diff --git a/sdk/spring/azure-spring-boot-samples/azure-spring-boot-sample-active-directory-resource-server-obo/src/main/java/com/azure/spring/sample/aad/configuration/AADSampleConfiguration.java b/sdk/spring/azure-spring-boot-samples/azure-spring-boot-sample-active-directory-resource-server-obo/src/main/java/com/azure/spring/sample/aad/configuration/AADSampleConfiguration.java
index 41ff9abd115e4..aa5d147e11475 100644
--- a/sdk/spring/azure-spring-boot-samples/azure-spring-boot-sample-active-directory-resource-server-obo/src/main/java/com/azure/spring/sample/aad/configuration/AADSampleConfiguration.java
+++ b/sdk/spring/azure-spring-boot-samples/azure-spring-boot-sample-active-directory-resource-server-obo/src/main/java/com/azure/spring/sample/aad/configuration/AADSampleConfiguration.java
@@ -2,11 +2,7 @@
 
 import org.springframework.context.annotation.Bean;
 import org.springframework.context.annotation.Configuration;
-import org.springframework.security.oauth2.client.OAuth2AuthorizedClientManager;
-import org.springframework.security.oauth2.client.OAuth2AuthorizedClientProvider;
-import org.springframework.security.oauth2.client.OAuth2AuthorizedClientProviderBuilder;
 import org.springframework.security.oauth2.client.registration.ClientRegistrationRepository;
-import org.springframework.security.oauth2.client.web.DefaultOAuth2AuthorizedClientManager;
 import org.springframework.security.oauth2.client.web.OAuth2AuthorizedClientRepository;
 import org.springframework.security.oauth2.client.web.reactive.function.client.ServletOAuth2AuthorizedClientExchangeFilterFunction;
 import org.springframework.web.reactive.function.client.WebClient;
diff --git a/sdk/spring/azure-spring-boot/src/main/java/com/azure/spring/aad/webapi/AADOAuth2OboAuthorizedClientRepository.java b/sdk/spring/azure-spring-boot/src/main/java/com/azure/spring/aad/webapi/AADOAuth2OboAuthorizedClientRepository.java
index 5e649b9265b6f..348f7426b209e 100644
--- a/sdk/spring/azure-spring-boot/src/main/java/com/azure/spring/aad/webapi/AADOAuth2OboAuthorizedClientRepository.java
+++ b/sdk/spring/azure-spring-boot/src/main/java/com/azure/spring/aad/webapi/AADOAuth2OboAuthorizedClientRepository.java
@@ -101,7 +101,7 @@ public <T extends OAuth2AuthorizedClient> T loadAuthorizedClient(String registra
             request.setAttribute(oboAuthorizedClientAttributeName, (T) oAuth2AuthorizedClient);
             return (T) oAuth2AuthorizedClient;
         } catch (ExecutionException exception) {
-            // Handle conditional access policy for obo flow.
+            // Handle conditional access policy, step 1.
             // A user interaction is required, but we are in a web API, and therefore, we need to report back to the
             // client through a 'WWW-Authenticate' header https://tools.ietf.org/html/rfc6750#section-3.1
             Optional.of(exception)
diff --git a/sdk/spring/azure-spring-boot/src/main/java/com/azure/spring/aad/webapp/AADHandleConditionalAccessFilter.java b/sdk/spring/azure-spring-boot/src/main/java/com/azure/spring/aad/webapp/AADHandleConditionalAccessFilter.java
index 8a5a8fff81d7b..469ea28b95e73 100644
--- a/sdk/spring/azure-spring-boot/src/main/java/com/azure/spring/aad/webapp/AADHandleConditionalAccessFilter.java
+++ b/sdk/spring/azure-spring-boot/src/main/java/com/azure/spring/aad/webapp/AADHandleConditionalAccessFilter.java
@@ -3,10 +3,10 @@
 
 package com.azure.spring.aad.webapp;
 
+import com.azure.spring.aad.AADClientRegistrationRepository;
 import com.azure.spring.autoconfigure.aad.Constants;
-import org.slf4j.Logger;
-import org.slf4j.LoggerFactory;
 import org.springframework.http.HttpHeaders;
+import org.springframework.security.oauth2.client.ClientAuthorizationRequiredException;
 import org.springframework.util.StringUtils;
 import org.springframework.web.filter.OncePerRequestFilter;
 import org.springframework.web.reactive.function.client.WebClientResponseException;
@@ -32,11 +32,11 @@
  */
 public class AADHandleConditionalAccessFilter extends OncePerRequestFilter {
 
-    private static final Logger LOGGER = LoggerFactory.getLogger(AADHandleConditionalAccessFilter.class);
 
     @Override
     protected void doFilterInternal(HttpServletRequest request, HttpServletResponse response,
                                     FilterChain filterChain) throws IOException, ServletException {
+        // Handle conditional access policy, step 2.
         try {
             filterChain.doFilter(request, response);
         } catch (Exception exception) {
@@ -53,18 +53,19 @@ protected void doFilterInternal(HttpServletRequest request, HttpServletResponse
             if (authParameters != null && authParameters.containsKey(Constants.CONDITIONAL_ACCESS_POLICY_CLAIMS)) {
                 request.getSession().setAttribute(Constants.CONDITIONAL_ACCESS_POLICY_CLAIMS,
                     authParameters.get(Constants.CONDITIONAL_ACCESS_POLICY_CLAIMS));
-                response.setStatus(302);
-                try {
-                    response.sendRedirect(Constants.DEFAULT_AUTHORITY_ENDPOINT_URI);
-                } catch (IOException e) {
-                    LOGGER.error("Failed to redirect at this response.", exception);
-                }
-                return;
+                // OAuth2AuthorizationRequestRedirectFilter will catch this exception to re-authorize.
+                throw new ClientAuthorizationRequiredException(AADClientRegistrationRepository.AZURE_CLIENT_REGISTRATION_ID);
             }
             throw exception;
         }
     }
 
+    /**
+     * Get claims filed form the header to re-authorize.
+     *
+     * @param wwwAuthenticateHeader httpHeader
+     * @return authParametersMap
+     */
     private Map<String, String> parseAuthParameters(String wwwAuthenticateHeader) {
         return Stream.of(wwwAuthenticateHeader)
                      .filter(header -> !StringUtils.isEmpty(header))
diff --git a/sdk/spring/azure-spring-boot/src/main/java/com/azure/spring/aad/webapp/AADOAuth2AuthorizedClientRepository.java b/sdk/spring/azure-spring-boot/src/main/java/com/azure/spring/aad/webapp/AADOAuth2AuthorizedClientRepository.java
index 0594b47efa49f..6e4fcd2a35710 100644
--- a/sdk/spring/azure-spring-boot/src/main/java/com/azure/spring/aad/webapp/AADOAuth2AuthorizedClientRepository.java
+++ b/sdk/spring/azure-spring-boot/src/main/java/com/azure/spring/aad/webapp/AADOAuth2AuthorizedClientRepository.java
@@ -7,6 +7,7 @@
 import org.slf4j.Logger;
 import org.slf4j.LoggerFactory;
 import org.springframework.security.core.Authentication;
+import org.springframework.security.oauth2.client.ClientAuthorizationRequiredException;
 import org.springframework.security.oauth2.client.OAuth2AuthorizationContext;
 import org.springframework.security.oauth2.client.OAuth2AuthorizedClient;
 import org.springframework.security.oauth2.client.OAuth2AuthorizedClientProvider;
@@ -68,6 +69,9 @@ public <T extends OAuth2AuthorizedClient> T loadAuthorizedClient(String id,
 
         if (repo.isClientNeedConsentWhenLogin(id)) {
             OAuth2AuthorizedClient azureClient = loadAuthorizedClient(getAzureClientId(), principal, request);
+            if (azureClient == null) {
+                throw new ClientAuthorizationRequiredException(AADClientRegistrationRepository.AZURE_CLIENT_REGISTRATION_ID);
+            }
             OAuth2AuthorizedClient fakeAuthzClient = createFakeAuthzClient(azureClient, id, principal);
             OAuth2AuthorizationContext.Builder contextBuilder =
                 OAuth2AuthorizationContext.withAuthorizedClient(fakeAuthzClient);
diff --git a/sdk/spring/azure-spring-boot/src/main/java/com/azure/spring/aad/webapp/AADWebSecurityConfigurerAdapter.java b/sdk/spring/azure-spring-boot/src/main/java/com/azure/spring/aad/webapp/AADWebSecurityConfigurerAdapter.java
index b29a4f63ef281..5de78993ee16c 100644
--- a/sdk/spring/azure-spring-boot/src/main/java/com/azure/spring/aad/webapp/AADWebSecurityConfigurerAdapter.java
+++ b/sdk/spring/azure-spring-boot/src/main/java/com/azure/spring/aad/webapp/AADWebSecurityConfigurerAdapter.java
@@ -13,9 +13,9 @@
 import org.springframework.security.oauth2.client.oidc.userinfo.OidcUserRequest;
 import org.springframework.security.oauth2.client.oidc.web.logout.OidcClientInitiatedLogoutSuccessHandler;
 import org.springframework.security.oauth2.client.userinfo.OAuth2UserService;
+import org.springframework.security.oauth2.client.web.OAuth2AuthorizationRequestRedirectFilter;
 import org.springframework.security.oauth2.client.web.OAuth2AuthorizationRequestResolver;
 import org.springframework.security.oauth2.core.oidc.user.OidcUser;
-import org.springframework.security.web.access.ExceptionTranslationFilter;
 import org.springframework.security.web.authentication.logout.LogoutSuccessHandler;
 import org.springframework.util.StringUtils;
 
@@ -51,7 +51,7 @@ protected void configure(HttpSecurity http) throws Exception {
             .logout()
                 .logoutSuccessHandler(oidcLogoutSuccessHandler())
                 .and()
-            .addFilterBefore(new AADHandleConditionalAccessFilter(), ExceptionTranslationFilter.class);
+            .addFilterAfter(new AADHandleConditionalAccessFilter(), OAuth2AuthorizationRequestRedirectFilter.class);
         // @formatter:off
     }