diff --git a/nifi-framework-bundle/nifi-framework/nifi-web/nifi-jetty/src/main/java/org/apache/nifi/web/server/JettyServer.java b/nifi-framework-bundle/nifi-framework/nifi-web/nifi-jetty/src/main/java/org/apache/nifi/web/server/JettyServer.java
index 0f577b76b5..917dd23e1c 100644
--- a/nifi-framework-bundle/nifi-framework/nifi-web/nifi-jetty/src/main/java/org/apache/nifi/web/server/JettyServer.java
+++ b/nifi-framework-bundle/nifi-framework/nifi-web/nifi-jetty/src/main/java/org/apache/nifi/web/server/JettyServer.java
@@ -153,6 +153,12 @@ public class JettyServer implements NiFiServer, ExtensionUiLoader {
     private static final String CONTEXT_PATH_NIFI_API = "/nifi-api";
     private static final String CONTEXT_PATH_NIFI_CONTENT_VIEWER = "/nifi-content-viewer";
     private static final String CONTEXT_PATH_NIFI_DOCS = "/nifi-docs";
+    private static final Set<String> REQUIRED_CONTEXT_PATHS = Set.of(
+            CONTEXT_PATH_NIFI,
+            CONTEXT_PATH_NIFI_API,
+            CONTEXT_PATH_NIFI_CONTENT_VIEWER,
+            CONTEXT_PATH_NIFI_DOCS
+    );
 
     private static final RequestFilterProvider REQUEST_FILTER_PROVIDER = new StandardRequestFilterProvider();
     private static final RequestFilterProvider REST_API_REQUEST_FILTER_PROVIDER = new RestApiRequestFilterProvider();
@@ -202,7 +208,7 @@ public class JettyServer implements NiFiServer, ExtensionUiLoader {
     private UiExtensionMapping componentUiExtensions;
     private Collection<WebAppContext> componentUiExtensionWebContexts;
 
-    private Map<BundleCoordinate, List<App>> appsByBundleCoordinate = new ConcurrentHashMap<>();
+    private final Map<BundleCoordinate, List<App>> appsByBundleCoordinate = new ConcurrentHashMap<>();
 
     /**
      * Default no-arg constructor for ServiceLoader
@@ -631,6 +637,9 @@ public class JettyServer implements NiFiServer, ExtensionUiLoader {
         webappContext.setErrorHandler(getErrorHandler());
         webappContext.setTempDirectory(getWebAppTempDirectory(warFile));
 
+        final boolean throwUnavailableOnStartupException = REQUIRED_CONTEXT_PATHS.contains(contextPath);
+        webappContext.setThrowUnavailableOnStartupException(throwUnavailableOnStartupException);
+
         final List<FilterHolder> requestFilters = CONTEXT_PATH_NIFI_API.equals(contextPath)
                 ? REST_API_REQUEST_FILTER_PROVIDER.getFilters(props)
                 : REQUEST_FILTER_PROVIDER.getFilters(props);
@@ -833,7 +842,7 @@ public class JettyServer implements NiFiServer, ExtensionUiLoader {
 
             // Additionally loaded NARs and collected flow resources must be in place before starting the flows
             narProviderService = new ExternalResourceProviderServiceBuilder("NAR Auto-Loader Provider", extensionManager)
-                    .providers(buildExternalResourceProviders(sslContext, extensionManager, NAR_PROVIDER_PREFIX, descriptor -> descriptor.getLocation().toLowerCase().endsWith(".nar")))
+                    .providers(buildExternalResourceProviders(sslContext, extensionManager, descriptor -> descriptor.getLocation().toLowerCase().endsWith(".nar")))
                     .targetDirectory(new File(props.getProperty(NiFiProperties.NAR_LIBRARY_AUTOLOAD_DIRECTORY, NiFiProperties.DEFAULT_NAR_LIBRARY_AUTOLOAD_DIR)))
                     .conflictResolutionStrategy(props.getProperty(NAR_PROVIDER_CONFLICT_RESOLUTION, DEFAULT_NAR_PROVIDER_CONFLICT_RESOLUTION))
                     .pollInterval(props.getProperty(NAR_PROVIDER_POLL_INTERVAL_PROPERTY, DEFAULT_NAR_PROVIDER_POLL_INTERVAL))
@@ -859,21 +868,8 @@ public class JettyServer implements NiFiServer, ExtensionUiLoader {
             narAutoLoader = new NarAutoLoader(props, narLoader);
             narAutoLoader.start();
 
-            // start the server
             server.start();
 
-            // ensure everything started successfully
-            for (Handler handler : server.getHandlers()) {
-                // see if the handler is a web app
-                if (handler instanceof final WebAppContext context) {
-                    // see if this webapp had any exceptions that would
-                    // cause it to be unavailable
-                    if (context.getUnavailableException() != null) {
-                        startUpFailure(context.getUnavailableException());
-                    }
-                }
-            }
-
             // ensure the appropriate wars deployed successfully before injecting the NiFi context and security filters
             // this must be done after starting the server (and ensuring there were no start up failures)
             if (webApiContext != null) {
@@ -977,22 +973,21 @@ public class JettyServer implements NiFiServer, ExtensionUiLoader {
     private Map<String, ExternalResourceProvider> buildExternalResourceProviders(
             final SSLContext sslContext,
             final ExtensionManager extensionManager,
-            final String providerPropertyPrefix,
             final Predicate<ExternalResourceDescriptor> filter
     )
         throws ClassNotFoundException, InstantiationException, IllegalAccessException, InvocationTargetException, NoSuchMethodException {
 
         final Map<String, ExternalResourceProvider> result = new HashMap<>();
-        final Set<String> externalSourceNames = props.getDirectSubsequentTokens(providerPropertyPrefix);
+        final Set<String> externalSourceNames = props.getDirectSubsequentTokens(NAR_PROVIDER_PREFIX);
 
         for (final String externalSourceName : externalSourceNames) {
             logger.info("External resource provider '{}' found in configuration", externalSourceName);
 
-            final String providerClass = props.getProperty(providerPropertyPrefix + externalSourceName + "." + NAR_PROVIDER_IMPLEMENTATION_PROPERTY);
+            final String providerClass = props.getProperty(NAR_PROVIDER_PREFIX + externalSourceName + "." + NAR_PROVIDER_IMPLEMENTATION_PROPERTY);
             final String providerId = UUID.randomUUID().toString();
 
             final ExternalResourceProviderInitializationContext context
-                    = new PropertyBasedExternalResourceProviderInitializationContext(sslContext, props, providerPropertyPrefix + externalSourceName + ".", filter);
+                    = new PropertyBasedExternalResourceProviderInitializationContext(sslContext, props, NAR_PROVIDER_PREFIX + externalSourceName + ".", filter);
             result.put(providerId, createProviderInstance(extensionManager, providerClass, providerId, context));
         }
 
@@ -1071,10 +1066,8 @@ public class JettyServer implements NiFiServer, ExtensionUiLoader {
         }
     }
 
-    private void startUpFailure(Throwable t) {
-        System.err.println("Failed to start web server: " + t.getMessage());
-        System.err.println("Shutting down...");
-        logger.error("Failed to start web server... shutting down.", t);
+    private void startUpFailure(final Throwable t) {
+        logger.error("Failed to start Server", t);
         System.exit(1);
     }
 
@@ -1092,8 +1085,8 @@ public class JettyServer implements NiFiServer, ExtensionUiLoader {
     public void stop() {
         try {
             server.stop();
-        } catch (Exception ex) {
-            logger.warn("Failed to stop web server", ex);
+        } catch (final Exception e) {
+            logger.warn("Failed to stop Server", e);
         }
 
         try {