diff --git a/rtl-spec/components/commands-publish-button.spec.tsx b/rtl-spec/components/commands-publish-button.spec.tsx
index 0871a16de8..4f6f561696 100644
--- a/rtl-spec/components/commands-publish-button.spec.tsx
+++ b/rtl-spec/components/commands-publish-button.spec.tsx
@@ -40,9 +40,21 @@ type GistCreateOpts = {
   public: boolean;
 };
 
+class RequestError extends Error {
+  public message: string;
+  public status: number;
+
+  public constructor(message: string, status: number) {
+    super(message);
+
+    this.message = message;
+    this.status = status;
+  }
+}
+
 describe('Action button component', () => {
   const description = 'Electron Fiddle Gist';
-  const errorMessage = '💀';
+  const error = new RequestError("Don't be blue 💙", 401);
   let app: App;
   let mocktokit: OctokitMock;
   let state: AppState;
@@ -228,8 +240,9 @@ describe('Action button component', () => {
     });
 
     it('handles an error in Gist publishing', async () => {
+      state.showGenericDialog = vi.fn().mockReturnValue({ confirm: true });
       mocktokit.gists.create.mockImplementation(() => {
-        throw new Error(errorMessage);
+        throw new RequestError(error.message, error.status);
       });
 
       state.editorMosaic.isEdited = true;
@@ -240,6 +253,11 @@ describe('Action button component', () => {
 
       // On failure the editor should still be considered edited
       expect(state.editorMosaic.isEdited).toBe(true);
+      expect(state.showGenericDialog).toHaveBeenCalledWith(
+        expect.objectContaining({
+          label: expect.stringContaining('Publishing Fiddle to GitHub failed.'),
+        }),
+      );
     });
 
     it('can publish private gists', async () => {
@@ -292,16 +310,16 @@ describe('Action button component', () => {
     });
 
     it('notifies the user if updating fails', async () => {
+      state.showGenericDialog = vi.fn().mockReturnValue({ confirm: true });
       mocktokit.gists.update.mockImplementation(() => {
-        throw new Error(errorMessage);
+        throw new RequestError(error.message, error.status);
       });
 
       await instance.performGistAction();
 
-      expect(window.ElectronFiddle.showWarningDialog).toHaveBeenCalledWith(
+      expect(state.showGenericDialog).toHaveBeenCalledWith(
         expect.objectContaining({
-          detail: expect.stringContaining(errorMessage),
-          message: expect.stringContaining('Updating Fiddle Gist failed.'),
+          label: expect.stringContaining('Updating Fiddle Gist failed.'),
         }),
       );
     });
@@ -325,16 +343,16 @@ describe('Action button component', () => {
     });
 
     it('notifies the user if deleting fails', async () => {
+      state.showGenericDialog = vi.fn().mockReturnValue({ confirm: true });
       mocktokit.gists.delete.mockImplementation(() => {
-        throw new Error(errorMessage);
+        throw new RequestError(error.message, error.status);
       });
 
       await instance.performGistAction();
 
-      expect(window.ElectronFiddle.showWarningDialog).toHaveBeenCalledWith(
+      expect(state.showGenericDialog).toHaveBeenCalledWith(
         expect.objectContaining({
-          detail: expect.stringContaining(errorMessage),
-          message: expect.stringContaining('Deleting Fiddle Gist failed.'),
+          label: expect.stringContaining('Deleting Fiddle Gist failed.'),
         }),
       );
     });
diff --git a/src/renderer/components/commands-action-button.tsx b/src/renderer/components/commands-action-button.tsx
index efb8aaddc0..128e411080 100644
--- a/src/renderer/components/commands-action-button.tsx
+++ b/src/renderer/components/commands-action-button.tsx
@@ -16,10 +16,12 @@ import { observer } from 'mobx-react';
 import {
   EditorId,
   EditorValues,
+  GenericDialogType,
   GistActionState,
   GistActionType,
   PACKAGE_NAME,
 } from '../../interfaces';
+import { FIDDLE_GIST_DESCRIPTION_PLACEHOLDER } from '../constants';
 import { AppState } from '../state';
 import { ensureRequiredFiles } from '../utils/editor-utils';
 import { getOctokit } from '../utils/octokit';
@@ -98,7 +100,7 @@ export const GistActionButton = observer(
     }
 
     private getFiddleDescriptionFromUser(): Promise<string | undefined> {
-      const placeholder = 'Electron Fiddle Gist' as const;
+      const placeholder = FIDDLE_GIST_DESCRIPTION_PLACEHOLDER;
       return this.props.appState.showInputDialog({
         defaultInput: placeholder,
         label: 'Please provide a brief description for your Fiddle Gist',
@@ -156,11 +158,23 @@ export const GistActionButton = observer(
       } catch (error: any) {
         console.warn(`Could not publish gist`, { error });
 
-        window.ElectronFiddle.showWarningDialog({
-          message:
-            'Publishing Fiddle to GitHub failed. Are you connected to the Internet?',
-          detail: `GitHub encountered the following error: ${error.message}`,
-        });
+        if (error.status === 401 || error.status === 403) {
+          const { confirm } = await this.props.appState.showGenericDialog({
+            label: `Publishing Fiddle to GitHub failed. GitHub encountered the following error: ${error.message}`,
+            ok: 'Update token',
+            cancel: 'Close',
+            type: GenericDialogType.warning,
+            wantsInput: false,
+          });
+
+          if (confirm) {
+            this.showGitHubTokenSettings();
+          }
+        } else {
+          await this.props.appState.showErrorDialog(
+            `Publishing Fiddle to GitHub failed. Are you connected to the Internet? GitHub encountered the following error: ${error.message}`,
+          );
+        }
 
         return false;
       }
@@ -230,12 +244,23 @@ export const GistActionButton = observer(
       } catch (error: any) {
         console.warn(`Could not update gist`, { error });
 
-        window.ElectronFiddle.showWarningDialog({
-          message:
-            'Updating Fiddle Gist failed. Are you connected to the Internet and is this your Gist?',
-          detail: `GitHub encountered the following error: ${error.message}`,
-          buttons: ['Ok'],
-        });
+        if (error.status === 401 || error.status === 403) {
+          const { confirm } = await this.props.appState.showGenericDialog({
+            label: `Updating Fiddle Gist failed. GitHub encountered the following error: ${error.message}`,
+            ok: 'Update token',
+            cancel: 'Close',
+            type: GenericDialogType.warning,
+            wantsInput: false,
+          });
+
+          if (confirm) {
+            this.showGitHubTokenSettings();
+          }
+        } else {
+          await this.props.appState.showErrorDialog(
+            `Updating Fiddle Gist failed. Are you connected to the Internet? GitHub encountered the following error: ${error.message}`,
+          );
+        }
       }
 
       appState.activeGistAction = GistActionState.none;
@@ -262,11 +287,23 @@ export const GistActionButton = observer(
       } catch (error: any) {
         console.warn(`Could not delete gist`, { error });
 
-        window.ElectronFiddle.showWarningDialog({
-          message:
-            'Deleting Fiddle Gist failed. Are you connected to the Internet, is this your Gist, and have you loaded it?',
-          detail: `GitHub encountered the following error: ${error.message}`,
-        });
+        if (error.status === 401 || error.status === 403) {
+          const { confirm } = await this.props.appState.showGenericDialog({
+            label: `Deleting Fiddle Gist failed. GitHub encountered the following error: ${error.message}`,
+            ok: 'Update token',
+            cancel: 'Close',
+            type: GenericDialogType.warning,
+            wantsInput: false,
+          });
+
+          if (confirm) {
+            this.showGitHubTokenSettings();
+          }
+        } else {
+          await this.props.appState.showErrorDialog(
+            `Deleting Fiddle Gist failed. Are you connected to the Internet? GitHub encountered the following error: ${error.message}`,
+          );
+        }
       }
 
       appState.gistId = undefined;
@@ -455,5 +492,10 @@ export const GistActionButton = observer(
           .map(([id, content]) => [id, { filename: id, content }]),
       );
     };
+
+    private showGitHubTokenSettings() {
+      this.props.appState.toggleSettings();
+      this.props.appState.toggleAuthDialog();
+    }
   },
 );