diff --git a/internal/devserver/ts_devserver.bzl b/internal/devserver/ts_devserver.bzl
index fe377ec..399bd4e 100644
--- a/internal/devserver/ts_devserver.bzl
+++ b/internal/devserver/ts_devserver.bzl
@@ -100,7 +100,7 @@
                 "/".join([ctx.bin_dir.path, ctx.label.package]),
                 "/".join([ctx.genfiles_dir.path, ctx.label.package]),
             ],
-            [f.path for f in ctx.files.static_files] + [bundle_script],
+            [_short_path_to_manifest_path(ctx, f.short_path) for f in ctx.files.static_files] + [bundle_script],
             injected_index,
         )
         devserver_runfiles += [injected_index]
diff --git a/internal/e2e/npm_packages/ts_devserver/BUILD.bazel b/internal/e2e/npm_packages/ts_devserver/BUILD.bazel
index dd6eeef..f7e2f11 100644
--- a/internal/e2e/npm_packages/ts_devserver/BUILD.bazel
+++ b/internal/e2e/npm_packages/ts_devserver/BUILD.bazel
@@ -14,6 +14,11 @@
 
 load("@npm_bazel_typescript//:defs.bzl", "ts_devserver", "ts_library")
 
+exports_files([
+    "red-body-style.css",
+    "tsconfig.json",
+])
+
 ts_library(
     name = "app",
     srcs = ["app.ts"],
diff --git a/internal/e2e/npm_packages/ts_devserver/package-template.json b/internal/e2e/npm_packages/ts_devserver/package-template.json
index 7001bfa..5a9c82e 100644
--- a/internal/e2e/npm_packages/ts_devserver/package-template.json
+++ b/internal/e2e/npm_packages/ts_devserver/package-template.json
@@ -10,6 +10,8 @@
   },
   "scripts": {
     "pretest": "webdriver-manager update $CHROMEDRIVER_VERSION_ARG",
-    "test": "bazel build ... && concurrently \"bazel run //:devserver\" \"while ! nc -z 127.0.0.1 8080; do sleep 1; done && protractor\" --kill-others --success first"
+    "wait-for-servers": "while [[ ! nc -z 127.0.0.1 8080 ]] || [[ ! nc -z 127.0.0.1 8081 ]]; do sleep 1; done",
+    "run-e2e-tests": "concurrently \"bazel run //:devserver\" \"yarn wait-for-servers\" --kill-others --success first",
+    "test": "bazel build ... && yarn run-e2e-tests"
   }
 }
diff --git a/internal/e2e/npm_packages/ts_devserver/protractor.conf.js b/internal/e2e/npm_packages/ts_devserver/protractor.conf.js
index 9691a64..725b81e 100644
--- a/internal/e2e/npm_packages/ts_devserver/protractor.conf.js
+++ b/internal/e2e/npm_packages/ts_devserver/protractor.conf.js
@@ -1,6 +1,6 @@
 exports.config = {
   specs: [
-    'bazel-bin/*_e2e_test.js',
+    'bazel-bin/**/*_e2e_test.js',
   ],
   capabilities: {
     browserName: 'chrome',
diff --git a/internal/e2e/npm_packages/ts_devserver/red-body-style.css b/internal/e2e/npm_packages/ts_devserver/red-body-style.css
new file mode 100644
index 0000000..5c5e887
--- /dev/null
+++ b/internal/e2e/npm_packages/ts_devserver/red-body-style.css
@@ -0,0 +1,3 @@
+body {
+    background: red;
+}
diff --git a/internal/e2e/npm_packages/ts_devserver/subpackage/BUILD.bazel b/internal/e2e/npm_packages/ts_devserver/subpackage/BUILD.bazel
new file mode 100644
index 0000000..b68ac44
--- /dev/null
+++ b/internal/e2e/npm_packages/ts_devserver/subpackage/BUILD.bazel
@@ -0,0 +1,33 @@
+# Copyright 2017 The Bazel Authors. All rights reserved.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#    http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+load("@npm_bazel_typescript//:defs.bzl", "ts_devserver", "ts_library")
+
+ts_devserver(
+    name = "devserver",
+    index_html = "index.html",
+    port = 8081,
+    static_files = ["//:red-body-style.css"],
+)
+
+ts_library(
+    name = "e2e",
+    testonly = 1,
+    srcs = ["subpackage_e2e_test.ts"],
+    deps = [
+        "@npm//@types/jasmine",
+        "@npm//@types/node",
+        "@npm//protractor",
+    ],
+)
diff --git a/internal/e2e/npm_packages/ts_devserver/subpackage/index.html b/internal/e2e/npm_packages/ts_devserver/subpackage/index.html
new file mode 100644
index 0000000..4ea2bf3
--- /dev/null
+++ b/internal/e2e/npm_packages/ts_devserver/subpackage/index.html
@@ -0,0 +1,10 @@
+<!doctype html>
+<html lang="en">
+<head>
+  <meta charset="UTF-8">
+  <title>Subpackage Devserver</title>
+</head>
+<body>
+  This is the devserver for a Bazel subpackage.
+</body>
+</html>
diff --git a/internal/e2e/npm_packages/ts_devserver/subpackage/subpackage_e2e_test.ts b/internal/e2e/npm_packages/ts_devserver/subpackage/subpackage_e2e_test.ts
new file mode 100644
index 0000000..281ea39
--- /dev/null
+++ b/internal/e2e/npm_packages/ts_devserver/subpackage/subpackage_e2e_test.ts
@@ -0,0 +1,17 @@
+import {browser, by, element} from 'protractor';
+
+describe('subpackage', () => {
+
+  beforeAll(async () => {
+    await browser.waitForAngularEnabled(false);
+    await browser.get('http://127.0.0.1:8081/');
+  });
+
+  // Ensures that the "ts_devserver" properly injects and loads static files which
+  // are in the current workspace, but not part of the current Bazel package. See
+  // related issue: https://github.com/bazelbuild/rules_typescript/issues/409
+  it('should be able to properly load the injected CSS file', async () => {
+    const bodyElement = element(by.css('body'));
+    expect(await bodyElement.getCssValue('background')).toContain('rgb(255, 0, 0)');
+  });
+});
diff --git a/internal/e2e/npm_packages/ts_devserver/tsconfig.json b/internal/e2e/npm_packages/ts_devserver/tsconfig.json
index e69de29..40dd225 100644
--- a/internal/e2e/npm_packages/ts_devserver/tsconfig.json
+++ b/internal/e2e/npm_packages/ts_devserver/tsconfig.json
@@ -0,0 +1,5 @@
+{
+  "compilerOptions": {
+    "lib": ["es2015", "dom"]
+  }
+}