diff --git a/src/main/java/org/ezcode/codetest/application/problem/service/ProblemService.java b/src/main/java/org/ezcode/codetest/application/problem/service/ProblemService.java
index afabe5f6..20481e19 100644
--- a/src/main/java/org/ezcode/codetest/application/problem/service/ProblemService.java
+++ b/src/main/java/org/ezcode/codetest/application/problem/service/ProblemService.java
@@ -12,6 +12,8 @@
 import org.ezcode.codetest.domain.user.service.UserDomainService;
 import org.ezcode.codetest.infrastructure.s3.S3Directory;
 import org.ezcode.codetest.infrastructure.s3.S3Uploader;
+import org.ezcode.codetest.infrastructure.s3.exception.S3Exception;
+import org.ezcode.codetest.infrastructure.s3.exception.code.S3ExceptionCode;
 import org.springframework.data.domain.Page;
 import org.springframework.data.domain.Pageable;
 import org.springframework.stereotype.Service;
@@ -19,9 +21,11 @@
 import org.springframework.web.multipart.MultipartFile;
 
 import lombok.RequiredArgsConstructor;
+import lombok.extern.slf4j.Slf4j;
 
 @Service
 @RequiredArgsConstructor
+@Slf4j
 public class ProblemService {
 
 	private final ProblemDomainService problemDomainService;
@@ -39,8 +43,8 @@ public ProblemDetailResponse createProblem(ProblemCreateRequest requestDto, Mult
 
 		// 문제 이미지 있다면?
 		if (image != null && !image.isEmpty()) {
-			String imageUrl = s3Uploader.upload(image, S3Directory.PROBLEM.getDir());
-			savedProblem.addImage(imageUrl);
+			String imageUrl = uploadImageAfterTransaction(image, savedProblem.getId());
+			updateProblemWithImage(savedProblem.getId(), imageUrl);
 		}
 
 		return ProblemDetailResponse.from(savedProblem);
@@ -91,5 +95,20 @@ public void removeProblem(Long problemId) {
 
 		problemDomainService.removeProblem(findProblem);
 	}
+
+	@Transactional
+	public void updateProblemWithImage(Long problemId, String imageUrl) {
+		Problem problem = problemDomainService.getProblem(problemId);
+		problem.addImage(imageUrl);
+	}
+
+	private String uploadImageAfterTransaction(MultipartFile image, Long problemId) {
+		try {
+			return s3Uploader.upload(image, S3Directory.PROBLEM.getDir());
+		} catch (Exception e) {
+			log.error("Problem {} 이미지 업로드 실패", problemId, e);
+			throw new S3Exception(S3ExceptionCode.S3_UPLOAD_FAILED);
+		}
+	}
 }