diff --git a/apps/obsidian/src/components/canvas/CustomContextMenu.tsx b/apps/obsidian/src/components/canvas/CustomContextMenu.tsx
index eeaf3a03c..de4b58460 100644
--- a/apps/obsidian/src/components/canvas/CustomContextMenu.tsx
+++ b/apps/obsidian/src/components/canvas/CustomContextMenu.tsx
@@ -10,7 +10,10 @@ import {
 } from "tldraw";
 import type { TFile } from "obsidian";
 import { usePlugin } from "~/components/PluginContext";
-import { convertToDiscourseNode } from "./utils/convertToDiscourseNode";
+import {
+  canConvertShapeToNode,
+  convertToDiscourseNode,
+} from "./utils/convertToDiscourseNode";
 import {
   convertArrowToDiscourseRelation,
   getValidRelationTypesForArrow,
@@ -34,9 +37,11 @@ export const CustomContextMenu = ({
     [editor],
   );
 
-  const shouldShowConvertTo =
-    selectedShape &&
-    (selectedShape.type === "text" || selectedShape.type === "image");
+  const shouldShowConvertTo = useValue(
+    "shouldShowConvertTo",
+    () => canConvertShapeToNode(editor, editor.getOnlySelectedShape()),
+    [editor],
+  );
 
   const isReadonly = useValue(
     "isReadonly",
@@ -86,7 +91,7 @@ export const CustomContextMenu = ({
           </TldrawUiMenuSubmenu>
         </TldrawUiMenuGroup>
       )}
-      {shouldShowConvertTo && (
+      {shouldShowConvertTo && selectedShape && (
         <TldrawUiMenuGroup id="convert-to">
           <TldrawUiMenuSubmenu id="convert-to-submenu" label="Convert To">
             {plugin.settings.nodeTypes.map((nodeType) => (
@@ -95,6 +100,7 @@ export const CustomContextMenu = ({
                 id={`convert-to-${nodeType.id}`}
                 label={"Convert to " + nodeType.name}
                 icon="file-type"
+                disabled={isReadonly}
                 onSelect={() => {
                   void convertToDiscourseNode({
                     editor,
diff --git a/apps/obsidian/src/components/canvas/utils/convertToDiscourseNode.ts b/apps/obsidian/src/components/canvas/utils/convertToDiscourseNode.ts
index 16d6fd738..afd05d6bf 100644
--- a/apps/obsidian/src/components/canvas/utils/convertToDiscourseNode.ts
+++ b/apps/obsidian/src/components/canvas/utils/convertToDiscourseNode.ts
@@ -3,7 +3,7 @@ import {
   TLShape,
   createShapeId,
   TLAssetId,
-  TLTextShape,
+  TLRichText,
   TLShapeId,
   renderPlaintextFromRichText,
 } from "tldraw";
@@ -20,6 +20,26 @@ import { showToast } from "./toastUtils";
 import ModifyNodeModal from "~/components/ModifyNodeModal";
 import { calcDiscourseNodeSize } from "~/utils/calcDiscourseNodeSize";
 
+// Only shapes storing a richText prop. Arrow is not one (it uses props.text) and
+// owns the "Relation" submenu instead.
+const RICH_TEXT_SHAPE_TYPES: readonly string[] = ["text", "geo", "note"];
+
+const getShapeText = (editor: Editor, shape: TLShape): string => {
+  if (!RICH_TEXT_SHAPE_TYPES.includes(shape.type)) return "";
+  const { richText } = shape.props as { richText?: TLRichText };
+  if (!richText) return "";
+  return renderPlaintextFromRichText(editor, richText).trim();
+};
+
+export const canConvertShapeToNode = (
+  editor: Editor,
+  shape: TLShape | null,
+): boolean => {
+  if (!shape) return false;
+  // Images are gated at conversion time, not here: the asset may not resolve to a vault file.
+  return shape.type === "image" || getShapeText(editor, shape) !== "";
+};
+
 type ConvertToDiscourseNodeArgs = {
   editor: Editor;
   shape: TLShape;
@@ -34,15 +54,15 @@ export const convertToDiscourseNode = async (
   try {
     const { shape } = args;
 
-    if (shape.type === "text") {
-      return await convertTextShapeToNode(args);
-    } else if (shape.type === "image") {
+    if (shape.type === "image") {
       return await convertImageShapeToNode(args);
+    } else if (RICH_TEXT_SHAPE_TYPES.includes(shape.type)) {
+      return convertTextBearingShapeToNode(args);
     } else {
       showToast({
         severity: "warning",
         title: "Cannot Convert",
-        description: "Only text and image shapes can be converted",
+        description: "Only shapes with text or images can be converted",
         targetCanvasId: args.canvasFile.path,
       });
     }
@@ -57,23 +77,20 @@ export const convertToDiscourseNode = async (
   }
 };
 
-const convertTextShapeToNode = ({
+const convertTextBearingShapeToNode = ({
   editor,
   shape,
   nodeType,
   plugin,
   canvasFile,
 }: ConvertToDiscourseNodeArgs): TLShapeId | undefined => {
-  const text = renderPlaintextFromRichText(
-    editor,
-    (shape as TLTextShape).props.richText,
-  );
+  const text = getShapeText(editor, shape);
 
-  if (!text.trim()) {
+  if (!text) {
     showToast({
       severity: "warning",
       title: "Cannot Convert",
-      description: "Text shape has no content to convert",
+      description: "Shape has no text to convert",
       targetCanvasId: canvasFile.path,
     });
     return undefined;
@@ -85,7 +102,7 @@ const convertTextShapeToNode = ({
     nodeTypes: plugin.settings.nodeTypes,
     plugin,
     initialNodeType: nodeType,
-    initialTitle: text.trim(),
+    initialTitle: text,
     onSubmit: async ({
       nodeType: selectedNodeType,
       title,
@@ -116,11 +133,11 @@ const convertTextShapeToNode = ({
         showToast({
           severity: "success",
           title: "Shape Converted",
-          description: `Converted text to ${selectedNodeType.name}`,
+          description: `Converted shape to ${selectedNodeType.name}`,
           targetCanvasId: canvasFile.path,
         });
       } catch (error) {
-        console.error("Error creating node from text:", error);
+        console.error("Error creating node from shape text:", error);
         throw error;
       }
     },