diff --git a/src/main/java/leets/weeth/domain/board/application/usecase/NoticeUsecaseImpl.java b/src/main/java/leets/weeth/domain/board/application/usecase/NoticeUsecaseImpl.java
index f0987ac2c..1de01a884 100644
--- a/src/main/java/leets/weeth/domain/board/application/usecase/NoticeUsecaseImpl.java
+++ b/src/main/java/leets/weeth/domain/board/application/usecase/NoticeUsecaseImpl.java
@@ -143,7 +143,11 @@ private CommentDTO.Response mapToDtoWithChildren(Comment comment, Map<Long, List
                 .map(child -> mapToDtoWithChildren(child, commentMap))
                 .collect(Collectors.toList());
 
-        return commentMapper.toCommentDto(comment, children);
+        List<FileResponse> files = fileGetService.findAllByComment(comment.getId()).stream()
+                .map(fileMapper::toFileResponse)
+                .toList();
+
+        return commentMapper.toCommentDto(comment, children, files);
     }
 
 }
diff --git a/src/main/java/leets/weeth/domain/board/application/usecase/PostUseCaseImpl.java b/src/main/java/leets/weeth/domain/board/application/usecase/PostUseCaseImpl.java
index 55bf65738..bf6a2fea5 100644
--- a/src/main/java/leets/weeth/domain/board/application/usecase/PostUseCaseImpl.java
+++ b/src/main/java/leets/weeth/domain/board/application/usecase/PostUseCaseImpl.java
@@ -1,10 +1,5 @@
 package leets.weeth.domain.board.application.usecase;
 
-import java.util.Collections;
-import java.util.Comparator;
-import java.util.List;
-import java.util.Map;
-import java.util.stream.Collectors;
 import leets.weeth.domain.board.application.dto.PartPostDTO;
 import leets.weeth.domain.board.application.dto.PostDTO;
 import leets.weeth.domain.board.application.exception.CategoryAccessDeniedException;
@@ -34,14 +29,16 @@
 import leets.weeth.domain.user.domain.service.UserCardinalGetService;
 import leets.weeth.domain.user.domain.service.UserGetService;
 import lombok.RequiredArgsConstructor;
-import org.springframework.data.domain.PageRequest;
-import org.springframework.data.domain.Pageable;
-import org.springframework.data.domain.Slice;
-import org.springframework.data.domain.SliceImpl;
-import org.springframework.data.domain.Sort;
+import org.springframework.data.domain.*;
 import org.springframework.stereotype.Service;
 import org.springframework.transaction.annotation.Transactional;
 
+import java.util.Collections;
+import java.util.Comparator;
+import java.util.List;
+import java.util.Map;
+import java.util.stream.Collectors;
+
 @Service
 @RequiredArgsConstructor
 public class PostUseCaseImpl implements PostUsecase {
@@ -106,7 +103,6 @@ public PostDTO.Response findPost(Long postId) {
                 .map(fileMapper::toFileResponse)
                 .toList();
 
-
         return mapper.toPostDto(post, response, filterParentComments(post.getComments()));
     }
 
@@ -232,7 +228,11 @@ private CommentDTO.Response mapToDtoWithChildren(Comment comment, Map<Long, List
                 .map(child -> mapToDtoWithChildren(child, commentMap))
                 .collect(Collectors.toList());
 
-        return commentMapper.toCommentDto(comment, children);
+        List<FileResponse> files = fileGetService.findAllByComment(comment.getId()).stream()
+                .map(fileMapper::toFileResponse)
+                .toList();
+
+        return commentMapper.toCommentDto(comment, children, files);
     }
 
     private void validatePageNumber(int pageNumber){
diff --git a/src/main/java/leets/weeth/domain/comment/application/dto/CommentDTO.java b/src/main/java/leets/weeth/domain/comment/application/dto/CommentDTO.java
index 7524c71ee..639e377d1 100644
--- a/src/main/java/leets/weeth/domain/comment/application/dto/CommentDTO.java
+++ b/src/main/java/leets/weeth/domain/comment/application/dto/CommentDTO.java
@@ -1,6 +1,10 @@
 package leets.weeth.domain.comment.application.dto;
 
+import jakarta.validation.Valid;
 import jakarta.validation.constraints.NotBlank;
+import jakarta.validation.constraints.NotNull;
+import leets.weeth.domain.file.application.dto.request.FileSaveRequest;
+import leets.weeth.domain.file.application.dto.response.FileResponse;
 import leets.weeth.domain.user.domain.entity.enums.Position;
 import leets.weeth.domain.user.domain.entity.enums.Role;
 import lombok.Builder;
@@ -13,12 +17,14 @@ public class CommentDTO {
     @Builder
     public record Save(
             Long parentCommentId,
-            @NotBlank String content
+            @NotBlank String content,
+            @Valid List<@NotNull FileSaveRequest> files
     ){}
 
     @Builder
     public record Update(
-            @NotBlank String content
+            @NotBlank String content,
+            @Valid List<@NotNull FileSaveRequest> files
     ){}
 
     @Builder
@@ -29,6 +35,7 @@ public record Response(
             Role role,
             String content,
             LocalDateTime time, //modifiedAt
+            List<FileResponse> fileUrls,
             List<CommentDTO.Response> children
     ){}
 
diff --git a/src/main/java/leets/weeth/domain/comment/application/mapper/CommentMapper.java b/src/main/java/leets/weeth/domain/comment/application/mapper/CommentMapper.java
index 6afc099ad..84941b7c7 100644
--- a/src/main/java/leets/weeth/domain/comment/application/mapper/CommentMapper.java
+++ b/src/main/java/leets/weeth/domain/comment/application/mapper/CommentMapper.java
@@ -4,6 +4,7 @@
 import leets.weeth.domain.board.domain.entity.Post;
 import leets.weeth.domain.comment.application.dto.CommentDTO;
 import leets.weeth.domain.comment.domain.entity.Comment;
+import leets.weeth.domain.file.application.dto.response.FileResponse;
 import leets.weeth.domain.user.domain.entity.User;
 import org.mapstruct.*;
 
@@ -44,5 +45,5 @@ public interface CommentMapper {
     @Mapping(target = "role", source = "comment.user.role")
     @Mapping(target = "time", source = "comment.modifiedAt")
     @Mapping(target = "children", source = "children")
-    CommentDTO.Response toCommentDto(Comment comment, List<CommentDTO.Response> children);
+    CommentDTO.Response toCommentDto(Comment comment, List<CommentDTO.Response> children, List<FileResponse> fileUrls);
 }
diff --git a/src/main/java/leets/weeth/domain/comment/application/usecase/NoticeCommentUsecaseImpl.java b/src/main/java/leets/weeth/domain/comment/application/usecase/NoticeCommentUsecaseImpl.java
index 7cd8fde1e..43c5f4c61 100644
--- a/src/main/java/leets/weeth/domain/comment/application/usecase/NoticeCommentUsecaseImpl.java
+++ b/src/main/java/leets/weeth/domain/comment/application/usecase/NoticeCommentUsecaseImpl.java
@@ -3,15 +3,20 @@
 import leets.weeth.domain.board.domain.entity.Notice;
 import leets.weeth.domain.board.domain.service.NoticeFindService;
 import leets.weeth.domain.comment.application.dto.CommentDTO;
+import leets.weeth.domain.comment.application.exception.CommentNotFoundException;
 import leets.weeth.domain.comment.application.mapper.CommentMapper;
 import leets.weeth.domain.comment.domain.entity.Comment;
 import leets.weeth.domain.comment.domain.service.CommentDeleteService;
 import leets.weeth.domain.comment.domain.service.CommentFindService;
 import leets.weeth.domain.comment.domain.service.CommentSaveService;
+import leets.weeth.domain.file.application.mapper.FileMapper;
+import leets.weeth.domain.file.domain.entity.File;
+import leets.weeth.domain.file.domain.service.FileDeleteService;
+import leets.weeth.domain.file.domain.service.FileGetService;
+import leets.weeth.domain.file.domain.service.FileSaveService;
+import leets.weeth.domain.user.application.exception.UserNotMatchException;
 import leets.weeth.domain.user.domain.entity.User;
 import leets.weeth.domain.user.domain.service.UserGetService;
-import leets.weeth.domain.comment.application.exception.CommentNotFoundException;
-import leets.weeth.domain.user.application.exception.UserNotMatchException;
 import lombok.RequiredArgsConstructor;
 import org.springframework.stereotype.Service;
 import org.springframework.transaction.annotation.Transactional;
@@ -26,6 +31,11 @@ public class NoticeCommentUsecaseImpl implements NoticeCommentUsecase {
     private final CommentFindService commentFindService;
     private final CommentDeleteService commentDeleteService;
 
+    private final FileSaveService fileSaveService;
+    private final FileGetService fileGetService;
+    private final FileDeleteService fileDeleteService;
+    private final FileMapper fileMapper;
+
     private final NoticeFindService noticeFindService;
 
     private final UserGetService userGetService;
@@ -44,6 +54,9 @@ public void saveNoticeComment(CommentDTO.Save dto, Long noticeId, Long userId) {
         Comment comment = commentMapper.fromCommentDto(dto, notice, user, parentComment);
         commentSaveService.save(comment);
 
+        List<File> files = fileMapper.toFileList(dto.files(), comment);
+        fileSaveService.save(files);
+
         // 부모 댓글이 없다면 새 댓글로 추가
         if(parentComment == null) {
             notice.addComment(comment);
@@ -61,6 +74,12 @@ public void updateNoticeComment(CommentDTO.Update dto, Long noticeId, Long comme
         Notice notice = noticeFindService.find(noticeId);
         Comment comment = validateOwner(commentId, userId);
 
+        List<File> fileList = getFiles(commentId);
+        fileDeleteService.delete(fileList);
+
+        List<File> files = fileMapper.toFileList(dto.files(), comment);
+        fileSaveService.save(files);
+
         comment.update(dto);
     }
 
@@ -109,4 +128,7 @@ private Comment validateOwner(Long commentId, Long userId) throws UserNotMatchEx
         return comment;
     }
 
+    private List<File> getFiles(Long commentId) {
+        return fileGetService.findAllByComment(commentId);
+    }
 }
diff --git a/src/main/java/leets/weeth/domain/comment/application/usecase/PostCommentUsecaseImpl.java b/src/main/java/leets/weeth/domain/comment/application/usecase/PostCommentUsecaseImpl.java
index 314987a29..c2b655499 100644
--- a/src/main/java/leets/weeth/domain/comment/application/usecase/PostCommentUsecaseImpl.java
+++ b/src/main/java/leets/weeth/domain/comment/application/usecase/PostCommentUsecaseImpl.java
@@ -3,15 +3,20 @@
 import leets.weeth.domain.board.domain.entity.Post;
 import leets.weeth.domain.board.domain.service.PostFindService;
 import leets.weeth.domain.comment.application.dto.CommentDTO;
+import leets.weeth.domain.comment.application.exception.CommentNotFoundException;
 import leets.weeth.domain.comment.application.mapper.CommentMapper;
 import leets.weeth.domain.comment.domain.entity.Comment;
 import leets.weeth.domain.comment.domain.service.CommentDeleteService;
 import leets.weeth.domain.comment.domain.service.CommentFindService;
 import leets.weeth.domain.comment.domain.service.CommentSaveService;
+import leets.weeth.domain.file.application.mapper.FileMapper;
+import leets.weeth.domain.file.domain.entity.File;
+import leets.weeth.domain.file.domain.service.FileDeleteService;
+import leets.weeth.domain.file.domain.service.FileGetService;
+import leets.weeth.domain.file.domain.service.FileSaveService;
+import leets.weeth.domain.user.application.exception.UserNotMatchException;
 import leets.weeth.domain.user.domain.entity.User;
 import leets.weeth.domain.user.domain.service.UserGetService;
-import leets.weeth.domain.comment.application.exception.CommentNotFoundException;
-import leets.weeth.domain.user.application.exception.UserNotMatchException;
 import lombok.RequiredArgsConstructor;
 import org.springframework.stereotype.Service;
 import org.springframework.transaction.annotation.Transactional;
@@ -26,6 +31,11 @@ public class PostCommentUsecaseImpl implements PostCommentUsecase {
     private final CommentFindService commentFindService;
     private final CommentDeleteService commentDeleteService;
 
+    private final FileSaveService fileSaveService;
+    private final FileGetService fileGetService;
+    private final FileDeleteService fileDeleteService;
+    private final FileMapper fileMapper;
+
     private final UserGetService userGetService;
 
     private final PostFindService postFindService;
@@ -45,6 +55,9 @@ public void savePostComment(CommentDTO.Save dto, Long postId, Long userId) {
         Comment comment = commentMapper.fromCommentDto(dto, post, user, parentComment);
         commentSaveService.save(comment);
 
+        List<File> files = fileMapper.toFileList(dto.files(), comment);
+        fileSaveService.save(files);
+
         // 부모 댓글이 없다면 새 댓글로 추가
         if (parentComment == null) {
             post.addComment(comment);
@@ -62,6 +75,12 @@ public void updatePostComment(CommentDTO.Update dto, Long postId, Long commentId
         Post post = postFindService.find(postId);
         Comment comment = validateOwner(commentId, userId);
 
+        List<File> fileList = getFiles(commentId);
+        fileDeleteService.delete(fileList);
+
+        List<File> files = fileMapper.toFileList(dto.files(), comment);
+        fileSaveService.save(files);
+
         comment.update(dto);
     }
 
@@ -120,4 +139,8 @@ private Comment validateOwner(Long commentId, Long userId) throws UserNotMatchEx
         return comment;
     }
 
+    private List<File> getFiles(Long commentId) {
+        return fileGetService.findAllByComment(commentId);
+    }
+
 }
diff --git a/src/main/java/leets/weeth/domain/file/application/mapper/FileMapper.java b/src/main/java/leets/weeth/domain/file/application/mapper/FileMapper.java
index 13fd228a4..3158efb75 100644
--- a/src/main/java/leets/weeth/domain/file/application/mapper/FileMapper.java
+++ b/src/main/java/leets/weeth/domain/file/application/mapper/FileMapper.java
@@ -4,6 +4,7 @@
 import leets.weeth.domain.board.domain.entity.Notice;
 import leets.weeth.domain.board.domain.entity.Post;
 import leets.weeth.domain.comment.application.mapper.CommentMapper;
+import leets.weeth.domain.comment.domain.entity.Comment;
 import leets.weeth.domain.file.application.dto.request.FileSaveRequest;
 import leets.weeth.domain.file.application.dto.response.FileResponse;
 import leets.weeth.domain.file.application.dto.response.UrlResponse;
@@ -15,6 +16,7 @@
 
 import java.util.Collections;
 import java.util.List;
+import java.util.function.Function;
 import java.util.stream.Collectors;
 
 @Mapper(componentModel = MappingConstants.ComponentModel.SPRING, uses = CommentMapper.class, unmappedTargetPolicy = ReportingPolicy.IGNORE)
@@ -32,39 +34,39 @@ public interface FileMapper {
     @Mapping(target = "receipt", source = "receipt")
     File toFileWithReceipt(String fileName, String fileUrl, Receipt receipt);
 
+    @Mapping(target = "id", ignore = true)
+    @Mapping(target = "comment", source = "comment")
+    @Mapping(target = "notice", ignore = true) // notice 필드는 매핑하지 않도록 명시
+    @Mapping(target = "post", ignore = true) // post 필드는 매핑하지 않도록 명시
+    File toFileWithComment(String fileName, String fileUrl, Comment comment);
+
     @Mapping(target = "fileId", source = "file.id")
     FileResponse toFileResponse(File file);
 
     UrlResponse toUrlResponse(String fileName, String putUrl);
 
-    default List<File> toFileList(List<FileSaveRequest> requests, Post post) {
-        List<FileSaveRequest> dto = requests;
-        if (dto == null || dto.isEmpty()) {
+    private List<File> mapRequestsToFiles(List<FileSaveRequest> requests, Function<FileSaveRequest, File> mapper) {
+        if (requests == null || requests.isEmpty()) {
             return Collections.emptyList();
         }
-
-        return dto.stream()
-                .map(request -> toFileWithPost(request.fileName(), request.fileUrl(), post))
+        return requests.stream()
+                .map(mapper)
                 .collect(Collectors.toList());
     }
 
-    default List<File> toFileList(List<FileSaveRequest> requests, Notice notice) {
-        if (requests == null || requests.isEmpty()) {
-            return Collections.emptyList();
-        }
+    default List<File> toFileList(List<FileSaveRequest> requests, Post post) {
+        return mapRequestsToFiles(requests, request -> toFileWithPost(request.fileName(), request.fileUrl(), post));
+    }
 
-        return requests.stream()
-                .map(request -> toFileWithNotice(request.fileName(), request.fileUrl(), notice))
-                .collect(Collectors.toList());
+    default List<File> toFileList(List<FileSaveRequest> requests, Notice notice) {
+        return mapRequestsToFiles(requests, request -> toFileWithNotice(request.fileName(), request.fileUrl(), notice));
     }
 
     default List<File> toFileList(List<FileSaveRequest> requests, Receipt receipt) {
-        if (requests == null || requests.isEmpty()) {
-            return Collections.emptyList();
-        }
+        return mapRequestsToFiles(requests, request -> toFileWithReceipt(request.fileName(), request.fileUrl(), receipt));
+    }
 
-        return requests.stream()
-                .map(request -> toFileWithReceipt(request.fileName(), request.fileUrl(), receipt))
-                .collect(Collectors.toList());
+    default List<File> toFileList(List<FileSaveRequest> requests, Comment comment) {
+        return mapRequestsToFiles(requests, request -> toFileWithComment(request.fileName(), request.fileUrl(), comment));
     }
 }
diff --git a/src/main/java/leets/weeth/domain/file/domain/entity/File.java b/src/main/java/leets/weeth/domain/file/domain/entity/File.java
index 059a5dd35..490921864 100644
--- a/src/main/java/leets/weeth/domain/file/domain/entity/File.java
+++ b/src/main/java/leets/weeth/domain/file/domain/entity/File.java
@@ -4,8 +4,12 @@
 import leets.weeth.domain.account.domain.entity.Receipt;
 import leets.weeth.domain.board.domain.entity.Notice;
 import leets.weeth.domain.board.domain.entity.Post;
+import leets.weeth.domain.comment.domain.entity.Comment;
 import leets.weeth.global.common.entity.BaseEntity;
-import lombok.*;
+import lombok.AccessLevel;
+import lombok.AllArgsConstructor;
+import lombok.Getter;
+import lombok.NoArgsConstructor;
 import lombok.experimental.SuperBuilder;
 
 @Getter
@@ -35,6 +39,10 @@ public class File extends BaseEntity {
     @JoinColumn(name = "receipt_id")
     private Receipt receipt;
 
+    @ManyToOne
+    @JoinColumn(name = "comment_id")
+    private Comment comment;
+
     public void update(String fileName, String fileUrl) {
         this.fileName = fileName;
         this.fileUrl = fileUrl;
diff --git a/src/main/java/leets/weeth/domain/file/domain/repository/FileRepository.java b/src/main/java/leets/weeth/domain/file/domain/repository/FileRepository.java
index 2daee1019..a9097038a 100644
--- a/src/main/java/leets/weeth/domain/file/domain/repository/FileRepository.java
+++ b/src/main/java/leets/weeth/domain/file/domain/repository/FileRepository.java
@@ -12,4 +12,6 @@ public interface FileRepository extends JpaRepository<File, Long> {
     List<File> findAllByNoticeId(Long noticeId);
 
     List<File> findAllByReceiptId(Long receiptId);
+
+    List<File> findAllByCommentId(Long commentId);
 }
diff --git a/src/main/java/leets/weeth/domain/file/domain/service/FileGetService.java b/src/main/java/leets/weeth/domain/file/domain/service/FileGetService.java
index a2f546e74..eb7212f93 100644
--- a/src/main/java/leets/weeth/domain/file/domain/service/FileGetService.java
+++ b/src/main/java/leets/weeth/domain/file/domain/service/FileGetService.java
@@ -1,6 +1,5 @@
 package leets.weeth.domain.file.domain.service;
 
-import leets.weeth.domain.board.domain.entity.Notice;
 import leets.weeth.domain.file.domain.entity.File;
 import leets.weeth.domain.file.domain.repository.FileRepository;
 import lombok.RequiredArgsConstructor;
@@ -26,4 +25,7 @@ public List<File> findAllByReceipt(Long receiptId) {
         return fileRepository.findAllByReceiptId(receiptId);
     }
 
+    public List<File> findAllByComment(Long commentId) {
+        return fileRepository.findAllByCommentId(commentId);
+    }
 }