diff --git a/server/src/main/java/server/haengdong/application/EventImageFacadeService.java b/server/src/main/java/server/haengdong/application/EventImageFacadeService.java
new file mode 100644
index 000000000..8c5bbe946
--- /dev/null
+++ b/server/src/main/java/server/haengdong/application/EventImageFacadeService.java
@@ -0,0 +1,25 @@
+package server.haengdong.application;
+
+import java.util.List;
+import lombok.RequiredArgsConstructor;
+import org.springframework.stereotype.Service;
+import org.springframework.web.multipart.MultipartFile;
+
+@RequiredArgsConstructor
+@Service
+public class EventImageFacadeService {
+
+    private final EventService eventService;
+    private final ImageService imageService;
+
+    public void uploadImages(String token, List<MultipartFile> images) {
+        eventService.validateImageCount(token, images.size());
+        List<String> imageNames = imageService.uploadImages(images);
+        eventService.saveImages(token, imageNames);
+    }
+
+    public void deleteImage(String token, Long imageId) {
+        String imageName = eventService.deleteImage(token, imageId);
+        imageService.deleteImage(imageName);
+    }
+}
diff --git a/server/src/main/java/server/haengdong/application/EventService.java b/server/src/main/java/server/haengdong/application/EventService.java
index 2eb80f265..cb0972f8c 100644
--- a/server/src/main/java/server/haengdong/application/EventService.java
+++ b/server/src/main/java/server/haengdong/application/EventService.java
@@ -5,6 +5,7 @@
 import lombok.RequiredArgsConstructor;
 import org.springframework.beans.factory.annotation.Value;
 import org.springframework.stereotype.Service;
+import org.springframework.transaction.annotation.Propagation;
 import org.springframework.transaction.annotation.Transactional;
 import server.haengdong.application.request.EventAppRequest;
 import server.haengdong.application.request.EventLoginAppRequest;
@@ -31,6 +32,8 @@
 @Service
 public class EventService {
 
+    private static final int MAX_IMAGE_COUNT = 10;
+
     private final EventRepository eventRepository;
     private final EventTokenProvider eventTokenProvider;
     private final BillRepository billRepository;
@@ -137,4 +140,14 @@ public String deleteImage(String token, Long imageId) {
         eventImageRepository.delete(eventImage);
         return eventImage.getName();
     }
+
+    public void validateImageCount(String token, int uploadImageCount) {
+        Event event = getEvent(token);
+        Long imageCount = eventImageRepository.countByEvent(event);
+        Long totalImageCount = imageCount + uploadImageCount;
+
+        if (totalImageCount > MAX_IMAGE_COUNT) {
+            throw new HaengdongException(HaengdongErrorCode.IMAGE_COUNT_INVALID, totalImageCount);
+        }
+    }
 }
diff --git a/server/src/main/java/server/haengdong/application/ImageService.java b/server/src/main/java/server/haengdong/application/ImageService.java
index b6d64b033..716ad8227 100644
--- a/server/src/main/java/server/haengdong/application/ImageService.java
+++ b/server/src/main/java/server/haengdong/application/ImageService.java
@@ -7,6 +7,7 @@
 import java.util.List;
 import java.util.UUID;
 import java.util.concurrent.CompletableFuture;
+import java.util.concurrent.CompletionException;
 import java.util.concurrent.ExecutionException;
 import java.util.concurrent.ExecutorService;
 import lombok.RequiredArgsConstructor;
@@ -39,12 +40,12 @@ public List<String> uploadImages(List<MultipartFile> images) {
                 .map(image -> CompletableFuture.supplyAsync(() -> uploadImage(image), executorService))
                 .toList();
 
-        CompletableFuture<List<String>> result = CompletableFuture.allOf(futures.toArray(new CompletableFuture[0]))
-                .thenApply(v -> futures.stream()
-                        .map(this::getFuture)
-                        .toList());
-
-        return result.join();
+        try {
+            CompletableFuture<List<String>> result = collectUploadResults(futures);
+            return result.join();
+        } catch (CompletionException e) {
+            throw new HaengdongException(HaengdongErrorCode.IMAGE_UPLOAD_FAIL, e);
+        }
     }
 
     private String uploadImage(MultipartFile image) {
@@ -71,7 +72,14 @@ private String uploadImageToStorage(InputStream inputStream, MultipartFile image
         return imageName;
     }
 
-    private String getFuture(CompletableFuture<String> future) {
+    private CompletableFuture<List<String>> collectUploadResults(List<CompletableFuture<String>> futures) {
+        return CompletableFuture.allOf(futures.toArray(new CompletableFuture[0]))
+                .thenApply(v -> futures.stream()
+                        .map(this::resolveFuture)
+                        .toList());
+    }
+
+    private String resolveFuture(CompletableFuture<String> future) {
         try {
             return future.get();
         } catch (InterruptedException | ExecutionException e) {
diff --git a/server/src/main/java/server/haengdong/domain/event/EventImageRepository.java b/server/src/main/java/server/haengdong/domain/event/EventImageRepository.java
index 00f84b8af..c8c9e82e4 100644
--- a/server/src/main/java/server/haengdong/domain/event/EventImageRepository.java
+++ b/server/src/main/java/server/haengdong/domain/event/EventImageRepository.java
@@ -8,4 +8,6 @@
 public interface EventImageRepository extends JpaRepository<EventImage, Long> {
 
     List<EventImage> findAllByEvent(Event event);
+
+    Long countByEvent(Event event);
 }
diff --git a/server/src/main/java/server/haengdong/exception/HaengdongErrorCode.java b/server/src/main/java/server/haengdong/exception/HaengdongErrorCode.java
index fc79123b9..39b1014b0 100644
--- a/server/src/main/java/server/haengdong/exception/HaengdongErrorCode.java
+++ b/server/src/main/java/server/haengdong/exception/HaengdongErrorCode.java
@@ -31,6 +31,7 @@ public enum HaengdongErrorCode {
     DIFFERENT_STEP_MEMBERS("참여자 목록이 일치하지 않습니다."),
 
     IMAGE_NOT_FOUND("존재하지 않는 이미지 입니다."),
+    IMAGE_COUNT_INVALID("이미지 수량은 %d개 까지 업로드할 수 있습니다."),
 
     /* Authentication */
 
diff --git a/server/src/main/java/server/haengdong/presentation/admin/AdminEventController.java b/server/src/main/java/server/haengdong/presentation/admin/AdminEventController.java
index 8fd913dae..0d47c2012 100644
--- a/server/src/main/java/server/haengdong/presentation/admin/AdminEventController.java
+++ b/server/src/main/java/server/haengdong/presentation/admin/AdminEventController.java
@@ -13,6 +13,7 @@
 import org.springframework.web.bind.annotation.RequestPart;
 import org.springframework.web.bind.annotation.RestController;
 import org.springframework.web.multipart.MultipartFile;
+import server.haengdong.application.EventImageFacadeService;
 import server.haengdong.application.EventService;
 import server.haengdong.application.ImageService;
 import server.haengdong.application.response.ImageNameAppResponse;
@@ -24,7 +25,7 @@
 public class AdminEventController {
 
     private final EventService eventService;
-    private final ImageService imageUploadService;
+    private final EventImageFacadeService eventImageFacadeService;
 
     @PostMapping("/api/admin/events/{eventId}/auth")
     public ResponseEntity<Void> authenticate() {
@@ -46,8 +47,7 @@ public ResponseEntity<Void> uploadImages(
             @PathVariable("eventId") String token,
             @RequestPart("images") List<MultipartFile> images
     ) {
-        List<String> imageNames = imageUploadService.uploadImages(images);
-        eventService.saveImages(token, imageNames);
+        eventImageFacadeService.uploadImages(token, images);
 
         return ResponseEntity.ok().build();
     }
@@ -57,8 +57,7 @@ public ResponseEntity<Void> deleteImage(
             @PathVariable("eventId") String token,
             @PathVariable("imageId") Long imageId
     ) {
-        String imageName = eventService.deleteImage(token, imageId);
-        imageUploadService.deleteImage(imageName);
+        eventImageFacadeService.deleteImage(token, imageId);
 
         return ResponseEntity.ok().build();
     }
diff --git a/server/src/test/java/server/haengdong/application/EventServiceTest.java b/server/src/test/java/server/haengdong/application/EventServiceTest.java
index bcfc0a3e4..a849209e1 100644
--- a/server/src/test/java/server/haengdong/application/EventServiceTest.java
+++ b/server/src/test/java/server/haengdong/application/EventServiceTest.java
@@ -2,6 +2,7 @@
 
 
 import static org.assertj.core.api.Assertions.assertThat;
+import static org.assertj.core.api.Assertions.assertThatThrownBy;
 import static org.assertj.core.api.AssertionsForClassTypes.tuple;
 import static org.junit.jupiter.api.Assertions.assertAll;
 import static org.mockito.BDDMockito.given;
@@ -28,6 +29,7 @@
 import server.haengdong.domain.event.Event;
 import server.haengdong.domain.event.EventRepository;
 import server.haengdong.domain.event.EventTokenProvider;
+import server.haengdong.exception.HaengdongException;
 import server.haengdong.support.fixture.Fixture;
 
 class EventServiceTest extends ServiceTestSupport {
@@ -228,4 +230,17 @@ void deleteImage() {
         assertThat(eventImageRepository.findById(eventImage.getId()))
                 .isEmpty();
     }
+
+    @DisplayName("행사 1개당 이미지는 10개까지 업로드 가능하다.")
+    @Test
+    void validateImageCount() {
+        Event event = Fixture.EVENT1;
+        eventRepository.save(event);
+        List<String> imageNames = List.of("image1.jpg", "image2.jpg");
+        String token = event.getToken();
+        eventService.saveImages(token, imageNames);
+
+        assertThatThrownBy(() -> eventService.validateImageCount(token, 9))
+                .isInstanceOf(HaengdongException.class);
+    }
 }
diff --git a/server/src/test/java/server/haengdong/application/ImageServiceTest.java b/server/src/test/java/server/haengdong/application/ImageServiceTest.java
new file mode 100644
index 000000000..16dc695a1
--- /dev/null
+++ b/server/src/test/java/server/haengdong/application/ImageServiceTest.java
@@ -0,0 +1,48 @@
+package server.haengdong.application;
+
+import static org.assertj.core.api.Assertions.assertThatThrownBy;
+import static org.awaitility.Awaitility.given;
+import static org.junit.jupiter.api.Assertions.*;
+import static org.mockito.ArgumentMatchers.any;
+import static org.mockito.Mockito.doThrow;
+import static org.mockito.Mockito.when;
+
+import java.util.List;
+import org.assertj.core.api.Assertions;
+import org.junit.jupiter.api.DisplayName;
+import org.junit.jupiter.api.Test;
+import org.springframework.beans.factory.annotation.Autowired;
+import org.springframework.boot.test.mock.mockito.MockBean;
+import org.springframework.mock.web.MockMultipartFile;
+import org.springframework.web.multipart.MultipartFile;
+import server.haengdong.exception.HaengdongException;
+import software.amazon.awssdk.core.sync.RequestBody;
+import software.amazon.awssdk.services.s3.S3Client;
+import software.amazon.awssdk.services.s3.model.PutObjectRequest;
+import software.amazon.awssdk.services.s3.model.S3Exception;
+
+
+class ImageServiceTest extends ServiceTestSupport {
+
+    @Autowired
+    private ImageService imageService;
+
+    @MockBean
+    private S3Client s3Client;
+
+    @DisplayName("이미지 업로드 도중 실패하면 예외가 커스텀 예외가 발생한다.")
+    @Test
+    void uploadImages() {
+        MultipartFile multipartFile1 = new MockMultipartFile("file1", "test1.txt", "text/plain", "hello1".getBytes());
+        MultipartFile multipartFile2 = new MockMultipartFile("file2", "test2.txt", "text/plain", "hello2".getBytes());
+        MultipartFile multipartFile3 = new MockMultipartFile("file3", "test3.txt", "text/plain", "hello3".getBytes());
+        MultipartFile multipartFile4 = new MockMultipartFile("file4", "test4.txt", "text/plain", "hello4".getBytes());
+        MultipartFile multipartFile5 = new MockMultipartFile("file5", "test5.txt", "text/plain", "hello5".getBytes());
+
+        doThrow(new RuntimeException("S3 upload failed"))
+                .when(s3Client).putObject(any(PutObjectRequest.class), any(RequestBody.class));
+
+        assertThatThrownBy(() -> imageService.uploadImages(List.of(multipartFile1, multipartFile2, multipartFile3, multipartFile4, multipartFile5)))
+                .isInstanceOf(HaengdongException.class);
+    }
+}
diff --git a/server/src/test/java/server/haengdong/docs/AdminEventControllerDocsTest.java b/server/src/test/java/server/haengdong/docs/AdminEventControllerDocsTest.java
index 658c57512..b5bb5cda8 100644
--- a/server/src/test/java/server/haengdong/docs/AdminEventControllerDocsTest.java
+++ b/server/src/test/java/server/haengdong/docs/AdminEventControllerDocsTest.java
@@ -26,19 +26,19 @@
 import org.springframework.http.MediaType;
 import org.springframework.mock.web.MockMultipartFile;
 import org.springframework.restdocs.payload.JsonFieldType;
+import server.haengdong.application.EventImageFacadeService;
 import server.haengdong.application.EventService;
-import server.haengdong.application.ImageService;
 import server.haengdong.presentation.admin.AdminEventController;
 import server.haengdong.presentation.request.EventUpdateRequest;
 
 class AdminEventControllerDocsTest extends RestDocsSupport {
 
     private final EventService eventService = mock(EventService.class);
-    private final ImageService imageUploadService = mock(ImageService.class);
+    private final EventImageFacadeService eventImageFacadeService = mock(EventImageFacadeService.class);
 
     @Override
     protected Object initController() {
-        return new AdminEventController(eventService, imageUploadService);
+        return new AdminEventController(eventService, eventImageFacadeService);
     }
 
     @DisplayName("행사 어드민 권한을 확인한다.")
diff --git a/server/src/test/java/server/haengdong/presentation/ControllerTestSupport.java b/server/src/test/java/server/haengdong/presentation/ControllerTestSupport.java
index 738823c40..3d7763ee0 100644
--- a/server/src/test/java/server/haengdong/presentation/ControllerTestSupport.java
+++ b/server/src/test/java/server/haengdong/presentation/ControllerTestSupport.java
@@ -10,6 +10,7 @@
 import org.springframework.web.servlet.config.annotation.WebMvcConfigurer;
 import server.haengdong.application.AuthService;
 import server.haengdong.application.BillService;
+import server.haengdong.application.EventImageFacadeService;
 import server.haengdong.application.EventService;
 import server.haengdong.application.ImageService;
 import server.haengdong.application.MemberService;
@@ -49,5 +50,5 @@ public abstract class ControllerTestSupport {
     protected BillService billService;
 
     @MockBean
-    protected ImageService imageUploadService;
+    protected EventImageFacadeService eventImageFacadeService;
 }