"""Content blueprint - New playlist-centric workflow."""
from flask import (Blueprint, render_template, request, redirect, url_for, 
                   flash, jsonify, current_app)
from flask_login import login_required
from werkzeug.utils import secure_filename
import os

from app.extensions import db, cache
from app.models import Content, Playlist, Player
from app.models.playlist import playlist_content
from app.utils.logger import log_action
from app.utils.uploads import process_video_file, set_upload_progress

content_bp = Blueprint('content', __name__, url_prefix='/content')


@content_bp.route('/')
@login_required
def content_list():
    """Main playlist management page."""
    playlists = Playlist.query.order_by(Playlist.created_at.desc()).all()
    media_files = Content.query.order_by(Content.uploaded_at.desc()).limit(3).all()  # Only last 3
    total_media_count = Content.query.count()  # Total count for display
    players = Player.query.order_by(Player.name).all()
    
    return render_template('content/content_list_new.html',
                         playlists=playlists,
                         media_files=media_files,
                         total_media_count=total_media_count,
                         players=players)


@content_bp.route('/media-library')
@login_required
def media_library():
    """View all media files in the library."""
    media_files = Content.query.order_by(Content.uploaded_at.desc()).all()
    
    # Group by content type
    images = [m for m in media_files if m.content_type == 'image']
    videos = [m for m in media_files if m.content_type == 'video']
    pdfs = [m for m in media_files if m.content_type == 'pdf']
    presentations = [m for m in media_files if m.content_type == 'pptx']
    others = [m for m in media_files if m.content_type not in ['image', 'video', 'pdf', 'pptx']]
    
    return render_template('content/media_library.html',
                         media_files=media_files,
                         images=images,
                         videos=videos,
                         pdfs=pdfs,
                         presentations=presentations,
                         others=others)


@content_bp.route('/media/<int:media_id>/delete', methods=['POST'])
@login_required
def delete_media(media_id: int):
    """Delete a media file and remove it from all playlists."""
    try:
        media = Content.query.get_or_404(media_id)
        filename = media.filename
        
        # Get all playlists containing this media
        affected_playlists = list(media.playlists.all())
        
        # Delete physical file
        file_path = os.path.join(current_app.config['UPLOAD_FOLDER'], media.filename)
        if os.path.exists(file_path):
            os.remove(file_path)
            log_action('info', f'Deleted physical file: {filename}')
        
        # Remove from all playlists (this will cascade properly)
        db.session.delete(media)
        
        # Increment version for all affected playlists
        for playlist in affected_playlists:
            playlist.version += 1
            log_action('info', f'Playlist "{playlist.name}" version updated to {playlist.version} (media removed)')
        
        db.session.commit()
        
        # Clear cache for affected playlists
        from app.blueprints.players import get_player_playlist
        from app.extensions import cache
        for playlist in affected_playlists:
            for player in playlist.players:
                cache.delete_memoized(get_player_playlist, player.id)
        
        if affected_playlists:
            flash(f'Deleted "{filename}" and removed from {len(affected_playlists)} playlist(s). Playlist versions updated.', 'success')
        else:
            flash(f'Deleted "{filename}" successfully.', 'success')
        
        log_action('info', f'Media deleted: {filename} (affected {len(affected_playlists)} playlists)')
        
    except Exception as e:
        db.session.rollback()
        log_action('error', f'Error deleting media: {str(e)}')
        flash(f'Error deleting media: {str(e)}', 'danger')
    
    return redirect(url_for('content.media_library'))


@content_bp.route('/playlist/create', methods=['POST'])
@login_required
def create_playlist():
    """Create a new playlist."""
    try:
        name = request.form.get('name', '').strip()
        description = request.form.get('description', '').strip()
        orientation = request.form.get('orientation', 'Landscape')
        
        if not name:
            flash('Playlist name is required.', 'warning')
            return redirect(url_for('content.content_list'))
        
        # Check if playlist name exists
        existing = Playlist.query.filter_by(name=name).first()
        if existing:
            flash(f'Playlist "{name}" already exists.', 'warning')
            return redirect(url_for('content.content_list'))
        
        playlist = Playlist(
            name=name,
            description=description or None,
            orientation=orientation
        )
        db.session.add(playlist)
        db.session.commit()
        
        log_action('info', f'Created playlist: {name}')
        flash(f'Playlist "{name}" created successfully!', 'success')
        
    except Exception as e:
        db.session.rollback()
        log_action('error', f'Error creating playlist: {str(e)}')
        flash('Error creating playlist.', 'danger')
    
    return redirect(url_for('content.content_list'))


@content_bp.route('/playlist/<int:playlist_id>/delete', methods=['POST'])
@login_required
def delete_playlist(playlist_id: int):
    """Delete a playlist."""
    playlist = Playlist.query.get_or_404(playlist_id)
    
    try:
        name = playlist.name
        
        # Unassign all players from this playlist
        Player.query.filter_by(playlist_id=playlist_id).update({'playlist_id': None})
        
        db.session.delete(playlist)
        db.session.commit()
        cache.clear()
        
        log_action('info', f'Deleted playlist: {name}')
        flash(f'Playlist "{name}" deleted successfully.', 'success')
        
    except Exception as e:
        db.session.rollback()
        log_action('error', f'Error deleting playlist: {str(e)}')
        flash('Error deleting playlist.', 'danger')
    
    return redirect(url_for('content.content_list'))


@content_bp.route('/playlist/<int:playlist_id>/manage')
@login_required
def manage_playlist_content(playlist_id: int):
    """Manage content in a specific playlist."""
    playlist = Playlist.query.get_or_404(playlist_id)
    
    # Get content in playlist (ordered)
    playlist_content = playlist.get_content_ordered()
    
    # Get all available content not in this playlist
    all_content = Content.query.all()
    playlist_content_ids = {c.id for c in playlist_content}
    available_content = [c for c in all_content if c.id not in playlist_content_ids]
    
    return render_template('content/manage_playlist_content.html',
                         playlist=playlist,
                         playlist_content=playlist_content,
                         available_content=available_content)


@content_bp.route('/playlist/<int:playlist_id>/add-content', methods=['POST'])
@login_required
def add_content_to_playlist(playlist_id: int):
    """Add content to playlist."""
    playlist = Playlist.query.get_or_404(playlist_id)
    
    try:
        content_id = request.form.get('content_id', type=int)
        duration = request.form.get('duration', type=int, default=10)
        
        if not content_id:
            flash('Please select content to add.', 'warning')
            return redirect(url_for('content.manage_playlist_content', playlist_id=playlist_id))
        
        content = Content.query.get_or_404(content_id)
        
        # Get max position
        from sqlalchemy import select, func
        from app.models.playlist import playlist_content
        
        max_pos = db.session.execute(
            select(func.max(playlist_content.c.position)).where(
                playlist_content.c.playlist_id == playlist_id
            )
        ).scalar() or 0
        
        # Add to playlist
        stmt = playlist_content.insert().values(
            playlist_id=playlist_id,
            content_id=content_id,
            position=max_pos + 1,
            duration=duration
        )
        db.session.execute(stmt)
        
        playlist.increment_version()
        db.session.commit()
        cache.clear()
        
        log_action('info', f'Added "{content.filename}" to playlist "{playlist.name}"')
        flash(f'Added "{content.filename}" to playlist.', 'success')
        
    except Exception as e:
        db.session.rollback()
        log_action('error', f'Error adding content to playlist: {str(e)}')
        flash('Error adding content to playlist.', 'danger')
    
    return redirect(url_for('content.manage_playlist_content', playlist_id=playlist_id))


@content_bp.route('/playlist/<int:playlist_id>/remove-content/<int:content_id>', methods=['POST'])
@login_required
def remove_content_from_playlist(playlist_id: int, content_id: int):
    """Remove content from playlist."""
    playlist = Playlist.query.get_or_404(playlist_id)
    
    try:
        from app.models.playlist import playlist_content
        
        # Remove from playlist
        stmt = playlist_content.delete().where(
            (playlist_content.c.playlist_id == playlist_id) &
            (playlist_content.c.content_id == content_id)
        )
        db.session.execute(stmt)
        
        playlist.increment_version()
        db.session.commit()
        cache.clear()
        
        log_action('info', f'Removed content from playlist "{playlist.name}"')
        flash('Content removed from playlist.', 'success')
        
    except Exception as e:
        db.session.rollback()
        log_action('error', f'Error removing content from playlist: {str(e)}')
        flash('Error removing content from playlist.', 'danger')
    
    return redirect(url_for('content.manage_playlist_content', playlist_id=playlist_id))


@content_bp.route('/playlist/<int:playlist_id>/reorder', methods=['POST'])
@login_required
def reorder_playlist_content(playlist_id: int):
    """Reorder content in playlist."""
    playlist = Playlist.query.get_or_404(playlist_id)
    
    try:
        data = request.get_json()
        content_ids = data.get('content_ids', [])
        
        if not content_ids:
            return jsonify({'success': False, 'message': 'No content IDs provided'}), 400
        
        from app.models.playlist import playlist_content
        
        # Update positions
        for idx, content_id in enumerate(content_ids, start=1):
            stmt = playlist_content.update().where(
                (playlist_content.c.playlist_id == playlist_id) &
                (playlist_content.c.content_id == content_id)
            ).values(position=idx)
            db.session.execute(stmt)
        
        playlist.increment_version()
        db.session.commit()
        cache.clear()
        
        log_action('info', f'Reordered playlist "{playlist.name}"')
        
        return jsonify({
            'success': True,
            'message': 'Playlist reordered successfully',
            'version': playlist.version
        })
        
    except Exception as e:
        db.session.rollback()
        log_action('error', f'Error reordering playlist: {str(e)}')
        return jsonify({'success': False, 'message': str(e)}), 500


@content_bp.route('/playlist/<int:playlist_id>/update-muted/<int:content_id>', methods=['POST'])
@login_required
def update_playlist_content_muted(playlist_id: int, content_id: int):
    """Update content muted setting in playlist."""
    playlist = Playlist.query.get_or_404(playlist_id)
    
    try:
        content = Content.query.get_or_404(content_id)
        muted = request.form.get('muted', 'true').lower() == 'true'
        
        from app.models.playlist import playlist_content
        from sqlalchemy import update
        
        # Update muted in association table
        stmt = update(playlist_content).where(
            (playlist_content.c.playlist_id == playlist_id) &
            (playlist_content.c.content_id == content_id)
        ).values(muted=muted)
        db.session.execute(stmt)
        
        # Increment playlist version
        playlist.increment_version()
        
        db.session.commit()
        cache.clear()
        
        log_action('info', f'Updated muted={muted} for "{content.filename}" in playlist "{playlist.name}"')
        
        return jsonify({
            'success': True,
            'message': 'Audio setting updated',
            'muted': muted,
            'version': playlist.version
        })
        
    except Exception as e:
        db.session.rollback()
        log_action('error', f'Error updating muted setting: {str(e)}')
        return jsonify({'success': False, 'message': str(e)}), 500


@content_bp.route('/upload-media-page')
@login_required
def upload_media_page():
    """Display upload media page."""
    playlists = Playlist.query.order_by(Playlist.name).all()
    return render_template('content/upload_media.html', playlists=playlists)


def process_image_file(filepath: str, filename: str) -> tuple[bool, str]:
    """Process and optimize image files."""
    try:
        from PIL import Image
        
        # Open and optimize image
        img = Image.open(filepath)
        
        # Convert RGBA to RGB for JPEGs
        if img.mode == 'RGBA' and filename.lower().endswith(('.jpg', '.jpeg')):
            rgb_img = Image.new('RGB', img.size, (255, 255, 255))
            rgb_img.paste(img, mask=img.split()[3])
            img = rgb_img
        
        # Resize if too large (max 1920x1080 for display efficiency)
        max_size = (1920, 1080)
        if img.width > max_size[0] or img.height > max_size[1]:
            img.thumbnail(max_size, Image.Resampling.LANCZOS)
            img.save(filepath, optimize=True, quality=85)
            log_action('info', f'Optimized image: {filename}')
        
        return True, "Image processed successfully"
    except Exception as e:
        return False, f"Image processing error: {str(e)}"


def process_video_file_extended(filepath: str, filename: str) -> tuple[bool, str]:
    """Process and optimize video files for Raspberry Pi playback."""
    try:
        # Basic video validation
        import subprocess
        
        # Check if video is playable
        result = subprocess.run(
            ['ffprobe', '-v', 'error', '-select_streams', 'v:0', 
             '-show_entries', 'stream=codec_name,width,height', 
             '-of', 'default=noprint_wrappers=1', filepath],
            capture_output=True, text=True, timeout=10
        )
        
        if result.returncode == 0:
            log_action('info', f'Video validated: {filename}')
            return True, "Video validated successfully"
        else:
            return False, "Video validation failed"
    except Exception as e:
        # If ffprobe not available, just accept the video
        log_action('warning', f'Video validation skipped (ffprobe unavailable): {filename}')
        return True, "Video accepted without validation"


def process_pdf_file(filepath: str, filename: str) -> tuple[bool, str]:
    """Process PDF files by converting each page to PNG images."""
    try:
        from pdf2image import convert_from_path
        from pathlib import Path
        
        # Basic PDF validation - check if it's a valid PDF
        with open(filepath, 'rb') as f:
            header = f.read(5)
            if header != b'%PDF-':
                return False, "Invalid PDF file"
        
        log_action('info', f'Converting PDF to images: {filename}')
        
        # Convert PDF pages to images at high DPI for quality
        images = convert_from_path(
            filepath,
            dpi=300,  # 300 DPI for sharp rendering
            fmt='png'
        )
        
        if not images:
            return False, "No pages found in PDF"
        
        # Generate base filename without extension
        base_filename = Path(filename).stem
        upload_folder = os.path.dirname(filepath)
        
        # Save each page with proper aspect ratio preservation
        converted_files = []
        for idx, image in enumerate(images, start=1):
            # Create filename for this page
            page_filename = f"{base_filename}_page{idx:03d}.png"
            page_filepath = os.path.join(upload_folder, page_filename)
            
            # Determine orientation and resize maintaining aspect ratio
            width, height = image.size
            is_portrait = height > width
            
            # Define Full HD dimensions based on orientation
            if is_portrait:
                # Portrait: max height 1920, max width 1080 (rotated Full HD)
                max_size = (1080, 1920)
            else:
                # Landscape: max width 1920, max height 1080 (standard Full HD)
                max_size = (1920, 1080)
            
            # Resize maintaining aspect ratio (thumbnail maintains ratio)
            from PIL import Image as PILImage
            image.thumbnail(max_size, PILImage.Resampling.LANCZOS)
            
            # Save the optimized image
            image.save(page_filepath, 'PNG', optimize=True, quality=95)
            
            converted_files.append((page_filepath, page_filename))
            log_action('info', f'Converted PDF page {idx}/{len(images)} ({width}x{height} -> {image.size[0]}x{image.size[1]}): {page_filename}')
        
        log_action('info', f'PDF converted successfully: {len(images)} pages from {filename}')
        
        # Return success with file info for later processing
        return True, f"PDF converted to {len(images)} images"
        
    except ImportError:
        return False, "pdf2image library not installed. Install with: pip install pdf2image"
    except Exception as e:
        import traceback
        error_details = traceback.format_exc()
        log_action('error', f'PDF processing error: {str(e)}\n{error_details}')
        return False, f"PDF processing error: {str(e)}"


def process_presentation_file(filepath: str, filename: str) -> tuple[bool, str]:
    """Process PowerPoint presentation files by converting slides to images."""
    try:
        import subprocess
        import tempfile
        import shutil
        from pathlib import Path
        
        # Basic validation - check file exists and has content
        file_size = os.path.getsize(filepath)
        if file_size < 1024:  # Less than 1KB is suspicious
            return False, "File too small to be a valid presentation"
        
        # Check if LibreOffice is available
        libreoffice_paths = [
            '/usr/bin/libreoffice',
            '/usr/bin/soffice',
            '/snap/bin/libreoffice',
            'libreoffice',  # Try in PATH
            'soffice'
        ]
        
        libreoffice_cmd = None
        for cmd in libreoffice_paths:
            try:
                result = subprocess.run([cmd, '--version'], 
                                      capture_output=True, 
                                      timeout=5)
                if result.returncode == 0:
                    libreoffice_cmd = cmd
                    log_action('info', f'Found LibreOffice at: {cmd}')
                    break
            except (FileNotFoundError, subprocess.TimeoutExpired):
                continue
        
        if not libreoffice_cmd:
            log_action('warning', f'LibreOffice not found, cannot convert: {filename}')
            return False, "LibreOffice is not installed. Please install it from the Admin Panel → System Dependencies to upload PowerPoint files."
        
        # Create temporary directory for conversion
        with tempfile.TemporaryDirectory() as temp_dir:
            temp_path = Path(temp_dir)
            
            # Copy presentation to temp directory
            temp_ppt = temp_path / filename
            shutil.copy2(filepath, temp_ppt)
            
            # Convert presentation to images (PNG format)
            # Using LibreOffice headless mode with custom resolution
            convert_cmd = [
                libreoffice_cmd,
                '--headless',
                '--convert-to', 'png',
                '--outdir', str(temp_path),
                str(temp_ppt)
            ]
            
            log_action('info', f'Converting presentation to images: {filename}')
            
            try:
                result = subprocess.run(
                    convert_cmd,
                    capture_output=True,
                    text=True,
                    timeout=120  # 2 minutes timeout
                )
                
                if result.returncode != 0:
                    log_action('error', f'LibreOffice conversion failed: {result.stderr}')
                    return True, "Presentation accepted without conversion (conversion failed)"
                
                # Find generated PNG files
                png_files = sorted(temp_path.glob('*.png'))
                
                if not png_files:
                    log_action('warning', f'No images generated from presentation: {filename}')
                    return True, "Presentation accepted without images"
                
                # Get upload folder from app config
                upload_folder = current_app.config['UPLOAD_FOLDER']
                base_name = os.path.splitext(filename)[0]
                
                # Move converted images to upload folder
                slide_count = 0
                for idx, png_file in enumerate(png_files, start=1):
                    # Create descriptive filename
                    slide_filename = f"{base_name}_slide_{idx:03d}.png"
                    destination = os.path.join(upload_folder, slide_filename)
                    
                    shutil.move(str(png_file), destination)
                    
                    # Optimize the image to Full HD (1920x1080)
                    optimize_image_to_fullhd(destination)
                    
                    slide_count += 1
                
                log_action('info', f'Converted {slide_count} slides from {filename} to images')
                
                # Remove original PPTX file as we now have the images
                os.remove(filepath)
                
                return True, f"Presentation converted to {slide_count} Full HD images"
                
            except subprocess.TimeoutExpired:
                log_action('error', f'LibreOffice conversion timeout for: {filename}')
                return True, "Presentation accepted without conversion (timeout)"
                
    except Exception as e:
        log_action('error', f'Presentation processing error: {str(e)}')
        return False, f"Presentation processing error: {str(e)}"


def create_fullhd_image(img):
    """Create a Full HD (1920x1080) image from PIL Image object, centered on white background."""
    from PIL import Image as PILImage
    
    target_size = (1920, 1080)
    
    # Resize maintaining aspect ratio
    img_copy = img.copy()
    img_copy.thumbnail(target_size, PILImage.Resampling.LANCZOS)
    
    # Create canvas with white background
    fullhd_img = PILImage.new('RGB', target_size, (255, 255, 255))
    
    # Center the image
    x = (target_size[0] - img_copy.width) // 2
    y = (target_size[1] - img_copy.height) // 2
    
    if img_copy.mode == 'RGBA':
        fullhd_img.paste(img_copy, (x, y), img_copy)
    else:
        fullhd_img.paste(img_copy, (x, y))
    
    return fullhd_img


def optimize_image_to_fullhd(filepath: str) -> bool:
    """Optimize and resize image file to Full HD (1920x1080) maintaining aspect ratio."""
    try:
        from PIL import Image
        
        img = Image.open(filepath)
        fullhd_img = create_fullhd_image(img)
        fullhd_img.save(filepath, 'PNG', optimize=True)
        
        return True
    except Exception as e:
        log_action('error', f'Image optimization error: {str(e)}')
        return False


@content_bp.route('/upload-media', methods=['POST'])
@login_required
def upload_media():
    """Upload media files to library with type-specific processing."""
    try:
        files = request.files.getlist('files')
        content_type = request.form.get('content_type', 'image')
        duration = request.form.get('duration', type=int, default=10)
        playlist_id = request.form.get('playlist_id', type=int)
        
        if not files or files[0].filename == '':
            flash('No files provided.', 'warning')
            return redirect(url_for('content.upload_media_page'))
        
        upload_folder = current_app.config['UPLOAD_FOLDER']
        os.makedirs(upload_folder, exist_ok=True)
        
        uploaded_count = 0
        processing_errors = []
        
        for file in files:
            if file.filename == '':
                continue
            
            filename = secure_filename(file.filename)
            filepath = os.path.join(upload_folder, filename)
            
            # Check if file already exists
            existing = Content.query.filter_by(filename=filename).first()
            if existing:
                log_action('warning', f'File {filename} already exists, skipping')
                continue
            
            # Save file first
            file.save(filepath)
            
            # Determine content type from extension
            file_ext = filename.rsplit('.', 1)[1].lower() if '.' in filename else ''
            
            # Process file based on type
            processing_success = True
            processing_message = ""
            
            if file_ext in ['jpg', 'jpeg', 'png', 'gif', 'bmp', 'webp']:
                detected_type = 'image'
                processing_success, processing_message = process_image_file(filepath, filename)
                
            elif file_ext in ['mp4', 'avi', 'mov', 'mkv', 'webm', 'flv', 'wmv']:
                detected_type = 'video'
                processing_success, processing_message = process_video_file_extended(filepath, filename)
                
            elif file_ext == 'pdf':
                detected_type = 'pdf'
                processing_success, processing_message = process_pdf_file(filepath, filename)
                
                # For PDFs, pages are converted to individual images
                # We need to add each page image as a separate content item
                if processing_success and "converted to" in processing_message.lower():
                    # Find all page images that were created
                    base_name = os.path.splitext(filename)[0]
                    page_pattern = f"{base_name}_page*.png"
                    import glob
                    page_files = sorted(glob.glob(os.path.join(upload_folder, page_pattern)))
                    
                    if page_files:
                        max_position = 0
                        if playlist_id:
                            playlist = Playlist.query.get(playlist_id)
                            max_position = db.session.query(db.func.max(playlist_content.c.position))\
                                .filter(playlist_content.c.playlist_id == playlist_id)\
                                .scalar() or 0
                        
                        # Add each page as separate content
                        for page_file in page_files:
                            page_filename = os.path.basename(page_file)
                            
                            # Create content record for page
                            page_content = Content(
                                filename=page_filename,
                                content_type='image',
                                duration=duration,
                                file_size=os.path.getsize(page_file)
                            )
                            db.session.add(page_content)
                            db.session.flush()
                            
                            # Add to playlist if specified
                            if playlist_id:
                                max_position += 1
                                stmt = playlist_content.insert().values(
                                    playlist_id=playlist_id,
                                    content_id=page_content.id,
                                    position=max_position,
                                    duration=duration
                                )
                                db.session.execute(stmt)
                            
                            uploaded_count += 1
                        
                        # Increment playlist version if pages were added
                        if playlist_id and page_files:
                            playlist.version += 1
                        
                        # Delete original PDF file
                        if os.path.exists(filepath):
                            os.remove(filepath)
                            log_action('info', f'Removed original PDF after conversion: {filename}')
                        
                        continue  # Skip normal content creation below
                
            elif file_ext in ['ppt', 'pptx']:
                detected_type = 'pptx'
                processing_success, processing_message = process_presentation_file(filepath, filename)
                
                # For presentations, slides are converted to individual images
                # We need to add each slide image as a separate content item
                if processing_success and "converted to" in processing_message.lower():
                    # Find all slide images that were created
                    base_name = os.path.splitext(filename)[0]
                    slide_pattern = f"{base_name}_slide_*.png"
                    import glob
                    slide_files = sorted(glob.glob(os.path.join(upload_folder, slide_pattern)))
                    
                    if slide_files:
                        max_position = 0
                        if playlist_id:
                            playlist = Playlist.query.get(playlist_id)
                            max_position = db.session.query(db.func.max(playlist_content.c.position))\
                                .filter(playlist_content.c.playlist_id == playlist_id)\
                                .scalar() or 0
                        
                        # Add each slide as separate content
                        for slide_file in slide_files:
                            slide_filename = os.path.basename(slide_file)
                            
                            # Create content record for slide
                            slide_content = Content(
                                filename=slide_filename,
                                content_type='image',
                                duration=duration,
                                file_size=os.path.getsize(slide_file)
                            )
                            db.session.add(slide_content)
                            db.session.flush()
                            
                            # Add to playlist if specified
                            if playlist_id:
                                max_position += 1
                                stmt = playlist_content.insert().values(
                                    playlist_id=playlist_id,
                                    content_id=slide_content.id,
                                    position=max_position,
                                    duration=duration
                                )
                                db.session.execute(stmt)
                            
                            uploaded_count += 1
                        
                        # Increment playlist version if slides were added
                        if playlist_id and slide_files:
                            playlist.version += 1
                        
                        # Delete original PPTX file
                        if os.path.exists(filepath):
                            os.remove(filepath)
                            log_action('info', f'Removed original PPTX after conversion: {filename}')
                        
                        continue  # Skip normal content creation below
                
            else:
                detected_type = 'other'
            
            if not processing_success:
                processing_errors.append(f"{filename}: {processing_message}")
                if os.path.exists(filepath):
                    os.remove(filepath)  # Remove failed file
                log_action('error', f'Processing failed for {filename}: {processing_message}')
                continue
            
            # Create content record (for non-presentation files or failed conversions)
            if os.path.exists(filepath):
                content = Content(
                    filename=filename,
                    content_type=detected_type,
                    duration=duration,
                    file_size=os.path.getsize(filepath)
                )
                db.session.add(content)
                db.session.flush()  # Get content ID
                
                # Add to playlist if specified
                if playlist_id:
                    playlist = Playlist.query.get(playlist_id)
                    if playlist:
                        # Get max position
                        max_position = db.session.query(db.func.max(playlist_content.c.position))\
                            .filter(playlist_content.c.playlist_id == playlist_id)\
                            .scalar() or 0
                        
                        # Add to playlist
                        stmt = playlist_content.insert().values(
                            playlist_id=playlist_id,
                            content_id=content.id,
                            position=max_position + 1,
                            duration=duration
                        )
                        db.session.execute(stmt)
                        
                        # Increment playlist version
                        playlist.version += 1
                
                uploaded_count += 1
        
        db.session.commit()
        cache.clear()
        
        log_action('info', f'Uploaded {uploaded_count} media files')
        
        # Show appropriate flash message
        if processing_errors:
            error_summary = '; '.join(processing_errors[:3])
            if len(processing_errors) > 3:
                error_summary += f' and {len(processing_errors) - 3} more...'
            flash(f'Uploaded {uploaded_count} file(s). Errors: {error_summary}', 'warning')
        elif playlist_id:
            playlist = Playlist.query.get(playlist_id)
            flash(f'Successfully uploaded {uploaded_count} file(s) to playlist "{playlist.name}"!', 'success')
        else:
            flash(f'Successfully uploaded {uploaded_count} file(s) to media library!', 'success')
        
    except Exception as e:
        db.session.rollback()
        log_action('error', f'Error uploading media: {str(e)}')
        flash('Error uploading media files.', 'danger')
    
    return redirect(url_for('content.upload_media_page'))


@content_bp.route('/player/<int:player_id>/assign-playlist', methods=['POST'])
@login_required
def assign_player_to_playlist(player_id: int):
    """Assign a player to a playlist."""
    player = Player.query.get_or_404(player_id)
    
    try:
        playlist_id = request.form.get('playlist_id', type=int)
        
        if playlist_id:
            playlist = Playlist.query.get_or_404(playlist_id)
            player.playlist_id = playlist_id
            log_action('info', f'Assigned player "{player.name}" to playlist "{playlist.name}"')
            flash(f'Player "{player.name}" assigned to playlist "{playlist.name}".', 'success')
        else:
            player.playlist_id = None
            log_action('info', f'Unassigned player "{player.name}" from playlist')
            flash(f'Player "{player.name}" unassigned from playlist.', 'success')
        
        db.session.commit()
        cache.clear()
        
    except Exception as e:
        db.session.rollback()
        log_action('error', f'Error assigning player to playlist: {str(e)}')
        flash('Error assigning player to playlist.', 'danger')
    
    return redirect(url_for('content.content_list'))