diff --git a/CHANGELOG.md b/CHANGELOG.md
index 339177b9..522dbcdf 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -5,6 +5,7 @@
 ### Changed
 
  - Added `language_version` key to be sent with metadata (#110)
+ - Added more debug logging to isolate issues easier (#111)
 
 ## [1.0.0] 2019-11-05
 
diff --git a/src/Agent.php b/src/Agent.php
index 8579b1f8..0adb993c 100644
--- a/src/Agent.php
+++ b/src/Agent.php
@@ -130,8 +130,17 @@ public static function fromConfig(Config $config, ?LoggerInterface $logger = nul
 
     public function connect() : void
     {
-        if (! $this->connector->connected() && $this->enabled()) {
-            $this->logger->info('Scout Core Agent Connection Failed, attempting to start');
+        if (! $this->enabled()) {
+            $this->logger->debug('Connection skipped, since monitoring is disabled');
+
+            return;
+        }
+
+        if (! $this->connector->connected()) {
+            $this->logger->info(sprintf(
+                'Scout Core Agent (app=%s) not connected yet, attempting to start',
+                $this->config->get(ConfigKey::APPLICATION_NAME)
+            ));
             $manager = new AutomaticDownloadAndLaunchManager(
                 $this->config,
                 $this->logger,
@@ -157,7 +166,10 @@ public function connect() : void
                 $this->logger->warning($failedToConnect->getMessage());
             }
         } else {
-            $this->logger->debug('Scout Core Agent Connected');
+            $this->logger->debug(sprintf(
+                'Scout Core Agent Connected (app=%s)',
+                $this->config->get(ConfigKey::APPLICATION_NAME)
+            ));
         }
     }
 
diff --git a/tests/Unit/AgentTest.php b/tests/Unit/AgentTest.php
index 6a114c9f..a016b240 100644
--- a/tests/Unit/AgentTest.php
+++ b/tests/Unit/AgentTest.php
@@ -119,7 +119,7 @@ public function testLogMessagesAreLoggedWhenUsingDefaultConfiguration() : void
             ->method('log')
             ->with(
                 LogLevel::DEBUG,
-                self::stringContains('Scout Core Agent Connected'),
+                self::stringContains('Connection skipped, since monitoring is disabled'),
                 []
             );