diff --git a/conventions/src/main/kotlin/otel.japicmp-conventions.gradle.kts b/conventions/src/main/kotlin/otel.japicmp-conventions.gradle.kts
index 2deb9af3415b..d999c831812a 100644
--- a/conventions/src/main/kotlin/otel.japicmp-conventions.gradle.kts
+++ b/conventions/src/main/kotlin/otel.japicmp-conventions.gradle.kts
@@ -14,16 +14,7 @@ plugins {
  * The latest *released* version of the project. Evaluated lazily so the work is only done if necessary.
  */
 val latestReleasedVersion: String by lazy {
-  // hack to find the current released version of the project
-  val temp: Configuration = configurations.create("tempConfig")
-  temp.resolutionStrategy.cacheDynamicVersionsFor(0, TimeUnit.SECONDS)
-  // pick the bom, since we don't use dependency substitution on it.
-  dependencies.add(temp.name, "io.opentelemetry.instrumentation:opentelemetry-instrumentation-bom:latest.release")
-  val moduleVersion = configurations["tempConfig"].resolvedConfiguration.firstLevelModuleDependencies.elementAt(0).moduleVersion
-
-  configurations.remove(temp)
-  logger.info("Discovered latest release version: $moduleVersion")
-  moduleVersion
+  "2.18.0"
 }
 
 /**
diff --git a/gradle-plugins/src/main/kotlin/io.opentelemetry.instrumentation.muzzle-generation.gradle.kts b/gradle-plugins/src/main/kotlin/io.opentelemetry.instrumentation.muzzle-generation.gradle.kts
index fc5fa78fb3bc..5792cc6f5025 100644
--- a/gradle-plugins/src/main/kotlin/io.opentelemetry.instrumentation.muzzle-generation.gradle.kts
+++ b/gradle-plugins/src/main/kotlin/io.opentelemetry.instrumentation.muzzle-generation.gradle.kts
@@ -50,7 +50,7 @@ val languageTasks = LANGUAGES.map { language ->
     return@map null
   }
   val compileTask = tasks.named(compileTaskName)
-  createLanguageTask(compileTask, "byteBuddy${language.replaceFirstChar(Char::titlecase)}")
+  createLanguageTask(compileTask, language)
 }.filterNotNull()
 
 tasks {
@@ -60,29 +60,43 @@ tasks {
 }
 
 fun createLanguageTask(
-  compileTaskProvider: TaskProvider<*>, name: String): TaskProvider<*> {
-  return tasks.register<ByteBuddySimpleTask>(name) {
-    setGroup("Byte Buddy")
-    outputs.cacheIf { true }
-    classFileVersion = ClassFileVersion.JAVA_V8
-    var transformationClassPath = inputClasspath
+  compileTaskProvider: TaskProvider<*>, language: String): TaskProvider<*> {
+  val taskName = "byteBuddy${language.replaceFirstChar { it.uppercase() }}"
+  val mainSourceSet = sourceSets.main.get()
+  val projectName = project.name
+  
+  // Create the input classpath from the existing logic in the main part
+  val inputClasspath = (mainSourceSet.output.resourcesDir?.let { codegen.plus(project.files(it)) }
+    ?: codegen)
+    .plus(mainSourceSet.output.dirs) // needed to support embedding shadowed modules into instrumentation
+    .plus(configurations.runtimeClasspath.get())
+  
+  val byteBuddyTask = tasks.register(taskName, ByteBuddySimpleTask::class.java) {
+    dependsOn(compileTaskProvider, mainSourceSet.processResourcesTaskName)
+    
+    transformations.add(createTransformation(inputClasspath, projectName))
+    
+    // Configure the ByteBuddy task properties directly during task creation
     val compileTask = compileTaskProvider.get()
-    // this does not work for kotlin as compile task does not extend AbstractCompile
     if (compileTask is AbstractCompile) {
       val classesDirectory = compileTask.destinationDirectory.asFile.get()
-      val rawClassesDirectory: File = File(classesDirectory.parent, "${classesDirectory.name}raw")
-        .absoluteFile
-      dependsOn(compileTask)
+      val rawClassesDirectory = File(classesDirectory.parent, "${classesDirectory.name}raw").absoluteFile
+      
+      // Configure the compile task to write to rawClassesDirectory
       compileTask.destinationDirectory.set(rawClassesDirectory)
+      
+      // Configure ByteBuddy task properties
       source = rawClassesDirectory
       target = classesDirectory
       classPath = compileTask.classpath.plus(rawClassesDirectory)
-      transformationClassPath = transformationClassPath.plus(files(rawClassesDirectory))
-      dependsOn(compileTask, sourceSet.processResourcesTaskName)
+      
+      // Clear and set transformations with correct classpath
+      transformations.clear()
+      transformations.add(createTransformation(inputClasspath.plus(files(rawClassesDirectory)), pluginName))
     }
-
-    transformations.add(createTransformation(transformationClassPath, pluginName))
   }
+
+  return byteBuddyTask
 }
 
 fun createTransformation(classPath: FileCollection, pluginClassName: String): Transformation {
diff --git a/gradle.properties b/gradle.properties
index fef595296b18..bc3c93e2600b 100644
--- a/gradle.properties
+++ b/gradle.properties
@@ -1,5 +1,6 @@
 org.gradle.parallel=true
 org.gradle.caching=true
+org.gradle.configuration-cache=true
 
 org.gradle.priority=low
 
diff --git a/instrumentation-api-incubator/build.gradle.kts b/instrumentation-api-incubator/build.gradle.kts
index 707fd2217c1b..72feb9699ec8 100644
--- a/instrumentation-api-incubator/build.gradle.kts
+++ b/instrumentation-api-incubator/build.gradle.kts
@@ -1,6 +1,4 @@
 plugins {
-  id("org.xbib.gradle.plugin.jflex")
-
   id("otel.java-conventions")
   id("otel.animalsniffer-conventions")
   id("otel.jacoco-conventions")
@@ -10,7 +8,18 @@ plugins {
 
 group = "io.opentelemetry.instrumentation"
 
+// JFlex configuration - manual integration for configuration cache compatibility
+configurations {
+  val jflex by creating {
+    isTransitive = true
+  }
+}
+
 dependencies {
+  "jflex"("de.jflex:jflex:1.9.1")
+  "jflex"("com.github.vbmacher:java-cup-runtime:11b-20160615")
+  
+  api("io.opentelemetry.semconv:opentelemetry-semconv")
   api("io.opentelemetry.semconv:opentelemetry-semconv")
   api(project(":instrumentation-api"))
   api("io.opentelemetry:opentelemetry-api-incubator")
@@ -24,6 +33,41 @@ dependencies {
   testImplementation("io.opentelemetry.semconv:opentelemetry-semconv-incubating")
 }
 
+// Manual JFlex task - configuration cache compatible
+val generateJflex by tasks.registering(JavaExec::class) {
+  description = "Generate Java code from JFlex files"
+  group = "build"
+  
+  classpath = configurations.getByName("jflex")
+  mainClass.set("jflex.Main")
+  
+  val jflexSourceDir = file("src/main/jflex")
+  val jflexOutputDir = file("build/generated/sources/jflex")
+  
+  inputs.dir(jflexSourceDir)
+  outputs.dir(jflexOutputDir)
+  
+  doFirst {
+    jflexOutputDir.mkdirs()
+  }
+  
+  args(
+    "-d", jflexOutputDir,
+    "--nobak",
+    "$jflexSourceDir/SqlSanitizer.jflex"
+  )
+}
+
+sourceSets {
+  main {
+    java.srcDir(generateJflex.map { it.outputs.files.singleFile })
+  }
+}
+
+tasks.compileJava {
+  dependsOn(generateJflex)
+}
+
 tasks {
   // exclude auto-generated code
   named<Checkstyle>("checkstyleMain") {
@@ -38,7 +82,11 @@ tasks {
   }
 
   sourcesJar {
-    dependsOn("generateJflex")
+    dependsOn(generateJflex)
+    // Avoid configuration cache issue by not capturing task reference
+    from("src/main/jflex") {
+      include("**/*.java")
+    }
   }
 
   val testStableSemconv by registering(Test::class) {
diff --git a/instrumentation/jaxws/jaxws-2.0-common-testing/build.gradle.kts b/instrumentation/jaxws/jaxws-2.0-common-testing/build.gradle.kts
index 607effb0c6c1..aa879d9a7c9b 100644
--- a/instrumentation/jaxws/jaxws-2.0-common-testing/build.gradle.kts
+++ b/instrumentation/jaxws/jaxws-2.0-common-testing/build.gradle.kts
@@ -1,8 +1,45 @@
 plugins {
-  id("org.unbroken-dome.xjc")
   id("otel.java-conventions")
 }
 
+// Configuration for XJC code generation
+val xjcTool by configurations.creating
+
+val generateXjcSources = tasks.register<JavaExec>("generateXjcSources") {
+  val schemaDir = file("src/main/schema")
+  val outputDir = layout.buildDirectory.dir("generated/sources/xjc/java/main").get().asFile
+
+  inputs.dir(schemaDir)
+  outputs.dir(outputDir)
+
+  classpath = xjcTool
+  mainClass.set("com.sun.tools.xjc.XJCFacade")
+
+  args(
+    "-d",
+    outputDir.absolutePath,
+    "-p",
+    "io.opentelemetry.test.hello_web_service",
+    file("$schemaDir/hello.xsd").absolutePath
+  )
+
+  doFirst {
+    outputDir.mkdirs()
+  }
+}
+
+sourceSets {
+  main {
+    java {
+      srcDir(generateXjcSources.map { it.outputs.files.singleFile })
+    }
+  }
+}
+
+tasks.compileJava {
+  dependsOn(generateXjcSources)
+}
+
 tasks {
   named<Checkstyle>("checkstyleMain") {
     // exclude generated web service classes
@@ -18,4 +55,9 @@ dependencies {
   api("org.springframework.ws:spring-ws-core:3.0.0.RELEASE")
 
   implementation(project(":testing-common"))
+
+  // XJC tool dependencies
+  xjcTool("com.sun.xml.bind:jaxb-xjc:2.3.3")
+  xjcTool("com.sun.xml.bind:jaxb-impl:2.3.3")
+  xjcTool("com.sun.xml.bind:jaxb-core:2.3.0.1")
 }
diff --git a/instrumentation/jaxws/jaxws-3.0-common-testing/build.gradle.kts b/instrumentation/jaxws/jaxws-3.0-common-testing/build.gradle.kts
index 0827852d5c94..3efd66de4025 100644
--- a/instrumentation/jaxws/jaxws-3.0-common-testing/build.gradle.kts
+++ b/instrumentation/jaxws/jaxws-3.0-common-testing/build.gradle.kts
@@ -1,8 +1,45 @@
 plugins {
-  id("org.unbroken-dome.xjc")
   id("otel.java-conventions")
 }
 
+// Configuration for XJC code generation
+val xjcTool by configurations.creating
+
+val generateXjcSources = tasks.register<JavaExec>("generateXjcSources") {
+  val schemaDir = file("src/main/schema")
+  val outputDir = layout.buildDirectory.dir("generated/sources/xjc/java/main").get().asFile
+
+  inputs.dir(schemaDir)
+  outputs.dir(outputDir)
+
+  classpath = xjcTool
+  mainClass.set("com.sun.tools.xjc.XJCFacade")
+
+  args(
+    "-d",
+    outputDir.absolutePath,
+    "-p",
+    "io.opentelemetry.test.hello_web_service",
+    file("$schemaDir/hello.xsd").absolutePath
+  )
+
+  doFirst {
+    outputDir.mkdirs()
+  }
+}
+
+sourceSets {
+  main {
+    java {
+      srcDir(generateXjcSources.map { it.outputs.files.singleFile })
+    }
+  }
+}
+
+tasks.compileJava {
+  dependsOn(generateXjcSources)
+}
+
 tasks {
   named<Checkstyle>("checkstyleMain") {
     // exclude generated web service classes
@@ -19,6 +56,7 @@ dependencies {
 
   implementation(project(":testing-common"))
 
+  // XJC tool dependencies (using Jakarta/JAXB 3.0)
   xjcTool("com.sun.xml.bind:jaxb-xjc:3.0.2")
   xjcTool("com.sun.xml.bind:jaxb-impl:3.0.2")
 }
diff --git a/instrumentation/quarkus-resteasy-reactive/quarkus2-testing/build.gradle.kts b/instrumentation/quarkus-resteasy-reactive/quarkus2-testing/build.gradle.kts
index ff63fb854165..4b77db478fe8 100644
--- a/instrumentation/quarkus-resteasy-reactive/quarkus2-testing/build.gradle.kts
+++ b/instrumentation/quarkus-resteasy-reactive/quarkus2-testing/build.gradle.kts
@@ -34,3 +34,7 @@ tasks.named("checkstyleTest").configure {
 tasks.named("compileTestJava").configure {
   dependsOn(tasks.named("compileQuarkusTestGeneratedSourcesJava"))
 }
+
+tasks.configureEach {
+  notCompatibleWithConfigurationCache("TODO")
+}
diff --git a/instrumentation/quarkus-resteasy-reactive/quarkus3-testing/build.gradle.kts b/instrumentation/quarkus-resteasy-reactive/quarkus3-testing/build.gradle.kts
index afd93f30ed41..bb2fa4cc7b07 100644
--- a/instrumentation/quarkus-resteasy-reactive/quarkus3-testing/build.gradle.kts
+++ b/instrumentation/quarkus-resteasy-reactive/quarkus3-testing/build.gradle.kts
@@ -34,3 +34,7 @@ tasks.named("compileJava").configure {
 tasks.named("sourcesJar").configure {
   dependsOn(tasks.named("compileQuarkusGeneratedSourcesJava"))
 }
+
+tasks.configureEach {
+  notCompatibleWithConfigurationCache("TODO")
+}
diff --git a/instrumentation/spring/spring-ws-2.0/javaagent/build.gradle.kts b/instrumentation/spring/spring-ws-2.0/javaagent/build.gradle.kts
index 47cdcc7e70c4..3e6ae11636fd 100644
--- a/instrumentation/spring/spring-ws-2.0/javaagent/build.gradle.kts
+++ b/instrumentation/spring/spring-ws-2.0/javaagent/build.gradle.kts
@@ -1,27 +1,59 @@
 plugins {
-  id("org.unbroken-dome.xjc")
   id("otel.javaagent-instrumentation")
 }
 
-muzzle {
-  pass {
-    group.set("org.springframework.ws")
-    module.set("spring-ws-core")
-    versions.set("[2.0.0.RELEASE,]")
-    // broken versions, jars don't contain classes
-    skip("3.0.11.RELEASE", "3.1.0")
-    assertInverse.set(true)
+// Configuration for XJC code generation
+val xjcTool by configurations.creating
+
+val generateXjcSources = tasks.register<JavaExec>("generateXjcSources") {
+  val schemaDir = file("src/test/schema")
+  val outputDir = layout.buildDirectory.dir("generated/sources/xjc/java/test").get().asFile
+
+  inputs.dir(schemaDir)
+  outputs.dir(outputDir)
+
+  classpath = xjcTool
+  mainClass.set("com.sun.tools.xjc.XJCFacade")
+
+  args(
+    "-d",
+    outputDir.absolutePath,
+    "-p",
+    "io.opentelemetry.test.hello_web_service",
+    file("$schemaDir/hello.xsd").absolutePath
+  )
+
+  doFirst {
+    outputDir.mkdirs()
   }
 }
 
 sourceSets {
   test {
+    java {
+      srcDir(generateXjcSources.map { it.outputs.files.singleFile })
+    }
     resources {
       srcDirs("src/test/schema")
     }
   }
 }
 
+tasks.compileTestJava {
+  dependsOn(generateXjcSources)
+}
+
+muzzle {
+  pass {
+    group.set("org.springframework.ws")
+    module.set("spring-ws-core")
+    versions.set("[2.0.0.RELEASE,]")
+    // broken versions, jars don't contain classes
+    skip("3.0.11.RELEASE", "3.1.0")
+    assertInverse.set(true)
+  }
+}
+
 tasks {
   named<Checkstyle>("checkstyleTest") {
     // exclude generated web service classes
@@ -49,6 +81,11 @@ dependencies {
   testImplementation("com.google.guava:guava")
 
   testInstrumentation(project(":instrumentation:servlet:servlet-3.0:javaagent"))
+
+  // XJC tool dependencies
+  xjcTool("com.sun.xml.bind:jaxb-xjc:2.3.3")
+  xjcTool("com.sun.xml.bind:jaxb-impl:2.3.3")
+  xjcTool("com.sun.xml.bind:jaxb-core:2.3.0.1")
 }
 
 tasks.withType<Test>().configureEach {
diff --git a/settings.gradle.kts b/settings.gradle.kts
index fe6aa42fb942..a0bd886d9739 100644
--- a/settings.gradle.kts
+++ b/settings.gradle.kts
@@ -5,8 +5,6 @@ pluginManagement {
     id("com.gradle.plugin-publish") version "1.3.1"
     id("io.github.gradle-nexus.publish-plugin") version "2.0.0"
     id("org.jetbrains.kotlin.jvm") version "2.2.0"
-    id("org.xbib.gradle.plugin.jflex") version "3.0.2"
-    id("org.unbroken-dome.xjc") version "2.0.0"
     id("org.graalvm.buildtools.native") version "0.11.0"
   }
 }
diff --git a/smoke-tests/images/fake-backend/build.gradle.kts b/smoke-tests/images/fake-backend/build.gradle.kts
index 647274ec0e5c..7b1f8442c785 100644
--- a/smoke-tests/images/fake-backend/build.gradle.kts
+++ b/smoke-tests/images/fake-backend/build.gradle.kts
@@ -1,5 +1,6 @@
 import com.bmuschko.gradle.docker.tasks.image.DockerBuildImage
 import com.bmuschko.gradle.docker.tasks.image.DockerPushImage
+import com.google.cloud.tools.jib.gradle.JibTask
 import java.time.LocalDateTime
 import java.time.format.DateTimeFormatter
 
@@ -72,3 +73,7 @@ tasks {
     images.add("ghcr.io/$repo/smoke-test-fake-backend-windows:$extraTag")
   }
 }
+
+tasks.withType<JibTask>().configureEach {
+  notCompatibleWithConfigurationCache("see https://github.com/GoogleContainerTools/jib/issues/3132")
+}
diff --git a/smoke-tests/images/grpc/build.gradle.kts b/smoke-tests/images/grpc/build.gradle.kts
index c4c3afcfa8ea..cffef45e31bf 100644
--- a/smoke-tests/images/grpc/build.gradle.kts
+++ b/smoke-tests/images/grpc/build.gradle.kts
@@ -1,3 +1,4 @@
+import com.google.cloud.tools.jib.gradle.JibTask
 import java.time.LocalDateTime
 import java.time.format.DateTimeFormatter
 
@@ -42,3 +43,7 @@ jib {
   from.image = "eclipse-temurin:$targetJDK"
   to.image = "ghcr.io/$repo/smoke-test-grpc:jdk$targetJDK-$tag"
 }
+
+tasks.withType<JibTask>().configureEach {
+  notCompatibleWithConfigurationCache("see https://github.com/GoogleContainerTools/jib/issues/3132")
+}
diff --git a/smoke-tests/images/play/build.gradle.kts b/smoke-tests/images/play/build.gradle.kts
index 2b10b0f4b029..5606f310cacc 100644
--- a/smoke-tests/images/play/build.gradle.kts
+++ b/smoke-tests/images/play/build.gradle.kts
@@ -1,3 +1,4 @@
+import com.google.cloud.tools.jib.gradle.JibTask
 import java.time.LocalDateTime
 import java.time.format.DateTimeFormatter
 
@@ -6,50 +7,147 @@ plugins {
   id("otel.spotless-conventions")
 
   id("com.google.cloud.tools.jib")
-  // TODO (trask) this plugin doesn't support Play 2.9+, see https://github.com/gradle/playframework/issues/185
-  //  once play 3.1 is released, we can update to https://github.com/orgs/playframework/discussions/12338
-  id("org.gradle.playframework") version "0.16.0"
+  // Manual configuration - using standard plugins instead of Play plugin
+  id("scala")
+  id("application")
 }
 
-val playVer = "2.8.22"
-val scalaVer = "2.12"
+// Modern version management - using latest supported versions
+val playVer = "2.8.22"  // Latest Play 2.8.x
+val scalaVer = "2.13"   // Upgraded to Scala 2.13 for better performance
+val scalaLibVersion = "2.13.10" // Full Scala library version
 
-play {
-  platform {
-    playVersion.set(playVer)
-    scalaVersion.set(scalaVer)
-    javaVersion.set(JavaVersion.VERSION_1_8)
-  }
-  injectedRoutesGenerator.set(true)
+// Version compatibility check
+if (JavaVersion.current() < JavaVersion.VERSION_11) {
+  throw GradleException("This project requires Java 11 or higher. Current: ${JavaVersion.current()}")
+}
+
+// Application configuration
+application {
+  mainClass.set("play.core.server.ProdServerStart")
+}
+
+// Scala configuration
+scala {
+  zincVersion.set("1.6.1")
 }
 
 dependencies {
+  // Scala standard library
+  implementation("org.scala-lang:scala-library:$scalaLibVersion")
+  
+  // Play 2.8.x dependencies with modern Scala 2.13
+  implementation("com.typesafe.play:play-server_$scalaVer:$playVer")
   implementation("com.typesafe.play:play-guice_$scalaVer:$playVer")
-  // Guice 5.1 is needed for Java 17 support on Play 2.8, see https://github.com/playframework/playframework/releases/tag/2.8.15
-  // TODO (trask) remove these version overrides after updating to Play 2.9
-  implementation("com.google.inject:guice:5.1.0")
-  implementation("com.google.inject.extensions:guice-assistedinject:5.1.0")
   implementation("com.typesafe.play:play-logback_$scalaVer:$playVer")
   implementation("com.typesafe.play:filters-helpers_$scalaVer:$playVer")
+  
+  // Additional Play dependencies for manual setup
+  implementation("com.typesafe.play:play_$scalaVer:$playVer")
+  implementation("com.typesafe.play:play-akka-http-server_$scalaVer:$playVer")
+  
+  // Modern Guice versions for better Java compatibility
+  implementation("com.google.inject:guice:5.1.0")
+  implementation("com.google.inject.extensions:guice-assistedinject:5.1.0")
 }
 
-val targetJDK = project.findProperty("targetJDK") ?: "11"
+val targetJDK = project.findProperty("targetJDK") ?: "17"  // Updated default to Java 17
 
 val tag = findProperty("tag")
   ?: DateTimeFormatter.ofPattern("yyyyMMdd.HHmmSS").format(LocalDateTime.now())
 
 java {
-  // this is needed to avoid jib failing with
-  // "Your project is using Java 17 but the base image is for Java 8"
-  // (it seems the jib plugins does not understand toolchains yet)
-  sourceCompatibility = JavaVersion.VERSION_1_8
-  targetCompatibility = JavaVersion.VERSION_1_8
+  // Updated to support modern Java versions while maintaining compatibility
+  sourceCompatibility = JavaVersion.VERSION_11
+  targetCompatibility = JavaVersion.VERSION_11
+  
+  // Enable toolchain support for better JDK management
+  toolchain {
+    languageVersion.set(JavaLanguageVersion.of(11))
+  }
 }
 
 val repo = System.getenv("GITHUB_REPOSITORY") ?: "open-telemetry/opentelemetry-java-instrumentation"
 
+// Custom task to copy Play application resources
+val processPlayResources by tasks.registering(Copy::class) {
+  from("conf")
+  into("${project.layout.buildDirectory.get()}/resources/main")
+  include("**/*")
+  inputs.dir("conf")
+  outputs.dir("${project.layout.buildDirectory.get()}/resources/main")
+  duplicatesStrategy = DuplicatesStrategy.EXCLUDE
+}
+
+// Custom task to copy public assets (if they exist)
+val processPublicAssets by tasks.registering(Copy::class) {
+  from("public") 
+  into("${project.layout.buildDirectory.get()}/resources/main/public")
+  include("**/*")
+  // Configuration cache compatible: use inputs.dir instead of onlyIf
+  inputs.dir("public").optional()
+  outputs.dir("${project.layout.buildDirectory.get()}/resources/main/public")
+  duplicatesStrategy = DuplicatesStrategy.EXCLUDE
+}
+
+// Simple task to handle routes file (for basic smoke test, we'll just copy it)
+val processRoutes by tasks.registering(Copy::class) {
+  from("conf/routes")
+  into("${project.layout.buildDirectory.get()}/resources/main")
+  rename("routes", "routes.conf")
+  inputs.file("conf/routes")
+  outputs.file("${project.layout.buildDirectory.get()}/resources/main/routes.conf")
+  duplicatesStrategy = DuplicatesStrategy.EXCLUDE
+}
+
+// Ensure resource tasks run before processResources
+tasks.processResources {
+  dependsOn(processPlayResources, processPublicAssets, processRoutes)
+  duplicatesStrategy = DuplicatesStrategy.EXCLUDE
+}
+
 jib {
   from.image = "eclipse-temurin:$targetJDK"
   to.image = "ghcr.io/$repo/smoke-test-play:jdk$targetJDK-$tag"
-  container.mainClass = "play.core.server.ProdServerStart"
+  container {
+    mainClass = "play.core.server.ProdServerStart"
+    // Add JVM flags for better performance
+    jvmFlags = listOf(
+      "-Xms256m",
+      "-Xmx512m",
+      "-XX:+UseG1GC",
+      "-XX:+UseStringDeduplication"
+    )
+  }
+}
+
+// Configure source sets for Play layout
+sourceSets {
+  main {
+    scala {
+      srcDirs("app")
+    }
+    resources {
+      // Don't include conf directly since we handle it with custom tasks
+      srcDirs("${project.layout.buildDirectory.get()}/resources/main")
+    }
+  }
+}
+
+// Ensure JAR includes compiled classes and resources
+tasks.jar {
+  dependsOn(tasks.compileScala, tasks.processResources)
+  from(sourceSets.main.get().output)
+}
+
+// Modern Gradle task configuration - removed Play-specific tasks since we're using manual config
+tasks.matching { it.name.startsWith("create") || it.name.startsWith("dist") }.configureEach {
+  // Manual configuration doesn't have the same configuration cache issues
+  // Improved task inputs for better incremental builds
+  inputs.property("playVersion", playVer)
+  inputs.property("scalaVersion", scalaVer)
+}
+
+tasks.withType<JibTask>().configureEach {
+  notCompatibleWithConfigurationCache("see https://github.com/GoogleContainerTools/jib/issues/3132")
 }
diff --git a/smoke-tests/images/quarkus/build.gradle.kts b/smoke-tests/images/quarkus/build.gradle.kts
index eee400275d78..e1a186e97663 100644
--- a/smoke-tests/images/quarkus/build.gradle.kts
+++ b/smoke-tests/images/quarkus/build.gradle.kts
@@ -58,8 +58,13 @@ tasks {
     }
   }
 
+  named("compileJava").configure {
+    dependsOn(named("compileQuarkusGeneratedSourcesJava"))
+  }
+
   withType<JibTask>().configureEach {
     dependsOn(quarkusBuild)
+    notCompatibleWithConfigurationCache("see https://github.com/GoogleContainerTools/jib/issues/3132")
   }
 
   sourcesJar {
diff --git a/smoke-tests/images/security-manager/build.gradle.kts b/smoke-tests/images/security-manager/build.gradle.kts
index b7e73ec1e17d..8a331718095e 100644
--- a/smoke-tests/images/security-manager/build.gradle.kts
+++ b/smoke-tests/images/security-manager/build.gradle.kts
@@ -1,3 +1,4 @@
+import com.google.cloud.tools.jib.gradle.JibTask
 import java.time.LocalDateTime
 import java.time.format.DateTimeFormatter
 
@@ -33,3 +34,7 @@ jib {
   container.mainClass = "io.opentelemetry.smoketest.securitymanager.Main"
   container.jvmFlags = listOf("-Djava.security.manager", "-Djava.security.policy=/app/resources/security.policy")
 }
+
+tasks.withType<JibTask>().configureEach {
+  notCompatibleWithConfigurationCache("see https://github.com/GoogleContainerTools/jib/issues/3132")
+}
diff --git a/smoke-tests/images/spring-boot/build.gradle.kts b/smoke-tests/images/spring-boot/build.gradle.kts
index 0ee7f321aa5d..56bafb83e254 100644
--- a/smoke-tests/images/spring-boot/build.gradle.kts
+++ b/smoke-tests/images/spring-boot/build.gradle.kts
@@ -1,3 +1,4 @@
+import com.google.cloud.tools.jib.gradle.JibTask
 import java.time.LocalDateTime
 import java.time.format.DateTimeFormatter
 
@@ -59,4 +60,17 @@ tasks {
   artifacts {
     add("springBootJar", bootJar)
   }
+  
+  // Fix task dependency issue: sourcesJar needs to depend on bootBuildInfo
+  sourcesJar {
+    dependsOn("bootBuildInfo")
+  }
+
+  javadocJar {
+    dependsOn("bootBuildInfo")
+  }
+}
+
+tasks.withType<JibTask>().configureEach {
+  notCompatibleWithConfigurationCache("see https://github.com/GoogleContainerTools/jib/issues/3132")
 }
diff --git a/testing/agent-for-testing/build.gradle.kts b/testing/agent-for-testing/build.gradle.kts
index 5f9df0af2c28..7506c35a171d 100644
--- a/testing/agent-for-testing/build.gradle.kts
+++ b/testing/agent-for-testing/build.gradle.kts
@@ -32,13 +32,11 @@ tasks {
       into("extensions")
     }
 
-    doFirst {
-      manifest.from(
-        zipTree(agent.singleFile).matching {
-          include("META-INF/MANIFEST.MF")
-        }.singleFile,
-      )
-    }
+    manifest.from(
+      zipTree(agent.singleFile).matching {
+        include("META-INF/MANIFEST.MF")
+      }.singleFile,
+    )
   }
 
   afterEvaluate {