diff --git a/distribution/tools/server-cli/src/main/java/org/elasticsearch/server/cli/SystemJvmOptions.java b/distribution/tools/server-cli/src/main/java/org/elasticsearch/server/cli/SystemJvmOptions.java
index 6fe7c18d68d27..285ac82a63aef 100644
--- a/distribution/tools/server-cli/src/main/java/org/elasticsearch/server/cli/SystemJvmOptions.java
+++ b/distribution/tools/server-cli/src/main/java/org/elasticsearch/server/cli/SystemJvmOptions.java
@@ -70,7 +70,7 @@ static List<String> systemJvmOptions(Settings nodeSettings, final Map<String, St
             maybeSetActiveProcessorCount(nodeSettings),
             maybeSetReplayFile(distroType, isHotspot),
             maybeWorkaroundG1Bug(),
-            maybeAllowSecurityManager(),
+            maybeAllowSecurityManager(useEntitlements),
             maybeAttachEntitlementAgent(useEntitlements)
         ).flatMap(s -> s).toList();
     }
@@ -148,9 +148,12 @@ private static Stream<String> maybeWorkaroundG1Bug() {
         return Stream.of();
     }
 
-    private static Stream<String> maybeAllowSecurityManager() {
-        // Will become conditional on useEntitlements once entitlements can run without SM
-        return Stream.of("-Djava.security.manager=allow");
+    private static Stream<String> maybeAllowSecurityManager(boolean useEntitlements) {
+        if (useEntitlements == false) {
+            // Will become conditional on useEntitlements once entitlements can run without SM
+            return Stream.of("-Djava.security.manager=allow");
+        }
+        return Stream.of();
     }
 
     private static Stream<String> maybeAttachEntitlementAgent(boolean useEntitlements) {
@@ -172,12 +175,16 @@ private static Stream<String> maybeAttachEntitlementAgent(boolean useEntitlement
         } catch (IOException e) {
             throw new IllegalStateException("Failed to list entitlement jars in: " + dir, e);
         }
+        // We instrument classes in these modules to call the bridge. Because the bridge gets patched
+        // into java.base, we must export the bridge from java.base to these modules.
+        String modulesContainingEntitlementInstrumentation = "java.logging";
         return Stream.of(
             "-Des.entitlements.enabled=true",
             "-XX:+EnableDynamicAgentLoading",
             "-Djdk.attach.allowAttachSelf=true",
             "--patch-module=java.base=" + bridgeJar,
-            "--add-exports=java.base/org.elasticsearch.entitlement.bridge=org.elasticsearch.entitlement"
+            "--add-exports=java.base/org.elasticsearch.entitlement.bridge=org.elasticsearch.entitlement,"
+                + modulesContainingEntitlementInstrumentation
         );
     }
 }
diff --git a/server/src/main/java/org/elasticsearch/bootstrap/Bootstrap.java b/server/src/main/java/org/elasticsearch/bootstrap/Bootstrap.java
index 56d185645e149..4c7fb96c5b1d5 100644
--- a/server/src/main/java/org/elasticsearch/bootstrap/Bootstrap.java
+++ b/server/src/main/java/org/elasticsearch/bootstrap/Bootstrap.java
@@ -33,6 +33,7 @@ class Bootstrap {
 
     // arguments from the CLI process
     private final ServerArgs args;
+    private final boolean useEntitlements;
 
     // controller for spawning component subprocesses
     private final Spawner spawner = new Spawner();
@@ -46,10 +47,11 @@ class Bootstrap {
     // loads information about plugins required for entitlements in phase 2, used by plugins service in phase 3
     private final SetOnce<PluginsLoader> pluginsLoader = new SetOnce<>();
 
-    Bootstrap(PrintStream out, PrintStream err, ServerArgs args) {
+    Bootstrap(PrintStream out, PrintStream err, ServerArgs args, boolean useEntitlements) {
         this.out = out;
         this.err = err;
         this.args = args;
+        this.useEntitlements = useEntitlements;
     }
 
     ServerArgs args() {
@@ -60,6 +62,10 @@ Spawner spawner() {
         return spawner;
     }
 
+    public boolean useEntitlements() {
+        return useEntitlements;
+    }
+
     void setSecureSettings(SecureSettings secureSettings) {
         this.secureSettings.set(secureSettings);
     }
diff --git a/server/src/main/java/org/elasticsearch/bootstrap/BootstrapChecks.java b/server/src/main/java/org/elasticsearch/bootstrap/BootstrapChecks.java
index 021ad8127a2d0..0adfdc5d3a7ae 100644
--- a/server/src/main/java/org/elasticsearch/bootstrap/BootstrapChecks.java
+++ b/server/src/main/java/org/elasticsearch/bootstrap/BootstrapChecks.java
@@ -211,7 +211,6 @@ static List<BootstrapCheck> checks() {
         checks.add(new OnErrorCheck());
         checks.add(new OnOutOfMemoryErrorCheck());
         checks.add(new EarlyAccessCheck());
-        checks.add(new AllPermissionCheck());
         checks.add(new DiscoveryConfiguredCheck());
         checks.add(new ByteOrderCheck());
         return Collections.unmodifiableList(checks);
diff --git a/server/src/main/java/org/elasticsearch/bootstrap/Elasticsearch.java b/server/src/main/java/org/elasticsearch/bootstrap/Elasticsearch.java
index 834465d29dd70..216f22ddfd2bb 100644
--- a/server/src/main/java/org/elasticsearch/bootstrap/Elasticsearch.java
+++ b/server/src/main/java/org/elasticsearch/bootstrap/Elasticsearch.java
@@ -51,6 +51,7 @@
 import java.nio.file.Path;
 import java.security.Permission;
 import java.security.Security;
+import java.util.ArrayList;
 import java.util.List;
 import java.util.Objects;
 import java.util.concurrent.CountDownLatch;
@@ -105,6 +106,7 @@ private static Bootstrap initPhase1() {
         final PrintStream out = getStdout();
         final PrintStream err = getStderr();
         final ServerArgs args;
+        final boolean useEntitlements = Boolean.parseBoolean(System.getProperty("es.entitlements.enabled"));
         try {
             initSecurityProperties();
 
@@ -113,12 +115,14 @@ private static Bootstrap initPhase1() {
              * the presence of a security manager or lack thereof act as if there is a security manager present (e.g., DNS cache policy).
              * This forces such policies to take effect immediately.
              */
-            org.elasticsearch.bootstrap.Security.setSecurityManager(new SecurityManager() {
-                @Override
-                public void checkPermission(Permission perm) {
-                    // grant all permissions so that we can later set the security manager to the one that we want
-                }
-            });
+            if (useEntitlements == false) {
+                org.elasticsearch.bootstrap.Security.setSecurityManager(new SecurityManager() {
+                    @Override
+                    public void checkPermission(Permission perm) {
+                        // grant all permissions so that we can later set the security manager to the one that we want
+                    }
+                });
+            }
             LogConfigurator.registerErrorListener();
 
             BootstrapInfo.init();
@@ -144,7 +148,7 @@ public void checkPermission(Permission perm) {
             return null; // unreachable, to satisfy compiler
         }
 
-        return new Bootstrap(out, err, args);
+        return new Bootstrap(out, err, args, useEntitlements);
     }
 
     /**
@@ -205,7 +209,7 @@ private static void initPhase2(Bootstrap bootstrap) throws IOException {
         var pluginsLoader = PluginsLoader.createPluginsLoader(nodeEnv.modulesFile(), nodeEnv.pluginsFile());
         bootstrap.setPluginsLoader(pluginsLoader);
 
-        if (Boolean.parseBoolean(System.getProperty("es.entitlements.enabled"))) {
+        if (bootstrap.useEntitlements()) {
             LogManager.getLogger(Elasticsearch.class).info("Bootstrapping Entitlements");
 
             List<EntitlementBootstrap.PluginData> pluginData = Stream.concat(
@@ -269,7 +273,11 @@ protected void validateNodeBeforeAcceptingRequests(
                 final BoundTransportAddress boundTransportAddress,
                 List<BootstrapCheck> checks
             ) throws NodeValidationException {
-                BootstrapChecks.check(context, boundTransportAddress, checks);
+                var additionalChecks = new ArrayList<>(checks);
+                if (bootstrap.useEntitlements() == false) {
+                    additionalChecks.add(new BootstrapChecks.AllPermissionCheck());
+                }
+                BootstrapChecks.check(context, boundTransportAddress, additionalChecks);
             }
         };
         INSTANCE = new Elasticsearch(bootstrap.spawner(), node);