diff --git a/backend/package-lock.json b/backend/package-lock.json
index 61e7d89..d834814 100644
--- a/backend/package-lock.json
+++ b/backend/package-lock.json
@@ -31,11 +31,13 @@
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         "helmet": "^8.1.0",
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         "passport-jwt": "^4.0.1",
         "passport-kakao": "^1.0.1",
+        "pdf-parse": "^2.4.5",
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         "reflect-metadata": "^0.2.2",
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+      "resolved": "https://registry.npmjs.org/@napi-rs/canvas-win32-x64-msvc/-/canvas-win32-x64-msvc-0.1.80.tgz",
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+      "optional": true,
+      "os": [
+        "win32"
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       "version": "2.1.1",
@@ -11605,7 +11897,6 @@
       "resolved": "https://registry.npmjs.org/rxjs/-/rxjs-7.8.2.tgz",
       "integrity": "sha512-dhKf903U/PQZY6boNNtAGdWbG85WAbjT/1xYoZIC7FAY0yWapOBQVsVrDl58W86//e1VpMNBtRV4MaXfdMySFA==",
       "license": "Apache-2.0",
-      "peer": true,
       "dependencies": {
         "tslib": "^2.1.0"
       }
@@ -11791,6 +12082,12 @@
         "node": ">= 0.4"
       }
     },
+    "node_modules/setimmediate": {
+      "version": "1.0.5",
+      "resolved": "https://registry.npmjs.org/setimmediate/-/setimmediate-1.0.5.tgz",
+      "integrity": "sha512-MATJdZp8sLqDl/68LfQmbP8zKPLQNV6BIZoIgrscFDQ+RsvK/BxeDQOgyxKKoh0y/8h3BqVFnCqQ/gd+reiIXA==",
+      "license": "MIT"
+    },
     "node_modules/setprototypeof": {
       "version": "1.2.0",
       "resolved": "https://registry.npmjs.org/setprototypeof/-/setprototypeof-1.2.0.tgz",
@@ -12012,7 +12309,6 @@
       "version": "1.0.3",
       "resolved": "https://registry.npmjs.org/sprintf-js/-/sprintf-js-1.0.3.tgz",
       "integrity": "sha512-D9cPgkvLlV3t3IzL0D0YLvGA9Ahk4PcvVwUbN0dSGr1aP0Nrt4AEnTUbuGvquEC0mA64Gqt1fzirlRs5ibXx8g==",
-      "dev": true,
       "license": "BSD-3-Clause"
     },
     "node_modules/sql-highlight": {
@@ -12434,7 +12730,6 @@
       "integrity": "sha512-Thbli+OlOj+iMPYFBVBfJ3OmCAnaSyNn4M1vz9T6Gka5Jt9ba/HIR56joy65tY6kx/FCF5VXNB819Y7/GUrBGA==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "fast-deep-equal": "^3.1.3",
         "fast-uri": "^3.0.1",
@@ -12811,7 +13106,6 @@
       "integrity": "sha512-f0FFpIdcHgn8zcPSbf1dRevwt047YMnaiJM3u2w2RewrB+fob/zePZcrOyQoLMMO7aBIddLcQIEK5dYjkLnGrQ==",
       "devOptional": true,
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "@cspotcode/source-map-support": "^0.8.0",
         "@tsconfig/node10": "^1.0.7",
@@ -12971,7 +13265,6 @@
       "resolved": "https://registry.npmjs.org/typeorm/-/typeorm-0.3.28.tgz",
       "integrity": "sha512-6GH7wXhtfq2D33ZuRXYwIsl/qM5685WZcODZb7noOOcRMteM9KF2x2ap3H0EBjnSV0VO4gNAfJT5Ukp0PkOlvg==",
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "@sqltools/formatter": "^1.2.5",
         "ansis": "^4.2.0",
@@ -13178,7 +13471,6 @@
       "integrity": "sha512-jl1vZzPDinLr9eUt3J/t7V6FgNEw9QjvBPdysz9KfQDD41fQrC2Y4vKQdiaUpFT4bXlb1RHhLpp8wtm6M5TgSw==",
       "devOptional": true,
       "license": "Apache-2.0",
-      "peer": true,
       "bin": {
         "tsc": "bin/tsc",
         "tsserver": "bin/tsserver"
@@ -13266,6 +13558,12 @@
         "through": "^2.3.8"
       }
     },
+    "node_modules/underscore": {
+      "version": "1.13.8",
+      "resolved": "https://registry.npmjs.org/underscore/-/underscore-1.13.8.tgz",
+      "integrity": "sha512-DXtD3ZtEQzc7M8m4cXotyHR+FAS18C64asBYY5vqZexfYryNNnDc02W4hKg3rdQuqOYas1jkseX0+nZXjTXnvQ==",
+      "license": "MIT"
+    },
     "node_modules/undici-types": {
       "version": "6.21.0",
       "resolved": "https://registry.npmjs.org/undici-types/-/undici-types-6.21.0.tgz",
@@ -13582,6 +13880,7 @@
       "integrity": "sha512-Wx0Kx52hxE7C18hkMEggYlEifqWZtYaRgouJor+WMdPnQyEK13vgEWyVNup7SoeeoLMsr4kf5h6dOW11I15MUA==",
       "dev": true,
       "license": "MIT",
+      "peer": true,
       "dependencies": {
         "ajv": "^8.0.0"
       },
@@ -13600,6 +13899,7 @@
       "integrity": "sha512-YCS/JNFAUyr5vAuhk1DWm1CBxRHW9LbJ2ozWeemrIqpbsqKjHVxYPyi5GC0rjZIT5JxJ3virVTS8wk4i/Z+krw==",
       "dev": true,
       "license": "MIT",
+      "peer": true,
       "dependencies": {
         "fast-deep-equal": "^3.1.3"
       },
@@ -13613,6 +13913,7 @@
       "integrity": "sha512-2NxwbF/hZ0KpepYN0cNbo+FN6XoK7GaHlQhgx/hIZl6Va0bF45RQOOwhLIy8lQDbuCiadSLCBnH2CFYquit5bw==",
       "dev": true,
       "license": "BSD-2-Clause",
+      "peer": true,
       "dependencies": {
         "esrecurse": "^4.3.0",
         "estraverse": "^4.1.1"
@@ -13627,6 +13928,7 @@
       "integrity": "sha512-39nnKffWz8xN1BU/2c79n9nB9HDzo0niYUqx6xyqUnyoAnQyyWpOTdZEeiCch8BBu515t4wp9ZmgVfVhn9EBpw==",
       "dev": true,
       "license": "BSD-2-Clause",
+      "peer": true,
       "engines": {
         "node": ">=4.0"
       }
@@ -13636,7 +13938,8 @@
       "resolved": "https://registry.npmjs.org/json-schema-traverse/-/json-schema-traverse-1.0.0.tgz",
       "integrity": "sha512-NM8/P9n3XjXhIZn1lLhkFaACTOURQXjWhV4BA/RnOv8xvgqtqpAX9IO4mRQxSx1Rlo4tqzeqb0sOlruaOy3dug==",
       "dev": true,
-      "license": "MIT"
+      "license": "MIT",
+      "peer": true
     },
     "node_modules/webpack/node_modules/schema-utils": {
       "version": "4.3.3",
@@ -13644,6 +13947,7 @@
       "integrity": "sha512-eflK8wEtyOE6+hsaRVPxvUKYCpRgzLqDTb8krvAsRIwOGlHoSgYLgBXoubGgLd2fT41/OUYdb48v4k4WWHQurA==",
       "dev": true,
       "license": "MIT",
+      "peer": true,
       "dependencies": {
         "@types/json-schema": "^7.0.9",
         "ajv": "^8.9.0",
@@ -13717,7 +14021,6 @@
       "resolved": "https://registry.npmjs.org/winston/-/winston-3.19.0.tgz",
       "integrity": "sha512-LZNJgPzfKR+/J3cHkxcpHKpKKvGfDZVPS4hfJCc4cCG0CgYzvlD6yE/S3CIL/Yt91ak327YCpiF/0MyeZHEHKA==",
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "@colors/colors": "^1.6.0",
         "@dabh/diagnostics": "^2.0.8",
@@ -13840,6 +14143,15 @@
         "node": "^14.17.0 || ^16.13.0 || >=18.0.0"
       }
     },
+    "node_modules/xmlbuilder": {
+      "version": "10.1.1",
+      "resolved": "https://registry.npmjs.org/xmlbuilder/-/xmlbuilder-10.1.1.tgz",
+      "integrity": "sha512-OyzrcFLL/nb6fMGHbiRDuPup9ljBycsdCypwuyg5AAHvyWzGfChJpCXMG88AGTIMFhGZ9RccFN1e6lhg3hkwKg==",
+      "license": "MIT",
+      "engines": {
+        "node": ">=4.0"
+      }
+    },
     "node_modules/xtend": {
       "version": "4.0.2",
       "resolved": "https://registry.npmjs.org/xtend/-/xtend-4.0.2.tgz",
diff --git a/backend/package.json b/backend/package.json
index 0ba549d..1d1decc 100644
--- a/backend/package.json
+++ b/backend/package.json
@@ -47,11 +47,13 @@
     "express-rate-limit": "^8.3.2",
     "helmet": "^8.1.0",
     "ioredis": "^5.11.1",
+    "mammoth": "^1.12.0",
     "nest-winston": "^1.10.0",
     "passport": "^0.7.0",
     "passport-google-oauth20": "^2.0.0",
     "passport-jwt": "^4.0.1",
     "passport-kakao": "^1.0.1",
+    "pdf-parse": "^2.4.5",
     "pg": "^8.20.0",
     "reflect-metadata": "^0.2.2",
     "rxjs": "^7.8.1",
diff --git a/backend/src/migrations/1782600000000-AddProjectAttachmentExtractedText.ts b/backend/src/migrations/1782600000000-AddProjectAttachmentExtractedText.ts
new file mode 100644
index 0000000..172401d
--- /dev/null
+++ b/backend/src/migrations/1782600000000-AddProjectAttachmentExtractedText.ts
@@ -0,0 +1,20 @@
+import { MigrationInterface, QueryRunner } from 'typeorm';
+
+// 프로젝트 첨부 문서의 추출 본문 캐시 컬럼 추가.
+// 업로드 시 1회 추출해 보관하고, AI 업무 추천에서 꺼내 읽는다.
+// 운영(migrationsRun)에서만 실행되며, dev 는 synchronize 로 자동 반영된다.
+export class AddProjectAttachmentExtractedText1782600000000 implements MigrationInterface {
+  name = 'AddProjectAttachmentExtractedText1782600000000';
+
+  public async up(queryRunner: QueryRunner): Promise<void> {
+    await queryRunner.query(
+      `ALTER TABLE "project_attachments" ADD "extracted_text" text`,
+    );
+  }
+
+  public async down(queryRunner: QueryRunner): Promise<void> {
+    await queryRunner.query(
+      `ALTER TABLE "project_attachments" DROP COLUMN "extracted_text"`,
+    );
+  }
+}
diff --git a/backend/src/modules/ai/ai.service.ts b/backend/src/modules/ai/ai.service.ts
index 92ebf44..de4ddc6 100644
--- a/backend/src/modules/ai/ai.service.ts
+++ b/backend/src/modules/ai/ai.service.ts
@@ -88,6 +88,7 @@ const SUGGEST_SYSTEM_PROMPT = [
   '- 각 카테고리에 필요한 항목을 충분히 제안하세요. 항목 수에 제한은 없습니다. 적합한 항목이 없으면 빈 배열([])로 두세요.',
   '- 각 항목은 한국어로 간결한 한 문장(체크리스트 항목)으로 작성합니다.',
   '- 업무·프로젝트 맥락에 구체적으로 맞추고 일반론은 피하세요.',
+  '- [프로젝트 문서] 섹션이 주어지면(첨부 문서에서 추출한 내용) 그 내용을 적극 반영해 더 구체적으로 제안하세요.',
   '',
   '[형식]',
   '{"groups":[{"category":"필수 기능","items":["..."]},{"category":"관리 기능","items":["..."]},{"category":"보안 기능","items":["..."]},{"category":"부가 기능","items":["..."]}]}',
@@ -199,9 +200,16 @@ export class AiService {
     // 프로젝트 정보(이름/설명) — 인증 사용자면 열람 가능. 없으면 404.
     const project = await this.projectService.findOne(input.projectId, userId);
     const content = (input.content ?? []).join('\n').trim() || '(없음)';
+    // 프로젝트 첨부 문서의 캐싱된 추출 본문(업로드 시 보관) — 있으면 추천에 반영
+    const docsText = await this.projectService.getAttachmentsTextForAi(
+      input.projectId,
+    );
     const userMsg = [
       `[프로젝트] 표시 제목: ${project.name}`,
       `설명: ${project.description ?? '(없음)'}`,
+      ...(docsText
+        ? ['', '[프로젝트 문서] (첨부 문서에서 추출한 내용)', docsText]
+        : []),
       '',
       `[업무] 제목: ${input.title}`,
       '내용:',
diff --git a/backend/src/modules/project/entities/project-attachment.entity.ts b/backend/src/modules/project/entities/project-attachment.entity.ts
index 9bc1b1f..2404f79 100644
--- a/backend/src/modules/project/entities/project-attachment.entity.ts
+++ b/backend/src/modules/project/entities/project-attachment.entity.ts
@@ -50,6 +50,16 @@ export class ProjectAttachment {
   @Column({ type: 'varchar' })
   kind!: AttachmentKind;
 
+  // AI 추천용 추출 본문 — 업로드 시 1회 추출·캐싱(매 호출 재파싱 방지).
+  // 추출 불가 형식/실패 시 null. 용량이 크므로 기본 조회에서는 제외(select:false).
+  @Column({
+    name: 'extracted_text',
+    type: 'text',
+    nullable: true,
+    select: false,
+  })
+  extractedText!: string | null;
+
   @CreateDateColumn({ name: 'created_at' })
   createdAt!: Date;
 }
diff --git a/backend/src/modules/project/extract-text.ts b/backend/src/modules/project/extract-text.ts
new file mode 100644
index 0000000..96899cc
--- /dev/null
+++ b/backend/src/modules/project/extract-text.ts
@@ -0,0 +1,69 @@
+import { readFile } from 'fs/promises';
+import { PDFParse } from 'pdf-parse';
+import { extractRawText } from 'mammoth';
+
+// 문서 1건당 추출 텍스트 상한(자) — DB 용량과 AI 토큰 사용량을 함께 보호한다.
+export const PER_DOC_TEXT_LIMIT = 8000;
+
+// 첨부 문서에서 평문 텍스트를 추출한다(업로드 시 1회). 추출 불가 형식/실패/빈 결과는 null.
+// 지원 형식: txt·csv(직접 읽기), pdf(pdf-parse), docx(mammoth).
+// 그 외(이미지·xlsx·ppt·압축 등)는 추출하지 않고 null 을 반환한다.
+export async function extractAttachmentText(
+  absPath: string,
+  mime: string,
+  name: string,
+): Promise<string | null> {
+  const lower = name.toLowerCase();
+  try {
+    // 1) 평문 텍스트 — 라이브러리 없이 그대로 읽는다
+    if (
+      mime === 'text/plain' ||
+      mime === 'text/csv' ||
+      lower.endsWith('.txt') ||
+      lower.endsWith('.csv')
+    ) {
+      const buf = await readFile(absPath);
+      return finalize(buf.toString('utf8'));
+    }
+
+    // 2) PDF — pdf-parse v2(PDFParse 클래스)로 페이지 텍스트 추출
+    if (mime === 'application/pdf' || lower.endsWith('.pdf')) {
+      const buf = await readFile(absPath);
+      const parser = new PDFParse({ data: buf });
+      try {
+        const result = await parser.getText();
+        return finalize(result.text);
+      } finally {
+        await parser.destroy();
+      }
+    }
+
+    // 3) Word(.docx) — mammoth 로 서식 제거한 본문만 추출
+    if (
+      mime ===
+        'application/vnd.openxmlformats-officedocument.wordprocessingml.document' ||
+      lower.endsWith('.docx')
+    ) {
+      const result = await extractRawText({ path: absPath });
+      return finalize(result.value);
+    }
+
+    return null;
+  } catch {
+    // 추출 실패는 무시한다 — 첨부 자체는 정상 저장되어야 한다.
+    return null;
+  }
+}
+
+// 공백·개행 정리 후 길이 상한 적용. 내용이 없으면 null.
+function finalize(text: string): string | null {
+  const cleaned = text
+    .replace(/\r\n/g, '\n')
+    .replace(/[ \t]+\n/g, '\n')
+    .replace(/\n{3,}/g, '\n\n')
+    .trim();
+  if (!cleaned) return null;
+  return cleaned.length > PER_DOC_TEXT_LIMIT
+    ? cleaned.slice(0, PER_DOC_TEXT_LIMIT)
+    : cleaned;
+}
diff --git a/backend/src/modules/project/project.service.ts b/backend/src/modules/project/project.service.ts
index 55a3144..52a4ea9 100644
--- a/backend/src/modules/project/project.service.ts
+++ b/backend/src/modules/project/project.service.ts
@@ -24,6 +24,7 @@ import {
   decodeOriginalName,
   type UploadedDiskFile,
 } from '../task/upload.config';
+import { extractAttachmentText } from './extract-text';
 import { CreateProjectDto } from './dto/create-project.dto';
 import { UpdateProjectDto } from './dto/update-project.dto';
 
@@ -218,6 +219,32 @@ export class ProjectService {
     return rows.map((a) => this.toAttachmentResponse(a, projectId));
   }
 
+  // AI 업무 추천용 — 프로젝트 문서들의 캐싱된 추출 본문을 문서명과 함께 합쳐 반환한다.
+  // 총량 상한으로 잘라 토큰 사용을 보호하며, 추출 텍스트가 없으면 빈 문자열.
+  // (extractedText 는 select:false 이므로 명시적으로 선택해 조회한다.)
+  async getAttachmentsTextForAi(projectId: string): Promise<string> {
+    const TOTAL_LIMIT = 16000;
+    const rows = await this.attachmentRepo
+      .createQueryBuilder('a')
+      .select(['a.name', 'a.extractedText'])
+      .where('a.project_id = :projectId', { projectId })
+      .orderBy('a.created_at', 'ASC')
+      .getMany();
+
+    const parts: string[] = [];
+    let used = 0;
+    for (const r of rows) {
+      const text = r.extractedText?.trim();
+      if (!text) continue;
+      const remaining = TOTAL_LIMIT - used;
+      if (remaining <= 0) break;
+      const slice = text.length > remaining ? text.slice(0, remaining) : text;
+      parts.push(`### ${r.name}\n${slice}`);
+      used += slice.length;
+    }
+    return parts.join('\n\n');
+  }
+
   // 첨부 업로드 — 관리자만. 디스크 저장은 multer 가 처리, 메타데이터만 영속
   async addFile(
     projectId: string,
@@ -229,6 +256,12 @@ export class ProjectService {
     const uploader = await this.userService.findById(userId);
 
     const name = decodeOriginalName(file.originalname);
+    // 업로드 시점에 텍스트를 1회 추출해 캐싱 — AI 추천에서 재파싱 없이 꺼내 쓴다.
+    const extractedText = await extractAttachmentText(
+      file.path,
+      file.mimetype,
+      name,
+    );
     const saved = await this.attachmentRepo.save(
       this.attachmentRepo.create({
         project: { id: project.id } as Project,
@@ -238,6 +271,7 @@ export class ProjectService {
         size: file.size,
         mime: file.mimetype,
         kind: deriveKind(file.mimetype, name),
+        extractedText,
       }),
     );
     return this.toAttachmentResponse(