diff --git a/build-logic/smoke-test/src/main/resources/datadog/buildlogic/smoketest/proxy-repositories.init.gradle.kts b/build-logic/smoke-test/src/main/resources/datadog/buildlogic/smoketest/proxy-repositories.init.gradle.kts
index 70fe8054b90..cd54686d921 100644
--- a/build-logic/smoke-test/src/main/resources/datadog/buildlogic/smoketest/proxy-repositories.init.gradle.kts
+++ b/build-logic/smoke-test/src/main/resources/datadog/buildlogic/smoketest/proxy-repositories.init.gradle.kts
@@ -1,10 +1,38 @@
 import org.gradle.api.Action
 import org.gradle.api.Project
+import org.gradle.api.artifacts.dsl.RepositoryHandler
+import org.gradle.api.artifacts.repositories.MavenArtifactRepository
 import org.gradle.api.initialization.Settings
 
 gradle.beforeSettings(Action<Settings> {
   val gradlePluginProxy = providers.gradleProperty("gradlePluginProxy").orNull
   val mavenRepositoryProxy = providers.gradleProperty("mavenRepositoryProxy").orNull
+  val mavenCentralUrls = setOf(
+    "https://repo.maven.apache.org/maven2",
+    "https://repo1.maven.org/maven2",
+  )
+
+  fun RepositoryHandler.redirectMavenCentral() {
+    val proxy = mavenRepositoryProxy?.takeIf { it.isNotBlank() } ?: return
+    withType(MavenArtifactRepository::class.java).configureEach {
+      if (url.toString().trimEnd('/') in mavenCentralUrls) {
+        url = java.net.URI(proxy)
+        isAllowInsecureProtocol = true
+      }
+    }
+  }
+
+  fun RepositoryHandler.removeDuplicateMavenProxy() {
+    val proxyUrl = mavenRepositoryProxy?.takeIf { it.isNotBlank() }?.trimEnd('/') ?: return
+    withType(MavenArtifactRepository::class.java)
+      .filter { it.url.toString().trimEnd('/') == proxyUrl }
+      .drop(1)
+      .forEach { remove(it) }
+  }
+
+  buildscript.repositories.redirectMavenCentral()
+  pluginManagement.repositories.redirectMavenCentral()
+  dependencyResolutionManagement.repositories.redirectMavenCentral()
 
   pluginManagement {
     repositories {
@@ -22,11 +50,19 @@ gradle.beforeSettings(Action<Settings> {
         }
       }
       gradlePluginPortal()
-      mavenCentral()
+      if (mavenRepositoryProxy.isNullOrBlank()) {
+        mavenCentral()
+      }
     }
   }
 
+  gradle.settingsEvaluated(Action<Settings> {
+    pluginManagement.repositories.removeDuplicateMavenProxy()
+  })
+
   gradle.beforeProject(Action<Project> {
+    repositories.redirectMavenCentral()
+    buildscript.repositories.redirectMavenCentral()
     repositories {
       mavenLocal()
       mavenRepositoryProxy?.takeIf { it.isNotBlank() }?.let { proxy ->
@@ -35,7 +71,13 @@ gradle.beforeSettings(Action<Settings> {
           isAllowInsecureProtocol = true
         }
       }
-      mavenCentral()
+      if (mavenRepositoryProxy.isNullOrBlank()) {
+        mavenCentral()
+      }
     }
   })
+
+  gradle.afterProject(Action<Project> {
+    repositories.removeDuplicateMavenProxy()
+  })
 })
diff --git a/build-logic/smoke-test/src/test/kotlin/datadog/buildlogic/smoketest/SmokeTestAppEndToEndTest.kt b/build-logic/smoke-test/src/test/kotlin/datadog/buildlogic/smoketest/SmokeTestAppEndToEndTest.kt
index 6aa17ed4b7c..da64a0d303e 100644
--- a/build-logic/smoke-test/src/test/kotlin/datadog/buildlogic/smoketest/SmokeTestAppEndToEndTest.kt
+++ b/build-logic/smoke-test/src/test/kotlin/datadog/buildlogic/smoketest/SmokeTestAppEndToEndTest.kt
@@ -265,7 +265,7 @@ class SmokeTestAppEndToEndTest {
   }
 
   @Test
-  fun `local proxy property prepends Maven proxy repositories exactly once`() {
+  fun `Maven proxy replaces Maven Central in nested repositories`() {
     writeOuterSettings()
     val proxyRepository = projectDir.resolve("proxy-maven-repo").toFile()
     val projectRepository = projectDir.resolve("project-maven-repo").toFile()
@@ -279,10 +279,29 @@ class SmokeTestAppEndToEndTest {
         sysProperty = "resolved.repositories.path",
       ),
     )
-    writeInnerSettings()
+    writeInnerSettings(
+      """
+      pluginManagement {
+        repositories {
+          mavenCentral()
+        }
+      }
+
+      gradle.settingsEvaluated {
+        val outputDir = java.io.File(providers.gradleProperty("appBuildDir").get())
+        outputDir.mkdirs()
+        outputDir.resolve("plugin-repositories.txt").writeText(
+          pluginManagement.repositories
+            .withType(org.gradle.api.artifacts.repositories.MavenArtifactRepository::class.java)
+            .joinToString(System.lineSeparator()) { "repository=" + it.url }
+        )
+      }
+      """.trimIndent(),
+    )
     writeInnerBuild(
       """
       repositories {
+        mavenCentral()
         maven {
           url = uri("${projectRepository.toURI()}")
         }
@@ -301,8 +320,12 @@ class SmokeTestAppEndToEndTest {
           val artifacts = configurations.compileClasspath.get()
             .sortedBy { it.name }
             .map { it.name + "=" + it.readText() }
+          val repositoryUrls = repositories
+            .withType(org.gradle.api.artifacts.repositories.MavenArtifactRepository::class.java)
+            .map { "repository=" + it.url }
           resolved.get().asFile.writeText(
-            (listOf("init-script-count=" + gradle.startParameter.initScripts.size) + artifacts)
+            (listOf("init-script-count=" + gradle.startParameter.initScripts.size) +
+              repositoryUrls + artifacts)
               .joinToString(System.lineSeparator())
           )
         }
@@ -319,11 +342,31 @@ class SmokeTestAppEndToEndTest {
     assertThat(result.task(":resolveRepositories")?.outcome).isEqualTo(TaskOutcome.SUCCESS)
     val resolvedFile = applicationOutput("resolved-repositories.txt")
     assertThat(resolvedFile).exists()
-    assertThat(resolvedFile.readLines()).containsExactly(
+    val resolvedLines = resolvedFile.readLines()
+    assertThat(resolvedLines).contains(
       "init-script-count=1",
+      "repository=${proxyRepository.toURI()}",
       "project-only-1.0.jar=project-only",
       "shared-1.0.jar=proxy",
     )
+    assertThat(resolvedLines).containsOnlyOnce(
+      "repository=${proxyRepository.toURI()}",
+    )
+    assertThat(resolvedLines).doesNotContain(
+      "repository=https://repo.maven.apache.org/maven2/",
+    )
+    val pluginRepositoriesFile = applicationOutput("plugin-repositories.txt")
+    assertThat(pluginRepositoriesFile).exists()
+    val pluginRepositoryLines = pluginRepositoriesFile.readLines()
+    assertThat(pluginRepositoryLines).contains(
+      "repository=${proxyRepository.toURI()}",
+    )
+    assertThat(pluginRepositoryLines).containsOnlyOnce(
+      "repository=${proxyRepository.toURI()}",
+    )
+    assertThat(pluginRepositoryLines).doesNotContain(
+      "repository=https://repo.maven.apache.org/maven2/",
+    )
   }
 
   @Test
@@ -649,10 +692,11 @@ class SmokeTestAppEndToEndTest {
       "fake-mvnw"
     }
 
-  private fun writeInnerSettings() {
+  private fun writeInnerSettings(additionalContent: String = "") {
     File(applicationDir, "settings.gradle.kts").writeText(
       """
       rootProject.name = "smoke-test-app-fixture-application"
+      $additionalContent
       """.trimIndent(),
     )
   }