_serializers.py
index 83e291b21..7f52da070 100644
--- a/packages/smithy-http/tests/unit/test_serializers.py
+++ b/packages/smithy-http/tests/unit/test_serializers.py
@@ -1,10 +1,10 @@
 #  Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
 #  SPDX-License-Identifier: Apache-2.0
 import datetime
-from asyncio import iscoroutinefunction
 from dataclasses import dataclass, field
 from datetime import UTC
 from decimal import Decimal
+from inspect import iscoroutinefunction
 from io import BytesIO
 from typing import Any, ClassVar, Protocol, Self
 
diff --git a/packages/smithy-json/.changes/0.2.1.json b/packages/smithy-json/.changes/0.2.1.json
new file mode 100644
index 000000000..cfaba4aa1
--- /dev/null
+++ b/packages/smithy-json/.changes/0.2.1.json
@@ -0,0 +1,8 @@
+{
+  "changes": [
+    {
+      "type": "dependency",
+      "description": "Removed strict pinning on `smithy-core` in favor of client managed versions."
+    }
+  ]
+}
\ No newline at end of file
diff --git a/packages/smithy-json/CHANGELOG.md b/packages/smithy-json/CHANGELOG.md
index d1f01ed00..924ce1878 100644
--- a/packages/smithy-json/CHANGELOG.md
+++ b/packages/smithy-json/CHANGELOG.md
@@ -1,5 +1,10 @@
 # Changelog
 
+## v0.2.1
+
+### Dependencies
+* Removed strict pinning on `smithy-core` in favor of client managed versions.
+
 ## v0.2.0
 
 ### Dependencies
diff --git a/packages/smithy-json/pyproject.toml b/packages/smithy-json/pyproject.toml
index d6ebe1452..b4c113e87 100644
--- a/packages/smithy-json/pyproject.toml
+++ b/packages/smithy-json/pyproject.toml
@@ -27,7 +27,7 @@ classifiers = [
 ]
 dependencies = [
     "ijson>=3.3.0",
-    "smithy-core~=0.2.0",
+    "smithy-core",
 ]
 
 [project.urls]
diff --git a/packages/smithy-json/src/smithy_json/__init__.py b/packages/smithy-json/src/smithy_json/__init__.py
index a16b4e4b4..25c23bc57 100644
--- a/packages/smithy-json/src/smithy_json/__init__.py
+++ b/packages/smithy-json/src/smithy_json/__init__.py
@@ -13,7 +13,7 @@
 from ._private.serializers import JSONShapeSerializer as _JSONShapeSerializer
 from .settings import JSONSettings
 
-__version__ = "0.2.0"
+__version__ = "0.2.1"
 __all__ = ("JSONCodec", "JSONDocument", "JSONSettings")
 
 
diff --git a/scripts/changelog/new-entry.py b/scripts/changelog/new-entry.py
index f21cb748a..aec8b511f 100755
--- a/scripts/changelog/new-entry.py
+++ b/scripts/changelog/new-entry.py
@@ -7,7 +7,7 @@
 
 import argparse
 import json
-from datetime import datetime
+import uuid
 from pathlib import Path
 
 PROJECT_ROOT_DIR = Path(__file__).resolve().parent.parent.parent
@@ -33,8 +33,8 @@ def create_change_entry(
     next_release_dir.mkdir(exist_ok=True)
 
     # Generate unique filename
-    timestamp = datetime.now().strftime("%Y%m%d%H%M%S")
-    filename = f"{package_name}-{change_type}-{timestamp}.json"
+    unique_id = uuid.uuid4().hex
+    filename = f"{package_name}-{change_type}-{unique_id}.json"
 
     entry_data = {
         "type": change_type,
diff --git a/uv.lock b/uv.lock
index 3bf8fb831..efa62699c 100644
--- a/uv.lock
+++ b/uv.lock
@@ -166,53 +166,88 @@ wheels = [
 
 [[package]]
 name = "coverage"
-version = "7.8.0"
+version = "7.12.0"
 source = { registry = "https://pypi.org/simple" }
-sdist = { url = "https://files.pythonhosted.org/packages/19/4f/2251e65033ed2ce1e68f00f91a0294e0f80c80ae8c3ebbe2f12828c4cd53/coverage-7.8.0.tar.gz", hash = "sha256:7a3d62b3b03b4b6fd41a085f3574874cf946cb4604d2b4d3e8dca8cd570ca501", size = 811872, upload-time = "2025-03-30T20:36:45.376Z" }
+sdist = { url = "https://files.pythonhosted.org/packages/89/26/4a96807b193b011588099c3b5c89fbb05294e5b90e71018e065465f34eb6/coverage-7.12.0.tar.gz", hash = "sha256:fc11e0a4e372cb5f282f16ef90d4a585034050ccda536451901abfb19a57f40c", size = 819341, upload-time = "2025-11-18T13:34:20.766Z" }
 wheels = [
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