diff --git a/packages/cli/src/services/web-ui.ts b/packages/cli/src/services/web-ui.ts
index ebb3d1b41ac..9a3615720a2 100644
--- a/packages/cli/src/services/web-ui.ts
+++ b/packages/cli/src/services/web-ui.ts
@@ -26,7 +26,7 @@ export const handler = Effect.fn("cli.web-ui.handler")(function* (options?: { re
 
 function serveUI(request: HttpServerRequest.HttpServerRequest, url: URL, assets: AssetMap) {
   const key = url.pathname.replace(/^\//, "")
-  if (key.startsWith("_assets/") && assets[key] === undefined)
+  if ((key.startsWith("_assets/") || key.startsWith("icons/")) && assets[key] === undefined)
     return Effect.succeed(HttpServerResponse.empty({ status: 404, headers: { "cache-control": "no-store" } }))
   const name = assets[key] !== undefined ? key : "index.html"
   const file = assets[name]
@@ -45,7 +45,7 @@ function serveUI(request: HttpServerRequest.HttpServerRequest, url: URL, assets:
   }
   return Effect.succeed(
     request.method === "HEAD"
-      ? HttpServerResponse.empty({ headers })
+      ? HttpServerResponse.empty({ status: 200, headers })
       : HttpServerResponse.raw(file, { headers, contentType: headers["content-type"] }),
   )
 }
diff --git a/packages/server/src/process.ts b/packages/server/src/process.ts
index bb25cbd5f3c..99f3b37f1b4 100644
--- a/packages/server/src/process.ts
+++ b/packages/server/src/process.ts
@@ -184,6 +184,7 @@ function dispatch(
     const app = yield* Ref.get(application)
     const ready = state.type === "ready" && Option.isSome(app)
     if (
+      (url.pathname === "/api" || url.pathname.startsWith("/api/") || url.pathname === "/openapi.json") &&
       (!ready || (!hasPtyConnectTicketURL(url) && !hasPersistentPtyConnectTicketURL(url))) &&
       !(yield* authorizedRequest(request, auth))
     )
diff --git a/packages/server/test/process.test.ts b/packages/server/test/process.test.ts
index 96f4f92b851..0b36bcfef6f 100644
--- a/packages/server/test/process.test.ts
+++ b/packages/server/test/process.test.ts
@@ -114,5 +114,13 @@ it.live("allows browser preflight requests without credentials", () =>
     expect(missing.headers.get("content-type")).toBe("text/plain")
     expect(missing.headers.get("vary")?.toLowerCase()).toContain("accept-encoding")
     expect(yield* Effect.promise(() => missing.text())).toBe(fallback)
+
+    yield* Effect.forEach(["/api", "/api/missing", "/openapi.json"], (pathname) =>
+      Effect.gen(function* () {
+        const response = yield* Effect.promise(() => fetch(new URL(pathname, HttpServer.formatAddress(server.address))))
+        expect(response.status).toBe(401)
+        expect(yield* Effect.promise(() => response.text())).toBe("")
+      }),
+    )
   }),
 )