diff --git a/core/src/main/java/org/acegisecurity/context/SecurityContext.java b/core/src/main/java/org/acegisecurity/context/SecurityContext.java
index a8ef06b1a669..3edc7cb4de9b 100644
--- a/core/src/main/java/org/acegisecurity/context/SecurityContext.java
+++ b/core/src/main/java/org/acegisecurity/context/SecurityContext.java
@@ -27,46 +27,67 @@
 import edu.umd.cs.findbugs.annotations.NonNull;
 import hudson.model.User;
 import hudson.security.ACL;
+import java.io.Serializable;
 import org.acegisecurity.Authentication;
+import org.kohsuke.accmod.Restricted;
+import org.kohsuke.accmod.restrictions.NoExternalUse;
 
 /**
  * @deprecated Use {@link ACL#as(User)} or {@link org.springframework.security.core.context.SecurityContext}
  */
 @Deprecated
-public interface SecurityContext {
+public interface SecurityContext extends Serializable {
 
     Authentication getAuthentication();
 
     void setAuthentication(Authentication a);
 
     static @NonNull SecurityContext fromSpring(@NonNull org.springframework.security.core.context.SecurityContext c) {
-        return new SecurityContext() {
-            @Override
-            public Authentication getAuthentication() {
-                org.springframework.security.core.Authentication a = c.getAuthentication();
-                return a != null ? Authentication.fromSpring(a) : null;
-            }
-
-            @Override
-            public void setAuthentication(Authentication a) {
-                c.setAuthentication(a != null ? a.toSpring() : null);
-            }
-        };
+        return new FromSpring(c);
+    }
+
+    @Restricted(NoExternalUse.class)
+    class FromSpring implements SecurityContext {
+        private final org.springframework.security.core.context.SecurityContext c;
+
+        FromSpring(org.springframework.security.core.context.SecurityContext c) {
+            this.c = c;
+        }
+
+        @Override
+        public Authentication getAuthentication() {
+            org.springframework.security.core.Authentication a = c.getAuthentication();
+            return a != null ? Authentication.fromSpring(a) : null;
+        }
+
+        @Override
+        public void setAuthentication(Authentication a) {
+            c.setAuthentication(a != null ? a.toSpring() : null);
+        }
     }
 
     default @NonNull org.springframework.security.core.context.SecurityContext toSpring() {
-        return new org.springframework.security.core.context.SecurityContext() {
-            @Override
-            public org.springframework.security.core.Authentication getAuthentication() {
-                Authentication a = SecurityContext.this.getAuthentication();
-                return a != null ? a.toSpring() : null;
-            }
-
-            @Override
-            public void setAuthentication(org.springframework.security.core.Authentication authentication) {
-                SecurityContext.this.setAuthentication(authentication != null ? Authentication.fromSpring(authentication) : null);
-            }
-        };
+        return new ToSpring(this);
+    }
+
+    @Restricted(NoExternalUse.class)
+    class ToSpring implements org.springframework.security.core.context.SecurityContext {
+        private final SecurityContext c;
+
+        ToSpring(SecurityContext c) {
+            this.c = c;
+        }
+
+        @Override
+        public org.springframework.security.core.Authentication getAuthentication() {
+            Authentication a = c.getAuthentication();
+            return a != null ? a.toSpring() : null;
+        }
+
+        @Override
+        public void setAuthentication(org.springframework.security.core.Authentication authentication) {
+            c.setAuthentication(authentication != null ? Authentication.fromSpring(authentication) : null);
+        }
     }
 
 }
diff --git a/core/src/test/java/org/acegisecurity/context/SecurityContextTest.java b/core/src/test/java/org/acegisecurity/context/SecurityContextTest.java
new file mode 100644
index 000000000000..27539a5cb9ef
--- /dev/null
+++ b/core/src/test/java/org/acegisecurity/context/SecurityContextTest.java
@@ -0,0 +1,69 @@
+/*
+ * The MIT License
+ *
+ * Copyright 2024 CloudBees, Inc.
+ *
+ * Permission is hereby granted, free of charge, to any person obtaining a copy
+ * of this software and associated documentation files (the "Software"), to deal
+ * in the Software without restriction, including without limitation the rights
+ * to use, copy, modify, merge, publish, distribute, sublicense, and/or sell
+ * copies of the Software, and to permit persons to whom the Software is
+ * furnished to do so, subject to the following conditions:
+ *
+ * The above copyright notice and this permission notice shall be included in
+ * all copies or substantial portions of the Software.
+ *
+ * THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+ * IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
+ * FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE
+ * AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
+ * LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,
+ * OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN
+ * THE SOFTWARE.
+ */
+
+package org.acegisecurity.context;
+
+import static org.hamcrest.MatcherAssert.assertThat;
+import static org.hamcrest.Matchers.is;
+
+import java.io.ByteArrayInputStream;
+import java.io.ByteArrayOutputStream;
+import java.io.ObjectInputStream;
+import java.io.ObjectOutputStream;
+import org.acegisecurity.providers.UsernamePasswordAuthenticationToken;
+import org.junit.jupiter.api.Test;
+
+@SuppressWarnings("deprecation")
+public class SecurityContextTest {
+
+    @Test
+    public void serializabilityFromSpring() throws Exception {
+        org.springframework.security.core.context.SecurityContext spring1 = new org.springframework.security.core.context.SecurityContextImpl();
+        spring1.setAuthentication(new org.springframework.security.authentication.UsernamePasswordAuthenticationToken("user", null));
+        SecurityContext acegi1 = SecurityContext.fromSpring(spring1);
+        SecurityContext acegi2 = serDeser(SecurityContext.class, acegi1);
+        org.springframework.security.core.context.SecurityContext spring2 = acegi2.toSpring();
+        assertThat(spring2.getAuthentication().getPrincipal(), is("user"));
+    }
+
+    @Test
+    public void serializabilityToSpring() throws Exception {
+        SecurityContext acegi1 = new SecurityContextImpl();
+        acegi1.setAuthentication(new UsernamePasswordAuthenticationToken("user", null));
+        org.springframework.security.core.context.SecurityContext spring1 = acegi1.toSpring();
+        org.springframework.security.core.context.SecurityContext spring2 = serDeser(org.springframework.security.core.context.SecurityContext.class, spring1);
+        SecurityContext acegi2 = SecurityContext.fromSpring(spring2);
+        assertThat(acegi2.getAuthentication().getPrincipal(), is("user"));
+    }
+
+    private static <T> T serDeser(Class<T> type, T object) throws Exception {
+        try (ByteArrayOutputStream baos = new ByteArrayOutputStream(); ObjectOutputStream oos = new ObjectOutputStream(baos)) {
+            oos.writeObject(object);
+            try (ByteArrayInputStream bais = new ByteArrayInputStream(baos.toByteArray()); ObjectInputStream ois = new ObjectInputStream(bais)) {
+                return type.cast(ois.readObject());
+            }
+        }
+    }
+
+}