diff --git a/webui/src/components/Sidebar.tsx b/webui/src/components/Sidebar.tsx
index 48725dce..66a8bd41 100644
--- a/webui/src/components/Sidebar.tsx
+++ b/webui/src/components/Sidebar.tsx
@@ -161,13 +161,6 @@ export function Sidebar(props: SidebarProps) {
           active={props.activeUtility === "apps"}
           icon={<Blocks className="h-4 w-4" />}
         />
-        <SidebarActionButton
-          collapsed={collapsed}
-          label={t("sidebar.automations", { defaultValue: "Automations" })}
-          onClick={props.onOpenAutomations}
-          active={props.activeUtility === "automations"}
-          icon={<CalendarClock className="h-4 w-4" />}
-        />
         <SidebarActionButton
           collapsed={collapsed}
           label={t("sidebar.skills.title")}
@@ -175,6 +168,13 @@ export function Sidebar(props: SidebarProps) {
           active={props.activeUtility === "skills"}
           icon={<Brain className="h-4 w-4" />}
         />
+        <SidebarActionButton
+          collapsed={collapsed}
+          label={t("sidebar.automations", { defaultValue: "Automations" })}
+          onClick={props.onOpenAutomations}
+          active={props.activeUtility === "automations"}
+          icon={<CalendarClock className="h-4 w-4" />}
+        />
         {props.archivedCount ? (
           <SidebarActionButton
             collapsed={collapsed}
diff --git a/webui/src/tests/app-layout.test.tsx b/webui/src/tests/app-layout.test.tsx
index 75ae92a8..59b22339 100644
--- a/webui/src/tests/app-layout.test.tsx
+++ b/webui/src/tests/app-layout.test.tsx
@@ -271,6 +271,23 @@ describe("App layout", () => {
     expect(asideClassNames.some((cls) => cls.includes("lg:block"))).toBe(true);
   });
 
+  it("places Automations after Skills in the main sidebar", async () => {
+    render(<App />);
+
+    await waitFor(() => expect(connectSpy).toHaveBeenCalled());
+    const sidebar = screen.getByRole("navigation", { name: "Sidebar navigation" });
+    const appsButton = within(sidebar).getByRole("button", { name: "Apps" });
+    const skillsButton = within(sidebar).getByRole("button", { name: "Skills" });
+    const automationsButton = within(sidebar).getByRole("button", { name: "Automations" });
+
+    expect(appsButton.compareDocumentPosition(skillsButton) & Node.DOCUMENT_POSITION_FOLLOWING)
+      .toBeTruthy();
+    expect(
+      skillsButton.compareDocumentPosition(automationsButton) &
+        Node.DOCUMENT_POSITION_FOLLOWING,
+    ).toBeTruthy();
+  });
+
   it("opens Skills from the main sidebar", async () => {
     mockFetchRoutes({
       "/api/settings": baseSettingsPayload(),