diff --git a/src/main/java/io/openliberty/tools/common/plugins/util/DevUtil.java b/src/main/java/io/openliberty/tools/common/plugins/util/DevUtil.java
index c8c3240e..73d6164e 100644
--- a/src/main/java/io/openliberty/tools/common/plugins/util/DevUtil.java
+++ b/src/main/java/io/openliberty/tools/common/plugins/util/DevUtil.java
@@ -2550,8 +2550,8 @@ public void runHotkeyReaderThread(ThreadPoolExecutor executor) {
                     // it's available
                     inputUnavailable.wait(500);
                 }
-                printDevModeMessages(inputUnavailable.get(), firstStartup);
-                firstStartup = false;
+                // firstStartup is false by the time this is called after initial startup.
+                printDevModeMessages(inputUnavailable.get(), false);
             } catch (InterruptedException e) {
                 debug("Interrupted while waiting to determine whether input can be read", e);
             } catch (PluginExecutionException pe) {
@@ -3199,6 +3199,17 @@ public void watchFiles(File outputDirectory, File testOutputDirectory, final Thr
                 }
             }
 
+            if (firstStartup) {
+                synchronized (inputUnavailable) {
+                    try {
+                        printDevModeMessages(inputUnavailable.get(), true);
+                    } catch (PluginExecutionException pe) {
+                        error(pe.getMessage());
+                    }
+                }
+                firstStartup = false;
+            }
+
             initWatchLoop();
 
             while (true) {