diff --git a/components/Landing.tsx b/components/Landing.tsx
index 0523c38..a1b56c0 100644
--- a/components/Landing.tsx
+++ b/components/Landing.tsx
@@ -1,14 +1,16 @@
 import React, { useState, useEffect } from 'react';
 import { motion, AnimatePresence } from 'framer-motion';
-import { BrainCircuit, Loader2, Play, PenTool, BookOpen, Upload, ChevronDown, ChevronUp, X, FileText, Settings, Image } from 'lucide-react';
+import { BrainCircuit, Loader2, Play, PenTool, BookOpen, Upload, X, FileText, Image, ScanText, Sparkles } from 'lucide-react';
 import { useAuth } from 'react-oidc-context';
 import { AuthButton } from './AuthButton';
 import { QuizLibrary } from './QuizLibrary';
 import { useQuizLibrary } from '../hooks/useQuizLibrary';
 import type { Quiz } from '../types';
 
+type GenerateMode = 'topic' | 'document';
+
 interface LandingProps {
-  onGenerate: (options: { topic?: string; questionCount?: number; file?: File }) => void;
+  onGenerate: (options: { topic?: string; questionCount?: number; files?: File[]; useOcr?: boolean }) => void;
   onCreateManual: () => void;
   onLoadQuiz: (quiz: Quiz) => void;
   onJoin: (pin: string, name: string) => void;
@@ -19,15 +21,20 @@ interface LandingProps {
 export const Landing: React.FC<LandingProps> = ({ onGenerate, onCreateManual, onLoadQuiz, onJoin, isLoading, error }) => {
   const auth = useAuth();
   const [mode, setMode] = useState<'HOST' | 'JOIN'>('HOST');
+  const [generateMode, setGenerateMode] = useState<GenerateMode>('topic');
   const [topic, setTopic] = useState('');
   const [pin, setPin] = useState('');
   const [name, setName] = useState('');
   const [libraryOpen, setLibraryOpen] = useState(false);
   
-  const [selectedFile, setSelectedFile] = useState<File | null>(null);
+  const [selectedFiles, setSelectedFiles] = useState<File[]>([]);
   const [questionCount, setQuestionCount] = useState(10);
-  const [showAdvanced, setShowAdvanced] = useState(false);
   const [isDragging, setIsDragging] = useState(false);
+  const [useOcr, setUseOcr] = useState(false);
+  
+  const hasImageFile = selectedFiles.some(f => f.type.startsWith('image/'));
+  const hasDocumentFile = selectedFiles.some(f => !f.type.startsWith('image/') && !['application/pdf', 'text/plain', 'text/markdown', 'text/csv', 'text/html'].includes(f.type));
+  const showOcrOption = hasImageFile || hasDocumentFile;
   
   const { 
     quizzes, 
@@ -48,21 +55,23 @@ export const Landing: React.FC<LandingProps> = ({ onGenerate, onCreateManual, on
   }, [libraryOpen, auth.isAuthenticated, fetchQuizzes]);
 
   const handleFileSelect = (e: React.ChangeEvent<HTMLInputElement>) => {
-    if (e.target.files && e.target.files[0]) {
-      setSelectedFile(e.target.files[0]);
+    if (e.target.files && e.target.files.length > 0) {
+      const newFiles = Array.from(e.target.files);
+      setSelectedFiles(prev => [...prev, ...newFiles]);
     }
   };
 
   const handleDrop = (e: React.DragEvent) => {
     e.preventDefault();
     setIsDragging(false);
-    if (e.dataTransfer.files && e.dataTransfer.files[0]) {
-      const file = e.dataTransfer.files[0];
-      const acceptedTypes = ['.pdf', '.txt', '.md', '.docx', '.jpg', '.jpeg', '.png', '.gif', '.webp'];
-      const fileExtension = '.' + file.name.split('.').pop()?.toLowerCase();
-      
-      if (acceptedTypes.includes(fileExtension) || file.type.startsWith('image/')) {
-        setSelectedFile(file);
+    if (e.dataTransfer.files && e.dataTransfer.files.length > 0) {
+      const acceptedTypes = ['.pdf', '.txt', '.md', '.docx', '.pptx', '.xlsx', '.odt', '.odp', '.ods', '.rtf', '.jpg', '.jpeg', '.png', '.gif', '.webp'];
+      const newFiles = Array.from(e.dataTransfer.files).filter((file: File) => {
+        const fileExtension = '.' + file.name.split('.').pop()?.toLowerCase();
+        return acceptedTypes.includes(fileExtension) || file.type.startsWith('image/');
+      });
+      if (newFiles.length > 0) {
+        setSelectedFiles(prev => [...prev, ...newFiles]);
       }
     }
   };
@@ -77,17 +86,28 @@ export const Landing: React.FC<LandingProps> = ({ onGenerate, onCreateManual, on
     setIsDragging(false);
   };
 
-  const removeFile = () => {
-    setSelectedFile(null);
+  const removeFile = (index: number) => {
+    setSelectedFiles(prev => prev.filter((_, i) => i !== index));
+    if (selectedFiles.length <= 1) {
+      setUseOcr(false);
+    }
   };
+  
+  const clearAllFiles = () => {
+    setSelectedFiles([]);
+    setUseOcr(false);
+  };
+
+  const canGenerate = generateMode === 'topic' ? topic.trim() : selectedFiles.length > 0;
 
   const handleHostSubmit = (e: React.FormEvent) => {
     e.preventDefault();
-    if ((topic.trim() || selectedFile) && !isLoading) {
+    if (canGenerate && !isLoading) {
       onGenerate({ 
-        topic: topic.trim(), 
+        topic: generateMode === 'topic' ? topic.trim() : undefined, 
         questionCount, 
-        file: selectedFile || undefined 
+        files: generateMode === 'document' ? selectedFiles : undefined,
+        useOcr: generateMode === 'document' && showOcrOption ? useOcr : undefined
       });
     }
   };
@@ -145,120 +165,187 @@ export const Landing: React.FC<LandingProps> = ({ onGenerate, onCreateManual, on
         </div>
 
         {mode === 'HOST' ? (
-          <div className="space-y-6">
+          <div className="space-y-4">
             <form onSubmit={handleHostSubmit} className="space-y-4">
-              <input
-                type="text"
-                placeholder="Topic (e.g. 'Space')"
-                value={topic}
-                onChange={(e) => setTopic(e.target.value)}
-                className="w-full p-4 text-xl font-bold border-2 border-gray-200 rounded-2xl focus:border-theme-primary focus:ring-4 focus:ring-theme-primary/20 outline-none transition-all placeholder:font-medium text-center"
-                disabled={isLoading}
-              />
-
-              <div className="border-2 border-gray-100 rounded-2xl overflow-hidden">
-                <button
-                    type="button"
-                    onClick={() => setShowAdvanced(!showAdvanced)}
-                    className="w-full p-3 bg-gray-50 flex items-center justify-center gap-2 text-gray-500 font-bold hover:bg-gray-100 transition-colors"
+              <div className="flex bg-gray-100 p-1.5 rounded-xl mb-2">
+                <button 
+                  type="button"
+                  onClick={() => setGenerateMode('topic')}
+                  className={`flex-1 py-2 px-3 rounded-lg font-bold text-sm transition-all duration-200 flex items-center justify-center gap-1.5 ${
+                    generateMode === 'topic' 
+                      ? 'bg-white shadow-sm text-theme-primary' 
+                      : 'text-gray-400 hover:text-gray-600'
+                  }`}
                 >
-                    <Settings size={18} />
-                    Advanced Options
-                    {showAdvanced ? <ChevronUp size={18} /> : <ChevronDown size={18} />}
+                  <Sparkles size={16} /> Topic
                 </button>
-                
-                <AnimatePresence>
-                    {showAdvanced && (
-                        <motion.div
-                            initial={{ height: 0, opacity: 0 }}
-                            animate={{ height: 'auto', opacity: 1 }}
-                            exit={{ height: 0, opacity: 0 }}
-                            transition={{ duration: 0.2 }}
-                        >
-                            <div className="p-4 space-y-4 bg-white border-t-2 border-gray-100">
-                                <div className="space-y-2">
-                                    <div className="flex justify-between items-center text-sm font-bold text-gray-600">
-                                        <span>Question Count</span>
-                                        <span className="bg-theme-primary text-white px-2 py-0.5 rounded-lg text-xs">{questionCount}</span>
-                                    </div>
-                                    <input
-                                        type="range"
-                                        min="5"
-                                        max="30"
-                                        value={questionCount}
-                                        onChange={(e) => setQuestionCount(Number(e.target.value))}
-                                        className="w-full accent-theme-primary h-2 bg-gray-200 rounded-lg appearance-none cursor-pointer"
-                                    />
-                                    <div className="flex justify-between text-xs text-gray-400 font-medium">
-                                        <span>5</span>
-                                        <span>30</span>
-                                    </div>
-                                </div>
+                <button 
+                  type="button"
+                  onClick={() => setGenerateMode('document')}
+                  className={`flex-1 py-2 px-3 rounded-lg font-bold text-sm transition-all duration-200 flex items-center justify-center gap-1.5 ${
+                    generateMode === 'document' 
+                      ? 'bg-white shadow-sm text-theme-primary' 
+                      : 'text-gray-400 hover:text-gray-600'
+                  }`}
+                >
+                  <FileText size={16} /> Document
+                </button>
+              </div>
 
-                                <div
-                                    onDrop={handleDrop}
-                                    onDragOver={handleDragOver}
-                                    onDragLeave={handleDragLeave}
-                                    onClick={() => document.getElementById('file-upload')?.click()}
-                                    className={`border-2 border-dashed rounded-xl p-4 text-center cursor-pointer transition-all ${
-                                        isDragging 
-                                            ? 'border-theme-primary bg-theme-primary/5 scale-[1.02]' 
-                                            : 'border-gray-300 hover:border-gray-400 hover:bg-gray-50'
-                                    }`}
-                                >
-                                    <input
-                                        id="file-upload"
-                                        type="file"
-                                        className="hidden"
-                                        onChange={handleFileSelect}
-                                        accept=".pdf,.txt,.md,.docx,.jpg,.jpeg,.png,.gif,.webp"
-                                    />
-                                    
-                                    {selectedFile ? (
-                                        <div className="flex items-center justify-between bg-gray-100 p-2 rounded-lg">
-                                            <div className="flex items-center gap-2 overflow-hidden text-left">
-                                                {selectedFile.type.startsWith('image/') ? (
-                                                    <Image size={20} className="text-theme-primary flex-shrink-0" />
-                                                ) : (
-                                                    <FileText size={20} className="text-theme-primary flex-shrink-0" />
-                                                )}
-                                                <div className="flex flex-col items-start min-w-0">
-                                                    <span className="text-sm font-bold text-gray-700 truncate max-w-[150px]">{selectedFile.name}</span>
-                                                    <span className="text-xs text-gray-500">{(selectedFile.size / 1024).toFixed(1)} KB</span>
-                                                </div>
-                                            </div>
-                                            <button
-                                                onClick={(e) => {
-                                                    e.stopPropagation();
-                                                    removeFile();
-                                                }}
-                                                className="p-1 hover:bg-gray-200 rounded-full text-gray-500 hover:text-red-500 transition-colors"
-                                            >
-                                                <X size={16} />
-                                            </button>
-                                        </div>
-                                    ) : (
-                                        <div className="space-y-1">
-                                            <Upload className={`mx-auto mb-2 ${isDragging ? 'text-theme-primary' : 'text-gray-400'}`} size={24} />
-                                            <p className="text-sm font-bold text-gray-600">
-                                                {isDragging ? 'Drop file here' : 'Upload Document'}
-                                            </p>
-                                            <p className="text-xs text-gray-400">PDF, TXT, DOCX, Images</p>
-                                        </div>
-                                    )}
+              <AnimatePresence mode="wait">
+                {generateMode === 'topic' ? (
+                  <motion.div
+                    key="topic"
+                    initial={{ opacity: 0, y: 10 }}
+                    animate={{ opacity: 1, y: 0 }}
+                    exit={{ opacity: 0, y: -10 }}
+                    transition={{ duration: 0.15 }}
+                  >
+                    <input
+                      type="text"
+                      placeholder="Enter a topic (e.g. 'Space')"
+                      value={topic}
+                      onChange={(e) => setTopic(e.target.value)}
+                      className="w-full p-4 text-xl font-bold border-2 border-gray-200 rounded-2xl focus:border-theme-primary focus:ring-4 focus:ring-theme-primary/20 outline-none transition-all placeholder:font-medium text-center"
+                      disabled={isLoading}
+                    />
+                  </motion.div>
+                ) : (
+                  <motion.div
+                    key="document"
+                    initial={{ opacity: 0, y: 10 }}
+                    animate={{ opacity: 1, y: 0 }}
+                    exit={{ opacity: 0, y: -10 }}
+                    transition={{ duration: 0.15 }}
+                    className="space-y-3"
+                  >
+                    <div
+                      onDrop={handleDrop}
+                      onDragOver={handleDragOver}
+                      onDragLeave={handleDragLeave}
+                      onClick={() => document.getElementById('file-upload')?.click()}
+                      className={`border-2 border-dashed rounded-2xl p-4 text-center cursor-pointer transition-all ${
+                        isDragging 
+                          ? 'border-theme-primary bg-theme-primary/5 scale-[1.02]' 
+                          : selectedFiles.length > 0
+                            ? 'border-theme-primary/50 bg-theme-primary/5'
+                            : 'border-gray-300 hover:border-gray-400 hover:bg-gray-50'
+                      }`}
+                    >
+                      <input
+                        id="file-upload"
+                        type="file"
+                        multiple
+                        className="hidden"
+                        onChange={handleFileSelect}
+                        accept=".pdf,.txt,.md,.docx,.pptx,.xlsx,.odt,.odp,.ods,.rtf,.jpg,.jpeg,.png,.gif,.webp"
+                      />
+                      
+                      <div className="space-y-2">
+                        <Upload className={`mx-auto ${isDragging ? 'text-theme-primary' : 'text-gray-400'}`} size={28} />
+                        <p className="text-sm font-bold text-gray-600">
+                          {isDragging ? 'Drop files here' : 'Drop files or click to browse'}
+                        </p>
+                        <p className="text-xs text-gray-400">PDF, DOCX, PPTX, XLSX, TXT, Images</p>
+                      </div>
+                    </div>
+                    
+                    {selectedFiles.length > 0 && (
+                      <div className="space-y-2">
+                        <div className="flex justify-between items-center">
+                          <span className="text-sm font-bold text-gray-600">{selectedFiles.length} file{selectedFiles.length > 1 ? 's' : ''} selected</span>
+                          <button
+                            type="button"
+                            onClick={(e) => {
+                              e.stopPropagation();
+                              clearAllFiles();
+                            }}
+                            className="text-xs font-bold text-gray-400 hover:text-red-500 transition-colors"
+                          >
+                            Clear all
+                          </button>
+                        </div>
+                        <div className="max-h-32 overflow-y-auto space-y-1.5">
+                          {selectedFiles.map((file, index) => (
+                            <div key={index} className="flex items-center justify-between bg-white p-2 rounded-lg shadow-sm">
+                              <div className="flex items-center gap-2 overflow-hidden text-left">
+                                <div className="p-1.5 bg-theme-primary/10 rounded">
+                                  {file.type.startsWith('image/') ? (
+                                    <Image size={14} className="text-theme-primary" />
+                                  ) : (
+                                    <FileText size={14} className="text-theme-primary" />
+                                  )}
                                 </div>
+                                <span className="text-xs font-medium text-gray-700 truncate max-w-[180px]">{file.name}</span>
+                              </div>
+                              <button
+                                type="button"
+                                onClick={(e) => {
+                                  e.stopPropagation();
+                                  removeFile(index);
+                                }}
+                                className="p-1 hover:bg-gray-100 rounded text-gray-400 hover:text-red-500 transition-colors"
+                              >
+                                <X size={14} />
+                              </button>
                             </div>
-                        </motion.div>
+                          ))}
+                        </div>
+                      </div>
                     )}
-                </AnimatePresence>
+                    
+                    {showOcrOption && (
+                      <label className="flex items-center gap-3 p-3 bg-gray-50 rounded-xl cursor-pointer hover:bg-gray-100 transition-colors">
+                        <div className="relative">
+                          <input
+                            type="checkbox"
+                            checked={useOcr}
+                            onChange={(e) => setUseOcr(e.target.checked)}
+                            className="sr-only peer"
+                          />
+                          <div className="w-10 h-6 bg-gray-300 rounded-full peer-checked:bg-theme-primary transition-colors"></div>
+                          <div className="absolute left-1 top-1 w-4 h-4 bg-white rounded-full peer-checked:translate-x-4 transition-transform"></div>
+                        </div>
+                        <div className="flex items-center gap-2">
+                          <ScanText size={18} className="text-gray-500" />
+                          <span className="text-sm font-bold text-gray-600">
+                            {hasImageFile && !hasDocumentFile ? 'Extract text with OCR' : 'OCR embedded images'}
+                          </span>
+                        </div>
+                      </label>
+                    )}
+                  </motion.div>
+                )}
+              </AnimatePresence>
+
+              <div className="space-y-2 pt-2">
+                <div className="flex justify-between items-center text-sm font-bold text-gray-500">
+                  <span>Questions</span>
+                  <span className="bg-gray-100 text-gray-600 px-2 py-0.5 rounded-lg text-xs">{questionCount}</span>
+                </div>
+                <input
+                  type="range"
+                  min="5"
+                  max="30"
+                  value={questionCount}
+                  onChange={(e) => setQuestionCount(Number(e.target.value))}
+                  className="w-full accent-theme-primary h-2 bg-gray-200 rounded-lg appearance-none cursor-pointer"
+                />
               </div>
 
               <button
                 type="submit"
-                disabled={isLoading || (!topic.trim() && !selectedFile)}
+                disabled={isLoading || !canGenerate}
                 className="w-full bg-[#333] text-white py-4 rounded-2xl text-xl font-black shadow-[0_6px_0_#000] active:shadow-none active:translate-y-[6px] transition-all hover:bg-black flex items-center justify-center gap-3 disabled:opacity-50 disabled:cursor-not-allowed"
               >
-                {isLoading ? <Loader2 className="animate-spin" /> : <><BrainCircuit size={24} /> {selectedFile && !topic.trim() ? 'Generate from Document' : 'Generate Quiz'}</>}
+                {isLoading ? (
+                  <Loader2 className="animate-spin" />
+                ) : (
+                  <>
+                    <BrainCircuit size={24} /> 
+                    {generateMode === 'document' ? 'Generate from Document' : 'Generate Quiz'}
+                  </>
+                )}
               </button>
             </form>
             
diff --git a/docker-compose.yml b/docker-compose.yml
index 0c001fa..0b0a3f7 100644
--- a/docker-compose.yml
+++ b/docker-compose.yml
@@ -110,7 +110,7 @@ services:
       OIDC_INTERNAL_JWKS_URI: http://authentik-server:9000/application/o/kaboot/jwks/
       CORS_ORIGIN: ${CORS_ORIGIN:-http://localhost:5173}
     volumes:
-      - kaboot-data:/data
+      - ./data:/data
     ports:
       - "${KABOOT_BACKEND_PORT:-3001}:3001"
     depends_on:
@@ -121,7 +121,6 @@ services:
 volumes:
   postgresql-data:
   redis-data:
-  kaboot-data:
 
 networks:
   kaboot-network:
diff --git a/hooks/useGame.ts b/hooks/useGame.ts
index 5bda1be..690b1a9 100644
--- a/hooks/useGame.ts
+++ b/hooks/useGame.ts
@@ -1,9 +1,11 @@
 import { useState, useEffect, useRef, useCallback } from 'react';
-import { Quiz, Player, GameState, GameRole, NetworkMessage, AnswerOption, Question } from '../types';
+import { Quiz, Player, GameState, GameRole, NetworkMessage, AnswerOption, Question, GenerateQuizOptions, ProcessedDocument } from '../types';
 import { generateQuiz } from '../services/geminiService';
 import { POINTS_PER_QUESTION, QUESTION_TIME, QUESTION_TIME_MS, PLAYER_COLORS } from '../constants';
 import { Peer, DataConnection } from 'peerjs';
 
+const BACKEND_URL = import.meta.env.VITE_BACKEND_URL || 'http://localhost:3001';
+
 export const useGame = () => {
   const [role, setRole] = useState<GameRole>('HOST');
   const [gameState, setGameState] = useState<GameState>('LANDING');
@@ -43,16 +45,50 @@ export const useGame = () => {
 
   // -- HOST LOGIC --
 
-  const startQuizGen = async (topic: string) => {
+  const uploadDocument = async (file: File, useOcr: boolean = false): Promise<ProcessedDocument> => {
+    const formData = new FormData();
+    formData.append('document', file);
+    formData.append('useOcr', String(useOcr));
+    
+    const response = await fetch(`${BACKEND_URL}/api/upload`, {
+      method: 'POST',
+      body: formData
+    });
+    
+    if (!response.ok) {
+      const error = await response.json();
+      throw new Error(error.error || 'Failed to upload document');
+    }
+    
+    return response.json();
+  };
+
+  const startQuizGen = async (options: { topic?: string; questionCount?: number; files?: File[]; useOcr?: boolean }) => {
     try {
       setGameState('GENERATING');
       setError(null);
       setRole('HOST');
-      const generatedQuiz = await generateQuiz(topic);
-      setPendingQuizToSave({ quiz: generatedQuiz, topic });
+      
+      let documents: ProcessedDocument[] | undefined;
+      if (options.files && options.files.length > 0) {
+        documents = await Promise.all(
+          options.files.map(file => uploadDocument(file, options.useOcr))
+        );
+      }
+      
+      const generateOptions: GenerateQuizOptions = {
+        topic: options.topic,
+        questionCount: options.questionCount,
+        documents
+      };
+      
+      const generatedQuiz = await generateQuiz(generateOptions);
+      const saveLabel = options.topic || options.files?.map(f => f.name).join(', ') || '';
+      setPendingQuizToSave({ quiz: generatedQuiz, topic: saveLabel });
       initializeHostGame(generatedQuiz);
     } catch (e) {
-      setError("Failed to generate quiz.");
+      const message = e instanceof Error ? e.message : "Failed to generate quiz.";
+      setError(message);
       setGameState('LANDING');
     }
   };
diff --git a/server/package-lock.json b/server/package-lock.json
index 4ea764d..53c3e55 100644
--- a/server/package-lock.json
+++ b/server/package-lock.json
@@ -13,6 +13,8 @@
         "express": "^4.21.2",
         "jsonwebtoken": "^9.0.2",
         "jwks-rsa": "^3.1.0",
+        "multer": "^2.0.2",
+        "officeparser": "^6.0.4",
         "uuid": "^11.0.5"
       },
       "devDependencies": {
@@ -20,6 +22,7 @@
         "@types/cors": "^2.8.17",
         "@types/express": "^5.0.0",
         "@types/jsonwebtoken": "^9.0.7",
+        "@types/multer": "^2.0.0",
         "@types/node": "^22.10.7",
         "@types/uuid": "^10.0.0",
         "tsx": "^4.19.2",
@@ -468,6 +471,262 @@
         "node": ">=18"
       }
     },
+    "node_modules/@napi-rs/canvas": {
+      "version": "0.1.88",
+      "resolved": "https://registry.npmjs.org/@napi-rs/canvas/-/canvas-0.1.88.tgz",
+      "integrity": "sha512-/p08f93LEbsL5mDZFQ3DBxcPv/I4QG9EDYRRq1WNlCOXVfAHBTHMSVMwxlqG/AtnSfUr9+vgfN7MKiyDo0+Weg==",
+      "license": "MIT",
+      "optional": true,
+      "workspaces": [
+        "e2e/*"
+      ],
+      "engines": {
+        "node": ">= 10"
+      },
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/Brooooooklyn"
+      },
+      "optionalDependencies": {
+        "@napi-rs/canvas-android-arm64": "0.1.88",
+        "@napi-rs/canvas-darwin-arm64": "0.1.88",
+        "@napi-rs/canvas-darwin-x64": "0.1.88",
+        "@napi-rs/canvas-linux-arm-gnueabihf": "0.1.88",
+        "@napi-rs/canvas-linux-arm64-gnu": "0.1.88",
+        "@napi-rs/canvas-linux-arm64-musl": "0.1.88",
+        "@napi-rs/canvas-linux-riscv64-gnu": "0.1.88",
+        "@napi-rs/canvas-linux-x64-gnu": "0.1.88",
+        "@napi-rs/canvas-linux-x64-musl": "0.1.88",
+        "@napi-rs/canvas-win32-arm64-msvc": "0.1.88",
+        "@napi-rs/canvas-win32-x64-msvc": "0.1.88"
+      }
+    },
+    "node_modules/@napi-rs/canvas-android-arm64": {
+      "version": "0.1.88",
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       "resolved": "https://registry.npmjs.org/napi-build-utils/-/napi-build-utils-2.0.0.tgz",
@@ -1660,6 +2080,26 @@
         "node": ">=10"
       }
     },
+    "node_modules/node-fetch": {
+      "version": "2.7.0",
+      "resolved": "https://registry.npmjs.org/node-fetch/-/node-fetch-2.7.0.tgz",
+      "integrity": "sha512-c4FRfUm/dbcWZ7U+1Wq0AwCyFL+3nt2bEw05wfxSz+DWpWsitgmSgYmy2dQdWyKC1694ELPqMs/YzUSNozLt8A==",
+      "license": "MIT",
+      "dependencies": {
+        "whatwg-url": "^5.0.0"
+      },
+      "engines": {
+        "node": "4.x || >=6.0.0"
+      },
+      "peerDependencies": {
+        "encoding": "^0.1.0"
+      },
+      "peerDependenciesMeta": {
+        "encoding": {
+          "optional": true
+        }
+      }
+    },
     "node_modules/object-assign": {
       "version": "4.1.1",
       "resolved": "https://registry.npmjs.org/object-assign/-/object-assign-4.1.1.tgz",
@@ -1681,6 +2121,26 @@
         "url": "https://github.com/sponsors/ljharb"
       }
     },
+    "node_modules/officeparser": {
+      "version": "6.0.4",
+      "resolved": "https://registry.npmjs.org/officeparser/-/officeparser-6.0.4.tgz",
+      "integrity": "sha512-zmxst4xbrUxCCY6w5BLmmtewJY5eHkLKNJ+2Z5OKY0JPh5qmtUSslFkg0fC3xc+0RG4DFdfQ36107B99yLMfuQ==",
+      "license": "MIT",
+      "dependencies": {
+        "@xmldom/xmldom": "^0.8.10",
+        "concat-stream": "^2.0.0",
+        "file-type": "^16.5.4",
+        "pdfjs-dist": "5.4.530",
+        "tesseract.js": "^6.0.0",
+        "yauzl": "^3.1.3"
+      },
+      "bin": {
+        "officeparser": "dist/index.js"
+      },
+      "engines": {
+        "node": ">=18.0.0"
+      }
+    },
     "node_modules/on-finished": {
       "version": "2.4.1",
       "resolved": "https://registry.npmjs.org/on-finished/-/on-finished-2.4.1.tgz",
@@ -1702,6 +2162,15 @@
         "wrappy": "1"
       }
     },
+    "node_modules/opencollective-postinstall": {
+      "version": "2.0.3",
+      "resolved": "https://registry.npmjs.org/opencollective-postinstall/-/opencollective-postinstall-2.0.3.tgz",
+      "integrity": "sha512-8AV/sCtuzUeTo8gQK5qDZzARrulB3egtLzFgteqB2tcT4Mw7B8Kt7JcDHmltjz6FOAHsvTevk70gZEbhM4ZS9Q==",
+      "license": "MIT",
+      "bin": {
+        "opencollective-postinstall": "index.js"
+      }
+    },
     "node_modules/parseurl": {
       "version": "1.3.3",
       "resolved": "https://registry.npmjs.org/parseurl/-/parseurl-1.3.3.tgz",
@@ -1717,6 +2186,37 @@
       "integrity": "sha512-RA1GjUVMnvYFxuqovrEqZoxxW5NUZqbwKtYz/Tt7nXerk0LbLblQmrsgdeOxV5SFHf0UDggjS/bSeOZwt1pmEQ==",
       "license": "MIT"
     },
+    "node_modules/pdfjs-dist": {
+      "version": "5.4.530",
+      "resolved": "https://registry.npmjs.org/pdfjs-dist/-/pdfjs-dist-5.4.530.tgz",
+      "integrity": "sha512-r1hWsSIGGmyYUAHR26zSXkxYWLXLMd6AwqcaFYG9YUZ0GBf5GvcjJSeo512tabM4GYFhxhl5pMCmPr7Q72Rq2Q==",
+      "license": "Apache-2.0",
+      "engines": {
+        "node": ">=20.16.0 || >=22.3.0"
+      },
+      "optionalDependencies": {
+        "@napi-rs/canvas": "^0.1.84"
+      }
+    },
+    "node_modules/peek-readable": {
+      "version": "4.1.0",
+      "resolved": "https://registry.npmjs.org/peek-readable/-/peek-readable-4.1.0.tgz",
+      "integrity": "sha512-ZI3LnwUv5nOGbQzD9c2iDG6toheuXSZP5esSHBjopsXH4dg19soufvpUGA3uohi5anFtGb2lhAVdHzH6R/Evvg==",
+      "license": "MIT",
+      "engines": {
+        "node": ">=8"
+      },
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/Borewit"
+      }
+    },
+    "node_modules/pend": {
+      "version": "1.2.0",
+      "resolved": "https://registry.npmjs.org/pend/-/pend-1.2.0.tgz",
+      "integrity": "sha512-F3asv42UuXchdzt+xXqfW1OGlVBe+mxa2mqI0pg5yAHZPvFmY3Y6drSf/GQ1A86WgWEN9Kzh/WrgKa6iGcHXLg==",
+      "license": "MIT"
+    },
     "node_modules/prebuild-install": {
       "version": "7.1.3",
       "resolved": "https://registry.npmjs.org/prebuild-install/-/prebuild-install-7.1.3.tgz",
@@ -1743,6 +2243,15 @@
         "node": ">=10"
       }
     },
+    "node_modules/process": {
+      "version": "0.11.10",
+      "resolved": "https://registry.npmjs.org/process/-/process-0.11.10.tgz",
+      "integrity": "sha512-cdGef/drWFoydD1JsMzuFf8100nZl+GT+yacc2bEced5f9Rjk4z+WtFUTBu9PhOi9j/jfmBPu0mMEY4wIdAF8A==",
+      "license": "MIT",
+      "engines": {
+        "node": ">= 0.6.0"
+      }
+    },
     "node_modules/proxy-addr": {
       "version": "2.0.7",
       "resolved": "https://registry.npmjs.org/proxy-addr/-/proxy-addr-2.0.7.tgz",
@@ -1834,6 +2343,68 @@
         "node": ">= 6"
       }
     },
+    "node_modules/readable-web-to-node-stream": {
+      "version": "3.0.4",
+      "resolved": "https://registry.npmjs.org/readable-web-to-node-stream/-/readable-web-to-node-stream-3.0.4.tgz",
+      "integrity": "sha512-9nX56alTf5bwXQ3ZDipHJhusu9NTQJ/CVPtb/XHAJCXihZeitfJvIRS4GqQ/mfIoOE3IelHMrpayVrosdHBuLw==",
+      "license": "MIT",
+      "dependencies": {
+        "readable-stream": "^4.7.0"
+      },
+      "engines": {
+        "node": ">=8"
+      },
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/Borewit"
+      }
+    },
+    "node_modules/readable-web-to-node-stream/node_modules/buffer": {
+      "version": "6.0.3",
+      "resolved": "https://registry.npmjs.org/buffer/-/buffer-6.0.3.tgz",
+      "integrity": "sha512-FTiCpNxtwiZZHEZbcbTIcZjERVICn9yq/pDFkTl95/AxzD1naBctN7YO68riM/gLSDY7sdrMby8hofADYuuqOA==",
+      "funding": [
+        {
+          "type": "github",
+          "url": "https://github.com/sponsors/feross"
+        },
+        {
+          "type": "patreon",
+          "url": "https://www.patreon.com/feross"
+        },
+        {
+          "type": "consulting",
+          "url": "https://feross.org/support"
+        }
+      ],
+      "license": "MIT",
+      "dependencies": {
+        "base64-js": "^1.3.1",
+        "ieee754": "^1.2.1"
+      }
+    },
+    "node_modules/readable-web-to-node-stream/node_modules/readable-stream": {
+      "version": "4.7.0",
+      "resolved": "https://registry.npmjs.org/readable-stream/-/readable-stream-4.7.0.tgz",
+      "integrity": "sha512-oIGGmcpTLwPga8Bn6/Z75SVaH1z5dUut2ibSyAMVhmUggWpmDn2dapB0n7f8nwaSiRtepAsfJyfXIO5DCVAODg==",
+      "license": "MIT",
+      "dependencies": {
+        "abort-controller": "^3.0.0",
+        "buffer": "^6.0.3",
+        "events": "^3.3.0",
+        "process": "^0.11.10",
+        "string_decoder": "^1.3.0"
+      },
+      "engines": {
+        "node": "^12.22.0 || ^14.17.0 || >=16.0.0"
+      }
+    },
+    "node_modules/regenerator-runtime": {
+      "version": "0.13.11",
+      "resolved": "https://registry.npmjs.org/regenerator-runtime/-/regenerator-runtime-0.13.11.tgz",
+      "integrity": "sha512-kY1AZVr2Ra+t+piVaJ4gxaFaReZVH40AKNo7UCX6W+dEwBo/2oZJzqfuN1qLq1oL45o56cPaTXELwrTh8Fpggg==",
+      "license": "MIT"
+    },
     "node_modules/resolve-pkg-maps": {
       "version": "1.0.0",
       "resolved": "https://registry.npmjs.org/resolve-pkg-maps/-/resolve-pkg-maps-1.0.0.tgz",
@@ -2059,6 +2630,14 @@
         "node": ">= 0.8"
       }
     },
+    "node_modules/streamsearch": {
+      "version": "1.1.0",
+      "resolved": "https://registry.npmjs.org/streamsearch/-/streamsearch-1.1.0.tgz",
+      "integrity": "sha512-Mcc5wHehp9aXz1ax6bZUyY5afg9u2rv5cqQI3mRrYkGC8rW2hM02jWuwjtL++LS5qinSyhj2QfLyNsuc+VsExg==",
+      "engines": {
+        "node": ">=10.0.0"
+      }
+    },
     "node_modules/string_decoder": {
       "version": "1.3.0",
       "resolved": "https://registry.npmjs.org/string_decoder/-/string_decoder-1.3.0.tgz",
@@ -2077,6 +2656,23 @@
         "node": ">=0.10.0"
       }
     },
+    "node_modules/strtok3": {
+      "version": "6.3.0",
+      "resolved": "https://registry.npmjs.org/strtok3/-/strtok3-6.3.0.tgz",
+      "integrity": "sha512-fZtbhtvI9I48xDSywd/somNqgUHl2L2cstmXCCif0itOf96jeW18MBSyrLuNicYQVkvpOxkZtkzujiTJ9LW5Jw==",
+      "license": "MIT",
+      "dependencies": {
+        "@tokenizer/token": "^0.3.0",
+        "peek-readable": "^4.1.0"
+      },
+      "engines": {
+        "node": ">=10"
+      },
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/Borewit"
+      }
+    },
     "node_modules/tar-fs": {
       "version": "2.1.4",
       "resolved": "https://registry.npmjs.org/tar-fs/-/tar-fs-2.1.4.tgz",
@@ -2105,6 +2701,30 @@
         "node": ">=6"
       }
     },
+    "node_modules/tesseract.js": {
+      "version": "6.0.1",
+      "resolved": "https://registry.npmjs.org/tesseract.js/-/tesseract.js-6.0.1.tgz",
+      "integrity": "sha512-/sPvMvrCtgxnNRCjbTYbr7BRu0yfWDsMZQ2a/T5aN/L1t8wUQN6tTWv6p6FwzpoEBA0jrN2UD2SX4QQFRdoDbA==",
+      "hasInstallScript": true,
+      "license": "Apache-2.0",
+      "dependencies": {
+        "bmp-js": "^0.1.0",
+        "idb-keyval": "^6.2.0",
+        "is-url": "^1.2.4",
+        "node-fetch": "^2.6.9",
+        "opencollective-postinstall": "^2.0.3",
+        "regenerator-runtime": "^0.13.3",
+        "tesseract.js-core": "^6.0.0",
+        "wasm-feature-detect": "^1.2.11",
+        "zlibjs": "^0.3.1"
+      }
+    },
+    "node_modules/tesseract.js-core": {
+      "version": "6.1.2",
+      "resolved": "https://registry.npmjs.org/tesseract.js-core/-/tesseract.js-core-6.1.2.tgz",
+      "integrity": "sha512-pv4GjmramjdObhDyR1q85Td8X60Puu/lGQn7Kw2id05LLgHhAcWgnz6xSdMCSxBMWjQDmMyDXPTC2aqADdpiow==",
+      "license": "Apache-2.0"
+    },
     "node_modules/toidentifier": {
       "version": "1.0.1",
       "resolved": "https://registry.npmjs.org/toidentifier/-/toidentifier-1.0.1.tgz",
@@ -2114,6 +2734,29 @@
         "node": ">=0.6"
       }
     },
+    "node_modules/token-types": {
+      "version": "4.2.1",
+      "resolved": "https://registry.npmjs.org/token-types/-/token-types-4.2.1.tgz",
+      "integrity": "sha512-6udB24Q737UD/SDsKAHI9FCRP7Bqc9D/MQUV02ORQg5iskjtLJlZJNdN4kKtcdtwCeWIwIHDGaUsTsCCAa8sFQ==",
+      "license": "MIT",
+      "dependencies": {
+        "@tokenizer/token": "^0.3.0",
+        "ieee754": "^1.2.1"
+      },
+      "engines": {
+        "node": ">=10"
+      },
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/Borewit"
+      }
+    },
+    "node_modules/tr46": {
+      "version": "0.0.3",
+      "resolved": "https://registry.npmjs.org/tr46/-/tr46-0.0.3.tgz",
+      "integrity": "sha512-N3WMsuqV66lT30CrXNbEjx4GEwlow3v6rr4mCcv6prnfwhS01rkgyFdjPNBYd9br7LpXV1+Emh01fHnq2Gdgrw==",
+      "license": "MIT"
+    },
     "node_modules/tsx": {
       "version": "4.21.0",
       "resolved": "https://registry.npmjs.org/tsx/-/tsx-4.21.0.tgz",
@@ -2159,6 +2802,12 @@
         "node": ">= 0.6"
       }
     },
+    "node_modules/typedarray": {
+      "version": "0.0.6",
+      "resolved": "https://registry.npmjs.org/typedarray/-/typedarray-0.0.6.tgz",
+      "integrity": "sha512-/aCDEGatGvZ2BIk+HmLf4ifCJFwvKFNb9/JeZPMulfgFracn9QFcAf5GO8B/mweUjSoblS5In0cWhqpfs/5PQA==",
+      "license": "MIT"
+    },
     "node_modules/typescript": {
       "version": "5.9.3",
       "resolved": "https://registry.npmjs.org/typescript/-/typescript-5.9.3.tgz",
@@ -2225,17 +2874,70 @@
         "node": ">= 0.8"
       }
     },
+    "node_modules/wasm-feature-detect": {
+      "version": "1.8.0",
+      "resolved": "https://registry.npmjs.org/wasm-feature-detect/-/wasm-feature-detect-1.8.0.tgz",
+      "integrity": "sha512-zksaLKM2fVlnB5jQQDqKXXwYHLQUVH9es+5TOOHwGOVJOCeRBCiPjwSg+3tN2AdTCzjgli4jijCH290kXb/zWQ==",
+      "license": "Apache-2.0"
+    },
+    "node_modules/webidl-conversions": {
+      "version": "3.0.1",
+      "resolved": "https://registry.npmjs.org/webidl-conversions/-/webidl-conversions-3.0.1.tgz",
+      "integrity": "sha512-2JAn3z8AR6rjK8Sm8orRC0h/bcl/DqL7tRPdGZ4I1CjdF+EaMLmYxBHyXuKL849eucPFhvBoxMsflfOb8kxaeQ==",
+      "license": "BSD-2-Clause"
+    },
+    "node_modules/whatwg-url": {
+      "version": "5.0.0",
+      "resolved": "https://registry.npmjs.org/whatwg-url/-/whatwg-url-5.0.0.tgz",
+      "integrity": "sha512-saE57nupxk6v3HY35+jzBwYa0rKSy0XR8JSxZPwgLr7ys0IBzhGviA1/TUGJLmSVqs8pb9AnvICXEuOHLprYTw==",
+      "license": "MIT",
+      "dependencies": {
+        "tr46": "~0.0.3",
+        "webidl-conversions": "^3.0.0"
+      }
+    },
     "node_modules/wrappy": {
       "version": "1.0.2",
       "resolved": "https://registry.npmjs.org/wrappy/-/wrappy-1.0.2.tgz",
       "integrity": "sha512-l4Sp/DRseor9wL6EvV2+TuQn63dMkPjZ/sp9XkghTEbV9KlPS1xUsZ3u7/IQO4wxtcFB4bgpQPRcR3QCvezPcQ==",
       "license": "ISC"
     },
+    "node_modules/xtend": {
+      "version": "4.0.2",
+      "resolved": "https://registry.npmjs.org/xtend/-/xtend-4.0.2.tgz",
+      "integrity": "sha512-LKYU1iAXJXUgAXn9URjiu+MWhyUXHsvfp7mcuYm9dSUKK0/CjtrUwFAxD82/mCWbtLsGjFIad0wIsod4zrTAEQ==",
+      "license": "MIT",
+      "engines": {
+        "node": ">=0.4"
+      }
+    },
     "node_modules/yallist": {
       "version": "4.0.0",
       "resolved": "https://registry.npmjs.org/yallist/-/yallist-4.0.0.tgz",
       "integrity": "sha512-3wdGidZyq5PB084XLES5TpOSRA3wjXAlIWMhum2kRcv/41Sn2emQ0dycQW4uZXLejwKvg6EsvbdlVL+FYEct7A==",
       "license": "ISC"
+    },
+    "node_modules/yauzl": {
+      "version": "3.2.0",
+      "resolved": "https://registry.npmjs.org/yauzl/-/yauzl-3.2.0.tgz",
+      "integrity": "sha512-Ow9nuGZE+qp1u4JIPvg+uCiUr7xGQWdff7JQSk5VGYTAZMDe2q8lxJ10ygv10qmSj031Ty/6FNJpLO4o1Sgc+w==",
+      "license": "MIT",
+      "dependencies": {
+        "buffer-crc32": "~0.2.3",
+        "pend": "~1.2.0"
+      },
+      "engines": {
+        "node": ">=12"
+      }
+    },
+    "node_modules/zlibjs": {
+      "version": "0.3.1",
+      "resolved": "https://registry.npmjs.org/zlibjs/-/zlibjs-0.3.1.tgz",
+      "integrity": "sha512-+J9RrgTKOmlxFSDHo0pI1xM6BLVUv+o0ZT9ANtCxGkjIVCCUdx9alUF8Gm+dGLKbkkkidWIHFDZHDMpfITt4+w==",
+      "license": "MIT",
+      "engines": {
+        "node": "*"
+      }
     }
   }
 }
diff --git a/server/package.json b/server/package.json
index 8ba79da..1e412dd 100644
--- a/server/package.json
+++ b/server/package.json
@@ -16,6 +16,8 @@
     "express": "^4.21.2",
     "jsonwebtoken": "^9.0.2",
     "jwks-rsa": "^3.1.0",
+    "multer": "^2.0.2",
+    "officeparser": "^6.0.4",
     "uuid": "^11.0.5"
   },
   "devDependencies": {
@@ -23,6 +25,7 @@
     "@types/cors": "^2.8.17",
     "@types/express": "^5.0.0",
     "@types/jsonwebtoken": "^9.0.7",
+    "@types/multer": "^2.0.0",
     "@types/node": "^22.10.7",
     "@types/uuid": "^10.0.0",
     "tsx": "^4.19.2",
diff --git a/server/src/index.ts b/server/src/index.ts
index 4557eba..886e7a9 100644
--- a/server/src/index.ts
+++ b/server/src/index.ts
@@ -3,6 +3,7 @@ import cors from 'cors';
 import { db } from './db/connection.js';
 import quizzesRouter from './routes/quizzes.js';
 import usersRouter from './routes/users.js';
+import uploadRouter from './routes/upload.js';
 
 const app = express();
 const PORT = process.env.PORT || 3001;
@@ -58,6 +59,7 @@ app.get('/health', (_req: Request, res: Response) => {
 
 app.use('/api/quizzes', quizzesRouter);
 app.use('/api/users', usersRouter);
+app.use('/api/upload', uploadRouter);
 
 app.use((err: Error, _req: Request, res: Response, _next: NextFunction) => {
   console.error('Unhandled error:', err);
diff --git a/server/src/routes/upload.ts b/server/src/routes/upload.ts
new file mode 100644
index 0000000..c120247
--- /dev/null
+++ b/server/src/routes/upload.ts
@@ -0,0 +1,71 @@
+import { Router } from 'express';
+import multer from 'multer';
+import { processDocument, SUPPORTED_TYPES } from '../services/documentParser.js';
+
+const router = Router();
+
+const storage = multer.memoryStorage();
+
+const upload = multer({
+  storage,
+  limits: {
+    fileSize: 50 * 1024 * 1024, // 50MB limit
+  },
+  fileFilter: (_req, file, cb) => {
+    if (SUPPORTED_TYPES.includes(file.mimetype)) {
+      cb(null, true);
+    } else {
+      cb(new Error(`Unsupported file type: ${file.mimetype}. Supported types: ${SUPPORTED_TYPES.join(', ')}`));
+    }
+  }
+});
+
+router.post('/', upload.single('document'), async (req, res) => {
+  try {
+    if (!req.file) {
+      return res.status(400).json({ error: 'No file uploaded' });
+    }
+
+    const useOcr = req.body?.useOcr === 'true' || req.body?.useOcr === true;
+    const processed = await processDocument(req.file.buffer, req.file.mimetype, { useOcr });
+
+    if (processed.type === 'native') {
+      res.json({
+        type: 'native',
+        content: (processed.content as Buffer).toString('base64'),
+        mimeType: processed.mimeType,
+        originalName: req.file.originalname
+      });
+    } else {
+      res.json({
+        type: 'text',
+        content: processed.content as string,
+        mimeType: processed.mimeType,
+        originalName: req.file.originalname
+      });
+    }
+  } catch (error) {
+    console.error('Upload processing error:', error);
+    res.status(500).json({ 
+      error: error instanceof Error ? error.message : 'Failed to process document' 
+    });
+  }
+});
+
+router.use((err: Error, _req: any, res: any, _next: any) => {
+  if (err instanceof multer.MulterError) {
+    if (err.code === 'LIMIT_FILE_SIZE') {
+      return res.status(400).json({ error: 'File too large. Maximum size is 50MB.' });
+    }
+    return res.status(400).json({ error: err.message });
+  }
+  
+  if (err.message.includes('Unsupported file type')) {
+    return res.status(400).json({ error: err.message });
+  }
+  
+  console.error('Upload error:', err);
+  res.status(500).json({ error: 'Upload failed' });
+});
+
+export default router;
diff --git a/server/src/services/documentParser.ts b/server/src/services/documentParser.ts
new file mode 100644
index 0000000..ad72b6f
--- /dev/null
+++ b/server/src/services/documentParser.ts
@@ -0,0 +1,123 @@
+import officeParser from 'officeparser';
+
+// MIME types that Gemini can handle natively (send as-is)
+export const GEMINI_NATIVE_TYPES = [
+  'application/pdf',
+  'text/plain',
+  'text/markdown',
+  'text/csv',
+  'text/html',
+  'image/jpeg',
+  'image/png',
+  'image/gif',
+  'image/webp'
+];
+
+// MIME types that officeparser can extract text from
+export const OFFICEPARSER_TYPES = [
+  'application/vnd.openxmlformats-officedocument.wordprocessingml.document',   // .docx
+  'application/vnd.openxmlformats-officedocument.presentationml.presentation', // .pptx
+  'application/vnd.openxmlformats-officedocument.spreadsheetml.sheet',         // .xlsx
+  'application/vnd.oasis.opendocument.text',                                   // .odt
+  'application/vnd.oasis.opendocument.presentation',                           // .odp
+  'application/vnd.oasis.opendocument.spreadsheet',                            // .ods
+  'application/rtf',                                                            // .rtf
+];
+
+// Image types that can use OCR for text extraction
+export const OCR_CAPABLE_TYPES = [
+  'image/jpeg',
+  'image/png',
+  'image/gif',
+  'image/webp'
+];
+
+export const SUPPORTED_TYPES = [...GEMINI_NATIVE_TYPES, ...OFFICEPARSER_TYPES];
+
+export interface ProcessedDocument {
+  type: 'native' | 'text';
+  content: Buffer | string;
+  mimeType: string;
+}
+
+export interface ProcessOptions {
+  useOcr?: boolean;
+}
+
+export function isSupportedType(mimeType: string): boolean {
+  return SUPPORTED_TYPES.includes(mimeType);
+}
+
+export function isGeminiNative(mimeType: string): boolean {
+  return GEMINI_NATIVE_TYPES.includes(mimeType);
+}
+
+export function isOcrCapable(mimeType: string): boolean {
+  return OCR_CAPABLE_TYPES.includes(mimeType);
+}
+
+export function needsOfficeParser(mimeType: string): boolean {
+  return OFFICEPARSER_TYPES.includes(mimeType);
+}
+
+async function extractWithOfficeParser(buffer: Buffer, useOcr: boolean = false): Promise<string> {
+  const config = useOcr ? {
+    extractAttachments: true,
+    ocr: true,
+    ocrLanguage: 'eng'
+  } : {};
+  
+  const ast = await officeParser.parseOffice(buffer, config);
+  let text = ast.toText();
+  
+  if (useOcr && ast.attachments) {
+    for (const attachment of ast.attachments) {
+      if (attachment.ocrText) {
+        text += '\n' + attachment.ocrText;
+      }
+    }
+  }
+  
+  return text;
+}
+
+export async function processDocument(
+  buffer: Buffer,
+  mimeType: string,
+  options: ProcessOptions = {}
+): Promise<ProcessedDocument> {
+  if (!isSupportedType(mimeType)) {
+    throw new Error(`Unsupported file type: ${mimeType}`);
+  }
+
+  // Images with OCR requested - extract text
+  if (isOcrCapable(mimeType) && options.useOcr) {
+    const text = await extractWithOfficeParser(buffer, true);
+    return {
+      type: 'text',
+      content: text,
+      mimeType: 'text/plain'
+    };
+  }
+
+  // Gemini-native types (including images without OCR) - pass through
+  if (isGeminiNative(mimeType)) {
+    return {
+      type: 'native',
+      content: buffer,
+      mimeType
+    };
+  }
+
+  // Office documents - extract text, OCR extracts text from embedded images
+  if (needsOfficeParser(mimeType)) {
+    const text = await extractWithOfficeParser(buffer, options.useOcr);
+    return {
+      type: 'text',
+      content: text,
+      mimeType: 'text/plain'
+    };
+  }
+
+  throw new Error(`No extraction handler for: ${mimeType}`);
+}
diff --git a/services/geminiService.ts b/services/geminiService.ts
index 4e4131a..5e1cd18 100644
--- a/services/geminiService.ts
+++ b/services/geminiService.ts
@@ -1,5 +1,5 @@
-import { GoogleGenAI, Type } from "@google/genai";
-import { Quiz, Question, AnswerOption } from "../types";
+import { GoogleGenAI, Type, createUserContent, createPartFromUri } from "@google/genai";
+import { Quiz, Question, AnswerOption, GenerateQuizOptions, ProcessedDocument } from "../types";
 import { v4 as uuidv4 } from 'uuid';
 
 const getClient = () => {
@@ -10,61 +10,62 @@ const getClient = () => {
   return new GoogleGenAI({ apiKey });
 };
 
-export const generateQuiz = async (topic: string): Promise<Quiz> => {
-  const ai = getClient();
-  
-  const prompt = `Generate a trivia quiz about "${topic}". Create 10 engaging multiple-choice questions. Each question must have exactly 4 options, and exactly one correct answer. Vary the difficulty. For each option, provide a brief reason explaining why it is correct or incorrect - this helps players learn.`;
-
-  const response = await ai.models.generateContent({
-    model: "gemini-3-flash-preview",
-    contents: prompt,
-    config: {
-      responseMimeType: "application/json",
-      responseSchema: {
+const QUIZ_SCHEMA = {
+  type: Type.OBJECT,
+  properties: {
+    title: { type: Type.STRING, description: "A catchy title for the quiz" },
+    questions: {
+      type: Type.ARRAY,
+      items: {
         type: Type.OBJECT,
         properties: {
-          title: { type: Type.STRING, description: "A catchy title for the quiz" },
-          questions: {
+          text: { type: Type.STRING, description: "The question text" },
+          options: {
             type: Type.ARRAY,
             items: {
               type: Type.OBJECT,
               properties: {
-                text: { type: Type.STRING, description: "The question text" },
-                options: {
-                  type: Type.ARRAY,
-                  items: {
-                    type: Type.OBJECT,
-                    properties: {
-                      text: { type: Type.STRING },
-                      isCorrect: { type: Type.BOOLEAN },
-                      reason: { type: Type.STRING, description: "Brief explanation of why this answer is correct or incorrect" }
-                    },
-                    required: ["text", "isCorrect", "reason"]
-                  },
-                }
+                text: { type: Type.STRING },
+                isCorrect: { type: Type.BOOLEAN },
+                reason: { type: Type.STRING, description: "Brief explanation of why this answer is correct or incorrect" }
               },
-              required: ["text", "options"]
-            }
+              required: ["text", "isCorrect", "reason"]
+            },
           }
         },
-        required: ["title", "questions"]
+        required: ["text", "options"]
       }
     }
-  });
+  },
+  required: ["title", "questions"]
+};
 
-  if (!response.text) {
-    throw new Error("Failed to generate quiz content");
-  }
-
-  const data = JSON.parse(response.text);
+function buildPrompt(options: GenerateQuizOptions, hasDocuments: boolean): string {
+  const questionCount = options.questionCount || 10;
+  
+  const baseInstructions = `Create ${questionCount} engaging multiple-choice questions. Each question must have exactly 4 options, and exactly one correct answer. Vary the difficulty.
+
+IMPORTANT: For each option's reason, write as if you are directly explaining facts - never reference "the document", "the text", "the material", or "the source". Write explanations as standalone factual statements.`;
+
+  if (hasDocuments) {
+    const topicContext = options.topic 
+      ? ` Focus on aspects related to "${options.topic}".` 
+      : '';
+    return `Generate a quiz based on the provided content.${topicContext}
+
+${baseInstructions}`;
+  }
+  
+  return `Generate a trivia quiz about "${options.topic}".
+
+${baseInstructions}`;
+}
+
+function transformToQuiz(data: any): Quiz {
+  const shapes = ['triangle', 'diamond', 'circle', 'square'] as const;
+  const colors = ['red', 'blue', 'yellow', 'green'] as const;
   
-  // Transform to our internal type with shapes/colors pre-assigned
   const questions: Question[] = data.questions.map((q: any) => {
-    const shapes = ['triangle', 'diamond', 'circle', 'square'] as const;
-    const colors = ['red', 'blue', 'yellow', 'green'] as const;
-    
-    // Shuffle options so the correct one isn't always first (though Gemini usually randomizes, safety first)
-    // Actually, to map shapes consistently, let's keep array order but assign props
     const options: AnswerOption[] = q.options.map((opt: any, index: number) => ({
       text: opt.text,
       isCorrect: opt.isCorrect,
@@ -85,4 +86,67 @@ export const generateQuiz = async (topic: string): Promise<Quiz> => {
     title: data.title,
     questions
   };
+}
+
+async function uploadNativeDocument(ai: GoogleGenAI, doc: ProcessedDocument): Promise<{ uri: string; mimeType: string }> {
+  const buffer = typeof doc.content === 'string'
+    ? Buffer.from(doc.content, 'base64')
+    : doc.content;
+  
+  const blob = new Blob([buffer], { type: doc.mimeType });
+  
+  const uploadedFile = await ai.files.upload({
+    file: blob,
+    config: { mimeType: doc.mimeType! }
+  });
+  
+  if (!uploadedFile.uri || !uploadedFile.mimeType) {
+    throw new Error("Failed to upload document to Gemini");
+  }
+  
+  return { uri: uploadedFile.uri, mimeType: uploadedFile.mimeType };
+}
+
+export const generateQuiz = async (options: GenerateQuizOptions): Promise<Quiz> => {
+  const ai = getClient();
+  
+  const docs = options.documents || [];
+  const hasDocuments = docs.length > 0;
+  const prompt = buildPrompt(options, hasDocuments);
+  
+  let contents: any;
+  
+  if (hasDocuments) {
+    const parts: any[] = [];
+    
+    for (const doc of docs) {
+      if (doc.type === 'native' && doc.mimeType) {
+        const uploaded = await uploadNativeDocument(ai, doc);
+        parts.push(createPartFromUri(uploaded.uri, uploaded.mimeType));
+      } else if (doc.type === 'text') {
+        parts.push({ text: doc.content as string });
+      }
+    }
+    
+    parts.push({ text: prompt });
+    contents = createUserContent(parts);
+  } else {
+    contents = prompt;
+  }
+
+  const response = await ai.models.generateContent({
+    model: "gemini-3-flash-preview",
+    contents,
+    config: {
+      responseMimeType: "application/json",
+      responseSchema: QUIZ_SCHEMA
+    }
+  });
+
+  if (!response.text) {
+    throw new Error("Failed to generate quiz content");
+  }
+
+  const data = JSON.parse(response.text);
+  return transformToQuiz(data);
 };
diff --git a/tsconfig.json b/tsconfig.json
index 2c6eed5..21643e7 100644
--- a/tsconfig.json
+++ b/tsconfig.json
@@ -11,7 +11,8 @@
     ],
     "skipLibCheck": true,
     "types": [
-      "node"
+      "node",
+      "vite/client"
     ],
     "moduleResolution": "bundler",
     "isolatedModules": true,
diff --git a/types.ts b/types.ts
index 6fc1adc..c9fc7c7 100644
--- a/types.ts
+++ b/types.ts
@@ -51,6 +51,18 @@ export interface QuizListItem {
   updatedAt: string;
 }
 
+export interface ProcessedDocument {
+  type: 'native' | 'text';
+  content: string | Buffer;
+  mimeType?: string;
+}
+
+export interface GenerateQuizOptions {
+  topic?: string;
+  questionCount?: number;
+  documents?: ProcessedDocument[];
+}
+
 export interface Player {
   id: string;
   name: string;