diff --git a/mcpjam-inspector/client/src/components/learn-more/LearnMoreHoverCard.tsx b/mcpjam-inspector/client/src/components/learn-more/LearnMoreHoverCard.tsx
index 6587f78b7..4d8e1ed4e 100644
--- a/mcpjam-inspector/client/src/components/learn-more/LearnMoreHoverCard.tsx
+++ b/mcpjam-inspector/client/src/components/learn-more/LearnMoreHoverCard.tsx
@@ -39,6 +39,8 @@ interface LearnMoreHoverCardProps {
   onExpand: (tabId: string, sourceRect: DOMRect | null) => void;
   triggerTooltip?: string;
   triggerTooltipDelayMs?: number;
+  /** Message shown inside the hover card for disabled items (e.g. "Available locally") */
+  disabledMessage?: string;
 }
 
 export function LearnMoreHoverCard({
@@ -47,6 +49,7 @@ export function LearnMoreHoverCard({
   onExpand,
   triggerTooltip,
   triggerTooltipDelayMs,
+  disabledMessage,
 }: LearnMoreHoverCardProps) {
   const entry = learnMoreContent[tabId];
   const wrapperRef = useRef<HTMLDivElement>(null);
@@ -194,6 +197,12 @@ export function LearnMoreHoverCard({
             />
           </div>
 
+          {disabledMessage && (
+            <p className="text-xs text-muted-foreground/80 italic mb-2">
+              {disabledMessage}
+            </p>
+          )}
+
           <div className="flex items-end justify-between gap-2">
             <p className="text-sm text-muted-foreground">{entry.description}</p>
             <button
diff --git a/mcpjam-inspector/client/src/components/sidebar/__tests__/nav-main.test.tsx b/mcpjam-inspector/client/src/components/sidebar/__tests__/nav-main.test.tsx
index a12031ee5..e9c6cfab6 100644
--- a/mcpjam-inspector/client/src/components/sidebar/__tests__/nav-main.test.tsx
+++ b/mcpjam-inspector/client/src/components/sidebar/__tests__/nav-main.test.tsx
@@ -27,8 +27,13 @@ vi.mock("@/components/ui/tooltip", () => ({
 }));
 
 vi.mock("@/components/learn-more/LearnMoreHoverCard", () => ({
-  LearnMoreHoverCard: ({ tabId, children }: any) => (
-    <div data-testid={`learn-more-${tabId}`}>{children}</div>
+  LearnMoreHoverCard: ({ tabId, children, disabledMessage }: any) => (
+    <div data-testid={`learn-more-${tabId}`}>
+      {disabledMessage && (
+        <span data-testid="disabled-message">{disabledMessage}</span>
+      )}
+      {children}
+    </div>
   ),
 }));
 
@@ -41,7 +46,7 @@ describe("NavMain", () => {
     mockSidebarOpen = true;
   });
 
-  it("keeps disabled items visible without allowing navigation", () => {
+  it("shows learn-more hover card for disabled items with learn-more content", () => {
     const onItemClick = vi.fn();
 
     render(
@@ -56,11 +61,19 @@ describe("NavMain", () => {
           },
         ]}
         onItemClick={onItemClick}
+        learnMore={{ onExpand: vi.fn() }}
       />,
     );
 
-    expect(screen.getByTitle(HOSTED_LOCAL_ONLY_TOOLTIP)).toBeInTheDocument();
-    expect(screen.getByText(HOSTED_LOCAL_ONLY_TOOLTIP)).toBeInTheDocument();
+    // Should show learn-more hover card with disabled message
+    expect(screen.getByTestId("learn-more-skills")).toBeInTheDocument();
+    expect(screen.getByTestId("disabled-message")).toHaveTextContent(
+      HOSTED_LOCAL_ONLY_TOOLTIP,
+    );
+    // No native title attribute (double tooltip fix)
+    expect(
+      screen.queryByTitle(HOSTED_LOCAL_ONLY_TOOLTIP),
+    ).not.toBeInTheDocument();
 
     const button = screen.getByRole("button", { name: "Skills" });
     expect(button).toHaveAttribute("aria-disabled", "true");
@@ -69,6 +82,48 @@ describe("NavMain", () => {
     expect(onItemClick).not.toHaveBeenCalled();
   });
 
+  it("shows plain tooltip for disabled items without learn-more content", () => {
+    render(
+      <NavMain
+        items={[
+          {
+            title: "SomeDisabled",
+            url: "#no-learn-more",
+            icon: FakeIcon,
+            disabled: true,
+            disabledTooltip: "Not available",
+          },
+        ]}
+        learnMore={{ onExpand: vi.fn() }}
+      />,
+    );
+
+    expect(
+      screen.queryByTestId("learn-more-no-learn-more"),
+    ).not.toBeInTheDocument();
+    expect(screen.getByText("Not available")).toBeInTheDocument();
+    expect(screen.queryByTitle("Not available")).not.toBeInTheDocument();
+  });
+
+  it("falls back to tooltip for disabled items when learnMore is not provided", () => {
+    render(
+      <NavMain
+        items={[
+          {
+            title: "Skills",
+            url: "#skills",
+            icon: FakeIcon,
+            disabled: true,
+            disabledTooltip: HOSTED_LOCAL_ONLY_TOOLTIP,
+          },
+        ]}
+      />,
+    );
+
+    expect(screen.queryByTestId("learn-more-skills")).not.toBeInTheDocument();
+    expect(screen.getByText(HOSTED_LOCAL_ONLY_TOOLTIP)).toBeInTheDocument();
+  });
+
   it("still handles clicks for enabled items", () => {
     const onItemClick = vi.fn();
 
diff --git a/mcpjam-inspector/client/src/components/sidebar/nav-main.tsx b/mcpjam-inspector/client/src/components/sidebar/nav-main.tsx
index 6da532281..568b78af0 100644
--- a/mcpjam-inspector/client/src/components/sidebar/nav-main.tsx
+++ b/mcpjam-inspector/client/src/components/sidebar/nav-main.tsx
@@ -91,6 +91,7 @@ export function NavMain({
         onExpand={learnMore.onExpand}
         triggerTooltip={!sidebarOpen ? item.title : undefined}
         triggerTooltipDelayMs={!sidebarOpen ? 1000 : undefined}
+        disabledMessage={item.disabled ? item.disabledTooltip : undefined}
       >
         {child}
       </LearnMoreHoverCard>
@@ -124,14 +125,22 @@ export function NavMain({
             );
 
             if (item.disabled) {
+              if (shouldShowHoverCard(item)) {
+                return (
+                  <SidebarMenuItem key={item.title}>
+                    {wrapWithHoverCard(
+                      item,
+                      <div className="w-full cursor-not-allowed">{button}</div>,
+                    )}
+                  </SidebarMenuItem>
+                );
+              }
+
               return (
                 <SidebarMenuItem key={item.title}>
                   <Tooltip>
                     <TooltipTrigger asChild>
-                      <div
-                        className="w-full cursor-not-allowed"
-                        title={item.disabledTooltip}
-                      >
+                      <div className="w-full cursor-not-allowed">
                         {button}
                       </div>
                     </TooltipTrigger>