diff --git a/tomcat/src/main/java/org/apache/coyote/http11/RequestMappingHandler.java b/tomcat/src/main/java/org/apache/catalina/RequestMappingHandler.java
similarity index 68%
rename from tomcat/src/main/java/org/apache/coyote/http11/RequestMappingHandler.java
rename to tomcat/src/main/java/org/apache/catalina/RequestMappingHandler.java
index 1c51b5f829..35c423044a 100644
--- a/tomcat/src/main/java/org/apache/coyote/http11/RequestMappingHandler.java
+++ b/tomcat/src/main/java/org/apache/catalina/RequestMappingHandler.java
@@ -1,5 +1,9 @@
-package org.apache.coyote.http11;
+package org.apache.catalina;
 
+import nextstep.jwp.LoginHandler;
+import nextstep.jwp.model.User;
+import org.apache.catalina.session.HttpSession;
+import org.apache.catalina.session.SessionManager;
 import org.apache.coyote.http11.request.HttpMethod;
 import org.apache.coyote.http11.request.HttpRequest;
 import org.apache.coyote.http11.response.*;
@@ -28,14 +32,34 @@ public enum RequestMappingHandler {
     }
 
     public static Controller findController(final HttpRequest request) {
-        String resourcePath = request.getRequestLine().getRequestUrl();
-        HttpMethod requestMethod = request.getRequestLine().getHttpMethod();
+        final String resourcePath = request.getRequestLine().getRequestUrl();
+        final HttpMethod requestMethod = request.getRequestLine().getHttpMethod();
 
-        return Arrays.stream(values())
+        final Controller findController = Arrays.stream(values())
                 .filter(value -> value.condition.test(resourcePath, requestMethod))
                 .findFirst()
                 .orElseThrow(() -> new IllegalArgumentException("잘못된 url 요청입니다."))
                 .getController();
+
+        if (findController instanceof LoginPostController
+                && (!request.hasJSessionId())) {
+            addSession(request);
+        }
+        if (findController instanceof LoginGetController
+                && request.hasJSessionId()
+                && SessionManager.isExist(request.getJSessionId())) {
+            request.setHasValidatedSessionTrue();
+        }
+        return findController;
+    }
+
+    private static void addSession(final HttpRequest request) {
+        final SessionManager sessionManager = new SessionManager();
+        final LoginHandler loginHandler = new LoginHandler();
+        final User user = loginHandler.getUser(request.getRequestBody());
+        final HttpSession httpSession = new HttpSession("user", user);
+        sessionManager.add(httpSession);
+        request.addJSessionId(httpSession.getId());
     }
 
     public static boolean isFileGetUrl(final String resourcePath, final HttpMethod requestMethod) {
diff --git a/tomcat/src/main/java/org/apache/coyote/http11/Http11Processor.java b/tomcat/src/main/java/org/apache/coyote/http11/Http11Processor.java
index 90ccda685b..8523e2e433 100644
--- a/tomcat/src/main/java/org/apache/coyote/http11/Http11Processor.java
+++ b/tomcat/src/main/java/org/apache/coyote/http11/Http11Processor.java
@@ -1,6 +1,7 @@
 package org.apache.coyote.http11;
 
 import nextstep.jwp.exception.UncheckedServletException;
+import org.apache.catalina.RequestMappingHandler;
 import org.apache.coyote.Processor;
 import org.apache.coyote.http11.request.HttpRequest;
 import org.apache.coyote.http11.response.Controller;
@@ -51,7 +52,4 @@ public void process(final Socket connection) {
         }
     }
 
-    // 쿠키값 빼내올때 문제점
-    // doPost, doGet 추가수정
-    // 세션 전략 세우기
 }
diff --git a/tomcat/src/main/java/org/apache/coyote/http11/request/HttpRequest.java b/tomcat/src/main/java/org/apache/coyote/http11/request/HttpRequest.java
index 0da6c372b7..a078d29b63 100644
--- a/tomcat/src/main/java/org/apache/coyote/http11/request/HttpRequest.java
+++ b/tomcat/src/main/java/org/apache/coyote/http11/request/HttpRequest.java
@@ -12,6 +12,7 @@ public class HttpRequest {
     private final RequestLine requestLine;
     private final RequestHeader requestHeader;
     private final String requestBody;
+    private boolean hasValidatedSession;
 
     public HttpRequest(final BufferedReader reader) throws IOException, URISyntaxException {
         final List<String> lines = readAllLines(reader);
@@ -19,6 +20,7 @@ public HttpRequest(final BufferedReader reader) throws IOException, URISyntaxExc
         requestLine = createRequestLine(lines);
         requestHeader = createRequestHeader(lines);
         requestBody = addRequestBody(lines, reader);
+        hasValidatedSession = false;
     }
 
     private static List<String> readAllLines(final BufferedReader reader) {
@@ -70,10 +72,18 @@ private int getContentLength(List<String> lines) {
         return 0;
     }
 
+    public void addJSessionId(final String jSessionId) {
+        requestHeader.addSession(jSessionId);
+    }
+
     public boolean hasJSessionId() {
         return requestHeader.hasJSessionId();
     }
 
+    public void setHasValidatedSessionTrue() {
+        this.hasValidatedSession = true;
+    }
+
     public String getJSessionId() {
         return requestHeader.getJSessionId();
     }
@@ -89,4 +99,8 @@ public RequestHeader getRequestHeader() {
     public String getRequestBody() {
         return requestBody;
     }
+
+    public boolean isHasValidatedSession() {
+        return hasValidatedSession;
+    }
 }
diff --git a/tomcat/src/main/java/org/apache/coyote/http11/request/RequestHeader.java b/tomcat/src/main/java/org/apache/coyote/http11/request/RequestHeader.java
index 3cbbd1e6f8..f75bb5d4a4 100644
--- a/tomcat/src/main/java/org/apache/coyote/http11/request/RequestHeader.java
+++ b/tomcat/src/main/java/org/apache/coyote/http11/request/RequestHeader.java
@@ -42,4 +42,8 @@ public String getJSessionId() {
         final String[] parts = cookie.split("=");
         return parts[1];
     }
+
+    public void addSession(String jSessionId){
+        headers.put(COOKIE, "JSessionId=" + jSessionId);
+    }
 }
diff --git a/tomcat/src/main/java/org/apache/coyote/http11/response/LoginGetController.java b/tomcat/src/main/java/org/apache/coyote/http11/response/LoginGetController.java
index 56a9757bf2..081f1f2160 100644
--- a/tomcat/src/main/java/org/apache/coyote/http11/response/LoginGetController.java
+++ b/tomcat/src/main/java/org/apache/coyote/http11/response/LoginGetController.java
@@ -2,7 +2,6 @@
 
 import org.apache.coyote.http11.ContentType;
 import org.apache.coyote.http11.request.HttpRequest;
-import org.apache.catalina.session.SessionManager;
 
 public class LoginGetController implements Controller {
 
@@ -12,14 +11,13 @@ public void service(final HttpRequest request,
         final String resourcePath = request.getRequestLine().getRequestUrl() + ".html";
         final String responseBody = ResourceResolver.resolve(resourcePath);
 
-        if (request.hasJSessionId() && SessionManager.isExist(request.getJSessionId())) {
-            response.setStatusCode(StatusCode.OK);
-            response.setResponseBody(ResourceResolver.resolve("/index.html"));
-            response.addHeader("Content-Type", ContentType.from("/index.html").getContentType() + ";charset=utf-8");
-            response.addHeader("Content-Length", String.valueOf(ResourceResolver.resolve("/index.html").getBytes().length));
+        if (request.isHasValidatedSession()) {
+            final String jSessionId = request.getJSessionId();
+            response.addJSessionId(jSessionId);
+            response.setStatusCode(StatusCode.FOUND);
+            response.addHeader("Location", "/index.html");
             return;
         }
-
         response.setStatusCode(StatusCode.OK);
         response.setResponseBody(ResourceResolver.resolve(resourcePath));
         response.addHeader("Content-Type", ContentType.from(resourcePath).getContentType() + ";charset=utf-8");
diff --git a/tomcat/src/main/java/org/apache/coyote/http11/response/LoginPostController.java b/tomcat/src/main/java/org/apache/coyote/http11/response/LoginPostController.java
index fbf89e651a..8d65816344 100644
--- a/tomcat/src/main/java/org/apache/coyote/http11/response/LoginPostController.java
+++ b/tomcat/src/main/java/org/apache/coyote/http11/response/LoginPostController.java
@@ -1,9 +1,6 @@
 package org.apache.coyote.http11.response;
 
 import nextstep.jwp.LoginHandler;
-import nextstep.jwp.model.User;
-import org.apache.catalina.session.HttpSession;
-import org.apache.catalina.session.SessionManager;
 import org.apache.coyote.http11.ContentType;
 import org.apache.coyote.http11.request.HttpRequest;
 
@@ -22,16 +19,8 @@ public void service(final HttpRequest request,
 
     private void successLoginResponse(final HttpRequest request,
                                       final HttpResponse response) {
-        final SessionManager sessionManager = new SessionManager();
-        if (!request.hasJSessionId()) {
-            final LoginHandler loginHandler = new LoginHandler();
-            final User user = loginHandler.getUser(request.getRequestBody());
-            final HttpSession httpSession = new HttpSession("user", user);
-            sessionManager.add(httpSession);
-
-            final HttpSession session = sessionManager.findSession(httpSession.getId());
-            response.addJSessionId(session.getId());
-        }
+        final String jSessionId = request.getJSessionId();
+        response.addJSessionId(jSessionId);
         response.setStatusCode(StatusCode.FOUND);
         response.addHeader("Location", "/index.html");
     }