diff --git a/edukit-api/src/main/resources/db/migration/V12__Add_ai_task_failure_tracking.sql b/edukit-api/src/main/resources/db/migration/V12__Add_ai_task_failure_tracking.sql
new file mode 100644
index 00000000..46e196ff
--- /dev/null
+++ b/edukit-api/src/main/resources/db/migration/V12__Add_ai_task_failure_tracking.sql
@@ -0,0 +1,5 @@
+-- Add failure tracking columns to student_record_ai_task table
+
+ALTER TABLE student_record_ai_task
+    ADD COLUMN failed_at DATETIME NULL AFTER completed_at,
+    ADD COLUMN error_type VARCHAR(50) NULL AFTER failed_at;
diff --git a/edukit-core/src/main/java/com/edukit/core/common/service/RedisStoreService.java b/edukit-core/src/main/java/com/edukit/core/common/service/RedisStoreService.java
index 997e27c2..f951566d 100644
--- a/edukit-core/src/main/java/com/edukit/core/common/service/RedisStoreService.java
+++ b/edukit-core/src/main/java/com/edukit/core/common/service/RedisStoreService.java
@@ -8,6 +8,8 @@ public interface RedisStoreService {
 
     String get(String key);
 
+    Boolean setIfAbsent(String key, String value, Duration ttl);
+
     void delete(String key);
 
     Long increment(String key, Duration ttl);
diff --git a/edukit-core/src/main/java/com/edukit/core/event/ai/AICompensationListener.java b/edukit-core/src/main/java/com/edukit/core/event/ai/AICompensationListener.java
new file mode 100644
index 00000000..9ec63840
--- /dev/null
+++ b/edukit-core/src/main/java/com/edukit/core/event/ai/AICompensationListener.java
@@ -0,0 +1,75 @@
+package com.edukit.core.event.ai;
+
+import com.edukit.core.common.service.RedisStoreService;
+import com.edukit.core.event.ai.dto.AITaskFailedEvent;
+import com.edukit.core.point.service.PointService;
+import com.edukit.core.studentrecord.db.entity.StudentRecordAITask;
+import com.edukit.core.studentrecord.service.AITaskService;
+import java.time.Duration;
+import lombok.RequiredArgsConstructor;
+import lombok.extern.slf4j.Slf4j;
+import org.springframework.boot.autoconfigure.condition.ConditionalOnBean;
+import org.springframework.context.event.EventListener;
+import org.springframework.scheduling.annotation.Async;
+import org.springframework.stereotype.Component;
+
+@Slf4j
+@Component
+@RequiredArgsConstructor
+@ConditionalOnBean(RedisStoreService.class)
+public class AICompensationListener {
+
+    private final PointService pointService;
+    private final AITaskService aiTaskService;
+    private final RedisStoreService redisStoreService;
+
+    private static final String COMPENSATION_KEY_PREFIX = "compensation:";
+    private static final int DEDUCTED_POINTS = 100;
+    private static final Duration COMPENSATION_RECORD_TTL = Duration.ofDays(7);
+
+    @Async("aiTaskExecutor")
+    @EventListener
+    public void handleAITaskFailure(final AITaskFailedEvent event) {
+        String taskId = event.taskId();
+        String compensationKey = COMPENSATION_KEY_PREFIX + taskId;
+
+        // 원자적 선점 - Redis SET NX로 중복 보상 방지
+        if (!tryClaimCompensation(compensationKey)) {
+            log.warn("Task {} already compensated by another instance, skipping", taskId);
+            return;
+        }
+
+        try {
+            // Task 정보 조회
+            StudentRecordAITask task = aiTaskService.getTaskById(Long.valueOf(taskId));
+
+            // Task를 실패로 마킹
+            aiTaskService.markTaskAsFailed(Long.valueOf(taskId), event.errorType());
+
+            // 포인트 보상
+            pointService.compensatePoints(
+                    task.getMember().getId(),
+                    DEDUCTED_POINTS,
+                    task.getId()
+            );
+
+            log.info("Successfully compensated {} points for taskId: {} (errorType: {})",
+                    DEDUCTED_POINTS, taskId, event.errorType());
+
+        } catch (Exception e) {
+            log.error("Failed to compensate points for taskId: {}", taskId, e);
+            // 보상 실패 시 Redis 키 삭제하여 재시도 가능하게 함
+            redisStoreService.delete(compensationKey);
+            throw e;
+        }
+    }
+
+    /**
+     * 원자적 선점 시도
+     * @return true: 선점 성공 (보상 실행), false: 이미 다른 인스턴스가 선점 (스킵)
+     */
+    private boolean tryClaimCompensation(final String compensationKey) {
+        Boolean claimed = redisStoreService.setIfAbsent(compensationKey, "COMPENSATED", COMPENSATION_RECORD_TTL);
+        return Boolean.TRUE.equals(claimed);
+    }
+}
diff --git a/edukit-core/src/main/java/com/edukit/core/event/ai/dto/AIErrorMessage.java b/edukit-core/src/main/java/com/edukit/core/event/ai/dto/AIErrorMessage.java
new file mode 100644
index 00000000..dc3999ce
--- /dev/null
+++ b/edukit-core/src/main/java/com/edukit/core/event/ai/dto/AIErrorMessage.java
@@ -0,0 +1,17 @@
+package com.edukit.core.event.ai.dto;
+
+import com.fasterxml.jackson.annotation.JsonProperty;
+
+public record AIErrorMessage(
+        @JsonProperty("task_id")
+        String taskId,
+        @JsonProperty("status")
+        String status,
+        @JsonProperty("error_type")
+        String errorType,
+        @JsonProperty("error_message")
+        String errorMessage,
+        @JsonProperty("retryable")
+        Boolean retryable
+) {
+}
diff --git a/edukit-core/src/main/java/com/edukit/core/event/ai/dto/AITaskFailedEvent.java b/edukit-core/src/main/java/com/edukit/core/event/ai/dto/AITaskFailedEvent.java
new file mode 100644
index 00000000..4cd38d33
--- /dev/null
+++ b/edukit-core/src/main/java/com/edukit/core/event/ai/dto/AITaskFailedEvent.java
@@ -0,0 +1,18 @@
+package com.edukit.core.event.ai.dto;
+
+public record AITaskFailedEvent(
+        String taskId,
+        String errorType
+) {
+
+    public static AITaskFailedEvent of(final String taskId, final String errorType) {
+        return new AITaskFailedEvent(taskId, errorType);
+    }
+
+    public static AITaskFailedEvent fromErrorMessage(final AIErrorMessage errorMessage) {
+        return AITaskFailedEvent.of(
+                errorMessage.taskId(),
+                errorMessage.errorType()
+        );
+    }
+}
diff --git a/edukit-core/src/main/java/com/edukit/core/event/ai/dto/SSEMessage.java b/edukit-core/src/main/java/com/edukit/core/event/ai/dto/SSEMessage.java
index d3ef7a5f..33e4e894 100644
--- a/edukit-core/src/main/java/com/edukit/core/event/ai/dto/SSEMessage.java
+++ b/edukit-core/src/main/java/com/edukit/core/event/ai/dto/SSEMessage.java
@@ -13,6 +13,10 @@ public static SSEMessage response(final String taskId, final String finalContent
         return new SSEMessage(taskId, "RESPONSE", new ResponseData(finalContent, version));
     }
 
+    public static SSEMessage error(final String taskId, final String errorType, final String errorMessage) {
+        return new SSEMessage(taskId, "ERROR", new ErrorData(errorType, errorMessage));
+    }
+
     public record ProgressData(
             String message,
             int version
@@ -24,4 +28,10 @@ public record ResponseData(
             Integer version
     ) {
     }
+
+    public record ErrorData(
+            String errorType,
+            String errorMessage
+    ) {
+    }
 }
diff --git a/edukit-core/src/main/java/com/edukit/core/member/db/entity/Member.java b/edukit-core/src/main/java/com/edukit/core/member/db/entity/Member.java
index c4cf95f4..538c6549 100644
--- a/edukit-core/src/main/java/com/edukit/core/member/db/entity/Member.java
+++ b/edukit-core/src/main/java/com/edukit/core/member/db/entity/Member.java
@@ -147,7 +147,11 @@ public void updateEmailAndChangeVerifyStatus(final String email) {
         this.role = MemberRole.PENDING_TEACHER;
     }
 
-    public void deductPoints(final int pointsToDeduct) {
-        this.point -= pointsToDeduct;
+    public void deductPoints(final int point) {
+        this.point -= point;
+    }
+
+    public void addPoints(final int point) {
+        this.point += point;
     }
 }
diff --git a/edukit-core/src/main/java/com/edukit/core/point/service/PointService.java b/edukit-core/src/main/java/com/edukit/core/point/service/PointService.java
index 329a9ade..8467199e 100644
--- a/edukit-core/src/main/java/com/edukit/core/point/service/PointService.java
+++ b/edukit-core/src/main/java/com/edukit/core/point/service/PointService.java
@@ -38,16 +38,14 @@ public void deductPoints(final Long memberId, final int pointsToDeduct, final Lo
     }
 
     @Transactional
-    public Member compensatePoints(final Long memberId, final int pointsToCompensate, final Long taskId) {
+    public void compensatePoints(final Long memberId, final int pointsToCompensate, final Long taskId) {
         Member member = memberRepository.findByIdWithLock(memberId)
                 .orElseThrow(() -> new MemberException(MemberErrorCode.MEMBER_NOT_FOUND));
 
-        member.deductPoints(-pointsToCompensate); // 음수 차감으로 복구
+        member.addPoints(pointsToCompensate); // 음수 차감으로 복구
 
         // 포인트 히스토리 기록
         PointHistory history = PointHistory.create(member, PointTransactionType.COMPENSATION, pointsToCompensate, taskId);
         pointHistoryRepository.save(history);
-
-        return member;
     }
 }
diff --git a/edukit-core/src/main/java/com/edukit/core/studentrecord/db/entity/StudentRecordAITask.java b/edukit-core/src/main/java/com/edukit/core/studentrecord/db/entity/StudentRecordAITask.java
index c08dc97d..32ea7850 100644
--- a/edukit-core/src/main/java/com/edukit/core/studentrecord/db/entity/StudentRecordAITask.java
+++ b/edukit-core/src/main/java/com/edukit/core/studentrecord/db/entity/StudentRecordAITask.java
@@ -3,8 +3,11 @@
 import static jakarta.persistence.FetchType.LAZY;
 
 import com.edukit.core.member.db.entity.Member;
+import com.edukit.core.studentrecord.db.enums.AIErrorType;
 import jakarta.persistence.Column;
 import jakarta.persistence.Entity;
+import jakarta.persistence.EnumType;
+import jakarta.persistence.Enumerated;
 import jakarta.persistence.GeneratedValue;
 import jakarta.persistence.GenerationType;
 import jakarta.persistence.Id;
@@ -39,6 +42,12 @@ public class StudentRecordAITask {
 
     private LocalDateTime completedAt;
 
+    private LocalDateTime failedAt;
+
+    @Enumerated(EnumType.STRING)
+    @Column(length = 50)
+    private AIErrorType errorType;
+
     @Builder(access = AccessLevel.PRIVATE)
     private StudentRecordAITask(final Member member, final String prompt, final LocalDateTime startedAt) {
         this.member = member;
@@ -60,4 +69,9 @@ public void start() {
     public void complete() {
         this.completedAt = LocalDateTime.now();
     }
+
+    public void markAsFailed(final AIErrorType errorType) {
+        this.failedAt = LocalDateTime.now();
+        this.errorType = errorType;
+    }
 }
diff --git a/edukit-core/src/main/java/com/edukit/core/studentrecord/db/enums/AIErrorType.java b/edukit-core/src/main/java/com/edukit/core/studentrecord/db/enums/AIErrorType.java
new file mode 100644
index 00000000..1acdc0b4
--- /dev/null
+++ b/edukit-core/src/main/java/com/edukit/core/studentrecord/db/enums/AIErrorType.java
@@ -0,0 +1,26 @@
+package com.edukit.core.studentrecord.db.enums;
+
+import java.util.Arrays;
+import lombok.Getter;
+import lombok.RequiredArgsConstructor;
+
+@Getter
+@RequiredArgsConstructor
+public enum AIErrorType {
+    OPENAI_API_ERROR("OpenAI API 호출 실패"),
+    LAMBDA_ERROR("Lambda 처리 오류"),
+    UNKNOWN_ERROR("알 수 없는 오류");
+
+    private final String description;
+
+    public static AIErrorType fromString(final String value) {
+        if (value == null || value.isBlank()) {
+            return UNKNOWN_ERROR;
+        }
+
+        return Arrays.stream(AIErrorType.values())
+                .filter(type -> type.name().equalsIgnoreCase(value))
+                .findFirst()
+                .orElse(UNKNOWN_ERROR);
+    }
+}
diff --git a/edukit-core/src/main/java/com/edukit/core/studentrecord/service/AITaskService.java b/edukit-core/src/main/java/com/edukit/core/studentrecord/service/AITaskService.java
index 60f4febb..1a5be677 100644
--- a/edukit-core/src/main/java/com/edukit/core/studentrecord/service/AITaskService.java
+++ b/edukit-core/src/main/java/com/edukit/core/studentrecord/service/AITaskService.java
@@ -2,6 +2,7 @@
 
 import com.edukit.core.member.db.entity.Member;
 import com.edukit.core.studentrecord.db.entity.StudentRecordAITask;
+import com.edukit.core.studentrecord.db.enums.AIErrorType;
 import com.edukit.core.studentrecord.db.repository.StudentRecordAITaskRepository;
 import com.edukit.core.studentrecord.exception.StudentRecordErrorCode;
 import com.edukit.core.studentrecord.exception.StudentRecordException;
@@ -37,6 +38,20 @@ public void validateUserTask(final long memberId, final String taskId) {
         }
     }
 
+    @Transactional(readOnly = true)
+    public StudentRecordAITask getTaskById(final Long taskId) {
+        return aiTaskRepository.findById(taskId)
+                .orElseThrow(() -> new StudentRecordException(StudentRecordErrorCode.AI_TASK_NOT_FOUND));
+    }
+
+    @Transactional
+    public void markTaskAsFailed(final Long taskId, final String errorType) {
+        StudentRecordAITask task = aiTaskRepository.findById(taskId)
+                .orElseThrow(() -> new StudentRecordException(StudentRecordErrorCode.AI_TASK_NOT_FOUND));
+        AIErrorType aiErrorType = AIErrorType.fromString(errorType);
+        task.markAsFailed(aiErrorType);
+    }
+
     private long parseTaskId(final String taskId) {
         try {
             return Long.parseLong(taskId);
diff --git a/edukit-core/src/main/java/com/edukit/core/studentrecord/service/RedisStreamConsumer.java b/edukit-core/src/main/java/com/edukit/core/studentrecord/service/RedisStreamConsumer.java
index 57626017..2e7d0338 100644
--- a/edukit-core/src/main/java/com/edukit/core/studentrecord/service/RedisStreamConsumer.java
+++ b/edukit-core/src/main/java/com/edukit/core/studentrecord/service/RedisStreamConsumer.java
@@ -1,9 +1,11 @@
 package com.edukit.core.studentrecord.service;
 
 import com.edukit.common.infra.ServerInstanceManager;
+import com.edukit.core.event.ai.dto.AIErrorMessage;
 import com.edukit.core.event.ai.dto.AIProgressMessage;
 import com.edukit.core.event.ai.dto.AIResponseMessage;
 import com.edukit.core.common.service.RedisStreamService;
+import com.edukit.core.event.ai.dto.AITaskFailedEvent;
 import com.edukit.core.studentrecord.exception.StudentRecordErrorCode;
 import com.edukit.core.studentrecord.exception.StudentRecordException;
 import com.edukit.core.studentrecord.service.enums.AITaskStatus;
@@ -20,6 +22,7 @@
 import lombok.RequiredArgsConstructor;
 import lombok.extern.slf4j.Slf4j;
 import org.springframework.boot.autoconfigure.condition.ConditionalOnBean;
+import org.springframework.context.ApplicationEventPublisher;
 import org.springframework.data.redis.connection.stream.Consumer;
 import org.springframework.data.redis.connection.stream.MapRecord;
 import org.springframework.data.redis.connection.stream.ReadOffset;
@@ -36,6 +39,7 @@ public class RedisStreamConsumer {
     private final ServerInstanceManager serverInstanceManager;
     private final SSEChannelManager sseChannelManager;
     private final ObjectMapper objectMapper;
+    private final ApplicationEventPublisher applicationEventPublisher;
 
     private static final String STREAM_KEY = "ai-response";
     private static final String CONSUMER_GROUP_PREFIX = "edukit-server-";
@@ -106,6 +110,13 @@ private void processMessage(final MapRecord<String, Object, Object> message) {
             String taskId = parseData(messageJson, "task_id");
             String status = parseData(messageJson, "status");
 
+            // 실패 상태 처리
+            if (AITaskStatus.isFailure(status)) {
+                AIErrorMessage errorMessage = objectMapper.readValue(messageJson, AIErrorMessage.class);
+                handleAITaskFailure(taskId, errorMessage);
+                return;
+            }
+
             if (sseChannelManager.hasActivateChannel(taskId)) {
                 if (AITaskStatus.isInProgress(status)) {
                     AIProgressMessage responseMessage = objectMapper.readValue(messageJson, AIProgressMessage.class);
@@ -127,6 +138,25 @@ private void processMessage(final MapRecord<String, Object, Object> message) {
         }
     }
 
+    private void handleAITaskFailure(final String taskId, final AIErrorMessage errorMessage) {
+        log.warn("AI task failed - taskId: {}, errorType: {}, message: {}",
+                taskId, errorMessage.errorType(), errorMessage.errorMessage());
+
+        // 보상 트랜잭션 이벤트 발행 (실패 시 예외를 상위로 전파하여 재처리)
+        applicationEventPublisher.publishEvent(
+                AITaskFailedEvent.fromErrorMessage(errorMessage)
+        );
+
+        // SSE로 실패 알림 전송 (실패해도 보상 로직에 영향 없음)
+        try {
+            if (sseChannelManager.hasActivateChannel(taskId)) {
+                sseChannelManager.sendErrorMessage(taskId, errorMessage);
+            }
+        } catch (Exception e) {
+            log.error("Failed to send SSE error message for taskId: {}, continuing with compensation", taskId, e);
+        }
+    }
+
     private String parseData(final String messageJson, final String target) {
         try {
             JsonNode node = objectMapper.readTree(messageJson);
diff --git a/edukit-core/src/main/java/com/edukit/core/studentrecord/service/SSEChannelManager.java b/edukit-core/src/main/java/com/edukit/core/studentrecord/service/SSEChannelManager.java
index 29572026..d5f1c77c 100644
--- a/edukit-core/src/main/java/com/edukit/core/studentrecord/service/SSEChannelManager.java
+++ b/edukit-core/src/main/java/com/edukit/core/studentrecord/service/SSEChannelManager.java
@@ -1,6 +1,7 @@
 package com.edukit.core.studentrecord.service;
 
 import com.edukit.common.infra.ServerInstanceManager;
+import com.edukit.core.event.ai.dto.AIErrorMessage;
 import com.edukit.core.event.ai.dto.AIProgressMessage;
 import com.edukit.core.event.ai.dto.AIResponseMessage;
 import com.edukit.core.event.ai.dto.SSEMessage;
@@ -107,6 +108,26 @@ public void sendProgressMessage(final String taskId, final AIProgressMessage aiP
         }
     }
 
+    public void sendErrorMessage(final String taskId, final AIErrorMessage errorMessage) {
+        SseEmitter emitter = activeChannels.get(taskId);
+        if (emitter != null) {
+            try {
+                SSEMessage sseMessage = SSEMessage.error(taskId, errorMessage.errorType(), errorMessage.errorMessage());
+                emitter.send(SseEmitter.event()
+                        .name(SSE_EVENT_NAME)
+                        .data(sseMessage));
+                log.info("Sent error message to SSE channel for taskId: {}", taskId);
+            } catch (IOException e) {
+                log.error("Failed to send error message to SSE channel for taskId: {}", taskId, e);
+            } finally {
+                // 에러 발생 시 채널 제거
+                removeChannel(taskId);
+            }
+        } else {
+            log.warn("No active SSE channel for taskId: {}, error message not sent", taskId);
+        }
+    }
+
     public void removeChannel(final String taskId) {
         SseEmitter emitter = activeChannels.remove(taskId);
         if (emitter != null) {
diff --git a/edukit-core/src/main/java/com/edukit/core/studentrecord/service/enums/AITaskStatus.java b/edukit-core/src/main/java/com/edukit/core/studentrecord/service/enums/AITaskStatus.java
index 6d21b91c..0a227972 100644
--- a/edukit-core/src/main/java/com/edukit/core/studentrecord/service/enums/AITaskStatus.java
+++ b/edukit-core/src/main/java/com/edukit/core/studentrecord/service/enums/AITaskStatus.java
@@ -12,7 +12,8 @@ public enum AITaskStatus {
     PHASE1_COMPLETED("PHASE1_COMPLETED", "생기부 초안 생성 완료.. - 다음 단계로 이동"),
     PHASE2_STARTED("PHASE2_STARTED", "금칙어 필터링 중.."),
     PHASE3_STARTED("PHASE3_STARTED", "바이트 수 최적화 중.."),
-    COMPLETED("COMPLETED", "생성 완료");
+    COMPLETED("COMPLETED", "생성 완료"),
+    FAILED("FAILED", "생성 실패 - 포인트가 복구됩니다");
 
     private final String status;
     private final String message;
@@ -25,6 +26,10 @@ public static AITaskStatus fromStatus(final String status) {
     }
 
     public static boolean isInProgress(final String currentStatus) {
-        return !COMPLETED.getStatus().equals(currentStatus);
+        return !COMPLETED.getStatus().equals(currentStatus) && !FAILED.getStatus().equals(currentStatus);
+    }
+
+    public static boolean isFailure(final String currentStatus) {
+        return FAILED.getStatus().equals(currentStatus);
     }
 }
diff --git a/edukit-external/src/main/java/com/edukit/external/redis/RedisStoreServiceImpl.java b/edukit-external/src/main/java/com/edukit/external/redis/RedisStoreServiceImpl.java
index b7e9cf9d..38797b8c 100644
--- a/edukit-external/src/main/java/com/edukit/external/redis/RedisStoreServiceImpl.java
+++ b/edukit-external/src/main/java/com/edukit/external/redis/RedisStoreServiceImpl.java
@@ -20,6 +20,10 @@ public String get(final String key) {
         return redisTemplate.opsForValue().get(key);
     }
 
+    public Boolean setIfAbsent(final String key, final String value, final Duration ttl) {
+        return redisTemplate.opsForValue().setIfAbsent(key, value, ttl);
+    }
+
     public void delete(final String key) {
         redisTemplate.delete(key);
     }