From f52ad48937ef43679d507d7a86997291aa58101b Mon Sep 17 00:00:00 2001
From: Charles Vien <charles.v@posthog.com>
Date: Mon, 5 Jan 2026 11:51:26 -0800
Subject: [PATCH 1/3] Preserve line breaks in user chat messages

---
 .../message-editor/tiptap/useDraftSync.ts     | 47 +++++++++++++++++--
 1 file changed, 43 insertions(+), 4 deletions(-)

diff --git a/apps/array/src/renderer/features/message-editor/tiptap/useDraftSync.ts b/apps/array/src/renderer/features/message-editor/tiptap/useDraftSync.ts
index b9857a73..c3136554 100644
--- a/apps/array/src/renderer/features/message-editor/tiptap/useDraftSync.ts
+++ b/apps/array/src/renderer/features/message-editor/tiptap/useDraftSync.ts
@@ -9,6 +9,10 @@ function tiptapJsonToEditorContent(json: JSONContent): EditorContent {
   const traverse = (node: JSONContent) => {
     if (node.type === "text" && node.text) {
       segments.push({ type: "text", text: node.text });
+    } else if (node.type === "hardBreak") {
+      // Shift+Enter creates a hard break within a paragraph
+      // Use two trailing spaces + newline for markdown line break (<br>)
+      segments.push({ type: "text", text: "  \n" });
     } else if (node.type === "mentionChip" && node.attrs) {
       segments.push({
         type: "chip",
@@ -18,6 +22,15 @@ function tiptapJsonToEditorContent(json: JSONContent): EditorContent {
           label: node.attrs.label,
         },
       });
+    } else if (node.type === "doc" && node.content) {
+      // Add double newlines between paragraphs for markdown rendering
+      // (single newlines in markdown become spaces, double newlines create paragraph breaks)
+      for (let i = 0; i < node.content.length; i++) {
+        if (i > 0) {
+          segments.push({ type: "text", text: "\n\n" });
+        }
+        traverse(node.content[i]);
+      }
     } else if (node.content) {
       for (const child of node.content) {
         traverse(child);
@@ -30,13 +43,33 @@ function tiptapJsonToEditorContent(json: JSONContent): EditorContent {
 }
 
 function editorContentToTiptapJson(content: EditorContent): JSONContent {
-  const paragraphContent: JSONContent[] = [];
+  const paragraphs: JSONContent[] = [];
+  let currentParagraphContent: JSONContent[] = [];
+
+  const flushParagraph = () => {
+    paragraphs.push({ type: "paragraph", content: currentParagraphContent });
+    currentParagraphContent = [];
+  };
 
   for (const seg of content.segments) {
     if (seg.type === "text") {
-      paragraphContent.push({ type: "text", text: seg.text });
+      const paragraphParts = seg.text.split("\n\n");
+      for (let i = 0; i < paragraphParts.length; i++) {
+        if (i > 0) {
+          flushParagraph();
+        }
+        const lineParts = paragraphParts[i].split(/  \n|\n/);
+        for (let j = 0; j < lineParts.length; j++) {
+          if (j > 0) {
+            currentParagraphContent.push({ type: "hardBreak" });
+          }
+          if (lineParts[j]) {
+            currentParagraphContent.push({ type: "text", text: lineParts[j] });
+          }
+        }
+      }
     } else {
-      paragraphContent.push({
+      currentParagraphContent.push({
         type: "mentionChip",
         attrs: {
           type: seg.chip.type,
@@ -47,9 +80,15 @@ function editorContentToTiptapJson(content: EditorContent): JSONContent {
     }
   }
 
+  flushParagraph();
+
+  if (paragraphs.length === 0) {
+    paragraphs.push({ type: "paragraph", content: [] });
+  }
+
   return {
     type: "doc",
-    content: [{ type: "paragraph", content: paragraphContent }],
+    content: paragraphs,
   };
 }
 

From 73a0a6248014fd6b9022f5fb10a78abc341597b3 Mon Sep 17 00:00:00 2001
From: Charles Vien <charles.v@posthog.com>
Date: Mon, 5 Jan 2026 12:49:24 -0800
Subject: [PATCH 2/3] Update useDraftSync.ts

---
 .../src/renderer/features/message-editor/tiptap/useDraftSync.ts | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/apps/array/src/renderer/features/message-editor/tiptap/useDraftSync.ts b/apps/array/src/renderer/features/message-editor/tiptap/useDraftSync.ts
index c3136554..615fb543 100644
--- a/apps/array/src/renderer/features/message-editor/tiptap/useDraftSync.ts
+++ b/apps/array/src/renderer/features/message-editor/tiptap/useDraftSync.ts
@@ -58,7 +58,7 @@ function editorContentToTiptapJson(content: EditorContent): JSONContent {
         if (i > 0) {
           flushParagraph();
         }
-        const lineParts = paragraphParts[i].split(/  \n|\n/);
+        const lineParts = paragraphParts[i].split(/ {2}\n|\n/);
         for (let j = 0; j < lineParts.length; j++) {
           if (j > 0) {
             currentParagraphContent.push({ type: "hardBreak" });

From 028f9443a4700e707e721d8c6efef6945aff50bb Mon Sep 17 00:00:00 2001
From: Charles Vien <charles.v@posthog.com>
Date: Tue, 6 Jan 2026 11:36:49 -0800
Subject: [PATCH 3/3] Update useTiptapEditor.ts

---
 .../renderer/features/message-editor/tiptap/useTiptapEditor.ts  | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/apps/array/src/renderer/features/message-editor/tiptap/useTiptapEditor.ts b/apps/array/src/renderer/features/message-editor/tiptap/useTiptapEditor.ts
index a4be146a..3486e304 100644
--- a/apps/array/src/renderer/features/message-editor/tiptap/useTiptapEditor.ts
+++ b/apps/array/src/renderer/features/message-editor/tiptap/useTiptapEditor.ts
@@ -173,7 +173,7 @@ export function useTiptapEditor(options: UseTiptapEditorOptions) {
 
             const textToInsert = paths.map((p) => `"${p}"`).join(" ");
 
-            view.dispatch(view.state.tr.insertText(textToInsert + " ", pos));
+            view.dispatch(view.state.tr.insertText(`${textToInsert} `, pos));
             return true;
           }