diff --git a/dd-java-agent/src/main/java/datadog/trace/agent/TracingAgent.java b/dd-java-agent/src/main/java/datadog/trace/agent/TracingAgent.java
index f137712ce4..ecc51e8b0d 100644
--- a/dd-java-agent/src/main/java/datadog/trace/agent/TracingAgent.java
+++ b/dd-java-agent/src/main/java/datadog/trace/agent/TracingAgent.java
@@ -276,7 +276,7 @@ public class TracingAgent {
 
     final String logManagerProp = System.getProperty("java.util.logging.manager");
     if (logManagerProp != null) {
-      final boolean onSysClasspath = ClassLoader.getSystemResource(logManagerProp) == null;
+      final boolean onSysClasspath = ClassLoader.getSystemResource(logManagerProp) != null;
       if (debugEnabled) {
         System.out.println("Prop - logging.manager: " + logManagerProp);
         System.out.println("logging.manager on system classpath: " + onSysClasspath);
diff --git a/dd-java-agent/src/test/groovy/datadog/trace/agent/CustomLogManagerTest.groovy b/dd-java-agent/src/test/groovy/datadog/trace/agent/CustomLogManagerTest.groovy
index 226f8a231e..c40c5655d1 100644
--- a/dd-java-agent/src/test/groovy/datadog/trace/agent/CustomLogManagerTest.groovy
+++ b/dd-java-agent/src/test/groovy/datadog/trace/agent/CustomLogManagerTest.groovy
@@ -30,14 +30,25 @@ class CustomLogManagerTest extends Specification {
     IntegrationTestUtils.runOnSeparateJvm(LogManagerSetter.getName()
       , [agentArg, "-Ddd.jmxfetch.enabled=true", "-Ddd.jmxfetch.refresh-beans-period=1", "-Ddatadog.slf4j.simpleLogger.defaultLogLevel=off"] as String[]
       , "" as String[]
+      , [:]
+      , true) == 0
+  }
+
+  def "jmxfetch starts up in premain if configured log manager on system classpath"() {
+    expect:
+    IntegrationTestUtils.runOnSeparateJvm(LogManagerSetter.getName()
+      , [agentArg, "-Ddd.jmxfetch.enabled=true", "-Ddd.jmxfetch.refresh-beans-period=1", "-Ddatadog.slf4j.simpleLogger.defaultLogLevel=off", "-Djava.util.logging.manager=jvmbootstraptest.CustomLogManager"] as String[]
+      , "" as String[]
+      , [:]
       , true) == 0
   }
 
   def "jmxfetch startup is delayed with java.util.logging.manager sysprop"() {
     expect:
     IntegrationTestUtils.runOnSeparateJvm(LogManagerSetter.getName()
-      , [agentArg, "-Ddd.jmxfetch.enabled=true", "-Ddd.jmxfetch.refresh-beans-period=1", "-Ddatadog.slf4j.simpleLogger.defaultLogLevel=off", "-Djava.util.logging.manager=jvmbootstraptest.CustomLogManager"] as String[]
+      , [agentArg, "-Ddd.jmxfetch.enabled=true", "-Ddd.jmxfetch.refresh-beans-period=1", "-Ddatadog.slf4j.simpleLogger.defaultLogLevel=off", "-Djava.util.logging.manager=jvmbootstraptest.MissingLogManager"] as String[]
       , "" as String[]
+      , [:]
       , true) == 0
   }
 
@@ -46,6 +57,16 @@ class CustomLogManagerTest extends Specification {
     IntegrationTestUtils.runOnSeparateJvm(LogManagerSetter.getName()
       , [agentArg, "-Ddd.jmxfetch.enabled=true", "-Ddd.jmxfetch.refresh-beans-period=1", "-Ddatadog.slf4j.simpleLogger.defaultLogLevel=off", "-Ddd.app.customlogmanager=true"] as String[]
       , "" as String[]
+      , [:]
+      , true) == 0
+  }
+
+  def "jmxfetch startup delayed with JBOSS_HOME environment variable"() {
+    expect:
+    IntegrationTestUtils.runOnSeparateJvm(LogManagerSetter.getName()
+      , [agentArg, "-Ddd.jmxfetch.enabled=true", "-Ddd.jmxfetch.refresh-beans-period=1", "-Ddatadog.slf4j.simpleLogger.defaultLogLevel=off", "-Ddd.app.customlogmanager=true"] as String[]
+      , "" as String[]
+      , ["JBOSS_HOME": "/"]
       , true) == 0
   }
 }
diff --git a/dd-java-agent/src/test/java/datadog/trace/agent/test/IntegrationTestUtils.java b/dd-java-agent/src/test/java/datadog/trace/agent/test/IntegrationTestUtils.java
index 7f9f856e36..af5c22b872 100644
--- a/dd-java-agent/src/test/java/datadog/trace/agent/test/IntegrationTestUtils.java
+++ b/dd-java-agent/src/test/java/datadog/trace/agent/test/IntegrationTestUtils.java
@@ -16,6 +16,7 @@ import java.net.URL;
 import java.util.ArrayList;
 import java.util.Arrays;
 import java.util.List;
+import java.util.Map;
 import java.util.UUID;
 import java.util.concurrent.Callable;
 import java.util.jar.Attributes;
@@ -198,12 +199,13 @@ public class IntegrationTestUtils {
       final String mainClassName,
       final String[] jvmArgs,
       final String[] mainMethodArgs,
+      final Map<String, String> envVars,
       final boolean printOutputStreams)
       throws Exception {
     final String separator = System.getProperty("file.separator");
     final String classpath = System.getProperty("java.class.path");
     final String path = System.getProperty("java.home") + separator + "bin" + separator + "java";
-    final List<String> commands = new ArrayList();
+    final List<String> commands = new ArrayList<>();
     commands.add(path);
     commands.addAll(Arrays.asList(jvmArgs));
     commands.add("-cp");
@@ -211,6 +213,7 @@ public class IntegrationTestUtils {
     commands.add(mainClassName);
     commands.addAll(Arrays.asList(mainMethodArgs));
     final ProcessBuilder processBuilder = new ProcessBuilder(commands.toArray(new String[0]));
+    processBuilder.environment().putAll(envVars);
     final Process process = processBuilder.start();
     final int result = process.waitFor();
 
diff --git a/dd-java-agent/src/test/java/jvmbootstraptest/LogManagerSetter.java b/dd-java-agent/src/test/java/jvmbootstraptest/LogManagerSetter.java
index f1d95a7b08..94aad7be17 100644
--- a/dd-java-agent/src/test/java/jvmbootstraptest/LogManagerSetter.java
+++ b/dd-java-agent/src/test/java/jvmbootstraptest/LogManagerSetter.java
@@ -3,20 +3,38 @@ package jvmbootstraptest;
 import java.util.logging.LogManager;
 
 public class LogManagerSetter {
-  public static void main(String... args) throws Exception {
+  public static void main(final String... args) throws Exception {
     if (System.getProperty("java.util.logging.manager") != null) {
-      customAssert(
-          isJmxfetchStarted(),
-          false,
-          "jmxfetch startup must be delayed when log manager system property is present.");
+      if (ClassLoader.getSystemResource(System.getProperty("java.util.logging.manager")) == null) {
+        customAssert(
+            isJmxfetchStarted(),
+            false,
+            "jmxfetch startup must be delayed when log manager system property is present.");
+        // Change back to a valid LogManager.
+        System.setProperty("java.util.logging.manager", CustomLogManager.class.getName());
+        customAssert(
+            LogManager.getLogManager().getClass(),
+            LogManagerSetter.class
+                .getClassLoader()
+                .loadClass(System.getProperty("java.util.logging.manager")),
+            "Javaagent should not prevent setting a custom log manager");
+        customAssert(isJmxfetchStarted(), true, "jmxfetch should start after loading LogManager.");
+      } else {
+        customAssert(
+            isJmxfetchStarted(),
+            true,
+            "jmxfetch should start in premain when custom log manager found on classpath.");
+      }
+    } else if (System.getProperty("dd.app.customlogmanager") != null) {
+      System.setProperty("java.util.logging.manager", CustomLogManager.class.getName());
       customAssert(
           LogManager.getLogManager().getClass(),
           LogManagerSetter.class
               .getClassLoader()
               .loadClass(System.getProperty("java.util.logging.manager")),
           "Javaagent should not prevent setting a custom log manager");
-      customAssert(isJmxfetchStarted(), true, "jmxfetch should start after loading LogManager.");
-    } else if (System.getProperty("dd.app.customlogmanager") != null) {
+
+    } else if (System.getenv("JBOSS_HOME") != null) {
       System.setProperty("java.util.logging.manager", CustomLogManager.class.getName());
       customAssert(
           LogManager.getLogManager().getClass(),
@@ -33,7 +51,8 @@ public class LogManagerSetter {
     }
   }
 
-  private static void customAssert(Object got, Object expected, String assertionMessage) {
+  private static void customAssert(
+      final Object got, final Object expected, final String assertionMessage) {
     if ((null == got && got != expected) || !got.equals(expected)) {
       throw new RuntimeException(
           "Assertion failed. Expected <" + expected + "> got <" + got + "> " + assertionMessage);
@@ -41,7 +60,7 @@ public class LogManagerSetter {
   }
 
   private static boolean isJmxfetchStarted() {
-    for (Thread thread : Thread.getAllStackTraces().keySet()) {
+    for (final Thread thread : Thread.getAllStackTraces().keySet()) {
       if ("dd-jmx-collector".equals(thread.getName())) {
         return true;
       }