diff --git a/src/main/java/com/example/cosmos_serversb/entities/User.java b/src/main/java/com/example/cosmos_serversb/entities/User.java
index eb1b59a..8a9e190 100644
--- a/src/main/java/com/example/cosmos_serversb/entities/User.java
+++ b/src/main/java/com/example/cosmos_serversb/entities/User.java
@@ -3,12 +3,14 @@
 import java.util.HashSet;
 import java.util.Set;
 
+import com.example.cosmos_serversb.models.SessionManager;
 import com.fasterxml.jackson.annotation.JsonIgnore;
 import com.fasterxml.jackson.annotation.JsonInclude;
 import com.fasterxml.jackson.annotation.JsonProperty;
 import com.fasterxml.jackson.annotation.JsonView;
 import lombok.Data;
 import com.example.cosmos_serversb.views.UsersView;
+import org.hibernate.Session;
 import org.hibernate.validator.constraints.Length;
 
 public class User {
@@ -55,7 +57,7 @@
         setName(name);
         setIconUri(iconUri);
         setFirstToken(token);
-        //addToken(this.dummyToken);
+        addToken(token);
         this.login = true;
     }
 
@@ -74,6 +76,7 @@
     public void setFirstToken(String firstToken) {
         this.firstToken = firstToken;
     }
+
     public Set<Token> getTokens() {
         return tokens;
     }
@@ -82,6 +85,11 @@
         this.tokens = tokens;
     }
 
+    public void addToken(String strToken){
+        Session session = SessionManager.getInstance().getSession();
+        this.tokens.add(session.get(Token.class, strToken));
+    }
+
     public String getUri() {
         return uri;
     }
diff --git a/src/main/java/com/example/cosmos_serversb/models/Users.java b/src/main/java/com/example/cosmos_serversb/models/Users.java
index 6beae5b..e85b1de 100644
--- a/src/main/java/com/example/cosmos_serversb/models/Users.java
+++ b/src/main/java/com/example/cosmos_serversb/models/Users.java
@@ -79,11 +79,11 @@
         Session session = SessionManager.getInstance().getSession();
         Token token = createToken(uId);
         LogUtils.info(token.token);
+        session.save(token);
         User testUser = new User(name, uId, uri, iconImage,token.token);
         Password password = new Password(pw, uId);
         session.save(testUser);
         session.save(password);
-        session.save(token);
         return testUser;
     }
 
@@ -149,6 +149,7 @@
     }
 
     public static DeleteResult deleteUser(String uId, String token) {
+        //リレーションがうまく機能していないため、すべてここで削除しています。
         if(checkToken(uId, token)){
             Session session = SessionManager.getInstance().getSession();
             User deleteUser = (User) session.get(User.class, uId);
@@ -163,6 +164,10 @@
                     }
                 }
                 deleteUser.groups.clear();
+                session.delete(session.get(Password.class, uId)); //パスワードの削除
+                for(Token deleteToken : deleteUser.getTokens()){
+                    session.delete(deleteToken); //tokenの削除
+                }
                 session.delete(deleteUser);
                 return DeleteResult.SUCCESS;
             }
@@ -202,8 +207,14 @@
                     return DeleteResult.FAILURE;
                 } else {
 //            Users.getInstance().getUserByToken(token).token.remove(Users.getInstance().getUserByToken(token).token.indexOf(token));
-                    session.delete(session.get(Token.class, token));
-                    return DeleteResult.SUCCESS;
+                    if(session.get(Token.class, token) != null) {
+                        user.getTokens().remove(session.get(Token.class, token));
+                        session.delete(session.get(Token.class, token));
+                        if(user.getTokens().size() == 0){
+                            user.login = false;
+                        }
+                        return DeleteResult.SUCCESS;
+                    }
                 }
             }
         }
diff --git a/src/main/resources/User.hbm.xml b/src/main/resources/User.hbm.xml
index d4528e7..f89e09f 100644
--- a/src/main/resources/User.hbm.xml
+++ b/src/main/resources/User.hbm.xml
@@ -29,6 +29,16 @@
                     column="GID">
             </many-to-many>
         </set>
+        <set name = "tokens"
+             table = "TOKENS"
+             lazy = "true"
+             cascade = "refresh">
+            <key column="UID"/>
+            <many-to-many
+                    class="Group"
+                    column="GID">
+            </many-to-many>
+        </set>
     </class>
 
 </hibernate-mapping>
\ No newline at end of file