diff --git a/.gitignore b/.gitignore
index 710a23e16b..268344ecb1 100644
--- a/.gitignore
+++ b/.gitignore
@@ -56,3 +56,6 @@ target/
 
 # tools
 .tool-versions
+
+# python
+__pycache__
diff --git a/codegen-core/src/main/kotlin/software/amazon/smithy/rust/codegen/core/smithy/generators/TypeConversionGenerator.kt b/codegen-core/src/main/kotlin/software/amazon/smithy/rust/codegen/core/smithy/generators/TypeConversionGenerator.kt
deleted file mode 100644
index b79200f952..0000000000
--- a/codegen-core/src/main/kotlin/software/amazon/smithy/rust/codegen/core/smithy/generators/TypeConversionGenerator.kt
+++ /dev/null
@@ -1,54 +0,0 @@
-/*
- * Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
- * SPDX-License-Identifier: Apache-2.0
- */
-
-package software.amazon.smithy.rust.codegen.core.smithy.generators
-
-import software.amazon.smithy.codegen.core.Symbol
-import software.amazon.smithy.model.Model
-import software.amazon.smithy.model.shapes.BlobShape
-import software.amazon.smithy.model.shapes.Shape
-import software.amazon.smithy.model.shapes.TimestampShape
-import software.amazon.smithy.rust.codegen.core.rustlang.Writable
-import software.amazon.smithy.rust.codegen.core.rustlang.rust
-import software.amazon.smithy.rust.codegen.core.rustlang.writable
-import software.amazon.smithy.rust.codegen.core.smithy.RuntimeConfig
-import software.amazon.smithy.rust.codegen.core.smithy.RuntimeType
-import software.amazon.smithy.rust.codegen.core.smithy.RustSymbolProvider
-import software.amazon.smithy.rust.codegen.core.smithy.rustType
-
-/*
- * Utility class used to force casting a non primitive type into one overriden by a new symbol provider,
- * by explicitly calling `from()` or into().
- *
- * For example we use this in the server Python implementation, where we override types like [Blob] and [DateTime]
- * with wrappers compatible with Python, without touching the original implementation coming from `aws-smithy-types`.
- */
-class TypeConversionGenerator(private val model: Model, private val symbolProvider: RustSymbolProvider, private val runtimeConfig: RuntimeConfig) {
-    private fun findOldSymbol(shape: Shape): Symbol {
-        return when (shape) {
-            is BlobShape -> RuntimeType.blob(runtimeConfig).toSymbol()
-            is TimestampShape -> RuntimeType.dateTime(runtimeConfig).toSymbol()
-            else -> symbolProvider.toSymbol(shape)
-        }
-    }
-
-    fun convertViaFrom(shape: Shape): Writable =
-        writable {
-            val oldSymbol = findOldSymbol(shape)
-            val newSymbol = symbolProvider.toSymbol(shape)
-            if (oldSymbol.rustType() != newSymbol.rustType()) {
-                rust(".map($newSymbol::from)")
-            }
-        }
-
-    fun convertViaInto(shape: Shape): Writable =
-        writable {
-            val oldSymbol = findOldSymbol(shape)
-            val newSymbol = symbolProvider.toSymbol(shape)
-            if (oldSymbol.rustType() != newSymbol.rustType()) {
-                rust(".into()")
-            }
-        }
-}
diff --git a/codegen-core/src/main/kotlin/software/amazon/smithy/rust/codegen/core/smithy/generators/http/HttpBindingGenerator.kt b/codegen-core/src/main/kotlin/software/amazon/smithy/rust/codegen/core/smithy/generators/http/HttpBindingGenerator.kt
index ab920bc53f..881d0f77af 100644
--- a/codegen-core/src/main/kotlin/software/amazon/smithy/rust/codegen/core/smithy/generators/http/HttpBindingGenerator.kt
+++ b/codegen-core/src/main/kotlin/software/amazon/smithy/rust/codegen/core/smithy/generators/http/HttpBindingGenerator.kt
@@ -88,6 +88,9 @@ sealed class HttpBindingSection(name: String) : Section(name) {
 
     data class AfterDeserializingIntoAHashMapOfHttpPrefixHeaders(val memberShape: MemberShape) :
         HttpBindingSection("AfterDeserializingIntoAHashMapOfHttpPrefixHeaders")
+
+    data class AfterDeserializingIntoADateTimeOfHttpHeaders(val memberShape: MemberShape) :
+        HttpBindingSection("AfterDeserializingIntoADateTimeOfHttpHeaders")
 }
 
 typealias HttpBindingCustomization = NamedCustomization<HttpBindingSection>
@@ -353,7 +356,7 @@ class HttpBindingGenerator(
             rustType to targetShape
         }
         val parsedValue = safeName()
-        if (coreType == dateTime) {
+        if (coreShape.isTimestampShape()) {
             val timestampFormat =
                 index.determineTimestampFormat(
                     memberShape,
@@ -362,10 +365,14 @@ class HttpBindingGenerator(
                 )
             val timestampFormatType = RuntimeType.parseTimestampFormat(codegenTarget, runtimeConfig, timestampFormat)
             rust(
-                "let $parsedValue: Vec<${coreType.render()}> = #T::many_dates(headers, #T)?;",
+                "let $parsedValue: Vec<${coreType.render()}> = #T::many_dates(headers, #T)?",
                 headerUtil,
                 timestampFormatType,
             )
+            for (customization in customizations) {
+                customization.section(HttpBindingSection.AfterDeserializingIntoADateTimeOfHttpHeaders(memberShape))(this)
+            }
+            rust(";")
         } else if (coreShape.isPrimitive()) {
             rust(
                 "let $parsedValue = #T::read_many_primitive::<${coreType.render()}>(headers)?;",
diff --git a/codegen-core/src/main/kotlin/software/amazon/smithy/rust/codegen/core/smithy/protocols/parse/JsonParserGenerator.kt b/codegen-core/src/main/kotlin/software/amazon/smithy/rust/codegen/core/smithy/protocols/parse/JsonParserGenerator.kt
index dd7255e47e..1566d84bf3 100644
--- a/codegen-core/src/main/kotlin/software/amazon/smithy/rust/codegen/core/smithy/protocols/parse/JsonParserGenerator.kt
+++ b/codegen-core/src/main/kotlin/software/amazon/smithy/rust/codegen/core/smithy/protocols/parse/JsonParserGenerator.kt
@@ -39,7 +39,6 @@ import software.amazon.smithy.rust.codegen.core.smithy.RuntimeType
 import software.amazon.smithy.rust.codegen.core.smithy.canUseDefault
 import software.amazon.smithy.rust.codegen.core.smithy.customize.NamedCustomization
 import software.amazon.smithy.rust.codegen.core.smithy.customize.Section
-import software.amazon.smithy.rust.codegen.core.smithy.generators.TypeConversionGenerator
 import software.amazon.smithy.rust.codegen.core.smithy.generators.UnionGenerator
 import software.amazon.smithy.rust.codegen.core.smithy.generators.renderUnknownVariant
 import software.amazon.smithy.rust.codegen.core.smithy.generators.setterName
@@ -61,6 +60,12 @@ import software.amazon.smithy.utils.StringUtils
  */
 sealed class JsonParserSection(name: String) : Section(name) {
     data class BeforeBoxingDeserializedMember(val shape: MemberShape) : JsonParserSection("BeforeBoxingDeserializedMember")
+
+    data class AfterTimestampDeserializedMember(val shape: MemberShape) : JsonParserSection("AfterTimestampDeserializedMember")
+
+    data class AfterBlobDeserializedMember(val shape: MemberShape) : JsonParserSection("AfterBlobDeserializedMember")
+
+    data class AfterDocumentDeserializedMember(val shape: MemberShape) : JsonParserSection("AfterDocumentDeserializedMember")
 }
 
 /**
@@ -94,7 +99,6 @@ class JsonParserGenerator(
     private val runtimeConfig = codegenContext.runtimeConfig
     private val codegenTarget = codegenContext.target
     private val smithyJson = CargoDependency.smithyJson(runtimeConfig).toType()
-    private val typeConversionGenerator = TypeConversionGenerator(model, symbolProvider, runtimeConfig)
     private val protocolFunctions = ProtocolFunctions(codegenContext)
     private val codegenScope = arrayOf(
         "Error" to smithyJson.resolve("deserialize::error::DeserializeError"),
@@ -276,13 +280,13 @@ class JsonParserGenerator(
             is StringShape -> deserializeString(target)
             is BooleanShape -> rustTemplate("#{expect_bool_or_null}(tokens.next())?", *codegenScope)
             is NumberShape -> deserializeNumber(target)
-            is BlobShape -> deserializeBlob()
+            is BlobShape -> deserializeBlob(memberShape)
             is TimestampShape -> deserializeTimestamp(target, memberShape)
             is CollectionShape -> deserializeCollection(target)
             is MapShape -> deserializeMap(target)
             is StructureShape -> deserializeStruct(target)
             is UnionShape -> deserializeUnion(target)
-            is DocumentShape -> rustTemplate("Some(#{expect_document}(tokens)?)", *codegenScope)
+            is DocumentShape -> deserializeDocument(memberShape)
             else -> PANIC("unexpected shape: $target")
         }
         val symbol = symbolProvider.toSymbol(memberShape)
@@ -294,11 +298,21 @@ class JsonParserGenerator(
         }
     }
 
-    private fun RustWriter.deserializeBlob() {
+    private fun RustWriter.deserializeDocument(member: MemberShape) {
+        rustTemplate("Some(#{expect_document}(tokens)?)", *codegenScope)
+        for (customization in customizations) {
+            customization.section(JsonParserSection.AfterDocumentDeserializedMember(member))(this)
+        }
+    }
+
+    private fun RustWriter.deserializeBlob(member: MemberShape) {
         rustTemplate(
             "#{expect_blob_or_null}(tokens.next())?",
             *codegenScope,
         )
+        for (customization in customizations) {
+            customization.section(JsonParserSection.AfterBlobDeserializedMember(member))(this)
+        }
     }
 
     private fun RustWriter.deserializeStringInner(target: StringShape, escapedStrName: String) {
@@ -349,9 +363,12 @@ class JsonParserGenerator(
             )
         val timestampFormatType = RuntimeType.parseTimestampFormat(codegenTarget, runtimeConfig, timestampFormat)
         rustTemplate(
-            "#{expect_timestamp_or_null}(tokens.next(), #{T})?#{ConvertFrom:W}",
-            "T" to timestampFormatType, "ConvertFrom" to typeConversionGenerator.convertViaFrom(shape), *codegenScope,
+            "#{expect_timestamp_or_null}(tokens.next(), #{T})?",
+            "T" to timestampFormatType, *codegenScope,
         )
+        for (customization in customizations) {
+            customization.section(JsonParserSection.AfterTimestampDeserializedMember(member))(this)
+        }
     }
 
     private fun RustWriter.deserializeCollection(shape: CollectionShape) {
diff --git a/codegen-server-test/python/build.gradle.kts b/codegen-server-test/python/build.gradle.kts
index 35144f42f0..87ff7cc5bd 100644
--- a/codegen-server-test/python/build.gradle.kts
+++ b/codegen-server-test/python/build.gradle.kts
@@ -54,14 +54,49 @@ val allCodegenTests = "../../codegen-core/common-test-models".let { commonModels
             // TODO(https://github.com/awslabs/smithy-rs/issues/1401) `@uniqueItems` is used.
             extraConfig = """, "codegen": { "ignoreUnsupportedConstraints": true } """,
         ),
-        // TODO(https://github.com/awslabs/smithy-rs/issues/2476)
+        CodegenTest(
+            "aws.protocoltests.json#JsonProtocol",
+            "json_rpc11",
+            extraConfig = """, "codegen": { "ignoreUnsupportedConstraints": true } """,
+        ),
+        CodegenTest("aws.protocoltests.json10#JsonRpc10", "json_rpc10"),
+        CodegenTest("aws.protocoltests.restjson#RestJson", "rest_json"),
+        CodegenTest(
+            "aws.protocoltests.restjson#RestJsonExtras",
+            "rest_json_extras",
+            imports = listOf("$commonModels/rest-json-extras.smithy"),
+        ),
+        // TODO(https://github.com/awslabs/smithy-rs/issues/2551)
         // CodegenTest(
-        //     "aws.protocoltests.json#JsonProtocol",
-        //     "json_rpc11",
+        //     "aws.protocoltests.restjson.validation#RestJsonValidation",
+        //     "rest_json_validation",
+        //     // `@range` trait is used on floating point shapes, which we deliberately don't want to support.
+        //     // See https://github.com/awslabs/smithy-rs/issues/1401.
         //     extraConfig = """, "codegen": { "ignoreUnsupportedConstraints": true } """,
         // ),
-        // TODO(https://github.com/awslabs/smithy-rs/issues/2479)
-        // CodegenTest("aws.protocoltests.json10#JsonRpc10", "json_rpc10"),
+        CodegenTest(
+            "com.amazonaws.constraints#ConstraintsService",
+            "constraints",
+            imports = listOf("$commonModels/constraints.smithy"),
+        ),
+        CodegenTest(
+            "com.amazonaws.constraints#ConstraintsService",
+            "constraints_without_public_constrained_types",
+            imports = listOf("$commonModels/constraints.smithy"),
+            extraConfig = """, "codegen": { "publicConstrainedTypes": false } """,
+        ),
+        CodegenTest(
+            "com.amazonaws.constraints#UniqueItemsService",
+            "unique_items",
+            imports = listOf("$commonModels/unique-items.smithy"),
+        ),
+        CodegenTest(
+            "naming_obs_structs#NamingObstacleCourseStructs",
+            "naming_test_structs",
+            imports = listOf("$commonModels/naming-obstacle-course-structs.smithy"),
+        ),
+        CodegenTest("casing#ACRONYMInside_Service", "naming_test_casing", imports = listOf("$commonModels/naming-obstacle-course-casing.smithy")),
+        CodegenTest("crate#Config", "naming_test_ops", imports = listOf("$commonModels/naming-obstacle-course-ops.smithy")),
     )
 }
 
diff --git a/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/PythonServerCodegenVisitor.kt b/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/PythonServerCodegenVisitor.kt
index 788b6e695f..fa1f8eeb65 100644
--- a/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/PythonServerCodegenVisitor.kt
+++ b/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/PythonServerCodegenVisitor.kt
@@ -8,6 +8,7 @@ package software.amazon.smithy.rust.codegen.server.python.smithy
 import software.amazon.smithy.build.PluginContext
 import software.amazon.smithy.model.Model
 import software.amazon.smithy.model.knowledge.NullableIndex
+import software.amazon.smithy.model.shapes.BlobShape
 import software.amazon.smithy.model.shapes.MemberShape
 import software.amazon.smithy.model.shapes.OperationShape
 import software.amazon.smithy.model.shapes.ServiceShape
@@ -22,6 +23,7 @@ import software.amazon.smithy.rust.codegen.core.smithy.RustSymbolProviderConfig
 import software.amazon.smithy.rust.codegen.core.smithy.generators.error.ErrorImplGenerator
 import software.amazon.smithy.rust.codegen.core.util.getTrait
 import software.amazon.smithy.rust.codegen.core.util.isEventStream
+import software.amazon.smithy.rust.codegen.server.python.smithy.generators.ConstrainedPythonBlobGenerator
 import software.amazon.smithy.rust.codegen.server.python.smithy.generators.PythonApplicationGenerator
 import software.amazon.smithy.rust.codegen.server.python.smithy.generators.PythonServerEnumGenerator
 import software.amazon.smithy.rust.codegen.server.python.smithy.generators.PythonServerEventStreamErrorGenerator
@@ -30,6 +32,7 @@ import software.amazon.smithy.rust.codegen.server.python.smithy.generators.Pytho
 import software.amazon.smithy.rust.codegen.server.python.smithy.generators.PythonServerOperationHandlerGenerator
 import software.amazon.smithy.rust.codegen.server.python.smithy.generators.PythonServerStructureGenerator
 import software.amazon.smithy.rust.codegen.server.python.smithy.generators.PythonServerUnionGenerator
+import software.amazon.smithy.rust.codegen.server.python.smithy.protocols.PythonServerProtocolLoader
 import software.amazon.smithy.rust.codegen.server.smithy.ServerCodegenContext
 import software.amazon.smithy.rust.codegen.server.smithy.ServerCodegenVisitor
 import software.amazon.smithy.rust.codegen.server.smithy.ServerModuleDocProvider
@@ -42,8 +45,9 @@ import software.amazon.smithy.rust.codegen.server.smithy.createInlineModuleCreat
 import software.amazon.smithy.rust.codegen.server.smithy.customize.ServerCodegenDecorator
 import software.amazon.smithy.rust.codegen.server.smithy.generators.UnconstrainedUnionGenerator
 import software.amazon.smithy.rust.codegen.server.smithy.generators.protocol.ServerProtocol
-import software.amazon.smithy.rust.codegen.server.smithy.protocols.ServerProtocolLoader
+import software.amazon.smithy.rust.codegen.server.smithy.isDirectlyConstrained
 import software.amazon.smithy.rust.codegen.server.smithy.traits.isReachableFromOperationInput
+import software.amazon.smithy.rust.codegen.server.smithy.withModuleOrWithStructureBuilderModule
 
 /**
  * Entrypoint for Python server-side code generation. This class will walk the in-memory model and
@@ -68,10 +72,10 @@ class PythonServerCodegenVisitor(
         val baseModel = baselineTransform(context.model)
         val service = settings.getService(baseModel)
         val (protocol, generator) =
-            ServerProtocolLoader(
+            PythonServerProtocolLoader(
                 codegenDecorator.protocols(
                     service.id,
-                    ServerProtocolLoader.DefaultProtocols,
+                    PythonServerProtocolLoader.defaultProtocols(settings.runtimeConfig),
                 ),
             )
                 .protocolFor(context.model, service)
@@ -258,4 +262,21 @@ class PythonServerCodegenVisitor(
             }
         }
     }
+
+    override fun blobShape(shape: BlobShape) {
+        logger.info("[python-server-codegen] Generating a service $shape")
+        super.blobShape(shape)
+
+        if (shape.isDirectlyConstrained(codegenContext.symbolProvider)) {
+            rustCrate.withModuleOrWithStructureBuilderModule(ServerRustModule.Model, shape, codegenContext) {
+                ConstrainedPythonBlobGenerator(
+                    codegenContext,
+                    rustCrate.createInlineModuleCreator(),
+                    this,
+                    shape,
+                    validationExceptionConversionGenerator,
+                ).render()
+            }
+        }
+    }
 }
diff --git a/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/generators/ConstrainedPythonBlobGenerator.kt b/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/generators/ConstrainedPythonBlobGenerator.kt
new file mode 100644
index 0000000000..a9c2021520
--- /dev/null
+++ b/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/generators/ConstrainedPythonBlobGenerator.kt
@@ -0,0 +1,100 @@
+/*
+ * Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
+ * SPDX-License-Identifier: Apache-2.0
+ */
+
+package software.amazon.smithy.rust.codegen.server.python.smithy.generators
+
+import software.amazon.smithy.codegen.core.Symbol
+import software.amazon.smithy.model.shapes.BlobShape
+import software.amazon.smithy.model.traits.LengthTrait
+import software.amazon.smithy.rust.codegen.core.rustlang.RustType
+import software.amazon.smithy.rust.codegen.core.rustlang.RustWriter
+import software.amazon.smithy.rust.codegen.core.rustlang.join
+import software.amazon.smithy.rust.codegen.core.rustlang.render
+import software.amazon.smithy.rust.codegen.core.rustlang.rust
+import software.amazon.smithy.rust.codegen.core.rustlang.rustTemplate
+import software.amazon.smithy.rust.codegen.core.smithy.RuntimeType
+import software.amazon.smithy.rust.codegen.core.smithy.makeMaybeConstrained
+import software.amazon.smithy.rust.codegen.core.smithy.rustType
+import software.amazon.smithy.rust.codegen.core.util.getTrait
+import software.amazon.smithy.rust.codegen.core.util.orNull
+import software.amazon.smithy.rust.codegen.server.python.smithy.PythonServerRuntimeType
+import software.amazon.smithy.rust.codegen.server.smithy.InlineModuleCreator
+import software.amazon.smithy.rust.codegen.server.smithy.PubCrateConstraintViolationSymbolProvider
+import software.amazon.smithy.rust.codegen.server.smithy.ServerCodegenContext
+import software.amazon.smithy.rust.codegen.server.smithy.generators.BlobLength
+import software.amazon.smithy.rust.codegen.server.smithy.generators.TraitInfo
+import software.amazon.smithy.rust.codegen.server.smithy.generators.ValidationExceptionConversionGenerator
+
+class ConstrainedPythonBlobGenerator(
+    val codegenContext: ServerCodegenContext,
+    private val inlineModuleCreator: InlineModuleCreator,
+    val writer: RustWriter,
+    val shape: BlobShape,
+    private val validationExceptionConversionGenerator: ValidationExceptionConversionGenerator,
+) {
+    val constrainedShapeSymbolProvider = codegenContext.constrainedShapeSymbolProvider
+    val publicConstrainedTypes = codegenContext.settings.codegenConfig.publicConstrainedTypes
+    private val constraintViolationSymbolProvider =
+        with(codegenContext.constraintViolationSymbolProvider) {
+            if (publicConstrainedTypes) {
+                this
+            } else {
+                PubCrateConstraintViolationSymbolProvider(this)
+            }
+        }
+    val constraintViolation = constraintViolationSymbolProvider.toSymbol(shape)
+    private val blobConstraintsInfo: List<BlobLength> = listOf(LengthTrait::class.java)
+        .mapNotNull { shape.getTrait(it).orNull() }
+        .map { BlobLength(it) }
+    private val constraintsInfo: List<TraitInfo> = blobConstraintsInfo.map { it.toTraitInfo() }
+
+    fun render() {
+        val symbol = constrainedShapeSymbolProvider.toSymbol(shape)
+        val blobType = PythonServerRuntimeType.blob(codegenContext.runtimeConfig).toSymbol().rustType()
+        renderFrom(symbol, blobType)
+        renderTryFrom(symbol, blobType)
+    }
+
+    fun renderFrom(symbol: Symbol, blobType: RustType) {
+        val name = symbol.name
+        val inner = blobType.render()
+        writer.rustTemplate(
+            """
+            impl #{From}<$inner> for #{MaybeConstrained} {
+                fn from(value: $inner) -> Self {
+                    Self::Unconstrained(value.into())
+                }
+            }
+
+            impl #{From}<$name> for $inner {
+                fn from(value: $name) -> Self {
+                    value.into_inner().into()
+                }
+            }
+            """,
+            "MaybeConstrained" to symbol.makeMaybeConstrained(),
+            "From" to RuntimeType.From,
+        )
+    }
+
+    fun renderTryFrom(symbol: Symbol, blobType: RustType) {
+        val name = symbol.name
+        val inner = blobType.render()
+        writer.rustTemplate(
+            """
+            impl #{TryFrom}<$inner> for $name {
+                type Error = #{ConstraintViolation};
+
+                fn try_from(value: $inner) -> Result<Self, Self::Error> {
+                    value.try_into()
+                }
+            }
+            """,
+            "TryFrom" to RuntimeType.TryFrom,
+            "ConstraintViolation" to constraintViolation,
+            "TryFromChecks" to constraintsInfo.map { it.tryFromCheck }.join("\n"),
+        )
+    }
+}
diff --git a/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/generators/PythonApplicationGenerator.kt b/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/generators/PythonApplicationGenerator.kt
index cc4804bb21..deec6f6b29 100644
--- a/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/generators/PythonApplicationGenerator.kt
+++ b/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/generators/PythonApplicationGenerator.kt
@@ -8,6 +8,7 @@ package software.amazon.smithy.rust.codegen.server.python.smithy.generators
 import software.amazon.smithy.model.knowledge.TopDownIndex
 import software.amazon.smithy.model.shapes.OperationShape
 import software.amazon.smithy.model.traits.DocumentationTrait
+import software.amazon.smithy.rust.codegen.core.rustlang.RustReservedWords
 import software.amazon.smithy.rust.codegen.core.rustlang.RustWriter
 import software.amazon.smithy.rust.codegen.core.rustlang.rust
 import software.amazon.smithy.rust.codegen.core.rustlang.rustBlockTemplate
@@ -203,14 +204,13 @@ class PythonApplicationGenerator(
                     *codegenScope,
                 )
                 for (operation in operations) {
-                    val operationName = symbolProvider.toSymbol(operation).name
-                    val name = operationName.toSnakeCase()
+                    val fnName = RustReservedWords.escapeIfNeeded(symbolProvider.toSymbol(operation).name.toSnakeCase())
                     rustTemplate(
                         """
-                        let ${name}_locals = #{pyo3_asyncio}::TaskLocals::new(event_loop);
-                        let handler = self.handlers.get("$name").expect("Python handler for operation `$name` not found").clone();
-                        let builder = builder.$name(move |input, state| {
-                            #{pyo3_asyncio}::tokio::scope(${name}_locals.clone(), crate::python_operation_adaptor::$name(input, state, handler.clone()))
+                        let ${fnName}_locals = #{pyo3_asyncio}::TaskLocals::new(event_loop);
+                        let handler = self.handlers.get("$fnName").expect("Python handler for operation `$fnName` not found").clone();
+                        let builder = builder.$fnName(move |input, state| {
+                            #{pyo3_asyncio}::tokio::scope(${fnName}_locals.clone(), crate::python_operation_adaptor::$fnName(input, state, handler.clone()))
                         });
                         """,
                         *codegenScope,
@@ -342,7 +342,7 @@ class PythonApplicationGenerator(
             )
             operations.map { operation ->
                 val operationName = symbolProvider.toSymbol(operation).name
-                val name = operationName.toSnakeCase()
+                val fnName = RustReservedWords.escapeIfNeeded(symbolProvider.toSymbol(operation).name.toSnakeCase())
 
                 val input = PythonType.Opaque("${operationName}Input", "crate::input")
                 val output = PythonType.Opaque("${operationName}Output", "crate::output")
@@ -363,15 +363,15 @@ class PythonApplicationGenerator(
 
                 rustTemplate(
                     """
-                    /// Method to register `$name` Python implementation inside the handlers map.
+                    /// Method to register `$fnName` Python implementation inside the handlers map.
                     /// It can be used as a function decorator in Python.
                     ///
                     /// :param func ${handler.renderAsDocstring()}:
                     /// :rtype ${PythonType.None.renderAsDocstring()}:
                     ##[pyo3(text_signature = "(${'$'}self, func)")]
-                    pub fn $name(&mut self, py: #{pyo3}::Python, func: #{pyo3}::PyObject) -> #{pyo3}::PyResult<()> {
+                    pub fn $fnName(&mut self, py: #{pyo3}::Python, func: #{pyo3}::PyObject) -> #{pyo3}::PyResult<()> {
                         use #{SmithyPython}::PyApp;
-                        self.register_operation(py, "$name", func)
+                        self.register_operation(py, "$fnName", func)
                     }
                     """,
                     *codegenScope,
diff --git a/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/generators/PythonServerModuleGenerator.kt b/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/generators/PythonServerModuleGenerator.kt
index 8a622c51ef..5baf6e83ea 100644
--- a/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/generators/PythonServerModuleGenerator.kt
+++ b/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/generators/PythonServerModuleGenerator.kt
@@ -15,6 +15,7 @@ import software.amazon.smithy.rust.codegen.core.rustlang.RustWriter
 import software.amazon.smithy.rust.codegen.core.rustlang.rustBlockTemplate
 import software.amazon.smithy.rust.codegen.core.rustlang.rustTemplate
 import software.amazon.smithy.rust.codegen.core.smithy.RustCrate
+import software.amazon.smithy.rust.codegen.core.util.toPascalCase
 import software.amazon.smithy.rust.codegen.core.util.toSnakeCase
 import software.amazon.smithy.rust.codegen.server.python.smithy.PythonServerCargoDependency
 import software.amazon.smithy.rust.codegen.server.python.smithy.PythonServerRustModule
@@ -71,13 +72,13 @@ class PythonServerModuleGenerator(
                 when (shape) {
                     is UnionShape -> rustTemplate(
                         """
-                        $moduleType.add_class::<crate::$moduleType::PyUnionMarker${shape.id.name}>()?;
+                        $moduleType.add_class::<crate::$moduleType::PyUnionMarker${shape.id.name.toPascalCase()}>()?;
                         """,
                         *codegenScope,
                     )
                     else -> rustTemplate(
                         """
-                        $moduleType.add_class::<crate::$moduleType::${shape.id.name}>()?;
+                        $moduleType.add_class::<crate::$moduleType::${shape.id.name.toPascalCase()}>()?;
                         """,
                         *codegenScope,
                     )
diff --git a/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/generators/PythonServerOperationHandlerGenerator.kt b/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/generators/PythonServerOperationHandlerGenerator.kt
index f107806098..e8a704ecdd 100644
--- a/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/generators/PythonServerOperationHandlerGenerator.kt
+++ b/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/generators/PythonServerOperationHandlerGenerator.kt
@@ -6,11 +6,13 @@
 package software.amazon.smithy.rust.codegen.server.python.smithy.generators
 
 import software.amazon.smithy.model.shapes.OperationShape
+import software.amazon.smithy.rust.codegen.core.rustlang.RustReservedWords
 import software.amazon.smithy.rust.codegen.core.rustlang.RustWriter
 import software.amazon.smithy.rust.codegen.core.rustlang.Writable
 import software.amazon.smithy.rust.codegen.core.rustlang.rustTemplate
 import software.amazon.smithy.rust.codegen.core.rustlang.writable
 import software.amazon.smithy.rust.codegen.core.smithy.CodegenContext
+import software.amazon.smithy.rust.codegen.core.util.toPascalCase
 import software.amazon.smithy.rust.codegen.core.util.toSnakeCase
 import software.amazon.smithy.rust.codegen.server.python.smithy.PythonServerCargoDependency
 
@@ -50,10 +52,11 @@ class PythonServerOperationHandlerGenerator(
 
     private fun renderPythonOperationHandlerImpl(writer: RustWriter) {
         val operationName = symbolProvider.toSymbol(operation).name
-        val input = "crate::input::${operationName}Input"
-        val output = "crate::output::${operationName}Output"
+        val input = "crate::input::${operationName.toPascalCase()}Input"
+        val output = "crate::output::${operationName.toPascalCase()}Output"
+        // TODO(https://github.com/awslabs/smithy-rs/issues/2552) - Use to pascalCase for error shapes.
         val error = "crate::error::${operationName}Error"
-        val fnName = operationName.toSnakeCase()
+        val fnName = RustReservedWords.escapeIfNeeded(symbolProvider.toSymbol(operation).name.toSnakeCase())
 
         writer.rustTemplate(
             """
diff --git a/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/generators/PythonServerStructureGenerator.kt b/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/generators/PythonServerStructureGenerator.kt
index 28b48d31e3..1502f5422a 100644
--- a/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/generators/PythonServerStructureGenerator.kt
+++ b/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/generators/PythonServerStructureGenerator.kt
@@ -60,6 +60,9 @@ class PythonServerStructureGenerator(
         writer.rustTemplate("#{ConstructorSignature:W}", "ConstructorSignature" to renderConstructorSignature())
         super.renderStructure()
         renderPyO3Methods()
+        if (!shape.hasTrait<ErrorTrait>()) {
+            renderPyBoxTraits()
+        }
     }
 
     override fun renderStructureMember(
@@ -101,6 +104,25 @@ class PythonServerStructureGenerator(
         )
     }
 
+    private fun renderPyBoxTraits() {
+        writer.rustTemplate(
+            """
+            impl<'source> #{pyo3}::FromPyObject<'source> for std::boxed::Box<$name> {
+                fn extract(ob: &'source #{pyo3}::PyAny) -> #{pyo3}::PyResult<Self> {
+                    ob.extract::<$name>().map(Box::new)
+                }
+            }
+
+            impl #{pyo3}::IntoPy<#{pyo3}::PyObject> for std::boxed::Box<$name> {
+                fn into_py(self, py: #{pyo3}::Python<'_>) -> #{pyo3}::PyObject {
+                    (*self).into_py(py)
+                }
+            }
+            """,
+            "pyo3" to pyO3,
+        )
+    }
+
     private fun renderStructSignatureMembers(): Writable =
         writable {
             forEachMember(members) { _, memberName, memberSymbol ->
diff --git a/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/generators/PythonServerUnionGenerator.kt b/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/generators/PythonServerUnionGenerator.kt
index df083751ae..6b7a7bee8a 100644
--- a/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/generators/PythonServerUnionGenerator.kt
+++ b/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/generators/PythonServerUnionGenerator.kt
@@ -121,7 +121,7 @@ class PythonServerUnionGenerator(
             )
             writer.rust("/// :rtype ${unionSymbol.name}:")
             writer.rustBlock("pub fn $funcNamePart() -> Self") {
-                rust("Self(${unionSymbol.name}::$variantName")
+                rust("Self(${unionSymbol.name}::$variantName)")
             }
         } else {
             val memberSymbol = symbolProvider.toSymbol(member)
@@ -157,7 +157,7 @@ class PythonServerUnionGenerator(
             writer.rustBlockTemplate("pub fn as_$funcNamePart(&self) -> #{pyo3}::PyResult<()>", "pyo3" to pyo3) {
                 rustTemplate(
                     """
-                    self.0.as_$funcNamePart().map_err(#{pyo3}::exceptions::PyValueError::new_err(
+                    self.0.as_$funcNamePart().map_err(|_| #{pyo3}::exceptions::PyValueError::new_err(
                         "${unionSymbol.name} variant is not None"
                     ))
                     """,
diff --git a/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/protocols/PythonServerProtocolLoader.kt b/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/protocols/PythonServerProtocolLoader.kt
new file mode 100644
index 0000000000..f84d35e7cb
--- /dev/null
+++ b/codegen-server/python/src/main/kotlin/software/amazon/smithy/rust/codegen/server/python/smithy/protocols/PythonServerProtocolLoader.kt
@@ -0,0 +1,125 @@
+
+/*
+ * Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
+ * SPDX-License-Identifier: Apache-2.0
+ */
+
+package software.amazon.smithy.rust.codegen.server.python.smithy.protocols
+
+import software.amazon.smithy.aws.traits.protocols.AwsJson1_0Trait
+import software.amazon.smithy.aws.traits.protocols.AwsJson1_1Trait
+import software.amazon.smithy.aws.traits.protocols.RestJson1Trait
+import software.amazon.smithy.rust.codegen.core.rustlang.Writable
+import software.amazon.smithy.rust.codegen.core.rustlang.rust
+import software.amazon.smithy.rust.codegen.core.rustlang.writable
+import software.amazon.smithy.rust.codegen.core.smithy.RuntimeConfig
+import software.amazon.smithy.rust.codegen.core.smithy.generators.http.HttpBindingCustomization
+import software.amazon.smithy.rust.codegen.core.smithy.generators.http.HttpBindingSection
+import software.amazon.smithy.rust.codegen.core.smithy.protocols.AwsJsonVersion
+import software.amazon.smithy.rust.codegen.core.smithy.protocols.ProtocolLoader
+import software.amazon.smithy.rust.codegen.core.smithy.protocols.ProtocolMap
+import software.amazon.smithy.rust.codegen.core.smithy.protocols.parse.JsonParserCustomization
+import software.amazon.smithy.rust.codegen.core.smithy.protocols.parse.JsonParserSection
+import software.amazon.smithy.rust.codegen.server.python.smithy.PythonServerRuntimeType
+import software.amazon.smithy.rust.codegen.server.smithy.ServerCodegenContext
+import software.amazon.smithy.rust.codegen.server.smithy.generators.protocol.ServerProtocolGenerator
+import software.amazon.smithy.rust.codegen.server.smithy.protocols.ServerAwsJsonFactory
+import software.amazon.smithy.rust.codegen.server.smithy.protocols.ServerHttpBoundProtocolCustomization
+import software.amazon.smithy.rust.codegen.server.smithy.protocols.ServerHttpBoundProtocolSection
+import software.amazon.smithy.rust.codegen.server.smithy.protocols.ServerRestJsonFactory
+
+/**
+ * Customization class used to force casting a non primitive type into one overriden by a new symbol provider,
+ * by explicitly calling `from()` on it.
+ *
+ * For example we use this in the server Python implementation, where we override types like [Blob], [DateTime] and [Document]
+ * with wrappers compatible with Python, without touching the original implementation coming from `aws-smithy-types`.
+ */
+class PythonServerAfterDeserializedMemberJsonParserCustomization(private val runtimeConfig: RuntimeConfig) :
+    JsonParserCustomization() {
+    override fun section(section: JsonParserSection): Writable = when (section) {
+        is JsonParserSection.AfterTimestampDeserializedMember -> writable {
+            rust(".map(#T::from)", PythonServerRuntimeType.dateTime(runtimeConfig).toSymbol())
+        }
+        is JsonParserSection.AfterBlobDeserializedMember -> writable {
+            rust(".map(#T::from)", PythonServerRuntimeType.blob(runtimeConfig).toSymbol())
+        }
+        is JsonParserSection.AfterDocumentDeserializedMember -> writable {
+            rust(".map(#T::from)", PythonServerRuntimeType.document(runtimeConfig).toSymbol())
+        }
+        else -> emptySection
+    }
+}
+
+/**
+ * Customization class used to force casting a non primitive type into one overriden by a new symbol provider,
+ * by explicitly calling `into()` on it.
+ */
+class PythonServerAfterDeserializedMemberServerHttpBoundCustomization() :
+    ServerHttpBoundProtocolCustomization() {
+    override fun section(section: ServerHttpBoundProtocolSection): Writable = when (section) {
+        is ServerHttpBoundProtocolSection.AfterTimestampDeserializedMember -> writable {
+            rust(".into()")
+        }
+        else -> emptySection
+    }
+}
+
+/**
+ * Customization class used to force casting a `Vec<DateTime>` into one a Python `Vec<DateTime>`
+ */
+class PythonServerAfterDeserializedMemberHttpBindingCustomization(private val runtimeConfig: RuntimeConfig) :
+    HttpBindingCustomization() {
+    override fun section(section: HttpBindingSection): Writable = when (section) {
+        is HttpBindingSection.AfterDeserializingIntoADateTimeOfHttpHeaders -> writable {
+            rust(".into_iter().map(#T::from).collect()", PythonServerRuntimeType.dateTime(runtimeConfig).toSymbol())
+        }
+        else -> emptySection
+    }
+}
+
+class PythonServerProtocolLoader(
+    private val supportedProtocols: ProtocolMap<ServerProtocolGenerator, ServerCodegenContext>,
+) : ProtocolLoader<ServerProtocolGenerator, ServerCodegenContext>(supportedProtocols) {
+
+    companion object {
+        fun defaultProtocols(runtimeConfig: RuntimeConfig) =
+            mapOf(
+                RestJson1Trait.ID to ServerRestJsonFactory(
+                    additionalParserCustomizations = listOf(
+                        PythonServerAfterDeserializedMemberJsonParserCustomization(runtimeConfig),
+                    ),
+                    additionalServerHttpBoundProtocolCustomizations = listOf(
+                        PythonServerAfterDeserializedMemberServerHttpBoundCustomization(),
+                    ),
+                    additionalHttpBindingCustomizations = listOf(
+                        PythonServerAfterDeserializedMemberHttpBindingCustomization(runtimeConfig),
+                    ),
+                ),
+                AwsJson1_0Trait.ID to ServerAwsJsonFactory(
+                    AwsJsonVersion.Json10,
+                    additionalParserCustomizations = listOf(
+                        PythonServerAfterDeserializedMemberJsonParserCustomization(runtimeConfig),
+                    ),
+                    additionalServerHttpBoundProtocolCustomizations = listOf(
+                        PythonServerAfterDeserializedMemberServerHttpBoundCustomization(),
+                    ),
+                    additionalHttpBindingCustomizations = listOf(
+                        PythonServerAfterDeserializedMemberHttpBindingCustomization(runtimeConfig),
+                    ),
+                ),
+                AwsJson1_1Trait.ID to ServerAwsJsonFactory(
+                    AwsJsonVersion.Json11,
+                    additionalParserCustomizations = listOf(
+                        PythonServerAfterDeserializedMemberJsonParserCustomization(runtimeConfig),
+                    ),
+                    additionalServerHttpBoundProtocolCustomizations = listOf(
+                        PythonServerAfterDeserializedMemberServerHttpBoundCustomization(),
+                    ),
+                    additionalHttpBindingCustomizations = listOf(
+                        PythonServerAfterDeserializedMemberHttpBindingCustomization(runtimeConfig),
+                    ),
+                ),
+            )
+    }
+}
diff --git a/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/generators/http/ServerRequestBindingGenerator.kt b/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/generators/http/ServerRequestBindingGenerator.kt
index 41201b8695..e1e6c747f7 100644
--- a/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/generators/http/ServerRequestBindingGenerator.kt
+++ b/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/generators/http/ServerRequestBindingGenerator.kt
@@ -28,6 +28,7 @@ class ServerRequestBindingGenerator(
     protocol: Protocol,
     codegenContext: ServerCodegenContext,
     operationShape: OperationShape,
+    additionalHttpBindingCustomizations: List<HttpBindingCustomization> = listOf(),
 ) {
     private val httpBindingGenerator =
         HttpBindingGenerator(
@@ -39,7 +40,7 @@ class ServerRequestBindingGenerator(
                 ServerRequestAfterDeserializingIntoAHashMapOfHttpPrefixHeadersWrapInUnconstrainedMapHttpBindingCustomization(
                     codegenContext,
                 ),
-            ),
+            ) + additionalHttpBindingCustomizations,
         )
 
     fun generateDeserializeHeaderFn(binding: HttpBindingDescriptor): RuntimeType =
@@ -81,5 +82,6 @@ class ServerRequestAfterDeserializingIntoAHashMapOfHttpPrefixHeadersWrapInUncons
                 )
             }
         }
+        else -> emptySection
     }
 }
diff --git a/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/generators/http/ServerResponseBindingGenerator.kt b/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/generators/http/ServerResponseBindingGenerator.kt
index cc47830054..01448d27a4 100644
--- a/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/generators/http/ServerResponseBindingGenerator.kt
+++ b/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/generators/http/ServerResponseBindingGenerator.kt
@@ -71,6 +71,7 @@ class ServerResponseBeforeIteratingOverMapBoundWithHttpPrefixHeadersUnwrapConstr
 
         is HttpBindingSection.BeforeRenderingHeaderValue,
         is HttpBindingSection.AfterDeserializingIntoAHashMapOfHttpPrefixHeaders,
+        is HttpBindingSection.AfterDeserializingIntoADateTimeOfHttpHeaders,
         -> emptySection
     }
 }
@@ -100,6 +101,7 @@ class ServerResponseBeforeRenderingHeadersHttpBindingCustomization(val codegenCo
 
         is HttpBindingSection.BeforeIteratingOverMapShapeBoundWithHttpPrefixHeaders,
         is HttpBindingSection.AfterDeserializingIntoAHashMapOfHttpPrefixHeaders,
+        is HttpBindingSection.AfterDeserializingIntoADateTimeOfHttpHeaders,
         -> emptySection
     }
 }
diff --git a/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/generators/protocol/ServerProtocol.kt b/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/generators/protocol/ServerProtocol.kt
index 0b466f95c2..3ee16c233f 100644
--- a/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/generators/protocol/ServerProtocol.kt
+++ b/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/generators/protocol/ServerProtocol.kt
@@ -106,6 +106,7 @@ fun jsonParserGenerator(
     codegenContext: ServerCodegenContext,
     httpBindingResolver: HttpBindingResolver,
     jsonName: (MemberShape) -> String,
+    additionalParserCustomizations: List<JsonParserCustomization> = listOf(),
 ): JsonParserGenerator =
     JsonParserGenerator(
         codegenContext,
@@ -114,12 +115,13 @@ fun jsonParserGenerator(
         returnSymbolToParseFn(codegenContext),
         listOf(
             ServerRequestBeforeBoxingDeserializedMemberConvertToMaybeConstrainedJsonParserCustomization(codegenContext),
-        ),
+        ) + additionalParserCustomizations,
     )
 
 class ServerAwsJsonProtocol(
     private val serverCodegenContext: ServerCodegenContext,
     awsJsonVersion: AwsJsonVersion,
+    private val additionalParserCustomizations: List<JsonParserCustomization> = listOf(),
 ) : AwsJson(serverCodegenContext, awsJsonVersion), ServerProtocol {
     private val runtimeConfig = codegenContext.runtimeConfig
 
@@ -130,7 +132,7 @@ class ServerAwsJsonProtocol(
         }
 
     override fun structuredDataParser(): StructuredDataParserGenerator =
-        jsonParserGenerator(serverCodegenContext, httpBindingResolver, ::awsJsonFieldName)
+        jsonParserGenerator(serverCodegenContext, httpBindingResolver, ::awsJsonFieldName, additionalParserCustomizations)
 
     override fun structuredDataSerializer(): StructuredDataSerializerGenerator =
         ServerAwsJsonSerializerGenerator(serverCodegenContext, httpBindingResolver, awsJsonVersion)
@@ -183,13 +185,14 @@ private fun restRouterType(runtimeConfig: RuntimeConfig) =
 
 class ServerRestJsonProtocol(
     private val serverCodegenContext: ServerCodegenContext,
+    private val additionalParserCustomizations: List<JsonParserCustomization> = listOf(),
 ) : RestJson(serverCodegenContext), ServerProtocol {
     val runtimeConfig = codegenContext.runtimeConfig
 
     override val protocolModulePath: String = "rest_json_1"
 
     override fun structuredDataParser(): StructuredDataParserGenerator =
-        jsonParserGenerator(serverCodegenContext, httpBindingResolver, ::restJsonFieldName)
+        jsonParserGenerator(serverCodegenContext, httpBindingResolver, ::restJsonFieldName, additionalParserCustomizations)
 
     override fun structuredDataSerializer(): StructuredDataSerializerGenerator =
         ServerRestJsonSerializerGenerator(serverCodegenContext, httpBindingResolver)
@@ -254,5 +257,6 @@ class ServerRequestBeforeBoxingDeserializedMemberConvertToMaybeConstrainedJsonPa
                 rust(".map(|x| x.into())")
             }
         }
+        else -> emptySection
     }
 }
diff --git a/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/protocols/ServerAwsJson.kt b/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/protocols/ServerAwsJson.kt
index 2a3467cd6b..920813e34d 100644
--- a/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/protocols/ServerAwsJson.kt
+++ b/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/protocols/ServerAwsJson.kt
@@ -10,11 +10,13 @@ import software.amazon.smithy.rust.codegen.core.rustlang.Writable
 import software.amazon.smithy.rust.codegen.core.rustlang.escape
 import software.amazon.smithy.rust.codegen.core.rustlang.rust
 import software.amazon.smithy.rust.codegen.core.rustlang.writable
+import software.amazon.smithy.rust.codegen.core.smithy.generators.http.HttpBindingCustomization
 import software.amazon.smithy.rust.codegen.core.smithy.generators.protocol.ProtocolSupport
 import software.amazon.smithy.rust.codegen.core.smithy.protocols.AwsJsonVersion
 import software.amazon.smithy.rust.codegen.core.smithy.protocols.HttpBindingResolver
 import software.amazon.smithy.rust.codegen.core.smithy.protocols.ProtocolGeneratorFactory
 import software.amazon.smithy.rust.codegen.core.smithy.protocols.awsJsonFieldName
+import software.amazon.smithy.rust.codegen.core.smithy.protocols.parse.JsonParserCustomization
 import software.amazon.smithy.rust.codegen.core.smithy.protocols.serialize.JsonSerializerCustomization
 import software.amazon.smithy.rust.codegen.core.smithy.protocols.serialize.JsonSerializerGenerator
 import software.amazon.smithy.rust.codegen.core.smithy.protocols.serialize.JsonSerializerSection
@@ -30,13 +32,22 @@ import software.amazon.smithy.rust.codegen.server.smithy.generators.protocol.Ser
  * AwsJson 1.0 and 1.1 server-side protocol factory. This factory creates the [ServerHttpBoundProtocolGenerator]
  * with AwsJson specific configurations.
  */
-class ServerAwsJsonFactory(private val version: AwsJsonVersion) :
-    ProtocolGeneratorFactory<ServerHttpBoundProtocolGenerator, ServerCodegenContext> {
+class ServerAwsJsonFactory(
+    private val version: AwsJsonVersion,
+    private val additionalParserCustomizations: List<JsonParserCustomization> = listOf(),
+    private val additionalServerHttpBoundProtocolCustomizations: List<ServerHttpBoundProtocolCustomization> = listOf(),
+    private val additionalHttpBindingCustomizations: List<HttpBindingCustomization> = listOf(),
+) : ProtocolGeneratorFactory<ServerHttpBoundProtocolGenerator, ServerCodegenContext> {
     override fun protocol(codegenContext: ServerCodegenContext): ServerProtocol =
-        ServerAwsJsonProtocol(codegenContext, version)
+        ServerAwsJsonProtocol(codegenContext, version, additionalParserCustomizations)
 
     override fun buildProtocolGenerator(codegenContext: ServerCodegenContext): ServerHttpBoundProtocolGenerator =
-        ServerHttpBoundProtocolGenerator(codegenContext, protocol(codegenContext))
+        ServerHttpBoundProtocolGenerator(
+            codegenContext,
+            protocol(codegenContext),
+            additionalServerHttpBoundProtocolCustomizations,
+            additionalHttpBindingCustomizations,
+        )
 
     override fun support(): ProtocolSupport {
         return ProtocolSupport(
diff --git a/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/protocols/ServerHttpBoundProtocolGenerator.kt b/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/protocols/ServerHttpBoundProtocolGenerator.kt
index 9a7e45f112..889967412e 100644
--- a/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/protocols/ServerHttpBoundProtocolGenerator.kt
+++ b/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/protocols/ServerHttpBoundProtocolGenerator.kt
@@ -16,6 +16,7 @@ import software.amazon.smithy.model.pattern.UriPattern
 import software.amazon.smithy.model.shapes.BooleanShape
 import software.amazon.smithy.model.shapes.CollectionShape
 import software.amazon.smithy.model.shapes.MapShape
+import software.amazon.smithy.model.shapes.MemberShape
 import software.amazon.smithy.model.shapes.NumberShape
 import software.amazon.smithy.model.shapes.OperationShape
 import software.amazon.smithy.model.shapes.Shape
@@ -42,8 +43,10 @@ import software.amazon.smithy.rust.codegen.core.rustlang.withBlockTemplate
 import software.amazon.smithy.rust.codegen.core.rustlang.writable
 import software.amazon.smithy.rust.codegen.core.smithy.CodegenTarget
 import software.amazon.smithy.rust.codegen.core.smithy.RuntimeType
+import software.amazon.smithy.rust.codegen.core.smithy.customize.NamedCustomization
 import software.amazon.smithy.rust.codegen.core.smithy.customize.OperationCustomization
-import software.amazon.smithy.rust.codegen.core.smithy.generators.TypeConversionGenerator
+import software.amazon.smithy.rust.codegen.core.smithy.customize.Section
+import software.amazon.smithy.rust.codegen.core.smithy.generators.http.HttpBindingCustomization
 import software.amazon.smithy.rust.codegen.core.smithy.generators.http.HttpMessageType
 import software.amazon.smithy.rust.codegen.core.smithy.generators.setterName
 import software.amazon.smithy.rust.codegen.core.smithy.isOptional
@@ -77,6 +80,18 @@ import software.amazon.smithy.rust.codegen.server.smithy.generators.protocol.Ser
 import software.amazon.smithy.rust.codegen.server.smithy.generators.serverBuilderSymbol
 import java.util.logging.Logger
 
+/**
+ * Class describing a ServerHttpBoundProtocol section that can be used in a customization.
+ */
+sealed class ServerHttpBoundProtocolSection(name: String) : Section(name) {
+    data class AfterTimestampDeserializedMember(val shape: MemberShape) : ServerHttpBoundProtocolSection("AfterTimestampDeserializedMember")
+}
+
+/**
+ * Customization for the ServerHttpBoundProtocol generator.
+ */
+typealias ServerHttpBoundProtocolCustomization = NamedCustomization<ServerHttpBoundProtocolSection>
+
 /**
  * Implement operations' input parsing and output serialization. Protocols can plug their own implementations
  * and overrides by creating a protocol factory inheriting from this class and feeding it to the [ServerProtocolLoader].
@@ -85,10 +100,12 @@ import java.util.logging.Logger
 class ServerHttpBoundProtocolGenerator(
     codegenContext: ServerCodegenContext,
     protocol: ServerProtocol,
+    customizations: List<ServerHttpBoundProtocolCustomization> = listOf(),
+    additionalHttpBindingCustomizations: List<HttpBindingCustomization> = listOf(),
 ) : ServerProtocolGenerator(
     codegenContext,
     protocol,
-    ServerHttpBoundProtocolTraitImplGenerator(codegenContext, protocol),
+    ServerHttpBoundProtocolTraitImplGenerator(codegenContext, protocol, customizations, additionalHttpBindingCustomizations),
 ) {
     // Define suffixes for operation input / output / error wrappers
     companion object {
@@ -104,6 +121,8 @@ class ServerHttpBoundProtocolGenerator(
 class ServerHttpBoundProtocolTraitImplGenerator(
     private val codegenContext: ServerCodegenContext,
     private val protocol: ServerProtocol,
+    private val customizations: List<ServerHttpBoundProtocolCustomization>,
+    private val additionalHttpBindingCustomizations: List<HttpBindingCustomization>,
 ) {
     private val logger = Logger.getLogger(javaClass.name)
     private val symbolProvider = codegenContext.symbolProvider
@@ -111,7 +130,6 @@ class ServerHttpBoundProtocolTraitImplGenerator(
     private val model = codegenContext.model
     private val runtimeConfig = codegenContext.runtimeConfig
     private val httpBindingResolver = protocol.httpBindingResolver
-    private val typeConversionGenerator = TypeConversionGenerator(model, symbolProvider, runtimeConfig)
     private val protocolFunctions = ProtocolFunctions(codegenContext)
 
     private val codegenScope = arrayOf(
@@ -568,9 +586,9 @@ class ServerHttpBoundProtocolTraitImplGenerator(
     private fun serverRenderHttpResponseCode(defaultCode: Int) = writable {
         check(defaultCode in 100..999) {
             """
-           Smithy library lied to us. According to https://smithy.io/2.0/spec/http-bindings.html#http-trait,
-           "The provided value SHOULD be between 100 and 599, and it MUST be between 100 and 999".
-           """.replace("\n", "").trimIndent()
+            Smithy library lied to us. According to https://smithy.io/2.0/spec/http-bindings.html#http-trait,
+            "The provided value SHOULD be between 100 and 599, and it MUST be between 100 and 999".
+            """.replace("\n", "").trimIndent()
         }
         rustTemplate(
             """
@@ -611,7 +629,7 @@ class ServerHttpBoundProtocolTraitImplGenerator(
         inputShape: StructureShape,
         bindings: List<HttpBindingDescriptor>,
     ) {
-        val httpBindingGenerator = ServerRequestBindingGenerator(protocol, codegenContext, operationShape)
+        val httpBindingGenerator = ServerRequestBindingGenerator(protocol, codegenContext, operationShape, additionalHttpBindingCustomizations)
         val structuredDataParser = protocol.structuredDataParser()
         Attribute.AllowUnusedMut.render(this)
         rust(
@@ -952,12 +970,15 @@ class ServerHttpBoundProtocolTraitImplGenerator(
                                 val timestampFormatType = RuntimeType.parseTimestampFormat(CodegenTarget.SERVER, runtimeConfig, timestampFormat)
                                 rustTemplate(
                                     """
-                                    let v = #{DateTime}::from_str(&v, #{format})?#{ConvertInto:W};
+                                    let v = #{DateTime}::from_str(&v, #{format})?
                                     """.trimIndent(),
                                     *codegenScope,
                                     "format" to timestampFormatType,
-                                    "ConvertInto" to typeConversionGenerator.convertViaInto(memberShape),
                                 )
+                                for (customization in customizations) {
+                                    customization.section(ServerHttpBoundProtocolSection.AfterTimestampDeserializedMember(it.member))(this)
+                                }
+                                rust(";")
                             }
                             else -> { // Number or boolean.
                                 rust(
@@ -1047,7 +1068,7 @@ class ServerHttpBoundProtocolTraitImplGenerator(
     }
 
     private fun serverRenderHeaderParser(writer: RustWriter, binding: HttpBindingDescriptor, operationShape: OperationShape) {
-        val httpBindingGenerator = ServerRequestBindingGenerator(protocol, codegenContext, operationShape)
+        val httpBindingGenerator = ServerRequestBindingGenerator(protocol, codegenContext, operationShape, additionalHttpBindingCustomizations)
         val deserializer = httpBindingGenerator.generateDeserializeHeaderFn(binding)
         writer.rustTemplate(
             """
@@ -1109,22 +1130,24 @@ class ServerHttpBoundProtocolTraitImplGenerator(
                             rustTemplate(
                                 """
                                 let value = #{PercentEncoding}::percent_decode_str(value).decode_utf8()?;
-                                let value = #{DateTime}::from_str(value.as_ref(), #{format})?#{ConvertInto:W};
+                                let value = #{DateTime}::from_str(value.as_ref(), #{format})?
                                 """,
                                 *codegenScope,
                                 "format" to timestampFormatType,
-                                "ConvertInto" to typeConversionGenerator.convertViaInto(target),
                             )
                         } else {
                             rustTemplate(
                                 """
-                                let value = #{DateTime}::from_str(value, #{format})?#{ConvertInto:W};
+                                let value = #{DateTime}::from_str(value, #{format})?
                                 """,
                                 *codegenScope,
                                 "format" to timestampFormatType,
-                                "ConvertInto" to typeConversionGenerator.convertViaInto(target),
                             )
                         }
+                        for (customization in customizations) {
+                            customization.section(ServerHttpBoundProtocolSection.AfterTimestampDeserializedMember(binding.member))(this)
+                        }
+                        rust(";")
                     }
                     else -> {
                         check(target is NumberShape || target is BooleanShape)
diff --git a/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/protocols/ServerRestJson.kt b/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/protocols/ServerRestJson.kt
index 744ef93bc5..ddf1ca08c3 100644
--- a/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/protocols/ServerRestJson.kt
+++ b/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/protocols/ServerRestJson.kt
@@ -5,10 +5,12 @@
 
 package software.amazon.smithy.rust.codegen.server.smithy.protocols
 
+import software.amazon.smithy.rust.codegen.core.smithy.generators.http.HttpBindingCustomization
 import software.amazon.smithy.rust.codegen.core.smithy.generators.protocol.ProtocolSupport
 import software.amazon.smithy.rust.codegen.core.smithy.protocols.HttpBindingResolver
 import software.amazon.smithy.rust.codegen.core.smithy.protocols.Protocol
 import software.amazon.smithy.rust.codegen.core.smithy.protocols.ProtocolGeneratorFactory
+import software.amazon.smithy.rust.codegen.core.smithy.protocols.parse.JsonParserCustomization
 import software.amazon.smithy.rust.codegen.core.smithy.protocols.restJsonFieldName
 import software.amazon.smithy.rust.codegen.core.smithy.protocols.serialize.JsonSerializerGenerator
 import software.amazon.smithy.rust.codegen.core.smithy.protocols.serialize.StructuredDataSerializerGenerator
@@ -21,11 +23,23 @@ import software.amazon.smithy.rust.codegen.server.smithy.generators.protocol.Ser
  * RestJson1 server-side protocol factory. This factory creates the [ServerHttpProtocolGenerator]
  * with RestJson1 specific configurations.
  */
-class ServerRestJsonFactory : ProtocolGeneratorFactory<ServerHttpBoundProtocolGenerator, ServerCodegenContext> {
-    override fun protocol(codegenContext: ServerCodegenContext): Protocol = ServerRestJsonProtocol(codegenContext)
+class ServerRestJsonFactory(
+    private val additionalParserCustomizations: List<JsonParserCustomization> = listOf(),
+    private val additionalServerHttpBoundProtocolCustomizations: List<ServerHttpBoundProtocolCustomization> = listOf(),
+    private val additionalHttpBindingCustomizations: List<HttpBindingCustomization> = listOf(),
+) : ProtocolGeneratorFactory<ServerHttpBoundProtocolGenerator, ServerCodegenContext> {
+    override fun protocol(codegenContext: ServerCodegenContext): Protocol = ServerRestJsonProtocol(codegenContext, additionalParserCustomizations)
 
     override fun buildProtocolGenerator(codegenContext: ServerCodegenContext): ServerHttpBoundProtocolGenerator =
-        ServerHttpBoundProtocolGenerator(codegenContext, ServerRestJsonProtocol(codegenContext))
+        ServerHttpBoundProtocolGenerator(
+            codegenContext,
+            ServerRestJsonProtocol(
+                codegenContext,
+                additionalParserCustomizations,
+            ),
+            additionalServerHttpBoundProtocolCustomizations,
+            additionalHttpBindingCustomizations,
+        )
 
     override fun support(): ProtocolSupport {
         return ProtocolSupport(
diff --git a/tools/ci-scripts/codegen-diff/diff_lib.py b/tools/ci-scripts/codegen-diff/diff_lib.py
index 60fa3d6edf..09f7edbf86 100644
--- a/tools/ci-scripts/codegen-diff/diff_lib.py
+++ b/tools/ci-scripts/codegen-diff/diff_lib.py
@@ -2,9 +2,9 @@
 #  SPDX-License-Identifier: Apache-2.0
 
 import os
-import sys
-import subprocess
 import shlex
+import subprocess
+import sys
 
 HEAD_BRANCH_NAME = "__tmp-localonly-head"
 BASE_BRANCH_NAME = "__tmp-localonly-base"
@@ -15,10 +15,10 @@ COMMIT_AUTHOR_EMAIL = "generated-code-action@github.com"
 
 CDN_URL = "https://d2luzm2xt3nokh.cloudfront.net"
 
-PYTHON_EXAMPLES_PATH = "rust-runtime/aws-smithy-http-server-python/examples"
-
 target_codegen_client = 'codegen-client-test'
 target_codegen_server = 'codegen-server-test'
+target_codegen_server_python = 'codegen-server-test:python'
+target_codegen_server_typescript = 'codegen-server-test:typescript'
 target_aws_sdk = 'aws:sdk'
 
 
@@ -38,19 +38,19 @@ def checkout_commit_and_generate(revision_sha, branch_name, targets=None):
 
 
 def generate_and_commit_generated_code(revision_sha, targets=None):
-    targets = targets or [target_codegen_client, target_codegen_server, target_aws_sdk]
+    targets = targets or [
+            target_codegen_client,
+            target_codegen_server,
+            target_aws_sdk,
+            target_codegen_server_python,
+            target_codegen_server_typescript
+        ]
     # Clean the build artifacts before continuing
+    assemble_tasks = ' '.join([f'{t}:assemble' for t in targets])
+    clean_tasks = ' '.join([f'{t}:clean' for t in targets])
     get_cmd_output("rm -rf aws/sdk/build")
-    if target_codegen_server in targets:
-        get_cmd_output("make distclean", shell=True, cwd=PYTHON_EXAMPLES_PATH)
-    get_cmd_output("./gradlew codegen-core:clean codegen-client:clean codegen-server:clean aws:sdk-codegen:clean")
-
-    # Generate code
-    tasks = ' '.join([f'{t}:assemble' for t in targets])
-    get_cmd_output(f"./gradlew --rerun-tasks {tasks}")
-    if target_codegen_server in targets:
-        get_cmd_output("make build", shell=True, check=False, cwd=PYTHON_EXAMPLES_PATH)
-        get_cmd_output(f"./gradlew --rerun-tasks codegen-server-test:typescript:assemble")
+    get_cmd_output(f"./gradlew --rerun-tasks {clean_tasks}")
+    get_cmd_output(f"./gradlew --rerun-tasks {assemble_tasks}")
 
     # Move generated code into codegen-diff/ directory
     get_cmd_output(f"rm -rf {OUTPUT_PATH}")
@@ -61,12 +61,8 @@ def generate_and_commit_generated_code(revision_sha, targets=None):
         if target in targets:
             get_cmd_output(f"mv {target}/build/smithyprojections/{target} {OUTPUT_PATH}/")
             if target == target_codegen_server:
-                get_cmd_output(
-                    f"mv {PYTHON_EXAMPLES_PATH}/pokemon-service-server-sdk/ {OUTPUT_PATH}/codegen-server-test-python/",
-                    check=False)
-                get_cmd_output(
-                    f"mv codegen-server-test/typescript/build/smithyprojections/codegen-server-test-typescript {OUTPUT_PATH}/",
-                    check=False)
+                get_cmd_output(f"mv {target}/python/build/smithyprojections/{target}-python {OUTPUT_PATH}/")
+                get_cmd_output(f"mv {target}/typescript/build/smithyprojections/{target}-typescript {OUTPUT_PATH}/")
 
     # Clean up the SDK directory
     get_cmd_output(f"rm -f {OUTPUT_PATH}/aws-sdk/versions.toml")
@@ -79,6 +75,7 @@ def generate_and_commit_generated_code(revision_sha, targets=None):
 
     # Clean up the server-test folder
     get_cmd_output(f"rm -rf {OUTPUT_PATH}/codegen-server-test/source")
+    get_cmd_output(f"rm -rf {OUTPUT_PATH}/codegen-server-test-python/source")
     get_cmd_output(f"rm -rf {OUTPUT_PATH}/codegen-server-test-typescript/source")
     run(f"find {OUTPUT_PATH}/codegen-server-test | "
         f"grep -E 'smithy-build-info.json|sources/manifest|model.json' | "