diff --git a/dev-python/flask/files/flask-1.1.1-py38.patch b/dev-python/flask/files/flask-1.1.1-py38.patch
new file mode 100644
index 0000000000000..a03aa445137b2
--- /dev/null
+++ b/dev-python/flask/files/flask-1.1.1-py38.patch
@@ -0,0 +1,38 @@
+commit c367a86cc5be70da4928b276d0218f98df6e854d
+Author: Fernanda Guimarães <fernandaguimaraes28@gmail.com>
+Date:   Mon Oct 28 21:37:25 2019 -0300
+
+    Test test_send_from_directory_bad_request no longer fails in Python 3.8.
+
+diff --git a/tests/test_helpers.py b/tests/test_helpers.py
+index 78a56221..21735af1 100644
+--- a/tests/test_helpers.py
++++ b/tests/test_helpers.py
+@@ -11,6 +11,7 @@
+ import datetime
+ import io
+ import os
++import sys
+ import uuid
+ 
+ import pytest
+@@ -780,12 +781,17 @@ class TestSendfile(object):
+         assert rv.data.strip() == b"Hello Subdomain"
+         rv.close()
+ 
+-    def test_send_from_directory_bad_request(self, app, req_ctx):
++    def test_send_from_directory_null_character(self, app, req_ctx):
+         app.root_path = os.path.join(
+             os.path.dirname(__file__), "test_apps", "subdomaintestmodule"
+         )
+ 
+-        with pytest.raises(BadRequest):
++        if sys.version_info >= (3, 8):
++            exception = NotFound
++        else:
++            exception = BadRequest
++
++        with pytest.raises(exception):
+             flask.send_from_directory("static", "bad\x00")
+ 
+ 
diff --git a/dev-python/flask/flask-1.1.1.ebuild b/dev-python/flask/flask-1.1.1.ebuild
index 6c634728d160e..df47780240215 100644
--- a/dev-python/flask/flask-1.1.1.ebuild
+++ b/dev-python/flask/flask-1.1.1.ebuild
@@ -3,7 +3,7 @@
 
 EAPI=7
 
-PYTHON_COMPAT=( python2_7 python3_{5,6,7} pypy{,3} )
+PYTHON_COMPAT=( python2_7 python3_{5,6,7,8} pypy{,3} )
 
 inherit distutils-r1
 
@@ -35,6 +35,11 @@ DEPEND="${RDEPEND}
 	doc? ( $(python_gen_any_dep 'dev-python/sphinx[${PYTHON_USEDEP}]') )
 	test? ( dev-python/pytest[${PYTHON_USEDEP}] )"
 
+PATCHES=(
+	# taken from upstream git, will be in next release
+	"${FILESDIR}/flask-1.1.1-py38.patch"
+)
+
 python_check_deps() {
 	use doc || return 0
 	has_version "dev-python/sphinx[${PYTHON_USEDEP}]"