diff --git a/docs/changelog/44536.yaml b/docs/changelog/44536.yaml
new file mode 100644
index 0000000000000..ddae6474d3d91
--- /dev/null
+++ b/docs/changelog/44536.yaml
@@ -0,0 +1,5 @@
+pr: 44536
+summary: Log summarised description of `StartupExceptions`
+area: Infra/Logging
+type: enhancement
+issues: []
diff --git a/server/src/main/java/org/elasticsearch/bootstrap/ElasticsearchUncaughtExceptionHandler.java b/server/src/main/java/org/elasticsearch/bootstrap/ElasticsearchUncaughtExceptionHandler.java
index 1c3c0ccf6b61f..c60a0d6015255 100644
--- a/server/src/main/java/org/elasticsearch/bootstrap/ElasticsearchUncaughtExceptionHandler.java
+++ b/server/src/main/java/org/elasticsearch/bootstrap/ElasticsearchUncaughtExceptionHandler.java
@@ -22,6 +22,8 @@
 import org.apache.logging.log4j.LogManager;
 import org.apache.logging.log4j.Logger;
 import org.apache.logging.log4j.message.ParameterizedMessage;
+import org.elasticsearch.ElasticsearchException;
+import org.elasticsearch.ExceptionsHelper;
 import org.elasticsearch.common.SuppressForbidden;
 
 import java.io.IOError;
@@ -53,6 +55,10 @@ public void uncaughtException(Thread t, Throwable e) {
                     halt(1);
                 }
             }
+        } else if (e instanceof StartupException) {
+            // StartupException means that this server didn't start, and we want to do everything we can to make that
+            // error clear to anyone who consults the logs so that they're not simply overwhelmed by a stack trace.
+            onStartupException(t.getName(), (StartupException) e);
         } else {
             onNonFatalUncaught(t.getName(), e);
         }
@@ -70,6 +76,41 @@ void onNonFatalUncaught(final String threadName, final Throwable t) {
         logger.warn(() -> new ParameterizedMessage("uncaught exception in thread [{}]", threadName), t);
     }
 
+    void onStartupException(final String threadName, final StartupException e) {
+        String bannerMessage = describeStartupException(e);
+        logger.error(bannerMessage);
+        logger.warn(() -> new ParameterizedMessage("uncaught exception in thread [{}]", threadName), e);
+        // Log the error message twice (before and after the stack trace) so that it is super-obvious to anyone reading the logs
+        logger.error(bannerMessage);
+    }
+
+    // accessible for testing
+    static String describeStartupException(StartupException e) {
+        StringBuilder bannerMessage = new StringBuilder("an exception was thrown that prevented this node from starting (")
+            // Append the top message so that it as clear as possible that this message is just a summary of the stacktrace next to it.
+            .append(e.getMessage())
+            .append(")");
+        // Find the first elasticsearch exception, that message is the most likely to provide a helpful explanation
+        ElasticsearchException esCause = (ElasticsearchException) ExceptionsHelper.unwrap(e, ElasticsearchException.class);
+        if (esCause != null) {
+            bannerMessage.append("\nthis was caused by:");
+            // Allow the elasticsearch exception to decide on the best root cause(s to report)
+            for (ElasticsearchException root : esCause.guessRootCauses()) {
+                bannerMessage.append("\n * ").append(root.getMessage())
+                    .append(" (").append(ElasticsearchException.getExceptionName(root)).append(")");
+                String indent = "   ";
+                Throwable cause = root.getCause();
+                for (int counter = 0; counter < 3 && cause != null; counter++) {
+                    bannerMessage.append('\n').append(indent).append("- caused by: ")
+                        .append(cause.getMessage()).append(" (").append(ElasticsearchException.getExceptionName(cause)).append(")");
+                    cause = cause.getCause();
+                    indent += "  ";
+                }
+            }
+        }
+        return bannerMessage.toString();
+    }
+
     void halt(int status) {
         AccessController.doPrivileged(new PrivilegedHaltAction(status));
     }
diff --git a/server/src/test/java/org/elasticsearch/bootstrap/ElasticsearchUncaughtExceptionHandlerTests.java b/server/src/test/java/org/elasticsearch/bootstrap/ElasticsearchUncaughtExceptionHandlerTests.java
index df415d713d103..f0c7b4ed4ed2e 100644
--- a/server/src/test/java/org/elasticsearch/bootstrap/ElasticsearchUncaughtExceptionHandlerTests.java
+++ b/server/src/test/java/org/elasticsearch/bootstrap/ElasticsearchUncaughtExceptionHandlerTests.java
@@ -19,6 +19,8 @@
 
 package org.elasticsearch.bootstrap;
 
+import org.elasticsearch.ElasticsearchException;
+import org.elasticsearch.ElasticsearchSecurityException;
 import org.elasticsearch.test.ESTestCase;
 
 import java.io.IOError;
@@ -129,6 +131,38 @@ public void testIsFatalCause() {
         assertNonFatal(new UncheckedIOException(new IOException()));
     }
 
+    public void testStartupExceptionMessageWithoutElasticsearchException() {
+        final StartupException exception = new StartupException(new IndexOutOfBoundsException("test"));
+        final String message = ElasticsearchUncaughtExceptionHandler.describeStartupException(exception);
+        assertThat(message, equalTo("an exception was thrown that prevented this node from starting" +
+            " (java.lang.IndexOutOfBoundsException: test)"));
+    }
+
+    public void testStartupExceptionMessageWithElasticsearchException() {
+        final StartupException exception = new StartupException(new RuntimeException("test",
+            new ElasticsearchException("es-exception", new RuntimeException("the-cause", new IndexOutOfBoundsException("root-cause")))));
+        final String message = ElasticsearchUncaughtExceptionHandler.describeStartupException(exception);
+        assertThat(message, equalTo(
+            "an exception was thrown that prevented this node from starting (java.lang.RuntimeException: test)\n" +
+                "this was caused by:\n" +
+                " * es-exception (exception)\n" +
+                "   - caused by: the-cause (runtime_exception)\n" +
+                "     - caused by: root-cause (index_out_of_bounds_exception)"));
+    }
+
+    public void testStartupExceptionMessageWithChainOfElasticsearchExceptions() {
+        final StartupException exception = new StartupException(new RuntimeException("test", new ElasticsearchException("es-exception-1",
+            new ElasticsearchSecurityException("es-exception-2", new RuntimeException("the-cause",
+                new IndexOutOfBoundsException("root-cause"))))));
+        final String message = ElasticsearchUncaughtExceptionHandler.describeStartupException(exception);
+        assertThat(message, equalTo(
+            "an exception was thrown that prevented this node from starting (java.lang.RuntimeException: test)\n" +
+                "this was caused by:\n" +
+                " * es-exception-2 (security_exception)\n" +
+                "   - caused by: the-cause (runtime_exception)\n" +
+                "     - caused by: root-cause (index_out_of_bounds_exception)"));
+    }
+
     private void assertFatal(Throwable cause) {
         assertTrue(ElasticsearchUncaughtExceptionHandler.isFatalUncaught(cause));
     }