smart_printer/smart_printer/PrintService.swift

import Cocoa
import CoreText
import PDFKit
import UniformTypeIdentifiers

enum PrintService {
    static func printContacts(_ contacts: [PrintableContact], from window: NSWindow? = nil) {
        guard !contacts.isEmpty else {
            showNoContactsAlert()
            return
        }
        let text = formattedContactsText(contacts)
        guard let document = pdfDocument(from: text) else {
            showPrintFailedAlert()
            return
        }
        printPDF(document, title: "Print Contacts", from: window ?? NSApp.keyWindow)
    }

    static func printCanvas(_ image: NSImage, from window: NSWindow? = nil) {
        guard image.size.width > 0, image.size.height > 0 else {
            showEmptyCanvasAlert()
            return
        }
        printImage(image, title: "Blank Canvas", from: window)
    }

    static func printPhoto(_ image: NSImage, title: String = "Photo", from window: NSWindow? = nil) {
        guard image.size.width > 0, image.size.height > 0 else {
            showPrintFailedAlert()
            return
        }
        printImage(image, title: title, from: window)
    }

    static func saveCanvasPDF(_ image: NSImage) {
        guard image.size.width > 0, image.size.height > 0 else {
            showEmptyCanvasAlert()
            return
        }
        guard let document = pdfDocument(from: image) else {
            showSaveFailedAlert()
            return
        }

        let panel = NSSavePanel()
        panel.title = "Save as PDF"
        panel.message = "Choose where to save your canvas."
        panel.prompt = "Save"
        panel.nameFieldStringValue = "Blank Canvas.pdf"
        panel.allowedContentTypes = [.pdf]
        panel.canCreateDirectories = true

        guard panel.runModal() == .OK, let url = panel.url else { return }
        guard document.write(to: url) else {
            showSaveFailedAlert()
            return
        }
    }

    static func printText(_ text: String, title: String = "Print Text", from window: NSWindow? = nil) {
        let trimmed = text.trimmingCharacters(in: .whitespacesAndNewlines)
        guard !trimmed.isEmpty else {
            showEmptyTextAlert()
            return
        }
        guard let document = pdfDocument(from: trimmed) else {
            showPrintFailedAlert()
            return
        }
        printPDF(document, title: title, from: window ?? NSApp.keyWindow)
    }

    static func saveAttributedTextAsPDF(
        _ attributed: NSAttributedString,
        defaultName: String = "Scan",
        from window: NSWindow? = nil
    ) {
        guard hasPrintableContent(attributed) else {
            showEmptyTextAlert()
            return
        }
        guard let document = pdfDocument(from: attributed) else {
            showSaveFailedAlert()
            return
        }

        let panel = NSSavePanel()
        panel.title = "Save as PDF"
        panel.message = "Choose where to save your document."
        panel.prompt = "Save"
        panel.nameFieldStringValue = "\(defaultName).pdf"
        panel.allowedContentTypes = [.pdf]
        panel.canCreateDirectories = true

        guard panel.runModal() == .OK, let url = panel.url else { return }
        guard document.write(to: url) else {
            showSaveFailedAlert()
            return
        }
    }

    static func printAttributedText(
        _ attributed: NSAttributedString,
        title: String = "Scan",
        from window: NSWindow? = nil
    ) {
        guard hasPrintableContent(attributed) else {
            showEmptyTextAlert()
            return
        }
        guard let document = pdfDocument(from: attributed) else {
            showPrintFailedAlert()
            return
        }
        printPDF(document, title: title, from: window ?? NSApp.keyWindow)
    }

    static func saveParsedScansAsPDF(
        pages: [ParsedScanPage],
        defaultName: String = "Scan",
        from window: NSWindow? = nil
    ) {
        guard !pages.isEmpty else {
            showEmptyTextAlert()
            return
        }
        guard let document = pdfDocument(from: pages) else {
            showSaveFailedAlert()
            return
        }

        let panel = NSSavePanel()
        panel.title = "Save as PDF"
        panel.message = "Choose where to save your document."
        panel.prompt = "Save"
        panel.nameFieldStringValue = "\(defaultName).pdf"
        panel.allowedContentTypes = [.pdf]
        panel.canCreateDirectories = true

        guard panel.runModal() == .OK, let url = panel.url else { return }
        guard document.write(to: url) else {
            showSaveFailedAlert()
            return
        }
    }

    static func printParsedScans(
        pages: [ParsedScanPage],
        title: String = "Scan",
        from window: NSWindow? = nil
    ) {
        guard !pages.isEmpty else {
            showEmptyTextAlert()
            return
        }
        guard let document = pdfDocument(from: pages) else {
            showPrintFailedAlert()
            return
        }
        printPDF(document, title: title, from: window ?? NSApp.keyWindow)
    }

    static func saveTextAsPDF(
        _ text: String,
        defaultName: String = "Scan",
        from window: NSWindow? = nil
    ) {
        let trimmed = text.trimmingCharacters(in: .whitespacesAndNewlines)
        guard !trimmed.isEmpty else {
            showEmptyTextAlert()
            return
        }
        guard let document = pdfDocument(from: trimmed) else {
            showSaveFailedAlert()
            return
        }

        let panel = NSSavePanel()
        panel.title = "Save as PDF"
        panel.message = "Choose where to save your document."
        panel.prompt = "Save"
        panel.nameFieldStringValue = "\(defaultName).pdf"
        panel.allowedContentTypes = [.pdf]
        panel.canCreateDirectories = true

        guard panel.runModal() == .OK, let url = panel.url else { return }
        guard document.write(to: url) else {
            showSaveFailedAlert()
            return
        }
    }

    static func print(urls: [URL], from window: NSWindow? = nil) {
        guard !urls.isEmpty else { return }

        let hostWindow = window ?? NSApp.keyWindow
        for url in urls {
            let accessed = url.startAccessingSecurityScopedResource()
            defer {
                if accessed { url.stopAccessingSecurityScopedResource() }
            }
            printFile(at: url, from: hostWindow)
        }
    }

    static func printFile(at url: URL, from window: NSWindow? = nil) {
        let title = url.lastPathComponent
        guard let document = printablePDFDocument(from: url) else {
            showUnsupportedAlert(for: url)
            return
        }
        printPDF(document, title: title, from: window ?? NSApp.keyWindow)
    }

    private static func contentType(for url: URL) -> UTType? {
        if let values = try? url.resourceValues(forKeys: [.contentTypeKey]),
           let type = values.contentType {
            return type
        }
        let ext = url.pathExtension.lowercased()
        guard !ext.isEmpty else { return nil }
        return UTType(filenameExtension: ext)
    }

    private static func printablePDFDocument(from url: URL) -> PDFDocument? {
        let type = contentType(for: url) ?? UTType(filenameExtension: url.pathExtension) ?? .data

        if type.conforms(to: .pdf), let source = PDFDocument(url: url) {
            return flattenedPDF(from: source)
        }

        if type.conforms(to: .image), let image = NSImage(contentsOf: url) {
            return pdfDocument(from: image)
        }
        if let image = NSImage(contentsOf: url), image.isValid {
            return pdfDocument(from: image)
        }

        if let text = DocumentContentService.plainTextForPrinting(from: url)?
            .trimmingCharacters(in: .whitespacesAndNewlines),
           !text.isEmpty,
           let document = pdfDocument(from: text) {
            return document
        }

        if let attributed = DocumentContentService.attributedString(for: url),
           !attributed.string.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty,
           let document = pdfDocument(from: attributed) {
            return document
        }

        return nil
    }

    private static func printPDF(_ document: PDFDocument, title: String, from window: NSWindow?) {
        guard let data = document.dataRepresentation(),
              let printable = PDFDocument(data: data) else {
            showPrintFailedAlert()
            return
        }

        let printInfo = configuredPrintInfo()
        guard let operation = printable.printOperation(
            for: printInfo,
            scalingMode: .pageScaleToFit,
            autoRotate: false
        ) else {
            showPrintFailedAlert()
            return
        }
        runPrintOperation(operation, title: title, from: window)
    }

    private static func printImage(_ image: NSImage, title: String, from window: NSWindow?) {
        guard let document = pdfDocument(from: image) else {
            showPrintFailedAlert()
            return
        }
        printPDF(document, title: title, from: window)
    }

    private static func runPrintOperation(_ operation: NSPrintOperation, title: String, from window: NSWindow?) {
        operation.showsPrintPanel = true
        operation.showsProgressPanel = false
        operation.jobTitle = title
        operation.printPanel.options.insert([
            .showsCopies,
            .showsPageRange,
            .showsPaperSize,
            .showsOrientation,
            .showsScaling,
        ])

        NSApp.activate(ignoringOtherApps: true)
        let parentWindow = window ?? NSApp.keyWindow ?? NSApp.mainWindow
        parentWindow?.makeKeyAndOrderFront(nil)

        let observer = observePrintPanelAppearance(relativeTo: parentWindow)
        defer { NotificationCenter.default.removeObserver(observer) }

        if let parentWindow {
            let callback = PrintRatingCallback(window: parentWindow)
            operation.runModal(
                for: parentWindow,
                delegate: callback,
                didRun: #selector(PrintRatingCallback.printOperationDidRun(_:success:contextInfo:)),
                contextInfo: nil
            )
            withExtendedLifetime(callback) {}
        } else {
            operation.run()
        }
    }

    private final class PrintRatingCallback: NSObject {
        private let window: NSWindow?

        init(window: NSWindow?) {
            self.window = window
        }

        @objc func printOperationDidRun(
            _ printOperation: NSPrintOperation,
            success: Bool,
            contextInfo: UnsafeMutableRawPointer?
        ) {
            guard success else { return }
            Task { @MainActor in
                AppRatingManager.shared.recordSuccessfulPrint(from: window)
            }
        }
    }

    private static func observePrintPanelAppearance(relativeTo parentWindow: NSWindow?) -> NSObjectProtocol {
        NotificationCenter.default.addObserver(
            forName: NSWindow.didBecomeKeyNotification,
            object: nil,
            queue: .main
        ) { notification in
            guard let panelWindow = notification.object as? NSWindow,
                  isPrintPanelWindow(panelWindow) else { return }
            configurePrintPanelWindow(panelWindow, relativeTo: parentWindow)
            DispatchQueue.main.async {
                configurePrintPanelWindow(panelWindow, relativeTo: parentWindow)
            }
        }
    }

    private static func configurePrintPanelWindow(_ panelWindow: NSWindow, relativeTo parentWindow: NSWindow?) {
        hideTrafficLights(on: panelWindow)
        if let parentWindow {
            center(panelWindow, relativeTo: parentWindow)
        }
    }

    private static func center(_ panelWindow: NSWindow, relativeTo parentWindow: NSWindow) {
        let parentFrame = parentWindow.frame
        var panelFrame = panelWindow.frame
        panelFrame.origin.x = parentFrame.midX - panelFrame.width / 2
        panelFrame.origin.y = parentFrame.midY - panelFrame.height / 2
        panelWindow.setFrame(panelFrame, display: true)
    }

    private static func isPrintPanelWindow(_ window: NSWindow) -> Bool {
        let className = String(describing: type(of: window))
        if className.localizedCaseInsensitiveContains("printpanel") {
            return true
        }
        return window.title == "Print"
    }

    private static func hideTrafficLights(on window: NSWindow) {
        for buttonType: NSWindow.ButtonType in [.closeButton, .miniaturizeButton, .zoomButton] {
            window.standardWindowButton(buttonType)?.isHidden = true
        }
    }

    private static func configuredPrintInfo() -> NSPrintInfo {
        let printInfo = (NSPrintInfo.shared.copy() as? NSPrintInfo) ?? NSPrintInfo()

        let printerName = AppSettings.effectiveDefaultPrinter
        if let printer = NSPrinter(name: printerName),
           NSPrinter.printerNames.contains(printerName) {
            printInfo.printer = printer
        }

        switch AppSettings.defaultPaperSize {
        case .a4: printInfo.paperName = NSPrinter.PaperName("iso-a4")
        case .letter: printInfo.paperName = NSPrinter.PaperName("na-letter")
        case .legal: printInfo.paperName = NSPrinter.PaperName("na-legal")
        }

        printInfo.horizontalPagination = .fit
        printInfo.verticalPagination = .fit
        printInfo.isHorizontallyCentered = true
        printInfo.isVerticallyCentered = false
        printInfo.topMargin = 36
        printInfo.bottomMargin = 36
        printInfo.leftMargin = 36
        printInfo.rightMargin = 36

        return printInfo
    }

    private static func hasPrintableContent(_ attributed: NSAttributedString) -> Bool {
        if !attributed.string.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty {
            return true
        }
        var hasAttachment = false
        attributed.enumerateAttribute(.attachment, in: NSRange(location: 0, length: attributed.length)) { value, _, stop in
            if value != nil {
                hasAttachment = true
                stop.pointee = true
            }
        }
        return hasAttachment
    }

    private static let scanFigureFraction: CGFloat = 0.52

    private static func pdfDocument(from pages: [ParsedScanPage]) -> PDFDocument? {
        guard !pages.isEmpty else { return nil }

        let combined = PDFDocument()
        for page in pages {
            guard let pdfPage = pdfPage(from: page) else { continue }
            combined.insert(pdfPage, at: combined.pageCount)
        }
        return combined.pageCount > 0 ? combined : nil
    }

    private static func pdfPage(from page: ParsedScanPage) -> PDFPage? {
        let bodyEmpty = page.body.plainText.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty
        let captionEmpty = page.caption?.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty ?? true

        if bodyEmpty && captionEmpty {
            return PDFPage(image: page.picture)
        }

        let printInfo = configuredPrintInfo()
        let pageSize = printInfo.paperSize
        guard pageSize.width > 0, pageSize.height > 0 else { return PDFPage(image: page.picture) }

        let contentWidth = pageSize.width - printInfo.leftMargin - printInfo.rightMargin
        let contentHeight = pageSize.height - printInfo.topMargin - printInfo.bottomMargin

        let pdfData = NSMutableData()
        var mediaBox = CGRect(origin: .zero, size: pageSize)
        guard let consumer = CGDataConsumer(data: pdfData as CFMutableData),
              let context = CGContext(consumer: consumer, mediaBox: &mediaBox, nil) else {
            return PDFPage(image: page.picture)
        }

        appendParsedScanPage(
            page,
            to: context,
            pageSize: pageSize,
            printInfo: printInfo,
            contentWidth: contentWidth,
            contentHeight: contentHeight
        )
        context.closePDF()

        guard let document = PDFDocument(data: pdfData as Data) else {
            return PDFPage(image: page.picture)
        }
        return document.page(at: 0)
    }

    private static func appendParsedScanPage(
        _ page: ParsedScanPage,
        to context: CGContext,
        pageSize: NSSize,
        printInfo: NSPrintInfo,
        contentWidth: CGFloat,
        contentHeight: CGFloat
    ) {
        let bodyText = page.body.plainText.trimmingCharacters(in: .whitespacesAndNewlines)
        let captionText = page.caption?.trimmingCharacters(in: .whitespacesAndNewlines) ?? ""
        let hasCaption = !captionText.isEmpty
        let hasBody = !bodyText.isEmpty
        let showsImage = page.showsPicture

        let imageFraction: CGFloat
        let captionFraction: CGFloat
        let textFraction: CGFloat
        if showsImage {
            imageFraction = hasBody || hasCaption ? 0.48 : 1.0
            captionFraction = hasCaption ? 0.05 : 0
            textFraction = hasBody ? max(0, 1 - imageFraction - captionFraction) : 0
        } else {
            imageFraction = 0
            captionFraction = hasCaption ? 0.05 : 0
            textFraction = hasBody ? max(0, 1 - captionFraction) : 0
        }

        let imageHeight = contentHeight * imageFraction
        let captionHeight = contentHeight * captionFraction
        let textHeight = contentHeight * textFraction

        context.beginPDFPage(nil)

        var cursorY = printInfo.bottomMargin + captionHeight + textHeight

        if showsImage {
            let imageRect = CGRect(
                x: printInfo.leftMargin,
                y: cursorY,
                width: contentWidth,
                height: imageHeight
            )
            drawScanImage(page.picture, in: imageRect, context: context)
        }

        if hasCaption {
            cursorY = printInfo.bottomMargin + textHeight
            let captionRect = CGRect(
                x: printInfo.leftMargin,
                y: cursorY,
                width: contentWidth,
                height: captionHeight
            )
            drawScanText(captionText, in: captionRect, context: context, pageSize: pageSize, alignment: .center)
        }

        if hasBody {
            switch page.body {
            case .single(let text):
                let textRect = CGRect(
                    x: printInfo.leftMargin,
                    y: printInfo.bottomMargin,
                    width: contentWidth,
                    height: textHeight
                )
                drawScanAttributedText(text, in: textRect, context: context, pageSize: pageSize)
            case .twoColumn(let left, let right):
                let columnGap: CGFloat = 14
                let columnWidth = (contentWidth - columnGap) / 2
                let leftRect = CGRect(
                    x: printInfo.leftMargin,
                    y: printInfo.bottomMargin,
                    width: columnWidth,
                    height: textHeight
                )
                let rightRect = CGRect(
                    x: printInfo.leftMargin + columnWidth + columnGap,
                    y: printInfo.bottomMargin,
                    width: columnWidth,
                    height: textHeight
                )
                drawScanAttributedText(left, in: leftRect, context: context, pageSize: pageSize)
                drawScanAttributedText(right, in: rightRect, context: context, pageSize: pageSize)
            }
        }

        context.endPDFPage()
    }

    private static func drawScanImage(_ image: NSImage, in rect: CGRect, context: CGContext) {
        var proposedRect = NSRect(origin: .zero, size: image.size)
        guard image.size.width > 0, image.size.height > 0,
              let cgImage = image.cgImage(forProposedRect: &proposedRect, context: nil, hints: nil) else { return }

        let scale = min(rect.width / image.size.width, rect.height / image.size.height)
        let drawSize = CGSize(width: image.size.width * scale, height: image.size.height * scale)
        let drawRect = CGRect(
            x: rect.midX - drawSize.width / 2,
            y: rect.midY - drawSize.height / 2,
            width: drawSize.width,
            height: drawSize.height
        )
        context.draw(cgImage, in: drawRect)
    }

    private static func drawScanText(
        _ text: String,
        in rect: CGRect,
        context: CGContext,
        pageSize: NSSize,
        alignment: NSTextAlignment = .left
    ) {
        guard !text.isEmpty else { return }
        let paragraphStyle = NSMutableParagraphStyle()
        paragraphStyle.alignment = alignment
        paragraphStyle.lineBreakMode = .byWordWrapping
        let attributes: [NSAttributedString.Key: Any] = [
            .font: NSFont.systemFont(ofSize: 11),
            .foregroundColor: NSColor.black,
            .paragraphStyle: paragraphStyle,
        ]
        drawScanAttributedText(
            NSAttributedString(string: text, attributes: attributes),
            in: rect,
            context: context,
            pageSize: pageSize
        )
    }

    private static func drawScanAttributedText(
        _ attributed: NSAttributedString,
        in rect: CGRect,
        context: CGContext,
        pageSize: NSSize
    ) {
        guard attributed.length > 0 else { return }
        let normalized = scanAttributedStringForPrinting(attributed)

        context.saveGState()
        context.translateBy(x: 0, y: pageSize.height)
        context.scaleBy(x: 1, y: -1)

        let flippedY = pageSize.height - rect.maxY
        let drawRect = CGRect(x: rect.origin.x, y: flippedY, width: rect.width, height: rect.height)

        NSGraphicsContext.saveGraphicsState()
        NSGraphicsContext.current = NSGraphicsContext(cgContext: context, flipped: true)
        normalized.draw(with: drawRect, options: [.usesLineFragmentOrigin, .usesFontLeading])
        NSGraphicsContext.restoreGraphicsState()
        context.restoreGState()
    }

    private static func scanAttributedStringForPrinting(_ source: NSAttributedString) -> NSAttributedString {
        let mutable = NSMutableAttributedString(attributedString: source)
        let fullRange = NSRange(location: 0, length: mutable.length)
        guard fullRange.length > 0 else { return mutable }

        mutable.addAttribute(.foregroundColor, value: NSColor.black, range: fullRange)
        mutable.enumerateAttribute(.font, in: fullRange) { value, range, _ in
            let font = (value as? NSFont) ?? NSFont.systemFont(ofSize: 11)
            let scaled = NSFontManager.shared.convert(font, toSize: 11)
            mutable.addAttribute(.font, value: scaled, range: range)
        }
        return mutable
    }

    private static func pdfDocument(from text: String) -> PDFDocument? {
        let paragraphStyle = NSMutableParagraphStyle()
        paragraphStyle.alignment = .left
        paragraphStyle.lineBreakMode = .byWordWrapping

        let attributes: [NSAttributedString.Key: Any] = [
            .font: NSFont.systemFont(ofSize: 12),
            .foregroundColor: NSColor.black,
            .paragraphStyle: paragraphStyle,
        ]
        return pdfDocument(from: NSAttributedString(string: text, attributes: attributes))
    }

    private static func pdfDocument(from attributed: NSAttributedString) -> PDFDocument? {
        let normalized = attributedStringForPrinting(attributed)
        guard normalized.length > 0 else { return nil }

        if let document = pdfDocumentUsingRenderedImages(from: normalized) {
            return document
        }
        return pdfDocumentUsingCoreText(from: normalized)
    }

    private static func attributedStringForPrinting(_ source: NSAttributedString) -> NSAttributedString {
        let mutable = NSMutableAttributedString(attributedString: source)
        let fullRange = NSRange(location: 0, length: mutable.length)
        guard fullRange.length > 0 else { return mutable }

        mutable.addAttribute(.foregroundColor, value: NSColor.black, range: fullRange)
        mutable.enumerateAttribute(.font, in: fullRange) { value, range, _ in
            if value == nil {
                mutable.addAttribute(.font, value: NSFont.systemFont(ofSize: 12), range: range)
            }
        }
        return mutable
    }

    private static func pdfDocumentUsingCoreText(from attributed: NSAttributedString) -> PDFDocument? {
        let printInfo = configuredPrintInfo()
        let pageSize = printInfo.paperSize
        guard pageSize.width > 0, pageSize.height > 0 else { return nil }

        let frameRect = CGRect(
            x: printInfo.leftMargin,
            y: printInfo.bottomMargin,
            width: pageSize.width - printInfo.leftMargin - printInfo.rightMargin,
            height: pageSize.height - printInfo.topMargin - printInfo.bottomMargin
        )

        let pdfData = NSMutableData()
        var mediaBox = CGRect(origin: .zero, size: pageSize)
        guard let consumer = CGDataConsumer(data: pdfData as CFMutableData),
              let context = CGContext(consumer: consumer, mediaBox: &mediaBox, nil) else {
            return nil
        }

        let framesetter = CTFramesetterCreateWithAttributedString(attributed as CFAttributedString)
        var currentIndex = 0
        var pageCount = 0

        while currentIndex < attributed.length {
            context.beginPDFPage(nil)

            let path = CGPath(rect: frameRect, transform: nil)
            let range = CFRange(location: currentIndex, length: attributed.length - currentIndex)
            let frame = CTFramesetterCreateFrame(framesetter, range, path, nil)
            CTFrameDraw(frame, context)

            let visibleRange = CTFrameGetVisibleStringRange(frame)
            context.endPDFPage()
            pageCount += 1

            guard visibleRange.length > 0 else { break }
            currentIndex += visibleRange.length
        }

        context.closePDF()
        guard pageCount > 0 else { return nil }
        return PDFDocument(data: pdfData as Data)
    }

    /// Renders each text page to a bitmap and embeds it in the PDF, matching the photo print pipeline.
    private static func pdfDocumentUsingRenderedImages(from attributed: NSAttributedString) -> PDFDocument? {
        let printInfo = configuredPrintInfo()
        let pageSize = printInfo.paperSize
        guard pageSize.width > 0, pageSize.height > 0 else { return nil }

        let textWidth = pageSize.width - printInfo.leftMargin - printInfo.rightMargin
        let textHeight = pageSize.height - printInfo.topMargin - printInfo.bottomMargin
        let containerSize = NSSize(width: textWidth, height: textHeight)

        let textStorage = NSTextStorage(attributedString: attributed)
        let layoutManager = NSLayoutManager()
        textStorage.addLayoutManager(layoutManager)

        let pdfData = NSMutableData()
        var mediaBox = CGRect(origin: .zero, size: pageSize)
        guard let consumer = CGDataConsumer(data: pdfData as CFMutableData),
              let context = CGContext(consumer: consumer, mediaBox: &mediaBox, nil) else {
            return nil
        }

        var pageCount = 0
        while true {
            let textContainer = NSTextContainer(size: containerSize)
            textContainer.lineFragmentPadding = 0
            layoutManager.addTextContainer(textContainer)
            layoutManager.ensureLayout(for: textContainer)

            let glyphRange = layoutManager.glyphRange(for: textContainer)
            guard glyphRange.length > 0 else { break }

            let charRange = layoutManager.characterRange(forGlyphRange: glyphRange, actualGlyphRange: nil)
            let pageText = attributed.attributedSubstring(from: charRange)
            let pageImage = renderTextPageImage(
                pageText: pageText,
                pageSize: pageSize,
                printInfo: printInfo
            )

            context.beginPDFPage(nil)
            if let cgImage = pageImage.cgImage(forProposedRect: nil, context: nil, hints: nil) {
                context.draw(cgImage, in: CGRect(origin: .zero, size: pageSize))
            }
            context.endPDFPage()
            pageCount += 1

            if NSMaxRange(glyphRange) >= layoutManager.numberOfGlyphs { break }
        }

        context.closePDF()
        guard pageCount > 0 else { return nil }
        return PDFDocument(data: pdfData as Data)
    }

    private static func renderTextPageImage(
        pageText: NSAttributedString,
        pageSize: NSSize,
        printInfo: NSPrintInfo
    ) -> NSImage {
        let textRect = NSRect(
            x: printInfo.leftMargin,
            y: printInfo.bottomMargin,
            width: pageSize.width - printInfo.leftMargin - printInfo.rightMargin,
            height: pageSize.height - printInfo.topMargin - printInfo.bottomMargin
        )

        let image = NSImage(size: pageSize)
        image.lockFocus()
        NSColor.white.setFill()
        NSRect(origin: .zero, size: pageSize).fill()
        pageText.draw(
            with: textRect,
            options: [.usesLineFragmentOrigin, .usesFontLeading]
        )
        image.unlockFocus()
        return image
    }

    private static func flattenedPDF(from source: PDFDocument) -> PDFDocument? {
        guard source.pageCount > 0 else { return nil }

        let printInfo = configuredPrintInfo()
        let pageSize = printInfo.paperSize
        guard pageSize.width > 0, pageSize.height > 0 else { return nil }

        let pdfData = NSMutableData()
        var mediaBox = CGRect(origin: .zero, size: pageSize)

        guard let consumer = CGDataConsumer(data: pdfData as CFMutableData),
              let context = CGContext(consumer: consumer, mediaBox: &mediaBox, nil) else {
            return nil
        }

        for index in 0..<source.pageCount {
            guard let page = source.page(at: index) else { continue }
            let pageBounds = page.bounds(for: .mediaBox)
            guard pageBounds.width > 0, pageBounds.height > 0 else { continue }

            context.beginPDFPage(nil)
            context.saveGState()

            let scale = min(pageSize.width / pageBounds.width, pageSize.height / pageBounds.height)
            let drawWidth = pageBounds.width * scale
            let drawHeight = pageBounds.height * scale
            let offsetX = (pageSize.width - drawWidth) / 2
            let offsetY = (pageSize.height - drawHeight) / 2

            context.translateBy(x: offsetX, y: offsetY)
            context.scaleBy(x: scale, y: scale)
            context.translateBy(x: -pageBounds.origin.x, y: -pageBounds.origin.y)
            page.draw(with: .mediaBox, to: context)

            context.restoreGState()
            context.endPDFPage()
        }

        context.closePDF()
        guard !(pdfData as Data).isEmpty else { return nil }
        return PDFDocument(data: pdfData as Data)
    }

    private static func pdfDocument(from image: NSImage) -> PDFDocument? {
        let printInfo = configuredPrintInfo()
        let pageSize = printInfo.paperSize
        guard pageSize.width > 0, pageSize.height > 0 else { return nil }

        let pdfData = NSMutableData()
        var mediaBox = CGRect(origin: .zero, size: pageSize)

        guard let consumer = CGDataConsumer(data: pdfData as CFMutableData),
              let context = CGContext(consumer: consumer, mediaBox: &mediaBox, nil) else {
            return nil
        }

        context.beginPDFPage(nil)

        let imageSize = image.size
        if imageSize.width > 0, imageSize.height > 0,
           let cgImage = image.cgImage(forProposedRect: nil, context: nil, hints: nil) {
            let scale = min(pageSize.width / imageSize.width, pageSize.height / imageSize.height)
            let drawSize = CGSize(width: imageSize.width * scale, height: imageSize.height * scale)
            let drawRect = CGRect(
                x: (pageSize.width - drawSize.width) / 2,
                y: (pageSize.height - drawSize.height) / 2,
                width: drawSize.width,
                height: drawSize.height
            )
            context.draw(cgImage, in: drawRect)
        }

        context.endPDFPage()
        context.closePDF()

        return PDFDocument(data: pdfData as Data)
    }

    private static func formattedContactsText(_ contacts: [PrintableContact]) -> String {
        contacts.map { contact in
            var lines = [contact.displayName]
            if let organization = contact.organization, !organization.isEmpty,
               organization.caseInsensitiveCompare(contact.displayName) != .orderedSame {
                lines.append("Organization: \(organization)")
            }
            for phone in contact.phoneNumbers {
                lines.append("Phone: \(phone)")
            }
            for email in contact.emailAddresses {
                lines.append("Email: \(email)")
            }
            for address in contact.postalAddresses {
                lines.append("Address:\n\(address)")
            }
            return lines.joined(separator: "\n")
        }
        .joined(separator: "\n\n" + String(repeating: "─", count: 40) + "\n\n")
    }

    private static func showNoContactsAlert() {
        let alert = NSAlert()
        alert.messageText = "No Contacts Selected"
        alert.informativeText = "Select at least one contact to print."
        alert.alertStyle = .informational
        alert.addButton(withTitle: "OK")
        alert.runModal()
    }

    private static func showPrintFailedAlert() {
        let alert = NSAlert()
        alert.messageText = "Print Failed"
        alert.informativeText = "The text could not be prepared for printing."
        alert.alertStyle = .warning
        alert.addButton(withTitle: "OK")
        alert.runModal()
    }

    private static func showSaveFailedAlert() {
        let alert = NSAlert()
        alert.messageText = "Save Failed"
        alert.informativeText = "The canvas could not be saved as a PDF."
        alert.alertStyle = .warning
        alert.addButton(withTitle: "OK")
        alert.runModal()
    }

    static func showEmptyCanvasAlert() {
        let alert = NSAlert()
        alert.messageText = "Nothing to Print"
        alert.informativeText = "Add a drawing, text, or image to the canvas before printing."
        alert.alertStyle = .informational
        alert.addButton(withTitle: "OK")
        alert.runModal()
    }

    private static func showEmptyTextAlert() {
        let alert = NSAlert()
        alert.messageText = "No Text to Print"
        alert.informativeText = "Enter some text before printing."
        alert.alertStyle = .informational
        alert.addButton(withTitle: "OK")
        alert.runModal()
    }

    private static func showUnsupportedAlert(for url: URL) {
        let alert = NSAlert()
        alert.messageText = "Unsupported File"
        alert.informativeText = "\"\(url.lastPathComponent)\" cannot be printed."
        alert.alertStyle = .warning
        alert.addButton(withTitle: "OK")
        alert.runModal()
    }
}