diff --git a/pom.xml b/pom.xml
index c71b9ec..937a71d 100644
--- a/pom.xml
+++ b/pom.xml
@@ -53,7 +53,7 @@
     <apache.httpclient.version>4.5.14</apache.httpclient.version>
     <apache.httpcore.version>4.4.16</apache.httpcore.version>
     <apache.httpmime.version>4.5.14</apache.httpmime.version>
-    <org.slf4j.version>2.0.7</org.slf4j.version>
+    <org.slf4j.version>2.0.12</org.slf4j.version>
 
     <!-- Test libraries versions -->
     <junit.version>5.9.2</junit.version>
diff --git a/src/main/java/com/redhat/insights/agent/AgentBasicReport.java b/src/main/java/com/redhat/insights/agent/AgentBasicReport.java
index 8caf93b..fb4cb74 100644
--- a/src/main/java/com/redhat/insights/agent/AgentBasicReport.java
+++ b/src/main/java/com/redhat/insights/agent/AgentBasicReport.java
@@ -1,4 +1,4 @@
-/* Copyright (C) Red Hat 2023 */
+/* Copyright (C) Red Hat 2023-2024 */
 package com.redhat.insights.agent;
 
 import com.redhat.insights.config.InsightsConfiguration;
@@ -10,7 +10,7 @@
 import java.util.Map;
 
 public class AgentBasicReport extends AbstractTopLevelReportBase {
-  private static final InsightsLogger logger = new SLF4JLogger(AgentBasicReport.class);
+  private static final InsightsLogger logger = AgentLogger.getLogger();
 
   private AgentBasicReport(
       InsightsConfiguration config, Map<String, InsightsSubreport> subReports) {
diff --git a/src/main/java/com/redhat/insights/agent/SLF4JLogger.java b/src/main/java/com/redhat/insights/agent/AgentLogger.java
similarity index 55%
rename from src/main/java/com/redhat/insights/agent/SLF4JLogger.java
rename to src/main/java/com/redhat/insights/agent/AgentLogger.java
index d510d94..f4447fb 100644
--- a/src/main/java/com/redhat/insights/agent/SLF4JLogger.java
+++ b/src/main/java/com/redhat/insights/agent/AgentLogger.java
@@ -1,18 +1,39 @@
-/* Copyright (C) Red Hat 2023 */
+/* Copyright (C) Red Hat 2023-2024 */
 package com.redhat.insights.agent;
 
 import com.redhat.insights.logging.InsightsLogger;
 import org.slf4j.Logger;
 import org.slf4j.LoggerFactory;
+import org.slf4j.simple.SimpleLogger;
 
-public class SLF4JLogger implements InsightsLogger {
+public class AgentLogger implements InsightsLogger {
 
-  private final Logger delegate;
+  private static AgentLogger instance;
 
-  public SLF4JLogger(Class<?> clazz) {
+  private Logger delegate;
+
+  private AgentLogger(Class<?> clazz) {
     this.delegate = LoggerFactory.getLogger(clazz);
   }
 
+  public static synchronized AgentLogger getLogger() {
+    if (instance == null) {
+      instance = new AgentLogger(AgentMain.class);
+    }
+    return instance;
+  }
+
+  static class DebugSimpleLogger extends SimpleLogger {
+    public DebugSimpleLogger() {
+      super("com.redhat.insights.agent.AgentLogger");
+      currentLogLevel = SimpleLogger.LOG_LEVEL_DEBUG;
+    }
+  }
+
+  public void setDebugDelegate() {
+    this.delegate = new DebugSimpleLogger();
+  }
+
   @Override
   public void debug(String message) {
     delegate.debug(message);
diff --git a/src/main/java/com/redhat/insights/agent/AgentMain.java b/src/main/java/com/redhat/insights/agent/AgentMain.java
index ca3ef91..b46325e 100644
--- a/src/main/java/com/redhat/insights/agent/AgentMain.java
+++ b/src/main/java/com/redhat/insights/agent/AgentMain.java
@@ -6,7 +6,6 @@
 import com.redhat.insights.http.InsightsFileWritingClient;
 import com.redhat.insights.http.InsightsHttpClient;
 import com.redhat.insights.jars.JarInfo;
-import com.redhat.insights.logging.InsightsLogger;
 import com.redhat.insights.reports.InsightsReport;
 import com.redhat.insights.tls.PEMSupport;
 import java.lang.instrument.Instrumentation;
@@ -22,7 +21,7 @@
 
 /** Main class for the agent. */
 public final class AgentMain {
-  private static final InsightsLogger logger = new SLF4JLogger(AgentMain.class);
+  private static final AgentLogger logger = AgentLogger.getLogger();
 
   private final AgentConfiguration configuration;
   private final BlockingQueue<JarInfo> waitingJars;
@@ -72,6 +71,10 @@ public static void startAgent(String agentArgs, Instrumentation instrumentation)
           "Config indicates Red Hat Insights agent is not to be run. Not starting agent capability.");
       return;
     }
+    if (config.isDebug()) {
+      logger.setDebugDelegate();
+      logger.debug("Running in debug mode");
+    }
 
     final BlockingQueue<JarInfo> jarsToSend = new LinkedBlockingQueue<>();
     try {
@@ -163,7 +166,7 @@ static Optional<AgentConfiguration> parseArgs(String agentArgs) {
 
   private static boolean shouldLookForCerts(AgentConfiguration config) {
     boolean hasToken = config.getMaybeAuthToken().isPresent();
-    return !hasToken && !config.isDebug() && !config.isFileOnly() && !config.isOptingOut();
+    return !hasToken && !config.isFileOnly() && !config.isOptingOut();
   }
 
   private void start() {
@@ -181,7 +184,7 @@ private void start() {
 
   private Supplier<InsightsHttpClient> getInsightsClientSupplier() {
     final Supplier<InsightsHttpClient> out;
-    if (configuration.isDebug() || configuration.isFileOnly()) {
+    if (configuration.isFileOnly()) {
       out = () -> new InsightsFileWritingClient(logger, configuration);
     } else if (configuration.isOCP()) {
       out = () -> new InsightsAgentHttpClient(configuration);
diff --git a/src/main/java/com/redhat/insights/agent/AgentSubreport.java b/src/main/java/com/redhat/insights/agent/AgentSubreport.java
index b0583c9..ac0f484 100644
--- a/src/main/java/com/redhat/insights/agent/AgentSubreport.java
+++ b/src/main/java/com/redhat/insights/agent/AgentSubreport.java
@@ -1,4 +1,4 @@
-/* Copyright (C) Red Hat 2023 */
+/* Copyright (C) Red Hat 2023-2024 */
 package com.redhat.insights.agent;
 
 import static java.lang.System.getProperty;
@@ -19,7 +19,7 @@
 import java.util.function.Function;
 
 public class AgentSubreport implements InsightsSubreport {
-  private static final InsightsLogger logger = new SLF4JLogger(AgentSubreport.class);
+  private static final InsightsLogger logger = AgentLogger.getLogger();
 
   private static final Class<?>[] EMPTY_CLASS_ARRAY = new Class[0];
   private static final Object[] EMPTY_OBJECT_ARRAY = new Object[0];
diff --git a/src/main/java/com/redhat/insights/agent/ClassNoticer.java b/src/main/java/com/redhat/insights/agent/ClassNoticer.java
index 2acb296..2a9af2b 100644
--- a/src/main/java/com/redhat/insights/agent/ClassNoticer.java
+++ b/src/main/java/com/redhat/insights/agent/ClassNoticer.java
@@ -1,4 +1,4 @@
-/* Copyright (C) Red Hat 2023 */
+/* Copyright (C) Red Hat 2023-2024 */
 package com.redhat.insights.agent;
 
 import com.redhat.insights.jars.JarAnalyzer;
@@ -15,7 +15,7 @@
 import java.util.concurrent.BlockingQueue;
 
 public final class ClassNoticer implements ClassFileTransformer {
-  private static final InsightsLogger logger = new SLF4JLogger(ClassNoticer.class);
+  private static final InsightsLogger logger = AgentLogger.getLogger();
 
   private final BlockingQueue<JarInfo> jarsToSend;
   private final JarAnalyzer analyzer;
diff --git a/src/main/java/com/redhat/insights/agent/InsightsAgentHttpClient.java b/src/main/java/com/redhat/insights/agent/InsightsAgentHttpClient.java
index c00c1a1..e3cdc77 100644
--- a/src/main/java/com/redhat/insights/agent/InsightsAgentHttpClient.java
+++ b/src/main/java/com/redhat/insights/agent/InsightsAgentHttpClient.java
@@ -28,7 +28,7 @@
 import org.apache.http.util.EntityUtils;
 
 public final class InsightsAgentHttpClient implements InsightsHttpClient {
-  private static final InsightsLogger logger = new SLF4JLogger(InsightsAgentHttpClient.class);
+  private static final InsightsLogger logger = AgentLogger.getLogger();
   private static final ContentType GENERAL_CONTENT_TYPE = ContentType.create(GENERAL_MIME_TYPE);
   private final Supplier<SSLContext> sslContextSupplier;
   private final InsightsConfiguration configuration;