diff --git a/apps/vscode/CHANGELOG.md b/apps/vscode/CHANGELOG.md
index a7e3592a..cde2e3c5 100644
--- a/apps/vscode/CHANGELOG.md
+++ b/apps/vscode/CHANGELOG.md
@@ -3,6 +3,7 @@
 ## 1.138.0 (Unreleased)
 
 - In Positron, running a Python cell in a knitr document now respects the `quarto.cells.useReticulate` setting, instead of always routing it through reticulate on the R console (<https://github.com/quarto-dev/quarto/pull/1116>).
+- In Positron, fixed how the "Render on Save" checkbox works in the visual editor (<https://github.com/quarto-dev/quarto/pull/1121>).
 
 ## 1.137.0 (Release on 2026-09-04)
 
diff --git a/apps/vscode/package.json b/apps/vscode/package.json
index 1902a494..a81429df 100644
--- a/apps/vscode/package.json
+++ b/apps/vscode/package.json
@@ -456,7 +456,7 @@
         "command": "quarto.toggleRenderOnSave",
         "title": "Render on Save",
         "category": "Quarto",
-        "enablement": "editorLangId == quarto",
+        "enablement": "editorLangId == quarto || activeCustomEditorId == 'quarto.visualEditor'",
         "actionBarOptions": {
           "controlType": "checkbox",
           "checked": "(quarto.editor.type == quarto && quarto.editor.renderOnSave) || (quarto.editor.type == 'quarto-shiny' && quarto.editor.renderOnSaveShiny)"
diff --git a/apps/vscode/src/providers/context-keys.ts b/apps/vscode/src/providers/context-keys.ts
index 65e88379..416f8401 100644
--- a/apps/vscode/src/providers/context-keys.ts
+++ b/apps/vscode/src/providers/context-keys.ts
@@ -32,26 +32,36 @@ export function activateContextKeySetter(
   engine: MarkdownEngine
 ) {
   // set the initial context keys
-  setEditorContextKeys(vscode.window.activeTextEditor, engine);
-  setLanguageContextKeys(vscode.window.activeTextEditor, engine);
+  setEditorContextKeys(vscode.window.activeTextEditor?.document, engine);
+  setLanguageContextKeys(vscode.window.activeTextEditor?.document, engine);
 
   // register for quarto.render.renderOnSave or quarto.render.renderOnSaveShiny configuration change notification
   context.subscriptions.push(vscode.workspace.onDidChangeConfiguration(event => {
     // if the change affects quarto.render.renderOnSave or quarto.render.renderOnSaveShiny, set the editor context keys.
     if (event.affectsConfiguration('quarto.render.renderOnSave') || event.affectsConfiguration('quarto.render.renderOnSaveShiny')) {
-      setEditorContextKeys(vscode.window.activeTextEditor, engine);
+      const document = vscode.window.activeTextEditor?.document ?? VisualEditorProvider.activeEditor()?.document;
+      setEditorContextKeys(document, engine);
     }
   }));
 
   // set context keys when active text editor changes
   vscode.window.onDidChangeActiveTextEditor(activeTextEditor => {
-    setEditorContextKeys(activeTextEditor, engine);
-    setLanguageContextKeys(activeTextEditor, engine);
+    setEditorContextKeys(activeTextEditor?.document, engine);
+    setLanguageContextKeys(activeTextEditor?.document, engine);
   },
     null,
     context.subscriptions
   );
 
+  // set context keys when a visual editor becomes active (custom editors
+  // don't fire onDidChangeActiveTextEditor)
+  context.subscriptions.push(
+    VisualEditorProvider.onDidChangeActiveEditor()(editor => {
+      setEditorContextKeys(editor.document, engine);
+      setLanguageContextKeys(editor.document, engine);
+    })
+  );
+
   // set context keys on changes to the document (if it's active)
   vscode.workspace.onDidChangeTextDocument(event => {
     const activeEditor = vscode.window.activeTextEditor;
@@ -59,8 +69,8 @@ export function activateContextKeySetter(
       // TODO: this debounce is being created and called immediately, which is not correct.
       debounce(
         () => {
-          setEditorContextKeys(activeEditor, engine);
-          setLanguageContextKeys(activeEditor, engine);
+          setEditorContextKeys(activeEditor.document, engine);
+          setLanguageContextKeys(activeEditor.document, engine);
         },
         debounceOnDidChangeDocumentMs
       )();
@@ -110,11 +120,11 @@ export function toggleRenderOnSaveOverride() {
 }
 
 // sets editor context keys
-function setEditorContextKeys(activeTextEditor: vscode.TextEditor | undefined, engine: MarkdownEngine) {
+function setEditorContextKeys(document: vscode.TextDocument | undefined, engine: MarkdownEngine) {
   // if a Quarto doc is active, set the editor context keys
-  if (isQuartoDoc(activeTextEditor?.document)) {
+  if (isQuartoDoc(document)) {
     // set the quarto.editor.type context key
-    quartoEditorType = !isQuartoShinyDoc(engine, activeTextEditor?.document)
+    quartoEditorType = !isQuartoShinyDoc(engine, document)
       ? 'quarto'
       : 'quarto-shiny';
     vscode.commands.executeCommand<string>(
@@ -145,13 +155,13 @@ function setEditorContextKeys(activeTextEditor: vscode.TextEditor | undefined, e
   }
 }
 
-function setLanguageContextKeys(activeTextEditor: vscode.TextEditor | undefined, engine: MarkdownEngine) {
-  if (!activeTextEditor || !isQuartoDoc(activeTextEditor.document)) {
+function setLanguageContextKeys(document: vscode.TextDocument | undefined, engine: MarkdownEngine) {
+  if (!document || !isQuartoDoc(document)) {
     return;
   }
 
   // expose main language for use in keybindings, etc
-  const tokens = engine.parse(activeTextEditor.document);
+  const tokens = engine.parse(document);
   const language = mainLanguage(tokens);
   vscode.commands.executeCommand(
     'setContext',
diff --git a/apps/vscode/src/providers/editor/editor.ts b/apps/vscode/src/providers/editor/editor.ts
index eebc811f..5c60fb33 100644
--- a/apps/vscode/src/providers/editor/editor.ts
+++ b/apps/vscode/src/providers/editor/editor.ts
@@ -26,7 +26,9 @@ import {
   Selection,
   TextEditorRevealType,
   GlobPattern,
-  TabInputText
+  TabInputText,
+  Event,
+  EventEmitter
 } from "vscode";
 
 import { projectDirForDocument, QuartoContext } from "quarto-core";
@@ -268,6 +270,11 @@ export class VisualEditorProvider implements CustomTextEditorProvider {
     this.editorPendingSwitchToVisual.add(document.uri.toString());
   }
 
+  // fires when a visual editor's webview panel becomes active
+  public static onDidChangeActiveEditor(): Event<TrackedEditor> {
+    return this.visualEditors.onDidChangeActiveEditor;
+  }
+
   public static activeEditor(includeVisible?: boolean): QuartoVisualEditor | undefined {
     const editor = this.visualEditors.activeEditor(includeVisible);
     if (editor) {
@@ -677,17 +684,27 @@ interface VisualEditorTracker {
   track: (document: TextDocument, webviewPanel: WebviewPanel, editor: VSCodeVisualEditor) => Disposable;
   editorForUri: (uri: Uri) => TrackedEditor | undefined;
   activeEditor: (includeVisible?: boolean) => TrackedEditor | undefined;
+  onDidChangeActiveEditor: Event<TrackedEditor>;
 }
 
 function visualEditorTracker(): VisualEditorTracker {
 
   const activeEditors = new Array<TrackedEditor>();
+  const onDidChangeActiveEditorEmitter = new EventEmitter<TrackedEditor>();
 
   return {
     track: (document: TextDocument, webviewPanel: WebviewPanel, editor: VSCodeVisualEditor): Disposable => {
-      activeEditors.push({ document, webviewPanel, editor });
+      const trackedEditor = { document, webviewPanel, editor };
+      activeEditors.push(trackedEditor);
+      // notify when this editor's webview panel becomes active
+      const viewStateDisposable = webviewPanel.onDidChangeViewState(e => {
+        if (e.webviewPanel.active) {
+          onDidChangeActiveEditorEmitter.fire(trackedEditor);
+        }
+      });
       return {
         dispose: () => {
+          viewStateDisposable.dispose();
           const idx = activeEditors.findIndex(editor => editor.webviewPanel === webviewPanel);
           if (idx !== -1) {
             activeEditors.splice(idx, 1);
@@ -711,7 +728,8 @@ function visualEditorTracker(): VisualEditorTracker {
         }
 
       });
-    }
+    },
+    onDidChangeActiveEditor: onDidChangeActiveEditorEmitter.event
   };
 }