diff --git a/src/main/kotlin/kr/co/vividnext/sodalive/chat/room/ChatMessage.kt b/src/main/kotlin/kr/co/vividnext/sodalive/chat/room/ChatMessage.kt
index 1013a3e..fb1c35e 100644
--- a/src/main/kotlin/kr/co/vividnext/sodalive/chat/room/ChatMessage.kt
+++ b/src/main/kotlin/kr/co/vividnext/sodalive/chat/room/ChatMessage.kt
@@ -1,14 +1,18 @@
 package kr.co.vividnext.sodalive.chat.room
 
+import kr.co.vividnext.sodalive.chat.character.image.CharacterImage
 import kr.co.vividnext.sodalive.common.BaseEntity
 import javax.persistence.Column
 import javax.persistence.Entity
+import javax.persistence.EnumType
+import javax.persistence.Enumerated
 import javax.persistence.FetchType
 import javax.persistence.JoinColumn
 import javax.persistence.ManyToOne
 
 @Entity
 class ChatMessage(
+    // 텍스트 메시지 본문. 현재는 NOT NULL 유지. IMAGE 타입 등 비텍스트 메시지는 빈 문자열("") 저장 방침.
     @Column(columnDefinition = "TEXT", nullable = false)
     val message: String,
 
@@ -20,5 +24,23 @@ class ChatMessage(
     @JoinColumn(name = "participant_id", nullable = false)
     val participant: ChatParticipant,
 
-    val isActive: Boolean = true
+    val isActive: Boolean = true,
+
+    @Enumerated(EnumType.STRING)
+    @Column(name = "message_type", nullable = false)
+    val messageType: ChatMessageType = ChatMessageType.TEXT,
+
+    // 미리 저장된 캐릭터 이미지 참조 (옵션)
+    @ManyToOne(fetch = FetchType.LAZY)
+    @JoinColumn(name = "character_image_id", nullable = true)
+    val characterImage: CharacterImage? = null,
+
+    // 이미지 정적 경로 스냅샷 (옵션)
+    @Column(name = "image_path", nullable = true, length = 1024)
+    val imagePath: String? = null,
+
+    // 메시지 가격 (옵션). 제공되는 경우 1 이상이어야 함.
+    // Bean Validation 사용 시 @field:Min(1) 추가 고려.
+    @Column(name = "price", nullable = true)
+    val price: Int? = null
 ) : BaseEntity()
diff --git a/src/main/kotlin/kr/co/vividnext/sodalive/chat/room/ChatMessageType.kt b/src/main/kotlin/kr/co/vividnext/sodalive/chat/room/ChatMessageType.kt
new file mode 100644
index 0000000..0a1756a
--- /dev/null
+++ b/src/main/kotlin/kr/co/vividnext/sodalive/chat/room/ChatMessageType.kt
@@ -0,0 +1,13 @@
+package kr.co.vividnext.sodalive.chat.room
+
+/**
+ * 채팅 메시지 타입
+ * - TEXT: 일반 텍스트 메시지
+ * - IMAGE: 이미지 메시지(캐릭터 이미지 등)
+ *
+ * 유의: 유료 여부는 별도 price 필드로 표현합니다.
+ */
+enum class ChatMessageType {
+    TEXT,
+    IMAGE
+}
diff --git a/src/main/kotlin/kr/co/vividnext/sodalive/chat/room/dto/ChatRoomDto.kt b/src/main/kotlin/kr/co/vividnext/sodalive/chat/room/dto/ChatRoomDto.kt
index e7691b6..267e67f 100644
--- a/src/main/kotlin/kr/co/vividnext/sodalive/chat/room/dto/ChatRoomDto.kt
+++ b/src/main/kotlin/kr/co/vividnext/sodalive/chat/room/dto/ChatRoomDto.kt
@@ -39,7 +39,11 @@ data class ChatMessageItemDto(
     val message: String,
     val profileImageUrl: String,
     val mine: Boolean,
-    val createdAt: Long
+    val createdAt: Long,
+    val messageType: String,
+    val imageUrl: String?,
+    val price: Int?,
+    val hasAccess: Boolean
 )
 
 /**
diff --git a/src/main/kotlin/kr/co/vividnext/sodalive/chat/room/service/ChatRoomService.kt b/src/main/kotlin/kr/co/vividnext/sodalive/chat/room/service/ChatRoomService.kt
index 04c9582..2521107 100644
--- a/src/main/kotlin/kr/co/vividnext/sodalive/chat/room/service/ChatRoomService.kt
+++ b/src/main/kotlin/kr/co/vividnext/sodalive/chat/room/service/ChatRoomService.kt
@@ -1,8 +1,11 @@
 package kr.co.vividnext.sodalive.chat.room.service
 
 import com.fasterxml.jackson.databind.ObjectMapper
+import kr.co.vividnext.sodalive.chat.character.image.CharacterImage
+import kr.co.vividnext.sodalive.chat.character.image.CharacterImageService
 import kr.co.vividnext.sodalive.chat.character.service.ChatCharacterService
 import kr.co.vividnext.sodalive.chat.room.ChatMessage
+import kr.co.vividnext.sodalive.chat.room.ChatMessageType
 import kr.co.vividnext.sodalive.chat.room.ChatParticipant
 import kr.co.vividnext.sodalive.chat.room.ChatRoom
 import kr.co.vividnext.sodalive.chat.room.ParticipantType
@@ -34,6 +37,7 @@ import org.springframework.transaction.annotation.Transactional
 import org.springframework.web.client.RestTemplate
 import java.time.Duration
 import java.time.LocalDateTime
+import java.time.ZoneId
 import java.util.UUID
 
 @Service
@@ -42,6 +46,7 @@ class ChatRoomService(
     private val participantRepository: ChatParticipantRepository,
     private val messageRepository: ChatMessageRepository,
     private val characterService: ChatCharacterService,
+    private val characterImageService: CharacterImageService,
 
     @Value("\${weraser.api-key}")
     private val apiKey: String,
@@ -293,14 +298,31 @@ class ChatRoomService(
                 ParticipantType.CHARACTER -> sender.character?.imagePath
             }
             val senderImageUrl = "$imageHost/${profilePath ?: "profile/default-profile.png"}"
-            val createdAtMillis = msg.createdAt?.atZone(java.time.ZoneId.systemDefault())?.toInstant()?.toEpochMilli()
+            val createdAtMillis = msg.createdAt?.atZone(ZoneId.systemDefault())?.toInstant()?.toEpochMilli()
                 ?: 0L
             ChatMessageItemDto(
                 messageId = msg.id!!,
                 message = msg.message,
                 profileImageUrl = senderImageUrl,
                 mine = sender.member?.id == member.id,
-                createdAt = createdAtMillis
+                createdAt = createdAtMillis,
+                messageType = msg.messageType.name,
+                imageUrl = msg.imagePath?.let { "$imageHost/$it" },
+                price = msg.price,
+                hasAccess = if (msg.messageType == ChatMessageType.IMAGE) {
+                    if (msg.price == null) {
+                        true
+                    } else {
+                        msg.characterImage?.id?.let {
+                            characterImageService.isOwnedImageByMember(
+                                it,
+                                member.id!!
+                            )
+                        } ?: true
+                    }
+                } else {
+                    true
+                }
             )
         }
 
@@ -455,15 +477,32 @@ class ChatRoomService(
                 ParticipantType.USER -> sender.member?.profileImage
                 ParticipantType.CHARACTER -> sender.character?.imagePath
             }
-            val imageUrl = "$imageHost/${profilePath ?: "profile/default-profile.png"}"
-            val createdAtMillis = msg.createdAt?.atZone(java.time.ZoneId.systemDefault())?.toInstant()?.toEpochMilli()
+            val senderImageUrl = "$imageHost/${profilePath ?: "profile/default-profile.png"}"
+            val createdAtMillis = msg.createdAt?.atZone(ZoneId.systemDefault())?.toInstant()?.toEpochMilli()
                 ?: 0L
             ChatMessageItemDto(
                 messageId = msg.id!!,
                 message = msg.message,
-                profileImageUrl = imageUrl,
+                profileImageUrl = senderImageUrl,
                 mine = sender.member?.id == member.id,
-                createdAt = createdAtMillis
+                createdAt = createdAtMillis,
+                messageType = msg.messageType.name,
+                imageUrl = msg.imagePath?.let { "$imageHost/$it" },
+                price = msg.price,
+                hasAccess = if (msg.messageType == ChatMessageType.IMAGE) {
+                    if (msg.price == null) {
+                        true
+                    } else {
+                        msg.characterImage?.id?.let {
+                            characterImageService.isOwnedImageByMember(
+                                it,
+                                member.id!!
+                            )
+                        } ?: true
+                    }
+                } else {
+                    true
+                }
             )
         }
 
@@ -509,30 +548,77 @@ class ChatRoomService(
         )
         messageRepository.save(myMsgEntity)
 
-        // 7) 캐릭터 메시지 저장
-        val characterMsgEntity = ChatMessage(
-            message = characterReply,
-            chatRoom = room,
-            participant = characterParticipant,
-            isActive = true
+        // 7) 캐릭터 텍스트 메시지 항상 저장
+        val characterTextMsg = messageRepository.save(
+            ChatMessage(
+                message = characterReply,
+                chatRoom = room,
+                participant = characterParticipant,
+                isActive = true
+            )
         )
-        val savedCharacterMsg = messageRepository.save(characterMsgEntity)
 
-        // 8) 응답 DTO 구성 (캐릭터 메시지 리스트 반환 - 단일 요소)
+        // 응답 프로필 이미지 URL 공통 구성
         val profilePath = characterParticipant.character?.imagePath
         val defaultPath = profilePath ?: "profile/default-profile.png"
-        val imageUrl = "$imageHost/$defaultPath"
-        val dto = ChatMessageItemDto(
-            messageId = savedCharacterMsg.id!!,
-            message = savedCharacterMsg.message,
-            profileImageUrl = imageUrl,
+        val senderImageUrl = "$imageHost/$defaultPath"
+
+        val textDto = ChatMessageItemDto(
+            messageId = characterTextMsg.id!!,
+            message = characterTextMsg.message,
+            profileImageUrl = senderImageUrl,
             mine = false,
-            createdAt = savedCharacterMsg.createdAt?.atZone(java.time.ZoneId.systemDefault())?.toInstant()
+            createdAt = characterTextMsg.createdAt?.atZone(ZoneId.systemDefault())?.toInstant()
                 ?.toEpochMilli()
-                ?: 0L
+                ?: 0L,
+            messageType = ChatMessageType.TEXT.name,
+            imageUrl = null,
+            price = null,
+            hasAccess = true
         )
 
-        return listOf(dto)
+        // 8) 트리거 매칭 → 이미지 메시지 추가 저장(있을 경우)
+        val matchedImage = findTriggeredCharacterImage(character.id!!, characterReply)
+        if (matchedImage != null) {
+            val owned = characterImageService.isOwnedImageByMember(matchedImage.id!!, member.id!!)
+            val priceInt: Int? = if (owned) {
+                null
+            } else {
+                val p = matchedImage.messagePriceCan
+                if (p <= 0L) null else if (p > Int.MAX_VALUE) Int.MAX_VALUE else p.toInt()
+            }
+            // 보유하지 않은 경우 블러 이미지로 전송
+            val snapshotPath = if (owned) matchedImage.imagePath else matchedImage.blurImagePath
+            val imageMsg = messageRepository.save(
+                ChatMessage(
+                    message = "",
+                    chatRoom = room,
+                    participant = characterParticipant,
+                    isActive = true,
+                    messageType = ChatMessageType.IMAGE,
+                    characterImage = matchedImage,
+                    imagePath = snapshotPath,
+                    price = priceInt
+                )
+            )
+
+            val imageDto = ChatMessageItemDto(
+                messageId = imageMsg.id!!,
+                message = imageMsg.message,
+                profileImageUrl = senderImageUrl,
+                mine = false,
+                createdAt = imageMsg.createdAt?.atZone(ZoneId.systemDefault())?.toInstant()
+                    ?.toEpochMilli()
+                    ?: 0L,
+                messageType = ChatMessageType.IMAGE.name,
+                imageUrl = imageMsg.imagePath?.let { "$imageHost/$it" },
+                price = imageMsg.price,
+                hasAccess = owned || imageMsg.price == null
+            )
+            return listOf(textDto, imageDto)
+        }
+
+        return listOf(textDto)
     }
 
     private fun callExternalApiForChatSendWithRetry(
@@ -603,4 +689,18 @@ class ChatRoomService(
         }
         return characterContent
     }
+
+    private fun findTriggeredCharacterImage(characterId: Long, replyText: String): CharacterImage? {
+        val text = replyText.lowercase()
+        val images: List<CharacterImage> = characterImageService.listActiveByCharacter(characterId)
+        for (img in images) {
+            val triggers = img.triggerMappings
+                .map { it.tag.word.trim().lowercase() }
+                .filter { it.isNotBlank() }
+            if (triggers.isEmpty()) continue
+            val allIncluded = triggers.all { t -> text.contains(t) }
+            if (allIncluded) return img
+        }
+        return null
+    }
 }