diff --git a/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/ServerCodegenContext.kt b/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/ServerCodegenContext.kt
index a0ad38f04f..28256ec15d 100644
--- a/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/ServerCodegenContext.kt
+++ b/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/ServerCodegenContext.kt
@@ -5,6 +5,7 @@
 
 package software.amazon.smithy.rust.codegen.server.smithy
 
+import software.amazon.smithy.codegen.core.Symbol
 import software.amazon.smithy.model.Model
 import software.amazon.smithy.model.shapes.ServiceShape
 import software.amazon.smithy.model.shapes.ShapeId
@@ -31,6 +32,7 @@ data class ServerCodegenContext(
     val constrainedShapeSymbolProvider: RustSymbolProvider,
     val constraintViolationSymbolProvider: ConstraintViolationSymbolProvider,
     val pubCrateConstrainedShapeSymbolProvider: PubCrateConstrainedShapeSymbolProvider,
+    val typesToInit: MutableSet<Symbol> = setOf<Symbol>().toMutableSet(),
 ) : CodegenContext(
     model, symbolProvider, serviceShape, protocol, settings, CodegenTarget.SERVER,
 )
diff --git a/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/generators/ConstrainedStringGenerator.kt b/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/generators/ConstrainedStringGenerator.kt
index be1df7fa8c..1b6ed8f080 100644
--- a/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/generators/ConstrainedStringGenerator.kt
+++ b/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/generators/ConstrainedStringGenerator.kt
@@ -87,6 +87,8 @@ class ConstrainedStringGenerator(
         if (constrainedTypeVisibility == Visibility.PUBCRATE) {
             Attribute.AllowUnused.render(writer)
         }
+        codegenContext.typesToInit.add(symbol)
+
         writer.rust(
             """
             impl $name {
diff --git a/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/generators/ServerServiceGenerator.kt b/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/generators/ServerServiceGenerator.kt
index e408248483..eddfb31b89 100644
--- a/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/generators/ServerServiceGenerator.kt
+++ b/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/generators/ServerServiceGenerator.kt
@@ -13,9 +13,9 @@ import software.amazon.smithy.rust.codegen.core.rustlang.RustModule
 import software.amazon.smithy.rust.codegen.core.rustlang.RustWriter
 import software.amazon.smithy.rust.codegen.core.rustlang.Visibility
 import software.amazon.smithy.rust.codegen.core.rustlang.rust
-import software.amazon.smithy.rust.codegen.core.smithy.CodegenContext
 import software.amazon.smithy.rust.codegen.core.smithy.RustCrate
 import software.amazon.smithy.rust.codegen.core.smithy.generators.protocol.ProtocolSupport
+import software.amazon.smithy.rust.codegen.server.smithy.ServerCodegenContext
 import software.amazon.smithy.rust.codegen.server.smithy.generators.protocol.ServerProtocol
 import software.amazon.smithy.rust.codegen.server.smithy.generators.protocol.ServerProtocolGenerator
 import software.amazon.smithy.rust.codegen.server.smithy.generators.protocol.ServerProtocolTestGenerator
@@ -31,7 +31,7 @@ open class ServerServiceGenerator(
     private val protocolGenerator: ServerProtocolGenerator,
     private val protocolSupport: ProtocolSupport,
     val protocol: ServerProtocol,
-    private val codegenContext: CodegenContext,
+    private val codegenContext: ServerCodegenContext,
 ) {
     private val index = TopDownIndex.of(codegenContext.model)
     protected val operations = index.getContainedOperations(codegenContext.serviceShape).sortedBy { it.id }
diff --git a/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/generators/ServerServiceGeneratorV2.kt b/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/generators/ServerServiceGeneratorV2.kt
index ca782f4da6..6d34bb58a8 100644
--- a/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/generators/ServerServiceGeneratorV2.kt
+++ b/codegen-server/src/main/kotlin/software/amazon/smithy/rust/codegen/server/smithy/generators/ServerServiceGeneratorV2.kt
@@ -16,14 +16,14 @@ import software.amazon.smithy.rust.codegen.core.rustlang.join
 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.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.smithy.ServerCargoDependency
+import software.amazon.smithy.rust.codegen.server.smithy.ServerCodegenContext
 import software.amazon.smithy.rust.codegen.server.smithy.generators.protocol.ServerProtocol
 
 class ServerServiceGeneratorV2(
-    private val codegenContext: CodegenContext,
+    private val codegenContext: ServerCodegenContext,
     private val protocol: ServerProtocol,
 ) {
     private val runtimeConfig = codegenContext.runtimeConfig
@@ -39,8 +39,11 @@ class ServerServiceGeneratorV2(
         )
     private val model = codegenContext.model
     private val symbolProvider = codegenContext.symbolProvider
-    val crateName = codegenContext.settings.moduleName.toSnakeCase()
+    private val crateName = codegenContext.settings.moduleName.toSnakeCase()
 
+    private val typeInitializations = codegenContext.typesToInit
+        .map { typeSymbol -> writable { rust("$typeSymbol::compile_regex();") } }
+        .join("\n")
     private val service = codegenContext.serviceShape
     private val serviceName = service.id.name.toPascalCase()
     private val builderName = "${serviceName}Builder"
@@ -203,6 +206,7 @@ class ServerServiceGeneratorV2(
             /// unspecified route requested.
             pub fn build(self) -> Result<$serviceName<#{SmithyHttpServer}::routing::Route<$builderBodyGenericTypeName>>, MissingOperationsError>
             {
+                #{TypeInitializations:W}
                 let router = {
                     use #{SmithyHttpServer}::operation::OperationShape;
                     let mut $missingOperationsVariableName = std::collections::HashMap::new();
@@ -221,6 +225,7 @@ class ServerServiceGeneratorV2(
             }
             """,
             "Router" to protocol.routerType(),
+            "TypeInitializations" to typeInitializations,
             "NullabilityChecks" to nullabilityChecks,
             "RoutesArrayElements" to routesArrayElements,
             "SmithyHttpServer" to smithyHttpServer,