diff --git a/sanic/__version__.py b/sanic/__version__.py
index faa7ddb9..9bccec66 100644
--- a/sanic/__version__.py
+++ b/sanic/__version__.py
@@ -1 +1 @@
-__version__ = "20.12.6"
+__version__ = "20.12.7"
diff --git a/sanic/static.py b/sanic/static.py
index 0a75d9dc..875fa3df 100644
--- a/sanic/static.py
+++ b/sanic/static.py
@@ -1,7 +1,6 @@
 from functools import partial, wraps
 from mimetypes import guess_type
-from os import path
-from re import sub
+from os import path, sep
 from time import gmtime, strftime
 from urllib.parse import unquote
 
@@ -26,28 +25,33 @@ async def _static_request_handler(
     content_type=None,
     file_uri=None,
 ):
-    # Using this to determine if the URL is trying to break out of the path
-    # served.  os.path.realpath seems to be very slow
-    if file_uri and "../" in file_uri:
-        raise InvalidUsage("Invalid URL")
     # Merge served directory and requested file if provided
-    # Strip all / that in the beginning of the URL to help prevent python
-    # from herping a derp and treating the uri as an absolute path
-    root_path = file_path = file_or_directory
-    if file_uri:
-        file_path = path.join(file_or_directory, sub("^[/]*", "", file_uri))
+    root_path = file_path = path.abspath(unquote(file_or_directory))
 
-    # URL decode the path sent by the browser otherwise we won't be able to
-    # match filenames which got encoded (filenames with spaces etc)
-    file_path = path.abspath(unquote(file_path))
-    if not file_path.startswith(path.abspath(unquote(root_path))):
+    if file_uri:
+        # Strip all / that in the beginning of the URL to help prevent
+        # python from herping a derp and treating the uri as an
+        # absolute path
+        unquoted_file_uri = unquote(file_uri).lstrip("/")
+
+        segments = unquoted_file_uri.split("/")
+        if ".." in segments or any(sep in segment for segment in segments):
+            raise InvalidUsage("Invalid URL")
+
+        file_path = path.join(file_or_directory, unquoted_file_uri)
+        file_path = path.abspath(file_path)
+
+    if not file_path.startswith(root_path):
         error_logger.exception(
             f"File not found: path={file_or_directory}, "
             f"relative_url={file_uri}"
         )
         raise FileNotFound(
-            "File not found", path=file_or_directory, relative_url=file_uri
+            "File not found",
+            path=file_or_directory,
+            relative_url=file_uri,
         )
+
     try:
         headers = {}
         # Check if the client has been sent this file before
diff --git a/tests/test_static.py b/tests/test_static.py
index 91635a45..e5ecd673 100644
--- a/tests/test_static.py
+++ b/tests/test_static.py
@@ -1,10 +1,14 @@
 import inspect
 import os
+import sys
 
+from pathlib import Path
 from time import gmtime, strftime
 
 import pytest
 
+from sanic.app import Sanic
+
 
 @pytest.fixture(scope="module")
 def static_file_directory():
@@ -15,6 +19,22 @@ def static_file_directory():
     return static_directory
 
 
+@pytest.fixture(scope="module")
+def double_dotted_directory_file(static_file_directory: str):
+    """Generate double dotted directory and its files"""
+    if sys.platform == "win32":
+        raise Exception("Windows doesn't support double dotted directories")
+
+    file_path = Path(static_file_directory) / "dotted.." / "dot.txt"
+    double_dotted_dir = file_path.parent
+    Path.mkdir(double_dotted_dir, exist_ok=True)
+    with open(file_path, "w") as f:
+        f.write("DOT\n")
+    yield file_path
+    Path.unlink(file_path)
+    Path.rmdir(double_dotted_dir)
+
+
 def get_file_path(static_file_directory, file_name):
     return os.path.join(static_file_directory, file_name)
 
@@ -374,3 +394,41 @@ def test_static_name(app, static_file_directory, static_name, file_name):
     request, response = app.test_client.get(f"/static/{file_name}")
 
     assert response.status == 200
+
+
+@pytest.mark.skipif(
+    sys.platform == "win32",
+    reason="Windows does not support double dotted directories",
+)
+def test_dotted_dir_ok(
+    app: Sanic, static_file_directory: str, double_dotted_directory_file: Path
+):
+    app.static("/foo", static_file_directory)
+    url = (
+        "/foo"
+        + str(double_dotted_directory_file)[len(static_file_directory) :]
+    )
+    _, response = app.test_client.get(url)
+    assert response.status == 200
+    assert response.body == b"DOT\n"
+
+
+def test_breakout(app: Sanic, static_file_directory: str):
+    app.static("/foo", static_file_directory)
+
+    _, response = app.test_client.get("/foo/..%2Fstatic/test.file")
+    assert response.status == 400
+
+
+@pytest.mark.skipif(
+    sys.platform != "win32", reason="Block backslash on Windows only"
+)
+def test_double_backslash_prohibited_on_win32(
+    app: Sanic, static_file_directory: str
+):
+    app.static("/foo", static_file_directory)
+
+    _, response = app.test_client.get("/foo/static/..\\static/test.file")
+    assert response.status == 400
+    _, response = app.test_client.get("/foo/static\\../static/test.file")
+    assert response.status == 400