diff --git a/lib/internal/bootstrap/pre_execution.js b/lib/internal/bootstrap/pre_execution.js
index 005b1b46c28227..e9700fc1f4639d 100644
--- a/lib/internal/bootstrap/pre_execution.js
+++ b/lib/internal/bootstrap/pre_execution.js
@@ -362,7 +362,7 @@ function initializePolicy() {
     // no bare specifiers for now
     let manifestURL;
     if (require('path').isAbsolute(experimentalPolicy)) {
-      manifestURL = new URL(`file:///${experimentalPolicy}`);
+      manifestURL = new URL(experimentalPolicy, 'file://');
     } else {
       const cwdURL = pathToFileURL(process.cwd());
       cwdURL.pathname += '/';
diff --git a/src/inspector_agent.cc b/src/inspector_agent.cc
index 4b7997a02fdc30..c54b2ab17fcb6e 100644
--- a/src/inspector_agent.cc
+++ b/src/inspector_agent.cc
@@ -640,7 +640,7 @@ class NodeInspectorClient : public V8InspectorClient {
     node::url::URL url = node::url::URL::FromFilePath(resource_name);
     // TODO(ak239spb): replace this code with url.href().
     // Refs: https://github.com/nodejs/node/issues/22610
-    return Utf8ToStringView(url.protocol() + "//" + url.path());
+    return Utf8ToStringView(url.protocol() + "/" + url.path());
   }
 
   node::Environment* env_;
diff --git a/src/node_url.cc b/src/node_url.cc
index b7aeb8b006284f..466f3c689a51f8 100644
--- a/src/node_url.cc
+++ b/src/node_url.cc
@@ -1904,16 +1904,19 @@ void URL::Parse(const char* input,
               state = kFragment;
               break;
             default:
+              url->query.clear();
+              if (base->flags & URL_FLAGS_HAS_HOST) {
+                url->flags |= URL_FLAGS_HAS_HOST;
+                url->host = base->host;
+              }
+              if (base->flags & URL_FLAGS_HAS_PATH) {
+                url->flags |= URL_FLAGS_HAS_PATH;
+                url->path = base->path;
+              }
               if (!StartsWithWindowsDriveLetter(p, end)) {
-                if (base->flags & URL_FLAGS_HAS_HOST) {
-                  url->flags |= URL_FLAGS_HAS_HOST;
-                  url->host = base->host;
-                }
-                if (base->flags & URL_FLAGS_HAS_PATH) {
-                  url->flags |= URL_FLAGS_HAS_PATH;
-                  url->path = base->path;
-                }
                 ShortenUrlPath(url);
+              } else {
+                url->path.clear();
               }
               state = kPath;
               continue;
@@ -1927,20 +1930,13 @@ void URL::Parse(const char* input,
         if (ch == '/' || ch == '\\') {
           state = kFileHost;
         } else {
-          if (has_base &&
-              base->scheme == "file:" &&
-              !StartsWithWindowsDriveLetter(p, end)) {
-            if (IsNormalizedWindowsDriveLetter(base->path[0])) {
+          if (has_base && base->scheme == "file:") {
+            url->flags |= URL_FLAGS_HAS_HOST;
+            url->host = base->host;
+            if (!StartsWithWindowsDriveLetter(p, end) &&
+                IsNormalizedWindowsDriveLetter(base->path[0])) {
               url->flags |= URL_FLAGS_HAS_PATH;
               url->path.push_back(base->path[0]);
-            } else {
-              if (base->flags & URL_FLAGS_HAS_HOST) {
-                url->flags |= URL_FLAGS_HAS_HOST;
-                url->host = base->host;
-              } else {
-                url->flags &= ~URL_FLAGS_HAS_HOST;
-                url->host.clear();
-              }
             }
           }
           state = kPath;
@@ -2024,29 +2020,19 @@ void URL::Parse(const char* input,
                 url->path.empty() &&
                 buffer.size() == 2 &&
                 IsWindowsDriveLetter(buffer)) {
-              if ((url->flags & URL_FLAGS_HAS_HOST) &&
-                  !url->host.empty()) {
-                url->host.clear();
-                url->flags |= URL_FLAGS_HAS_HOST;
-              }
               buffer[1] = ':';
             }
             url->flags |= URL_FLAGS_HAS_PATH;
             url->path.emplace_back(std::move(buffer));
           }
           buffer.clear();
-          if (url->scheme == "file:" &&
-              (ch == kEOL ||
-               ch == '?' ||
-               ch == '#')) {
-            while (url->path.size() > 1 && url->path[0].empty()) {
-              url->path.erase(url->path.begin());
-            }
-          }
           if (ch == '?') {
             url->flags |= URL_FLAGS_HAS_QUERY;
+            url->query.clear();
             state = kQuery;
           } else if (ch == '#') {
+            url->flags |= URL_FLAGS_HAS_FRAGMENT;
+            url->fragment.clear();
             state = kFragment;
           }
         } else {
diff --git a/test/cctest/test_url.cc b/test/cctest/test_url.cc
index 2e78b24a5e3424..806fe1a4d2a600 100644
--- a/test/cctest/test_url.cc
+++ b/test/cctest/test_url.cc
@@ -148,14 +148,14 @@ TEST_F(URLTest, FromFilePath) {
 #else
   file_url = URL::FromFilePath("/");
   EXPECT_EQ("file:", file_url.protocol());
-  EXPECT_EQ("/", file_url.path());
+  EXPECT_EQ("//", file_url.path());
 
   file_url = URL::FromFilePath("/a/b/c");
   EXPECT_EQ("file:", file_url.protocol());
-  EXPECT_EQ("/a/b/c", file_url.path());
+  EXPECT_EQ("//a/b/c", file_url.path());
 
   file_url = URL::FromFilePath("/a/%%.js");
   EXPECT_EQ("file:", file_url.protocol());
-  EXPECT_EQ("/a/%25%25.js", file_url.path());
+  EXPECT_EQ("//a/%25%25.js", file_url.path());
 #endif
 }
diff --git a/test/fixtures/wpt/README.md b/test/fixtures/wpt/README.md
index 9f6f20f5f47e89..d5ddd9b8c83f84 100644
--- a/test/fixtures/wpt/README.md
+++ b/test/fixtures/wpt/README.md
@@ -12,7 +12,7 @@ Last update:
 
 - console: https://github.com/web-platform-tests/wpt/tree/3b1f72e99a/console
 - encoding: https://github.com/web-platform-tests/wpt/tree/d7f9e16c9a/encoding
-- url: https://github.com/web-platform-tests/wpt/tree/e2ddf48b78/url
+- url: https://github.com/web-platform-tests/wpt/tree/050308a616/url
 - resources: https://github.com/web-platform-tests/wpt/tree/1d14e821b9/resources
 - interfaces: https://github.com/web-platform-tests/wpt/tree/15e47f779c/interfaces
 - html/webappapis/microtask-queuing: https://github.com/web-platform-tests/wpt/tree/2c5c3c4c27/html/webappapis/microtask-queuing
diff --git a/test/fixtures/wpt/url/resources/setters_tests.json b/test/fixtures/wpt/url/resources/setters_tests.json
index d06fb2cfe629b8..8aa74d6b8a28d9 100644
--- a/test/fixtures/wpt/url/resources/setters_tests.json
+++ b/test/fixtures/wpt/url/resources/setters_tests.json
@@ -1672,8 +1672,8 @@
             "href": "file://monkey/",
             "new_value": "\\\\",
             "expected": {
-                "href": "file://monkey/",
-                "pathname": "/"
+                "href": "file://monkey//",
+                "pathname": "//"
             }
         },
         {
@@ -1681,8 +1681,8 @@
             "href": "file:///unicorn",
             "new_value": "//\\/",
             "expected": {
-                "href": "file:///",
-                "pathname": "/"
+                "href": "file://////",
+                "pathname": "////"
             }
         },
         {
@@ -1690,8 +1690,8 @@
             "href": "file:///unicorn",
             "new_value": "//monkey/..//",
             "expected": {
-                "href": "file:///",
-                "pathname": "/"
+                "href": "file://///",
+                "pathname": "///"
             }
         },
         {
diff --git a/test/fixtures/wpt/url/resources/urltestdata.json b/test/fixtures/wpt/url/resources/urltestdata.json
index 76a8b3a015dcbc..dba7237d88a682 100644
--- a/test/fixtures/wpt/url/resources/urltestdata.json
+++ b/test/fixtures/wpt/url/resources/urltestdata.json
@@ -5389,84 +5389,84 @@
   {
     "input": "file:\\\\//",
     "base": "about:blank",
-    "href": "file:///",
+    "href": "file:////",
     "protocol": "file:",
     "username": "",
     "password": "",
     "host": "",
     "hostname": "",
     "port": "",
-    "pathname": "/",
+    "pathname": "//",
     "search": "",
     "hash": ""
   },
   {
     "input": "file:\\\\\\\\",
     "base": "about:blank",
-    "href": "file:///",
+    "href": "file:////",
     "protocol": "file:",
     "username": "",
     "password": "",
     "host": "",
     "hostname": "",
     "port": "",
-    "pathname": "/",
+    "pathname": "//",
     "search": "",
     "hash": ""
   },
   {
     "input": "file:\\\\\\\\?fox",
     "base": "about:blank",
-    "href": "file:///?fox",
+    "href": "file:////?fox",
     "protocol": "file:",
     "username": "",
     "password": "",
     "host": "",
     "hostname": "",
     "port": "",
-    "pathname": "/",
+    "pathname": "//",
     "search": "?fox",
     "hash": ""
   },
   {
     "input": "file:\\\\\\\\#guppy",
     "base": "about:blank",
-    "href": "file:///#guppy",
+    "href": "file:////#guppy",
     "protocol": "file:",
     "username": "",
     "password": "",
     "host": "",
     "hostname": "",
     "port": "",
-    "pathname": "/",
+    "pathname": "//",
     "search": "",
     "hash": "#guppy"
   },
   {
     "input": "file://spider///",
     "base": "about:blank",
-    "href": "file://spider/",
+    "href": "file://spider///",
     "protocol": "file:",
     "username": "",
     "password": "",
     "host": "spider",
     "hostname": "spider",
     "port": "",
-    "pathname": "/",
+    "pathname": "///",
     "search": "",
     "hash": ""
   },
   {
     "input": "file:\\\\localhost//",
     "base": "about:blank",
-    "href": "file:///",
+    "href": "file:////",
     "protocol": "file:",
     "username": "",
     "password": "",
     "host": "",
     "hostname": "",
     "port": "",
-    "pathname": "/",
+    "pathname": "//",
     "search": "",
     "hash": ""
   },
@@ -5487,42 +5487,42 @@
   {
     "input": "file://\\/localhost//cat",
     "base": "about:blank",
-    "href": "file:///localhost//cat",
+    "href": "file:////localhost//cat",
     "protocol": "file:",
     "username": "",
     "password": "",
     "host": "",
     "hostname": "",
     "port": "",
-    "pathname": "/localhost//cat",
+    "pathname": "//localhost//cat",
     "search": "",
     "hash": ""
   },
   {
     "input": "file://localhost//a//../..//",
     "base": "about:blank",
-    "href": "file:///",
+    "href": "file://///",
     "protocol": "file:",
     "username": "",
     "password": "",
     "host": "",
     "hostname": "",
     "port": "",
-    "pathname": "/",
+    "pathname": "///",
     "search": "",
     "hash": ""
   },
   {
     "input": "/////mouse",
     "base": "file:///elephant",
-    "href": "file:///mouse",
+    "href": "file://///mouse",
     "protocol": "file:",
     "username": "",
     "password": "",
     "host": "",
     "hostname": "",
     "port": "",
-    "pathname": "/mouse",
+    "pathname": "///mouse",
     "search": "",
     "hash": ""
   },
@@ -5543,42 +5543,42 @@
   {
     "input": "\\/localhost//pig",
     "base": "file://lion/",
-    "href": "file:///pig",
+    "href": "file:////pig",
     "protocol": "file:",
     "username": "",
     "password": "",
     "host": "",
     "hostname": "",
     "port": "",
-    "pathname": "/pig",
+    "pathname": "//pig",
     "search": "",
     "hash": ""
   },
   {
     "input": "//localhost//pig",
     "base": "file://lion/",
-    "href": "file:///pig",
+    "href": "file:////pig",
     "protocol": "file:",
     "username": "",
     "password": "",
     "host": "",
     "hostname": "",
     "port": "",
-    "pathname": "/pig",
+    "pathname": "//pig",
     "search": "",
     "hash": ""
   },
   {
     "input": "/..//localhost//pig",
     "base": "file://lion/",
-    "href": "file://lion/localhost//pig",
+    "href": "file://lion//localhost//pig",
     "protocol": "file:",
     "username": "",
     "password": "",
     "host": "lion",
     "hostname": "lion",
     "port": "",
-    "pathname": "/localhost//pig",
+    "pathname": "//localhost//pig",
     "search": "",
     "hash": ""
   },
@@ -5629,12 +5629,12 @@
   {
     "input": "C|",
     "base": "file://host/dir/file",
-    "href": "file:///C:",
+    "href": "file://host/C:",
     "protocol": "file:",
     "username": "",
     "password": "",
-    "host": "",
-    "hostname": "",
+    "host": "host",
+    "hostname": "host",
     "port": "",
     "pathname": "/C:",
     "search": "",
@@ -5643,12 +5643,12 @@
   {
     "input": "C|#",
     "base": "file://host/dir/file",
-    "href": "file:///C:#",
+    "href": "file://host/C:#",
     "protocol": "file:",
     "username": "",
     "password": "",
-    "host": "",
-    "hostname": "",
+    "host": "host",
+    "hostname": "host",
     "port": "",
     "pathname": "/C:",
     "search": "",
@@ -5657,12 +5657,12 @@
   {
     "input": "C|?",
     "base": "file://host/dir/file",
-    "href": "file:///C:?",
+    "href": "file://host/C:?",
     "protocol": "file:",
     "username": "",
     "password": "",
-    "host": "",
-    "hostname": "",
+    "host": "host",
+    "hostname": "host",
     "port": "",
     "pathname": "/C:",
     "search": "",
@@ -5671,12 +5671,12 @@
   {
     "input": "C|/",
     "base": "file://host/dir/file",
-    "href": "file:///C:/",
+    "href": "file://host/C:/",
     "protocol": "file:",
     "username": "",
     "password": "",
-    "host": "",
-    "hostname": "",
+    "host": "host",
+    "hostname": "host",
     "port": "",
     "pathname": "/C:/",
     "search": "",
@@ -5685,12 +5685,12 @@
   {
     "input": "C|\n/",
     "base": "file://host/dir/file",
-    "href": "file:///C:/",
+    "href": "file://host/C:/",
     "protocol": "file:",
     "username": "",
     "password": "",
-    "host": "",
-    "hostname": "",
+    "host": "host",
+    "hostname": "host",
     "port": "",
     "pathname": "/C:/",
     "search": "",
@@ -5699,12 +5699,12 @@
   {
     "input": "C|\\",
     "base": "file://host/dir/file",
-    "href": "file:///C:/",
+    "href": "file://host/C:/",
     "protocol": "file:",
     "username": "",
     "password": "",
-    "host": "",
-    "hostname": "",
+    "host": "host",
+    "hostname": "host",
     "port": "",
     "pathname": "/C:/",
     "search": "",
@@ -5784,27 +5784,27 @@
   {
     "input": "/c:/foo/bar",
     "base": "file://host/path",
-    "href": "file:///c:/foo/bar",
+    "href": "file://host/c:/foo/bar",
     "protocol": "file:",
     "username": "",
     "password": "",
-    "host": "",
-    "hostname": "",
+    "host": "host",
+    "hostname": "host",
     "port": "",
     "pathname": "/c:/foo/bar",
     "search": "",
     "hash": ""
   },
-  "# Windows drive letter quirk with not empty host",
+  "# Do not drop the host in the presence of a drive letter",
   {
     "input": "file://example.net/C:/",
     "base": "about:blank",
-    "href": "file:///C:/",
+    "href": "file://example.net/C:/",
     "protocol": "file:",
     "username": "",
     "password": "",
-    "host": "",
-    "hostname": "",
+    "host": "example.net",
+    "hostname": "example.net",
     "port": "",
     "pathname": "/C:/",
     "search": "",
@@ -5813,12 +5813,12 @@
   {
     "input": "file://1.2.3.4/C:/",
     "base": "about:blank",
-    "href": "file:///C:/",
+    "href": "file://1.2.3.4/C:/",
     "protocol": "file:",
     "username": "",
     "password": "",
-    "host": "",
-    "hostname": "",
+    "host": "1.2.3.4",
+    "hostname": "1.2.3.4",
     "port": "",
     "pathname": "/C:/",
     "search": "",
@@ -5827,12 +5827,12 @@
   {
     "input": "file://[1::8]/C:/",
     "base": "about:blank",
-    "href": "file:///C:/",
+    "href": "file://[1::8]/C:/",
     "protocol": "file:",
     "username": "",
     "password": "",
-    "host": "",
-    "hostname": "",
+    "host": "[1::8]",
+    "hostname": "[1::8]",
     "port": "",
     "pathname": "/C:/",
     "search": "",
@@ -6034,6 +6034,133 @@
     "base": "about:blank",
     "failure": true
   },
+  "# Additional file URL tetsts for (https://github.com/whatwg/url/issues/405)",
+  {
+    "input": "file://localhost//a//../..//foo",
+    "base": "about:blank",
+    "href": "file://///foo",
+    "protocol": "file:",
+    "username": "",
+    "password": "",
+    "host": "",
+    "hostname": "",
+    "port": "",
+    "pathname": "///foo",
+    "search": "",
+    "hash": ""
+  },
+  {
+    "input": "file://localhost////foo",
+    "base": "about:blank",
+    "href": "file://////foo",
+    "protocol": "file:",
+    "username": "",
+    "password": "",
+    "host": "",
+    "hostname": "",
+    "port": "",
+    "pathname": "////foo",
+    "search": "",
+    "hash": ""
+  },
+  {
+    "input": "file:////foo",
+    "base": "about:blank",
+    "href": "file:////foo",
+    "protocol": "file:",
+    "username": "",
+    "password": "",
+    "host": "",
+    "hostname": "",
+    "port": "",
+    "pathname": "//foo",
+    "search": "",
+    "hash": ""
+  },
+  {
+    "input": "file:///one/two",
+    "base": "file:///",
+    "href": "file:///one/two",
+    "protocol": "file:",
+    "username": "",
+    "password": "",
+    "host": "",
+    "hostname": "",
+    "port": "",
+    "pathname": "/one/two",
+    "search": "",
+    "hash": ""
+  },
+  {
+    "input": "file:////one/two",
+    "base": "file:///",
+    "href": "file:////one/two",
+    "protocol": "file:",
+    "username": "",
+    "password": "",
+    "host": "",
+    "hostname": "",
+    "port": "",
+    "pathname": "//one/two",
+    "search": "",
+    "hash": ""
+  },
+  {
+    "input": "//one/two",
+    "base": "file:///",
+    "href": "file://one/two",
+    "protocol": "file:",
+    "username": "",
+    "password": "",
+    "host": "one",
+    "hostname": "one",
+    "port": "",
+    "pathname": "/two",
+    "search": "",
+    "hash": ""
+  },
+  {
+    "input": "///one/two",
+    "base": "file:///",
+    "href": "file:///one/two",
+    "protocol": "file:",
+    "username": "",
+    "password": "",
+    "host": "",
+    "hostname": "",
+    "port": "",
+    "pathname": "/one/two",
+    "search": "",
+    "hash": ""
+  },
+  {
+    "input": "////one/two",
+    "base": "file:///",
+    "href": "file:////one/two",
+    "protocol": "file:",
+    "username": "",
+    "password": "",
+    "host": "",
+    "hostname": "",
+    "port": "",
+    "pathname": "//one/two",
+    "search": "",
+    "hash": ""
+  },
+  {
+    "input": "file:///.//",
+    "base": "file:////",
+    "href": "file:////",
+    "protocol": "file:",
+    "username": "",
+    "password": "",
+    "host": "",
+    "hostname": "",
+    "port": "",
+    "pathname": "//",
+    "search": "",
+    "hash": ""
+  },
   "# IPv6 tests",
   {
     "input": "http://[1:0::]",
diff --git a/test/fixtures/wpt/versions.json b/test/fixtures/wpt/versions.json
index d1d47d6d27caac..1977524052eea4 100644
--- a/test/fixtures/wpt/versions.json
+++ b/test/fixtures/wpt/versions.json
@@ -8,7 +8,7 @@
     "path": "encoding"
   },
   "url": {
-    "commit": "e2ddf48b78209d0aef4fa513b53a9f28243c9335",
+    "commit": "050308a616a8388f1ad5d6e87eac0270fd35023f",
     "path": "url"
   },
   "resources": {