diff --git a/ui/litellm-dashboard/src/utils/migratedPages.test.ts b/ui/litellm-dashboard/src/utils/migratedPages.test.ts
index 5812c1eec40..7e7ba8adc34 100644
--- a/ui/litellm-dashboard/src/utils/migratedPages.test.ts
+++ b/ui/litellm-dashboard/src/utils/migratedPages.test.ts
@@ -221,12 +221,22 @@ describe("legacyKeyForPathname", () => {
     expect(legacyKeyForPathname("/ui/skills")).toBe("skills");
   });
 
+  it("maps a nested tab route back to its sidebar key via the first path segment", async () => {
+    vi.doMock("@/components/networking", () => ({ serverRootPath: "/" }));
+    const { legacyKeyForPathname } = await import("./migratedPages");
+
+    expect(legacyKeyForPathname("/ui/caching/health")).toBe("caching");
+    expect(legacyKeyForPathname("/ui/caching/coordination-redis/")).toBe("caching");
+    expect(legacyKeyForPathname("/ui/models-and-endpoints/add")).toBe("models");
+  });
+
   it("returns null for a not-yet-migrated path", async () => {
     vi.doMock("@/components/networking", () => ({ serverRootPath: "/" }));
     const { legacyKeyForPathname } = await import("./migratedPages");
 
     expect(legacyKeyForPathname("/ui/")).toBeNull();
     expect(legacyKeyForPathname("/ui/some-legacy-page")).toBeNull();
+    expect(legacyKeyForPathname("/ui/some-legacy-page/nested")).toBeNull();
   });
 
   it("strips a non-root serverRootPath prefix before matching", async () => {
diff --git a/ui/litellm-dashboard/src/utils/migratedPages.ts b/ui/litellm-dashboard/src/utils/migratedPages.ts
index 73ab71ce4ac..34908a31f65 100644
--- a/ui/litellm-dashboard/src/utils/migratedPages.ts
+++ b/ui/litellm-dashboard/src/utils/migratedPages.ts
@@ -76,8 +76,10 @@ export function legacyPageHref(pageKey: string): string {
 export function legacyKeyForPathname(pathname: string): string | null {
   const base = uiBase();
   const rel = (pathname.startsWith(base) ? pathname.slice(base.length) : pathname).replace(/^\/+|\/+$/g, "");
+  const firstSegment = rel.split("/")[0] ?? "";
+  if (!firstSegment) return null;
   for (const [key, segment] of Object.entries(MIGRATED_PAGES)) {
-    if (rel === segment) return key;
+    if (firstSegment === segment) return key;
   }
   return null;
 }