diff --git a/src/main/kotlin/com/weeth/domain/file/application/dto/request/FileSaveRequest.kt b/src/main/kotlin/com/weeth/domain/file/application/dto/request/FileSaveRequest.kt
index 93cf515a..5dba7f8b 100644
--- a/src/main/kotlin/com/weeth/domain/file/application/dto/request/FileSaveRequest.kt
+++ b/src/main/kotlin/com/weeth/domain/file/application/dto/request/FileSaveRequest.kt
@@ -17,7 +17,13 @@ data class FileSaveRequest(
     @field:Schema(description = "파일 크기(bytes)", example = "102400")
     @field:Positive
     val fileSize: Long,
-    @field:Schema(description = "파일 Content-Type. `image/png, image/jpeg, application/pdf` 지원", example = "image/png")
+    @field:Schema(
+        description =
+            "파일 Content-Type. `image/png`, `image/jpeg`, `image/webp`, `application/pdf`, " +
+                "`application/vnd.openxmlformats-officedocument.presentationml.presentation`(pptx), " +
+                "`application/vnd.openxmlformats-officedocument.wordprocessingml.document`(docx) 지원",
+        example = "image/png",
+    )
     @field:NotBlank
     val contentType: String,
 )
diff --git a/src/main/kotlin/com/weeth/domain/file/domain/vo/FileType.kt b/src/main/kotlin/com/weeth/domain/file/domain/vo/FileType.kt
index e2e2f025..2d11a9c3 100644
--- a/src/main/kotlin/com/weeth/domain/file/domain/vo/FileType.kt
+++ b/src/main/kotlin/com/weeth/domain/file/domain/vo/FileType.kt
@@ -8,6 +8,17 @@ enum class FileType(
     PNG("image/png", setOf("png")),
     WEBP("image/webp", setOf("webp")),
     PDF("application/pdf", setOf("pdf")),
+
+    // V3 마이그레이션 대상에 세션 자료(pptx 27건)와 문서(docx 2건)가 포함되어 추가했다.
+    // svg는 XML이라 <script>를 품을 수 있어 인라인 서빙 시 XSS 벡터가 되므로 허용하지 않는다.
+    PPTX(
+        "application/vnd.openxmlformats-officedocument.presentationml.presentation",
+        setOf("pptx"),
+    ),
+    DOCX(
+        "application/vnd.openxmlformats-officedocument.wordprocessingml.document",
+        setOf("docx"),
+    ),
     ;
 
     companion object {
diff --git a/src/main/kotlin/com/weeth/domain/schedule/application/dto/request/ScheduleSaveRequest.kt b/src/main/kotlin/com/weeth/domain/schedule/application/dto/request/ScheduleSaveRequest.kt
index d32c6b91..91fa4066 100644
--- a/src/main/kotlin/com/weeth/domain/schedule/application/dto/request/ScheduleSaveRequest.kt
+++ b/src/main/kotlin/com/weeth/domain/schedule/application/dto/request/ScheduleSaveRequest.kt
@@ -12,7 +12,7 @@ data class ScheduleSaveRequest(
     @field:NotBlank
     val title: String,
     @field:Schema(description = "일정 내용", example = "1박 2일 MT입니다.")
-    @field:Size(max = 500)
+    @field:Size(max = 1000)
     val content: String? = null,
     @field:Schema(description = "장소", example = "가평")
     val location: String? = null,
diff --git a/src/main/kotlin/com/weeth/domain/schedule/application/dto/request/ScheduleUpdateRequest.kt b/src/main/kotlin/com/weeth/domain/schedule/application/dto/request/ScheduleUpdateRequest.kt
index 93c6799b..0e9aee3b 100644
--- a/src/main/kotlin/com/weeth/domain/schedule/application/dto/request/ScheduleUpdateRequest.kt
+++ b/src/main/kotlin/com/weeth/domain/schedule/application/dto/request/ScheduleUpdateRequest.kt
@@ -8,7 +8,7 @@ data class ScheduleUpdateRequest(
     @field:Schema(description = "일정 제목 (null=변경 안 함)", example = "MT")
     val title: String?,
     @field:Schema(description = "일정 내용 (null=변경 안 함)", example = "1박 2일 MT입니다.")
-    @field:Size(max = 500)
+    @field:Size(max = 1000)
     val content: String?,
     @field:Schema(description = "장소 (null=변경 안 함)", example = "가평")
     val location: String?,
diff --git a/src/main/kotlin/com/weeth/domain/schedule/domain/entity/Event.kt b/src/main/kotlin/com/weeth/domain/schedule/domain/entity/Event.kt
index 7d2c05f9..c98895af 100644
--- a/src/main/kotlin/com/weeth/domain/schedule/domain/entity/Event.kt
+++ b/src/main/kotlin/com/weeth/domain/schedule/domain/entity/Event.kt
@@ -17,7 +17,7 @@ import java.time.LocalDateTime
 class Event(
     club: Club,
     var title: String,
-    @Column(length = 500)
+    @Column(columnDefinition = "TEXT")
     var content: String? = null,
     var location: String? = null,
     var cardinal: Int,
diff --git a/src/main/kotlin/com/weeth/domain/session/application/dto/request/SessionCreateRequest.kt b/src/main/kotlin/com/weeth/domain/session/application/dto/request/SessionCreateRequest.kt
index 3acb49a1..aae9578b 100644
--- a/src/main/kotlin/com/weeth/domain/session/application/dto/request/SessionCreateRequest.kt
+++ b/src/main/kotlin/com/weeth/domain/session/application/dto/request/SessionCreateRequest.kt
@@ -12,7 +12,7 @@ data class SessionCreateRequest(
     @field:NotBlank
     val title: String,
     @field:Schema(description = "세션 내용", example = "OT 및 자기소개")
-    @field:Size(max = 500)
+    @field:Size(max = 1000)
     val content: String?,
     @field:Schema(description = "모임 장소", example = "공학관 401호")
     val location: String?,
diff --git a/src/main/kotlin/com/weeth/domain/session/application/dto/request/SessionUpdateRequest.kt b/src/main/kotlin/com/weeth/domain/session/application/dto/request/SessionUpdateRequest.kt
index 9c14f0ee..414652c3 100644
--- a/src/main/kotlin/com/weeth/domain/session/application/dto/request/SessionUpdateRequest.kt
+++ b/src/main/kotlin/com/weeth/domain/session/application/dto/request/SessionUpdateRequest.kt
@@ -8,7 +8,7 @@ data class SessionUpdateRequest(
     @field:Schema(description = "세션 제목 (null=변경 안 함)", example = "1차 정기모임")
     val title: String?,
     @field:Schema(description = "세션 내용 (null=변경 안 함)", example = "OT 및 자기소개")
-    @field:Size(max = 500)
+    @field:Size(max = 1000)
     val content: String?,
     @field:Schema(description = "모임 장소 (null=변경 안 함)", example = "공학관 401호")
     val location: String?,
diff --git a/src/main/kotlin/com/weeth/domain/session/domain/entity/Session.kt b/src/main/kotlin/com/weeth/domain/session/domain/entity/Session.kt
index 4df5bfd0..0a71cd67 100644
--- a/src/main/kotlin/com/weeth/domain/session/domain/entity/Session.kt
+++ b/src/main/kotlin/com/weeth/domain/session/domain/entity/Session.kt
@@ -56,7 +56,7 @@ class Session(
     var title: String = title
         private set
 
-    @Column(length = 500)
+    @Column(columnDefinition = "TEXT")
     var content: String? = content
         private set
 
diff --git a/src/main/resources/db/migration/V12__add_club_warning_and_penalty_rule.sql b/src/main/resources/db/migration/V12__add_club_warning_and_penalty_rule.sql
new file mode 100644
index 00000000..c1fa3759
--- /dev/null
+++ b/src/main/resources/db/migration/V12__add_club_warning_and_penalty_rule.sql
@@ -0,0 +1,9 @@
+ALTER TABLE club
+    ADD COLUMN warning_enabled BOOLEAN NOT NULL DEFAULT FALSE,
+    ADD COLUMN penalty_rule    VARCHAR(500);
+
+ALTER TABLE club_member
+    ADD COLUMN warning_count INT NOT NULL DEFAULT 0;
+
+ALTER TABLE penalty
+    ADD COLUMN score INT NOT NULL DEFAULT 1;
diff --git a/src/main/resources/db/migration/V13__add_user_privacy_settings.sql b/src/main/resources/db/migration/V13__add_user_privacy_settings.sql
new file mode 100644
index 00000000..05d228f9
--- /dev/null
+++ b/src/main/resources/db/migration/V13__add_user_privacy_settings.sql
@@ -0,0 +1,4 @@
+ALTER TABLE users
+    ADD COLUMN tel_public       TINYINT(1) NOT NULL DEFAULT 1,
+    ADD COLUMN email_public     TINYINT(1) NOT NULL DEFAULT 1,
+    ADD COLUMN student_info_public TINYINT(1) NOT NULL DEFAULT 1;
diff --git a/src/main/resources/db/migration/V14__fix_penalty_type_column.sql b/src/main/resources/db/migration/V14__fix_penalty_type_column.sql
new file mode 100644
index 00000000..e986a563
--- /dev/null
+++ b/src/main/resources/db/migration/V14__fix_penalty_type_column.sql
@@ -0,0 +1,2 @@
+ALTER TABLE penalty
+    MODIFY COLUMN penalty_type ENUM ('PENALTY', 'WARNING') NOT NULL DEFAULT 'PENALTY';
diff --git a/src/main/resources/db/migration/V15__alter_event_session_content_to_text.sql b/src/main/resources/db/migration/V15__alter_event_session_content_to_text.sql
new file mode 100644
index 00000000..aeb091bb
--- /dev/null
+++ b/src/main/resources/db/migration/V15__alter_event_session_content_to_text.sql
@@ -0,0 +1,7 @@
+-- V3 마이그레이션 대상 데이터의 event.content 최대 길이가 632자로 varchar(500) 한도를 초과한다.
+-- session.content(최대 431자)도 여유가 적어 함께 TEXT로 통일한다.
+ALTER TABLE event
+    MODIFY COLUMN content TEXT;
+
+ALTER TABLE session
+    MODIFY COLUMN content TEXT;
diff --git a/src/test/kotlin/com/weeth/domain/file/domain/vo/FileTypeTest.kt b/src/test/kotlin/com/weeth/domain/file/domain/vo/FileTypeTest.kt
index 8c376512..d7f8f970 100644
--- a/src/test/kotlin/com/weeth/domain/file/domain/vo/FileTypeTest.kt
+++ b/src/test/kotlin/com/weeth/domain/file/domain/vo/FileTypeTest.kt
@@ -16,5 +16,23 @@ class FileTypeTest :
                 FileType.fromExtension("jpeg") shouldBe FileType.JPEG
                 FileType.fromExtension("webp") shouldBe FileType.WEBP
             }
+
+            it("문서 타입을 조회한다") {
+                FileType.fromExtension("pptx") shouldBe FileType.PPTX
+                FileType.fromExtension("docx") shouldBe FileType.DOCX
+                FileType.fromContentType(
+                    "application/vnd.openxmlformats-officedocument.presentationml.presentation",
+                ) shouldBe FileType.PPTX
+                FileType.fromContentType(
+                    "application/vnd.openxmlformats-officedocument.wordprocessingml.document",
+                ) shouldBe FileType.DOCX
+            }
+
+            it("허용 목록 밖의 타입은 null을 반환한다") {
+                // svg는 XML이라 스크립트 삽입이 가능해 의도적으로 제외한다
+                FileType.fromExtension("svg") shouldBe null
+                FileType.fromContentType("image/svg+xml") shouldBe null
+                FileType.fromExtension("mp4") shouldBe null
+            }
         }
     })