oAI/Services/ConversationExportService.swift

@@ -76,7 +76,8 @@ enum ConversationExportService {
     font-size: 14px; color: #1a1a1a; background: #ffffff; max-width: 820px; margin: 40px auto; \
     padding: 0 24px; line-height: 1.5; }
     h1 { font-size: 22px; border-bottom: 1px solid #ddd; padding-bottom: 12px; }
-    .message { margin: 20px 0; padding: 12px 16px; border-radius: 8px; border-left: 4px solid transparent; }
+    .message { margin: 20px 0; padding: 12px 16px; border-radius: 8px; border-left: 4px solid transparent; \
+    break-inside: avoid; page-break-inside: avoid; }
     .message.user { background: #f5f7fa; border-left-color: #4a90d9; }
     .message.assistant { background: #fafafa; border-left-color: #8a8a8a; }
     .role { font-size: 11px; font-weight: 600; text-transform: uppercase; letter-spacing: 0.04em; \
@@ -115,16 +116,22 @@ enum ConversationExportService {
 
     // MARK: - PDF
 
+    enum PDFError: LocalizedError {
+        case generationFailed
+        var errorDescription: String? { "Failed to generate PDF" }
+    }
+
+    /// Uses WKWebView's real print pipeline (NSPrintOperation), not createPDF(). Confirmed
+    /// empirically by comparing against a normal reference PDF: createPDF() never paginates —
+    /// it captures the webview's frame verbatim, or auto-grows to ONE continuous page matching
+    /// full content height for overflow (a single page many thousands of points tall for a long
+    /// conversation). That's a fundamentally different, non-standard document shape from any
+    /// normal PDF, which is what actually made ordinarily-sized text read as "huge" — there was
+    /// no page of a familiar size to judge it against. Printing through NSPrintOperation with a
+    /// real US Letter paper size gives genuine multi-page pagination, matching what any other
+    /// app's "export/print to PDF" produces.
     static func pdfData(name: String, messages: [Message]) async throws -> Data {
         let htmlString = html(name: name, messages: messages)
-        // Confirmed empirically (not guessed): with WKPDFConfiguration.rect left at its
-        // default, createPDF captures exactly the webview's frame size verbatim for content
-        // that fits within it, and auto-grows to a single tall page matching the full
-        // scrollable content when it overflows — it does not paginate. Manually resizing the
-        // frame to match content height beforehand (a previous attempt at this) actively
-        // breaks that: the captured page ends up NOT matching the resized frame at all,
-        // producing a small, oddly-proportioned page that made ordinary-sized text look
-        // enormous relative to it. So: set a sane starting frame and leave it alone.
         let webView = WKWebView(frame: NSRect(x: 0, y: 0, width: 850, height: 1100))
         webView.pageZoom = 1.0
         // PDF content is baked at export time, so it can't respond to prefers-color-scheme
@@ -134,11 +141,34 @@ enum ConversationExportService {
         webView.navigationDelegate = delegate
         try await delegate.load(htmlString, in: webView)
 
-        return try await withCheckedThrowingContinuation { continuation in
-            webView.createPDF(configuration: WKPDFConfiguration()) { result in
-                continuation.resume(with: result)
+        let tempURL = FileManager.default.temporaryDirectory.appendingPathComponent(UUID().uuidString + ".pdf")
+        defer { try? FileManager.default.removeItem(at: tempURL) }
+
+        let printInfo = NSPrintInfo()
+        printInfo.paperSize = NSSize(width: 612, height: 792) // US Letter
+        printInfo.topMargin = 36
+        printInfo.bottomMargin = 36
+        printInfo.leftMargin = 36
+        printInfo.rightMargin = 36
+        printInfo.horizontalPagination = .fit
+        printInfo.jobDisposition = .save
+        printInfo.dictionary()[NSPrintInfo.AttributeKey.jobSavingURL] = tempURL
+
+        let printOp = webView.printOperation(with: printInfo)
+        printOp.showsPrintPanel = false
+        printOp.showsProgressPanel = false
+
+        // NSPrintOperation.run() blocks synchronously, so it's dispatched off the main actor
+        // to avoid freezing the UI while a long conversation paginates.
+        let success = await withCheckedContinuation { (continuation: CheckedContinuation<Bool, Never>) in
+            DispatchQueue.global(qos: .userInitiated).async {
+                continuation.resume(returning: printOp.run())
             }
         }
+        guard success, let data = try? Data(contentsOf: tempURL) else {
+            throw PDFError.generationFailed
+        }
+        return data
     }
 
     private final class PDFLoadDelegate: NSObject, WKNavigationDelegate {