diff --git a/agent/agent/src/main/resources/inst/META-INF/services/io.opentelemetry.sdk.autoconfigure.spi.metrics.ConfigurableMetricExporterProvider b/agent/agent/src/main/resources/inst/META-INF/services/io.opentelemetry.sdk.autoconfigure.spi.metrics.ConfigurableMetricExporterProvider
new file mode 100644
index 00000000000..93d8d0ee99a
--- /dev/null
+++ b/agent/agent/src/main/resources/inst/META-INF/services/io.opentelemetry.sdk.autoconfigure.spi.metrics.ConfigurableMetricExporterProvider
@@ -0,0 +1 @@
+io.opentelemetry.exporter.otlp.internal.OtlpMetricExporterProvider
diff --git a/buildSrc/build.gradle.kts b/buildSrc/build.gradle.kts
index fad471e9378..05375fa4d76 100644
--- a/buildSrc/build.gradle.kts
+++ b/buildSrc/build.gradle.kts
@@ -32,11 +32,11 @@ dependencies {
   // When updating, update above in plugins too
   implementation("com.diffplug.spotless:spotless-plugin-gradle:8.0.0")
   implementation("com.github.spotbugs.snom:spotbugs-gradle-plugin:6.3.0")
-  implementation("com.gradleup.shadow:shadow-gradle-plugin:8.3.9")
+  implementation("com.gradleup.shadow:shadow-gradle-plugin:9.2.2")
 
   implementation("org.owasp:dependency-check-gradle:12.1.8")
 
-  implementation("io.opentelemetry.instrumentation:gradle-plugins:2.19.0-alpha")
+  implementation("io.opentelemetry.instrumentation:gradle-plugins:2.21.0-alpha")
 
   implementation("net.ltgt.gradle:gradle-errorprone-plugin:4.3.0")
   implementation("net.ltgt.gradle:gradle-nullaway-plugin:2.3.0")
@@ -44,6 +44,4 @@ dependencies {
   implementation("gradle.plugin.io.morethan.jmhreport:gradle-jmh-report:0.9.6")
   implementation("me.champeau.jmh:jmh-gradle-plugin:0.7.3")
 
-  // earlier versions aren't compatible with Gradle 8.1.1
-  implementation("org.springframework.boot:spring-boot-gradle-plugin:2.5.12")
 }
diff --git a/buildSrc/src/main/kotlin/ai.shadow-conventions.gradle.kts b/buildSrc/src/main/kotlin/ai.shadow-conventions.gradle.kts
index 35f12ccf566..2ac0649ce38 100644
--- a/buildSrc/src/main/kotlin/ai.shadow-conventions.gradle.kts
+++ b/buildSrc/src/main/kotlin/ai.shadow-conventions.gradle.kts
@@ -1,13 +1,38 @@
 import com.github.jengelman.gradle.plugins.shadow.tasks.ShadowJar
+import org.gradle.api.file.DuplicatesStrategy
 
 plugins {
   id("com.gradleup.shadow")
 }
 
 tasks.withType<ShadowJar>().configureEach {
+  duplicatesStrategy = DuplicatesStrategy.EXCLUDE
+  mergeServiceFiles()
+  mergeServiceFiles("META-INF/services/**")
   mergeServiceFiles {
-    include("inst/META-INF/services/*")
+    include("inst/META-INF/services/**")
+    path = "inst/META-INF/services"
   }
+  filesMatching("META-INF/services/**") {
+    duplicatesStrategy = DuplicatesStrategy.INCLUDE
+  }
+  filesMatching("inst/META-INF/services/**") {
+    duplicatesStrategy = DuplicatesStrategy.INCLUDE
+  }
+  exclude("META-INF/services/javax.servlet.ServletContainerInitializer")
+  exclude("inst/META-INF/services/javax.servlet.ServletContainerInitializer")
+  exclude("META-INF/*.SF", "META-INF/*.DSA", "META-INF/*.RSA")
+  exclude(
+    "META-INF/LICENSE",
+    "META-INF/NOTICE",
+    "META-INF/LICENSE.txt",
+    "META-INF/NOTICE.txt",
+    "META-INF/INDEX.LIST",
+    "META-INF/io.netty.versions.properties",
+    "META-INF/AL2.0",
+    "META-INF/LGPL2.1"
+  )
+  exclude("META-INF/maven/**")
 
   exclude("**/module-info.class")
 
diff --git a/buildSrc/src/main/kotlin/ai.smoke-test-jar.gradle.kts b/buildSrc/src/main/kotlin/ai.smoke-test-jar.gradle.kts
index bf6a7dcb5ac..a9ae5df5599 100644
--- a/buildSrc/src/main/kotlin/ai.smoke-test-jar.gradle.kts
+++ b/buildSrc/src/main/kotlin/ai.smoke-test-jar.gradle.kts
@@ -1,11 +1,33 @@
+import com.github.jengelman.gradle.plugins.shadow.tasks.ShadowJar
 import com.microsoft.applicationinsights.gradle.AiSmokeTestExtension
+import org.gradle.api.file.DuplicatesStrategy
 
 plugins {
   id("ai.smoke-test")
-  id("org.springframework.boot")
+  id("com.gradleup.shadow")
 }
 
 val aiSmokeTest = extensions.getByType(AiSmokeTestExtension::class)
 
-aiSmokeTest.testAppArtifactDir.set(tasks.bootJar.flatMap { it.destinationDirectory })
-aiSmokeTest.testAppArtifactFilename.set(tasks.bootJar.flatMap { it.archiveFileName })
+val shadowJar = tasks.named<ShadowJar>("shadowJar") {
+  archiveClassifier.set("")
+  archiveVersion.set("")
+  duplicatesStrategy = DuplicatesStrategy.EXCLUDE
+
+  mergeServiceFiles()
+  mergeServiceFiles("META-INF/spring.factories")
+  mergeServiceFiles("META-INF/spring.handlers")
+  mergeServiceFiles("META-INF/spring.schemas")
+  mergeServiceFiles("META-INF/spring/org.springframework.boot.autoconfigure.AutoConfiguration.imports")
+
+  manifest {
+    attributes["Main-Class"] = "com.microsoft.applicationinsights.smoketestapp.SpringBootApp"
+  }
+}
+
+tasks.named("assemble") {
+  dependsOn(shadowJar)
+}
+
+aiSmokeTest.testAppArtifactDir.set(shadowJar.flatMap { it.destinationDirectory })
+aiSmokeTest.testAppArtifactFilename.set(shadowJar.flatMap { it.archiveFileName })
diff --git a/etw/etw-testapp/build.gradle.kts b/etw/etw-testapp/build.gradle.kts
index 2e6a486c0f3..629b4a2845b 100644
--- a/etw/etw-testapp/build.gradle.kts
+++ b/etw/etw-testapp/build.gradle.kts
@@ -1,6 +1,6 @@
 plugins {
   id("ai.java-conventions")
-  id("org.springframework.boot" version "2.5.12")
+  id("org.springframework.boot" version "2.7.18")
   id("war")
 }
 
diff --git a/gradle/wrapper/gradle-wrapper.properties b/gradle/wrapper/gradle-wrapper.properties
index d4081da476b..2e1113280ef 100644
--- a/gradle/wrapper/gradle-wrapper.properties
+++ b/gradle/wrapper/gradle-wrapper.properties
@@ -1,6 +1,6 @@
 distributionBase=GRADLE_USER_HOME
 distributionPath=wrapper/dists
-distributionUrl=https\://services.gradle.org/distributions/gradle-8.14.3-bin.zip
+distributionUrl=https\://services.gradle.org/distributions/gradle-9.1.0-bin.zip
 networkTimeout=10000
 validateDistributionUrl=true
 zipStoreBase=GRADLE_USER_HOME
diff --git a/smoke-tests/apps/ReadOnly/src/main/java/com/microsoft/applicationinsights/smoketestapp/App.java b/smoke-tests/apps/ReadOnly/src/main/java/com/microsoft/applicationinsights/smoketestapp/SpringBootApp.java
similarity index 94%
rename from smoke-tests/apps/ReadOnly/src/main/java/com/microsoft/applicationinsights/smoketestapp/App.java
rename to smoke-tests/apps/ReadOnly/src/main/java/com/microsoft/applicationinsights/smoketestapp/SpringBootApp.java
index 382610b2ff8..05103c90ea0 100644
--- a/smoke-tests/apps/ReadOnly/src/main/java/com/microsoft/applicationinsights/smoketestapp/App.java
+++ b/smoke-tests/apps/ReadOnly/src/main/java/com/microsoft/applicationinsights/smoketestapp/SpringBootApp.java
@@ -8,7 +8,7 @@
 
 // Spring boot doesn't support read-only containers
 // (https://github.com/spring-projects/spring-boot/issues/8578)
-public class App {
+public class SpringBootApp {
 
   private static final Logger logger = Logger.getLogger("smoketestapp");
 
diff --git a/smoke-tests/apps/gRPC/build.gradle.kts b/smoke-tests/apps/gRPC/build.gradle.kts
index eae03a2ecef..99802a6e67d 100644
--- a/smoke-tests/apps/gRPC/build.gradle.kts
+++ b/smoke-tests/apps/gRPC/build.gradle.kts
@@ -2,7 +2,7 @@ import com.google.protobuf.gradle.*
 
 plugins {
   id("ai.smoke-test-jar")
-  id("com.google.protobuf") version "0.8.19"
+  id("com.google.protobuf") version "0.9.5"
 }
 
 val grpcVersion = "1.26.0" // first version with support for arm64