diff --git a/app/controllers/concerns/inline_script_hashes.rb b/app/controllers/concerns/inline_script_hashes.rb
index 357a70d..4577292 100644
--- a/app/controllers/concerns/inline_script_hashes.rb
+++ b/app/controllers/concerns/inline_script_hashes.rb
@@ -24,7 +24,9 @@ module InlineScriptHashes
     # The importmap is resolved by Rails' asset helpers, so its URLs already
     # carry any relative root and asset host, however the host is written:
     # with or without a scheme, protocol-relative, a %d set, or a proc. Each
-    # is allowed up to its asset directory; one outside it is allowed exactly.
+    # is allowed up to its asset directory, the last one in its path, since an
+    # asset host's own path may contain one too; a URL outside it is allowed
+    # exactly.
     #
     # This origin's own sources leave out the scheme, so they match the page's
     # scheme even behind a proxy that terminates TLS without saying so.
@@ -37,7 +39,7 @@ module InlineScriptHashes
       JSON.parse(importmap)["imports"].values.map do |url|
         url = URI.join(request.base_url, url)
         origin = url.origin == request.base_url ? request.host_with_port : url.origin
-        directory = url.path[0, url.path.index(assets) + assets.length] if url.path.include?(assets)
+        directory = url.path[0, url.path.rindex(assets) + assets.length] if url.path.include?(assets)
         "#{origin}#{directory || url.path}"
       end.uniq
     end
diff --git a/test/integration/content_security_policy_test.rb b/test/integration/content_security_policy_test.rb
index b4672e0..7a3aaf6 100644
--- a/test/integration/content_security_policy_test.rb
+++ b/test/integration/content_security_policy_test.rb
@@ -56,6 +56,27 @@ class ContentSecurityPolicyTest < ActionDispatch::IntegrationTest
     end
   end
 
+  test "an asset host whose path contains the asset directory is limited to the directory it serves" do
+    with_asset_host("https://cdn.example.test/assets") do
+      get PAGE_PATH
+      follow_redirect! while response.redirect?
+
+      script_src = response.headers["Content-Security-Policy"][/script-src ([^;]+)/, 1].split
+      assert_includes script_src, "https://cdn.example.test/assets/assets/"
+      assert_not allowed_by_path?(script_src, "https://cdn.example.test/assets/rails/active_storage/blobs/proxy/x/upload.js")
+    end
+  end
+
+  test "the sign-in page is limited to the asset directory too" do
+    cookies.delete(:session_token)
+    get new_session_url
+    assert_response :success
+
+    script_src = response.headers["Content-Security-Policy"][/script-src ([^;]+)/, 1].split
+    assert_not_includes script_src, "'self'"
+    assert_includes script_src, "www.example.com/assets/"
+  end
+
   test "scripts are limited to the asset directory under a relative root" do
     with_relative_url_root("/chat") do
       get PAGE_PATH