diff --git a/web/src/main/java/org/springframework/security/web/context/HttpSessionSecurityContextRepository.java b/web/src/main/java/org/springframework/security/web/context/HttpSessionSecurityContextRepository.java
index 95cc2db912..817feb6967 100644
--- a/web/src/main/java/org/springframework/security/web/context/HttpSessionSecurityContextRepository.java
+++ b/web/src/main/java/org/springframework/security/web/context/HttpSessionSecurityContextRepository.java
@@ -18,6 +18,7 @@ import org.springframework.security.core.context.SecurityContextHolder;
 import org.springframework.security.core.context.SecurityContextHolderStrategy;
 import org.springframework.util.Assert;
 import org.springframework.util.ClassUtils;
+import org.springframework.web.util.WebUtils;
 
 /**
  * A {@code SecurityContextRepository} implementation which stores the security context in the {@code HttpSession}
@@ -105,7 +106,10 @@ public class HttpSessionSecurityContextRepository implements SecurityContextRepo
     }
 
     public void saveContext(SecurityContext context, HttpServletRequest request, HttpServletResponse response) {
-        SaveContextOnUpdateOrErrorResponseWrapper responseWrapper = (SaveContextOnUpdateOrErrorResponseWrapper)response;
+        SaveContextOnUpdateOrErrorResponseWrapper responseWrapper = WebUtils.getNativeResponse(response, SaveContextOnUpdateOrErrorResponseWrapper.class);
+        if(responseWrapper == null) {
+            throw new IllegalStateException("Cannot invoke saveContext on response " + response + ". You must use the HttpRequestResponseHolder.response after invoking loadContext");
+        }
         // saveContext() might already be called by the response wrapper
         // if something in the chain called sendError() or sendRedirect(). This ensures we only call it
         // once per request.
diff --git a/web/src/test/java/org/springframework/security/web/context/HttpSessionSecurityContextRepositoryTests.java b/web/src/test/java/org/springframework/security/web/context/HttpSessionSecurityContextRepositoryTests.java
index 6a7b65e359..4f9c7e3610 100644
--- a/web/src/test/java/org/springframework/security/web/context/HttpSessionSecurityContextRepositoryTests.java
+++ b/web/src/test/java/org/springframework/security/web/context/HttpSessionSecurityContextRepositoryTests.java
@@ -29,9 +29,7 @@ import static org.springframework.security.web.context.HttpSessionSecurityContex
 
 import javax.servlet.ServletOutputStream;
 import javax.servlet.ServletRequest;
-import javax.servlet.http.HttpServletRequest;
-import javax.servlet.http.HttpServletResponse;
-import javax.servlet.http.HttpSession;
+import javax.servlet.http.*;
 
 import org.junit.After;
 import org.junit.Test;
@@ -495,4 +493,33 @@ public class HttpSessionSecurityContextRepositoryTests {
         HttpSessionSecurityContextRepository repo = new HttpSessionSecurityContextRepository();
         repo.setTrustResolver(null);
     }
-}
+
+    // SEC-2578
+    @Test
+    public void traverseWrappedRequests() {
+        HttpSessionSecurityContextRepository repo = new HttpSessionSecurityContextRepository();
+        MockHttpServletRequest request = new MockHttpServletRequest();
+        MockHttpServletResponse response = new MockHttpServletResponse();
+        HttpRequestResponseHolder holder = new HttpRequestResponseHolder(request, response);
+        SecurityContext context = repo.loadContext(holder);
+        assertNull(request.getSession(false));
+        // Simulate authentication during the request
+        context.setAuthentication(testToken);
+
+        repo.saveContext(context, new HttpServletRequestWrapper(holder.getRequest()), new HttpServletResponseWrapper(holder.getResponse()));
+
+        assertNotNull(request.getSession(false));
+        assertEquals(context, request.getSession().getAttribute(SPRING_SECURITY_CONTEXT_KEY));
+    }
+
+    @Test(expected = IllegalStateException.class)
+    public void failsWithStandardResponse() {
+        HttpSessionSecurityContextRepository repo = new HttpSessionSecurityContextRepository();
+        MockHttpServletRequest request = new MockHttpServletRequest();
+        MockHttpServletResponse response = new MockHttpServletResponse();
+        SecurityContext context = SecurityContextHolder.createEmptyContext();
+        context.setAuthentication(testToken);
+
+        repo.saveContext(context,request,response);
+    }
+}
\ No newline at end of file