diff --git a/.gitignore b/.gitignore
index 385805d2ab8..5ca2bec15ea 100644
--- a/.gitignore
+++ b/.gitignore
@@ -60,6 +60,7 @@ replay_pid*
 .bsp/
 **/src/*/generated/*
 !dd-java-agent/benchmark/releases/*.jar
+*.jar
 
 # Magic for local JMC built
 /vendor/jmc-libs
diff --git a/dd-java-agent/agent-bootstrap/src/main/java/datadog/trace/bootstrap/InitializationTelemetry.java b/dd-java-agent/agent-bootstrap/src/main/java/datadog/trace/bootstrap/InitializationTelemetry.java
index d6cf0958ca9..c192d1c4600 100644
--- a/dd-java-agent/agent-bootstrap/src/main/java/datadog/trace/bootstrap/InitializationTelemetry.java
+++ b/dd-java-agent/agent-bootstrap/src/main/java/datadog/trace/bootstrap/InitializationTelemetry.java
@@ -8,7 +8,7 @@
  * Thread safe wrapper around BootstrapInitializationTelemetry used inside the Datadog ClassLoader.
  *
  * <p>Right now, this is needed because of the build separation between the two portions of the
- * bootstrap. We should consider adjusting the build to allow Agent et al to reference
+ * bootstrap. We should consider adjusting the build to allow Agent et al. to reference
  * BootstrapInitializationTelemetry, then we could remove this proxy.
  */
 public abstract class InitializationTelemetry {
@@ -48,7 +48,7 @@ public static final InitializationTelemetry noOpInstance() {
   public abstract void onFatalError(Throwable t);
 
   /**
-   * Indicates that an exception conditional occurred during the bootstrapping process. By default
+   * Indicates that an exception conditional occurred during the bootstrapping process. By default,
    * the exceptional condition is assumed to NOT have fully stopped the initialization of the
    * tracer.
    *
diff --git a/dd-java-agent/src/main/java/datadog/trace/bootstrap/BootstrapInitializationTelemetry.java b/dd-java-agent/src/main/java/datadog/trace/bootstrap/BootstrapInitializationTelemetry.java
index 6e09fa0f30a..a276ff9e8a2 100644
--- a/dd-java-agent/src/main/java/datadog/trace/bootstrap/BootstrapInitializationTelemetry.java
+++ b/dd-java-agent/src/main/java/datadog/trace/bootstrap/BootstrapInitializationTelemetry.java
@@ -92,6 +92,7 @@ public static final class JsonBased extends BootstrapInitializationTelemetry {
 
     // one way false to true
     private volatile boolean incomplete = false;
+    private volatile boolean error = false;
 
     JsonBased(JsonSender sender) {
       this.sender = sender;
@@ -111,11 +112,14 @@ public void initMetaInfo(String attr, String value) {
     public void onAbort(String reasonCode) {
       onPoint("library_entrypoint.abort", "reason:" + reasonCode);
       markIncomplete();
+      setMetadata("abort", mapResultClass(reasonCode), reasonCode);
     }
 
     @Override
     public void onError(Throwable t) {
+      error = true;
       onPoint("library_entrypoint.error", "error_type:" + t.getClass().getName());
+      setMetadata("error", "internal_error", t.getMessage());
     }
 
     @Override
@@ -126,7 +130,32 @@ public void onFatalError(Throwable t) {
 
     @Override
     public void onError(String reasonCode) {
+      error = true;
       onPoint("library_entrypoint.error", "error_type:" + reasonCode);
+      setMetadata("error", mapResultClass(reasonCode), reasonCode);
+    }
+
+    private void setMetadata(String result, String resultClass, String resultReason) {
+      initMetaInfo("result", result);
+      initMetaInfo("result_class", resultClass);
+      initMetaInfo("result_reason", resultReason);
+    }
+
+    private String mapResultClass(String reasonCode) {
+      if (reasonCode == null) {
+        return "success";
+      }
+
+      switch (reasonCode) {
+        case "already_initialized":
+          return "already_instrumented";
+        case "other-java-agents":
+          return "incompatible_library";
+        case "jdk_tool":
+          return "unsupported_binary";
+        default:
+          return "unknown";
+      }
     }
 
     private void onPoint(String name, String tag) {
@@ -143,6 +172,10 @@ public void markIncomplete() {
 
     @Override
     public void finish() {
+      if (!this.incomplete && !this.error) {
+        setMetadata("success", "success", "Successfully configured ddtrace package");
+      }
+
       try (JsonWriter writer = new JsonWriter()) {
         writer.beginObject();
         writer.name("metadata").beginObject();
diff --git a/dd-java-agent/src/main/java6/datadog/trace/bootstrap/AgentPreCheck.java b/dd-java-agent/src/main/java6/datadog/trace/bootstrap/AgentPreCheck.java
index a2919226eb5..6503ff44d10 100644
--- a/dd-java-agent/src/main/java6/datadog/trace/bootstrap/AgentPreCheck.java
+++ b/dd-java-agent/src/main/java6/datadog/trace/bootstrap/AgentPreCheck.java
@@ -11,6 +11,7 @@
 
 /** Special lightweight pre-main class that skips installation on incompatible JVMs. */
 public class AgentPreCheck {
+  public static final int MIN_JAVA_VERSION = 8;
   public static void premain(final String agentArgs, final Instrumentation inst) {
     agentmain(agentArgs, inst);
   }
@@ -59,6 +60,10 @@ static void sendTelemetry(String forwarderPath, String javaVersion, String agent
             + "\"points\":[{"
             + "\"name\":\"library_entrypoint.abort\","
             + "\"tags\":[\"reason:incompatible_runtime\"]"
+            + "\"result:error\","
+            + "\"result_class:incompatible_runtime\","
+            + "\"result_reason:java version" + MIN_JAVA_VERSION + "+ required\""
+            + "]"
             + "}]"
             + "}";
 
@@ -87,7 +92,7 @@ private static boolean compatible() {
   static boolean compatible(String javaVersion, String javaHome, PrintStream output) {
     int majorJavaVersion = parseJavaMajorVersion(javaVersion);
 
-    if (majorJavaVersion >= 8) {
+    if (majorJavaVersion >= MIN_JAVA_VERSION) {
       return true;
     }
 
diff --git a/dd-java-agent/src/test/groovy/datadog/trace/bootstrap/BootstrapInitializationTelemetryTest.groovy b/dd-java-agent/src/test/groovy/datadog/trace/bootstrap/BootstrapInitializationTelemetryTest.groovy
index da0dafa6d4a..2a0cfbcfa74 100644
--- a/dd-java-agent/src/test/groovy/datadog/trace/bootstrap/BootstrapInitializationTelemetryTest.groovy
+++ b/dd-java-agent/src/test/groovy/datadog/trace/bootstrap/BootstrapInitializationTelemetryTest.groovy
@@ -26,19 +26,47 @@ class BootstrapInitializationTelemetryTest extends Specification {
     initTelemetryProxy.setAdaptee(initTelemetry)
 
     this.initTelemetry = initTelemetryProxy
+    this.initTelemetry.initMetaInfo("runtime_name", "java")
+    this.initTelemetry.initMetaInfo("runtime_version", "1.8.0_382")
     this.capture = capture
   }
 
-  def "real example"() {
+  def "test success"() {
     when:
-    initTelemetry.initMetaInfo("runtime_name", "java")
-    initTelemetry.initMetaInfo("runtime_version", "1.8.0_382")
+    initTelemetry.finish()
+
+    then:
+    capture.json() == json("success", "success", "Successfully configured ddtrace package", 
+                           [[name: "library_entrypoint.complete"]])
+  }
 
+  def "real example"() {
+    when:
     initTelemetry.onError(new Exception("foo"))
     initTelemetry.finish()
 
     then:
-    capture.json() == '{"metadata":{"runtime_name":"java","runtime_version":"1.8.0_382"},"points":[{"name":"library_entrypoint.error","tags":["error_type:java.lang.Exception"]},{"name":"library_entrypoint.complete"}]}'
+    capture.json() == json("error", "internal_error", "foo", [
+      [name: "library_entrypoint.error", tags: ["error_type:java.lang.Exception"]],
+      [name: "library_entrypoint.complete"]
+    ])
+  }
+
+  def "test abort"() {
+    when:
+    initTelemetry.onAbort(reasonCode)
+    initTelemetry.finish()
+
+    then:
+    capture.json() == json("abort", resultClass, reasonCode, 
+                           [[name: "library_entrypoint.abort", tags: ["reason:${reasonCode}"]]])
+
+    where:
+    reasonCode            | resultClass
+    "jdk_tool"            | "unsupported_binary"
+    "already_initialized" | "already_instrumented"
+    "other-java-agents"   | "incompatible_library"
+    "foo"                 | "unknown"
   }
 
   def "trivial completion check"() {
@@ -65,6 +93,8 @@ class BootstrapInitializationTelemetryTest extends Specification {
 
     then:
     !capture.json().contains("library_entrypoint.complete")
+    capture.json() == json("error", "internal_error", "foo", 
+                           [[name: "library_entrypoint.error", tags: ["error_type:java.lang.Exception"]]])
   }
 
   def "incomplete on abort"() {
@@ -76,6 +106,10 @@ class BootstrapInitializationTelemetryTest extends Specification {
     !capture.json().contains("library_entrypoint.complete")
   }
 
+  private String json(String result, String resultClass, String resultReason, List points) {
+    return """{"metadata":{"runtime_name":"java","runtime_version":"1.8.0_382","result":"${result}","result_class":"${resultClass}","result_reason":"${resultReason}"},"points":${new groovy.json.JsonBuilder(points)}}"""
+  }
+
   static class Capture implements BootstrapInitializationTelemetry.JsonSender {
     String json