diff --git a/apps/backend/src/server/app.ts b/apps/backend/src/server/app.ts
index 40631e44c..047278972 100644
--- a/apps/backend/src/server/app.ts
+++ b/apps/backend/src/server/app.ts
@@ -4,10 +4,10 @@ import { NextNotFoundError } from "@/lib/runtime/navigation";
 import { parseCookieHeader, requestContextALS, type RequestContext } from "@/lib/runtime/request-context";
 import { node } from "@elysiajs/node";
 import { getEnvVariable, getNodeEnvironment } from "@hexclave/shared/dist/utils/env";
-import { captureError } from "@hexclave/shared/dist/utils/errors";
 import { Elysia } from "elysia";
-import { runRequestPipeline } from "./middleware";
 import { createBackendRequest } from "./backend-request";
+import { handleUncaughtBackendError } from "./error-handler";
+import { runRequestPipeline } from "./middleware";
 import { MalformedRouteParamError, matchRoute } from "./registry";
 
 const globalSecurityHeaders = {
@@ -40,13 +40,7 @@ export const app = new Elysia({
     const pathname = new URL(request.url).pathname;
     console.log(`[Elysia] ${request.method} ${pathname} ${set.status} ${elapsedMilliseconds}ms`);
   })
-  .onError(({ error }) => {
-    // Smart route handlers sanitize their own errors. This is the final boundary
-    // for errors from raw routes and framework code, which Elysia would otherwise
-    // return to the client verbatim.
-    captureError("elysia-request-handler", error);
-    return internalServerErrorResponse();
-  })
+  .onError(({ error }) => withGlobalHeaders(handleUncaughtBackendError(error)))
   .get("/", () => htmlResponse(homeHtml()))
   .get("/dev-stats", () => htmlResponse(devStatsHtml()))
   .get("/health/error-handler-debug", () => htmlResponse(errorHandlerDebugHtml()))
@@ -169,23 +163,6 @@ function htmlResponse(body: string, status = 200) {
   }));
 }
 
-function internalServerErrorResponse() {
-  return withGlobalHeaders(new Response("Internal Server Error", {
-    status: 500,
-    headers: {
-      "content-type": "text/plain; charset=utf-8",
-    },
-  }));
-}
-
-import.meta.vitest?.test("unhandled errors do not expose their message", async ({ expect }) => {
-  const response = internalServerErrorResponse();
-
-  expect(response.status).toBe(500);
-  expect(await response.text()).toBe("Internal Server Error");
-  expect(response.headers.get("x-content-type-options")).toBe("nosniff");
-});
-
 import.meta.vitest?.test("API version migrations do not expose their internal rewrite", async ({ expect }) => {
   const { vi } = import.meta.vitest!;
   vi.stubEnv("HEXCLAVE_ARTIFICIAL_DEVELOPMENT_DELAY_MS", "0");
diff --git a/apps/backend/src/server/error-handler.ts b/apps/backend/src/server/error-handler.ts
new file mode 100644
index 000000000..fa7caf051
--- /dev/null
+++ b/apps/backend/src/server/error-handler.ts
@@ -0,0 +1,31 @@
+import { captureError } from "@hexclave/shared/dist/utils/errors";
+
+function createUncaughtErrorResponse() {
+  return new Response("Internal Server Error", {
+    status: 500,
+    headers: {
+      "content-type": "text/plain; charset=utf-8",
+    },
+  });
+}
+
+export function handleUncaughtBackendError(error: unknown) {
+  captureError("backend-global-error", error);
+  return createUncaughtErrorResponse();
+}
+
+import.meta.vitest?.test("uncaught backend errors do not expose internal details", async ({ expect }) => {
+  const response = createUncaughtErrorResponse();
+
+  expect({
+    status: response.status,
+    contentType: response.headers.get("content-type"),
+    body: await response.text(),
+  }).toMatchInlineSnapshot(`
+    {
+      "body": "Internal Server Error",
+      "contentType": "text/plain; charset=utf-8",
+      "status": 500,
+    }
+  `);
+});
diff --git a/apps/backend/src/smart-router.tsx b/apps/backend/src/smart-router.tsx
index ceca8831b..2dfa3e992 100644
--- a/apps/backend/src/smart-router.tsx
+++ b/apps/backend/src/smart-router.tsx
@@ -103,9 +103,11 @@ function parseApiVersionStringToArray(version: string): [number, number] {
 
 
 function matchPath(path: string, toMatchWith: string): Record<string, string | string[]> | false {
-  // get the relative part, and modify it to have a leading slash, without a trailing slash, without ./.., etc.
-  const url = new URL(path + "/", "http://example.com");
-  const modifiedPath = url.pathname.slice(1, -1);
+  // Normalize to relative path segments without a trailing slash. Appending "/" before URL parsing
+  // turns an already-trailing path into "//", which URL interprets as a protocol-relative URL during
+  // the final recursive match and rejects because it has no host.
+  const url = new URL(path === "" ? "/" : path, "http://example.com");
+  const modifiedPath = url.pathname.slice(1).replace(/\/+$/, "");
   const modifiedToMatchWith = toMatchWith.slice(1);
 
   if (modifiedPath === "" && modifiedToMatchWith === "") {
@@ -146,6 +148,20 @@ function matchPath(path: string, toMatchWith: string): Record<string, string | s
   }
 }
 
+import.meta.vitest?.test("matches routes with trailing slashes", ({ expect }) => {
+  expect({
+    staticRoute: SmartRouter.matchNormalizedPath("/api/v1/", "/api/v1"),
+    dynamicRoute: SmartRouter.matchNormalizedPath("/users/user-123/", "/users/[user_id]"),
+  }).toMatchInlineSnapshot(`
+    {
+      "dynamicRoute": {
+        "user_id": "user-123",
+      },
+      "staticRoute": {},
+    }
+  `);
+});
+
 /**
  * Modified from: https://github.com/vercel/next.js/blob/6ff13369bb18045657d0f84ddc86b540340603a1/packages/next/src/shared/lib/router/utils/app-paths.ts#L23
  */
diff --git a/apps/e2e/tests/backend/endpoints/api/v1/index.test.ts b/apps/e2e/tests/backend/endpoints/api/v1/index.test.ts
index 9f636f92f..74ae165d4 100644
--- a/apps/e2e/tests/backend/endpoints/api/v1/index.test.ts
+++ b/apps/e2e/tests/backend/endpoints/api/v1/index.test.ts
@@ -10,6 +10,21 @@ describe("without project ID", () => {
 
   it("should load", async ({ expect }) => {
     const response = await niceBackendFetch("/api/v1");
+    expect(response).toMatchInlineSnapshot(`
+      NiceResponse {
+        "status": 200,
+        "body": deindent\`
+          Welcome to the Hexclave API endpoint! Please refer to the documentation at https://docs.hexclave.com.
+
+          Authentication: None
+        \`,
+        "headers": Headers { <some fields may have been hidden> },
+      }
+    `);
+  });
+
+  it("should load with a trailing slash", async ({ expect }) => {
+    const response = await niceBackendFetch("/api/v1/");
     expect(response).toMatchInlineSnapshot(`
       NiceResponse {
         "status": 200,