diff --git a/src/main/java/org/harang/server/controller/MatchingController.java b/src/main/java/org/harang/server/controller/MatchingController.java
index 687fd33..fb9f0de 100644
--- a/src/main/java/org/harang/server/controller/MatchingController.java
+++ b/src/main/java/org/harang/server/controller/MatchingController.java
@@ -44,4 +44,11 @@ public ApiResponse<?> finishMatching(final @NotNull @PathVariable("postId") Long
     public ApiResponse<?> getWaitinglist(final @NotNull @PathVariable("postId") Long postId) {
         return ApiResponse.success(matchingService.getWaitingList(postId));
     }
+
+    @PostMapping("/{postId}/chats")
+    public ApiResponse<?> createMatchingWaiting(@MemberId Long memberId,
+            final @NotNull @PathVariable("postId") Long postId) {
+        matchingService.createMatchingWaiting(memberId, postId);
+        return ApiResponse.success(SuccessMessage.OK);
+    }
 }
diff --git a/src/main/java/org/harang/server/controller/MockJwtController.java b/src/main/java/org/harang/server/controller/MockJwtController.java
index a84e5c9..09f6692 100644
--- a/src/main/java/org/harang/server/controller/MockJwtController.java
+++ b/src/main/java/org/harang/server/controller/MockJwtController.java
@@ -18,6 +18,6 @@ public class MockJwtController {
 
     @GetMapping
     public JwtTokenResponse getToken(){
-        return jwtUtil.generateTokens(Long.valueOf(1), Type.SPROUT);
+        return jwtUtil.generateTokens(Long.valueOf(2), Type.SPROUT);
     }
 }
diff --git a/src/main/java/org/harang/server/controller/PostController.java b/src/main/java/org/harang/server/controller/PostController.java
index 99dd598..271046b 100644
--- a/src/main/java/org/harang/server/controller/PostController.java
+++ b/src/main/java/org/harang/server/controller/PostController.java
@@ -31,6 +31,12 @@ public ApiResponse<?> createPost(@MemberId Long memberId, @Valid @RequestBody Po
         return ApiResponse.success(SuccessMessage.CREATED);
     }
 
+    @DeleteMapping("/{postId}")
+    public ApiResponse<?> deletePost(@MemberId Long memberId, @PathVariable Long postId) {
+        postService.deletePost(memberId, postId);
+        return ApiResponse.success(SuccessMessage.OK);
+    }
+
     @GetMapping
     public ApiResponse<List<PostResponse>> getAllPosts() {
         return ApiResponse.success(postService.getAllPosts());
diff --git a/src/main/java/org/harang/server/domain/Category.java b/src/main/java/org/harang/server/domain/Category.java
index f3f79d3..36d6854 100644
--- a/src/main/java/org/harang/server/domain/Category.java
+++ b/src/main/java/org/harang/server/domain/Category.java
@@ -21,7 +21,7 @@ public class Category {
     @Column(name = "name", nullable = false)
     private String name;
 
-    @OneToMany(mappedBy = "category")
+    @OneToMany(mappedBy = "category", cascade = CascadeType.ALL)
     private List<PostCategory> postCategoryList = new ArrayList<>();
 
     @Builder
diff --git a/src/main/java/org/harang/server/domain/Help.java b/src/main/java/org/harang/server/domain/Help.java
index 07dd418..9a0f2e1 100644
--- a/src/main/java/org/harang/server/domain/Help.java
+++ b/src/main/java/org/harang/server/domain/Help.java
@@ -22,7 +22,7 @@ public class Help {
     private String name;
 
     /* Relation Parent Mapping */
-    @OneToMany(mappedBy = "help")
+    @OneToMany(mappedBy = "help", cascade = CascadeType.ALL)
     private List<MemberHelp> memberHelpList = new ArrayList<>();
 
     @Builder
diff --git a/src/main/java/org/harang/server/domain/Location.java b/src/main/java/org/harang/server/domain/Location.java
index ad08ce8..f54751c 100644
--- a/src/main/java/org/harang/server/domain/Location.java
+++ b/src/main/java/org/harang/server/domain/Location.java
@@ -15,7 +15,7 @@ public class Location {
     @Column(name = "id", nullable = false)
     private Long id;
 
-    @OneToOne(fetch = FetchType.LAZY)
+    @OneToOne(fetch = FetchType.LAZY, cascade = CascadeType.ALL)
     @JoinColumn(name = "post_id")
     private Post post;
 
diff --git a/src/main/java/org/harang/server/domain/MemberInfo.java b/src/main/java/org/harang/server/domain/MemberInfo.java
index 4dc4339..94509e3 100644
--- a/src/main/java/org/harang/server/domain/MemberInfo.java
+++ b/src/main/java/org/harang/server/domain/MemberInfo.java
@@ -32,10 +32,10 @@ public class MemberInfo {
     private String refreshToken;
 
     /* Relation Parent Mapping */
-    @OneToMany(mappedBy = "memberInfo")
+    @OneToMany(mappedBy = "memberInfo", cascade = CascadeType.ALL)
     private List<MemberHelp> memberHelpList = new ArrayList<>();
 
-    @OneToMany(mappedBy = "memberInfo")
+    @OneToMany(mappedBy = "memberInfo", cascade = CascadeType.ALL)
     private List<Certification> certificationList = new ArrayList<>();
 
     @Builder
diff --git a/src/main/java/org/harang/server/domain/Post.java b/src/main/java/org/harang/server/domain/Post.java
index 381f609..1ed35ef 100644
--- a/src/main/java/org/harang/server/domain/Post.java
+++ b/src/main/java/org/harang/server/domain/Post.java
@@ -55,13 +55,13 @@ public class Post {
     private Status status = Status.WAITING;
 
     /* Relation Parent Mapping */
-    @OneToMany(mappedBy = "post")
+    @OneToMany(mappedBy = "post", cascade = CascadeType.ALL)
     private List<Matching> matchingList = new ArrayList<>();
 
-    @OneToMany(mappedBy = "post")
+    @OneToMany(mappedBy = "post", cascade = CascadeType.ALL)
     private List<PostCategory> postCategoryList = new ArrayList<>();
 
-    @OneToMany(mappedBy = "post")
+    @OneToMany(mappedBy = "post", cascade = CascadeType.ALL)
     private List<Waiting> waitingList = new ArrayList<>();
 
     @Builder
diff --git a/src/main/java/org/harang/server/dto/type/ErrorMessage.java b/src/main/java/org/harang/server/dto/type/ErrorMessage.java
index 61ad981..03032a7 100644
--- a/src/main/java/org/harang/server/dto/type/ErrorMessage.java
+++ b/src/main/java/org/harang/server/dto/type/ErrorMessage.java
@@ -49,6 +49,7 @@ public enum ErrorMessage {
     MATCHING_ALREADY_DONE("50004", HttpStatus.INTERNAL_SERVER_ERROR, "이미 종료된 매칭입니다."),
     ONLY_SPROUT_CAN_CREATE_MATCH("50005", HttpStatus.INTERNAL_SERVER_ERROR, "새싹인 유저만 매칭을 생성할 수 있습니다."),
     ONLY_WATERING_CAN_HELP_SPROUT("50006", HttpStatus.INTERNAL_SERVER_ERROR, "물뿌리개인 유저만 새싹을 도와줄 수 있습니다."),
+    CHAT_ALREADY_STARTED("50007", HttpStatus.INTERNAL_SERVER_ERROR, "이미 채팅을 시작한 게시글입니다."),
     ;
 
     private String code;
diff --git a/src/main/java/org/harang/server/repository/LocationRepository.java b/src/main/java/org/harang/server/repository/LocationRepository.java
index 05ce167..a950b26 100644
--- a/src/main/java/org/harang/server/repository/LocationRepository.java
+++ b/src/main/java/org/harang/server/repository/LocationRepository.java
@@ -1,7 +1,16 @@
 package org.harang.server.repository;
 
+import jakarta.transaction.Transactional;
 import org.harang.server.domain.Location;
 import org.springframework.data.jpa.repository.JpaRepository;
+import org.springframework.data.jpa.repository.Modifying;
+import org.springframework.data.jpa.repository.Query;
 
 public interface LocationRepository extends JpaRepository<Location, Long> {
-}
+    Location findByPostId(Long PostId);
+
+    @Transactional
+    @Modifying
+    @Query("DELETE FROM Location l WHERE l.post.id = :postId")
+    void deleteByPostId(Long postId);
+}
\ No newline at end of file
diff --git a/src/main/java/org/harang/server/service/MatchingService.java b/src/main/java/org/harang/server/service/MatchingService.java
index 5090e17..54c9ed5 100644
--- a/src/main/java/org/harang/server/service/MatchingService.java
+++ b/src/main/java/org/harang/server/service/MatchingService.java
@@ -94,4 +94,31 @@ public List<WaitingResponse> getWaitingList(Long postId) {
                         .build()).toList();
         return waitingListResponse;
     }
+
+    @Transactional
+    public void createMatchingWaiting(Long memberId, Long postId) {
+        Post post = postRepository.findByIdOrThrow(postId);
+        Member member = memberRepository.findByIdOrThrow(memberId);
+
+        // 이미 사용자가 채팅을 시작한 글이라면 예외 발생
+        List<Long> waitingMemberIdList = waitingRepository.findAllByPostId(postId)
+                .stream().map(w -> w.getMember().getId()).toList();
+        for (Long m : waitingMemberIdList) {
+            if (m.equals(memberId)) {
+                throw new CustomException(ErrorMessage.CHAT_ALREADY_STARTED);
+            }
+        }
+
+        // 사용자가 물뿌리개가 아니라면 예외 발생
+        if (!member.getType().equals(Type.WATERING)) {
+            throw new CustomException(ErrorMessage.ONLY_WATERING_CAN_HELP_SPROUT);
+        }
+
+        Waiting newWaiting = Waiting.builder()
+                .post(post)
+                .member(member)
+                .build();
+
+        waitingRepository.save(newWaiting);
+    }
 }
diff --git a/src/main/java/org/harang/server/service/PostService.java b/src/main/java/org/harang/server/service/PostService.java
index 19c6ab1..023a694 100644
--- a/src/main/java/org/harang/server/service/PostService.java
+++ b/src/main/java/org/harang/server/service/PostService.java
@@ -82,5 +82,13 @@ public List<PostResponse> getSearchResults(String title) {
                 .stream()
                 .map(p -> PostResponse.of(p))
                 .toList();
+
+    @Transactional
+    public void deletePost(Long memberId, Long postId) {
+        Post post = postRepository.findByIdOrThrow(postId);
+
+        locationRepository.deleteByPostId(postId);
+        postRepository.delete(post);
+
     }
 }