diff --git a/core/src/main/java/hudson/init/InitStrategy.java b/core/src/main/java/hudson/init/InitStrategy.java
index be3312a1ff8a..95c31b94bf53 100644
--- a/core/src/main/java/hudson/init/InitStrategy.java
+++ b/core/src/main/java/hudson/init/InitStrategy.java
@@ -9,6 +9,7 @@
 import java.util.ArrayList;
 import java.util.Arrays;
 import java.util.Collection;
+import java.util.Comparator;
 import java.util.Iterator;
 import java.util.List;
 import java.util.ServiceLoader;
@@ -64,7 +65,11 @@ private void listPluginFiles(PluginManager pm, String extension, Collection<File
         if (files == null)
             throw new IOException("Jenkins is unable to create " + pm.rootDir + "\nPerhaps its security privilege is insufficient");
 
-        all.addAll(Arrays.asList(files));
+        List<File> pluginFiles = new ArrayList<>();
+        pluginFiles.addAll(List.of(files));
+        pluginFiles.sort(Comparator.comparing(File::getName));
+
+        all.addAll(pluginFiles);
     }
 
     /**
@@ -76,15 +81,16 @@ private void listPluginFiles(PluginManager pm, String extension, Collection<File
     protected void getBundledPluginsFromProperty(final List<File> r) {
         String hplProperty = SystemProperties.getString("hudson.bundled.plugins");
         if (hplProperty != null) {
+            List<File> pluginFiles = new ArrayList<>();
             for (String hplLocation : hplProperty.split(",")) {
                 File hpl = new File(hplLocation.trim());
                 if (hpl.exists()) {
-                    r.add(hpl);
+                    pluginFiles.add(hpl);
                 } else if (hpl.getName().contains("*")) {
                     try {
                         new DirScanner.Glob(hpl.getName(), null).scan(hpl.getParentFile(), new FileVisitor() {
                             @Override public void visit(File f, String relativePath) throws IOException {
-                                r.add(f);
+                                pluginFiles.add(f);
                             }
                         });
                     } catch (IOException x) {
@@ -94,6 +100,8 @@ protected void getBundledPluginsFromProperty(final List<File> r) {
                     LOGGER.warning("bundled plugin " + hplLocation + " does not exist");
                 }
             }
+            pluginFiles.sort(Comparator.comparing(File::getName));
+            r.addAll(pluginFiles);
         }
     }