diff --git a/otel/src/main/kotlin/com/ryandens/javaagent/otel/JavaagentOTelModificationPlugin.kt b/otel/src/main/kotlin/com/ryandens/javaagent/otel/JavaagentOTelModificationPlugin.kt
index 3ea724f5..2a944948 100644
--- a/otel/src/main/kotlin/com/ryandens/javaagent/otel/JavaagentOTelModificationPlugin.kt
+++ b/otel/src/main/kotlin/com/ryandens/javaagent/otel/JavaagentOTelModificationPlugin.kt
@@ -89,6 +89,11 @@ class JavaagentOTelModificationPlugin : Plugin<Project> {
                     it.into("inst")
                 }
             }
-        project.dependencies.add("javaagent", extendedAgent.map { project.files(it.outputs.files.singleFile) })
+        // Add the extendedAgent output via the task provider (not extendedAgent.outputs.files.singleFile,
+        // which resolves to a plain File and loses provenance). project.files(TaskProvider) carries the
+        // producing task as a builtBy dependency, so consumers of the javaagent configuration that track it
+        // as an input — e.g. the run task in JavaagentApplicationRunPlugin — establish a dependency on
+        // :extendedAgent instead of failing Gradle's implicit-dependency validation.
+        project.dependencies.add("javaagent", project.files(extendedAgent))
     }
 }
diff --git a/plugin/src/functionalTest/kotlin/com/ryandens/javaagent/JavaagentPluginFunctionalTest.kt b/plugin/src/functionalTest/kotlin/com/ryandens/javaagent/JavaagentPluginFunctionalTest.kt
index a7640dc7..ef8adb94 100644
--- a/plugin/src/functionalTest/kotlin/com/ryandens/javaagent/JavaagentPluginFunctionalTest.kt
+++ b/plugin/src/functionalTest/kotlin/com/ryandens/javaagent/JavaagentPluginFunctionalTest.kt
@@ -74,6 +74,30 @@ class JavaagentPluginFunctionalTest {
         assertTrue(ccResult.output.contains("Reusing configuration cache."))
     }
 
+    @Test fun `run task depends on the tasks that build the javaagent artifacts`() {
+        val dependencies = """
+            javaagent project(':simple-agent')
+        """
+
+        createJavaagentProject(dependencies)
+
+        // The run task adds the agent jars via a CommandLineArgumentProvider that is not itself a tracked
+        // input, so the plugin registers the javaagent configuration as a task input to make Gradle schedule
+        // :simple-agent:jar before :hello-world:run. Without that, the run task can launch with
+        // -javaagent:<jar> before that jar has been produced, failing with "Error opening zip file or JAR
+        // manifest missing" (the `can attach to application run task` test above reproduces that
+        // intermittently under parallel scheduling). --dry-run prints the task execution graph in order
+        // without running anything, so asserting the ordering here catches the regression deterministically,
+        // independent of scheduling timing.
+        val result = runBuild(listOf("--dry-run", ":hello-world:run"))
+
+        val agentJarIndex = result.output.indexOf(":simple-agent:jar")
+        val runIndex = result.output.indexOf(":hello-world:run")
+        assertTrue(agentJarIndex >= 0, "expected :simple-agent:jar to be scheduled ahead of :hello-world:run")
+        assertTrue(runIndex >= 0, "expected :hello-world:run to be scheduled")
+        assertTrue(agentJarIndex < runIndex, "expected :simple-agent:jar to be scheduled before :hello-world:run")
+    }
+
     @Test fun `can attach to test task`() {
         // A real third-party javaagent used to verify the plugin attaches it and it logs its version banner.
         val otelVersion = "2.29.0"
diff --git a/plugin/src/main/kotlin/com/ryandens/javaagent/JavaagentApplicationRunPlugin.kt b/plugin/src/main/kotlin/com/ryandens/javaagent/JavaagentApplicationRunPlugin.kt
index 0c645702..d446e04c 100644
--- a/plugin/src/main/kotlin/com/ryandens/javaagent/JavaagentApplicationRunPlugin.kt
+++ b/plugin/src/main/kotlin/com/ryandens/javaagent/JavaagentApplicationRunPlugin.kt
@@ -21,6 +21,19 @@ class JavaagentApplicationRunPlugin :
     ) {
         // configure the run task to use the `javaagent` flag pointing to the dependency stored in the local Maven repository
         project.tasks.named(ApplicationPlugin.TASK_RUN_NAME, JavaExec::class.java).configure {
+            // The agent jars are passed to the JVM via a CommandLineArgumentProvider (see
+            // JavaForkOptionsConfigurer), which resolves the configuration's files at execution time but is
+            // not a tracked task input. Without registering the configuration as an input, Gradle
+            // establishes no ordering between the run task and the tasks that build the agent jars, so under
+            // parallel execution the run task can launch with -javaagent:<jar> before that jar has been
+            // produced, failing with "Error opening zip file or JAR manifest missing".
+            //
+            // A Configuration is Buildable, so registering it as an input makes the run task depend on the
+            // tasks that build the agent jars, the same way JavaagentApplicationDistributionPlugin does for
+            // the start-script task. This requires every artifact added to the javaagent configuration to
+            // carry its producing-task dependency (builtBy); consumers that synthesize a plain File must
+            // preserve it (see the otel example's extendedAgent wiring).
+            it.inputs.files(javaagentConfiguration)
             JavaForkOptionsConfigurer.configureJavaForkOptions(it, javaagentConfiguration.map { configuration -> configuration.files })
         }
     }