From 5050a18a0057df4cda6f6b00483d12d29cb59239 Mon Sep 17 00:00:00 2001
From: James Warne <15948170+bebleo@users.noreply.github.com>
Date: Mon, 18 Apr 2022 08:52:01 -0400
Subject: [PATCH] evaluate --cert before --key

---
 CHANGES.rst       | 2 ++
 src/flask/cli.py  | 5 ++++-
 tests/test_cli.py | 5 +++++
 3 files changed, 11 insertions(+), 1 deletion(-)

diff --git a/CHANGES.rst b/CHANGES.rst
index 0d96a61e71..68ef94fd2a 100644
--- a/CHANGES.rst
+++ b/CHANGES.rst
@@ -7,6 +7,8 @@ Unreleased
 
 -   Fix type annotation for ``json.loads``, it accepts str or bytes.
     :issue:`4519`
+-   The ``--cert`` and ``--key`` options on ``flask run`` can be given
+    in either order. :issue:`4459`
 
 
 Version 2.1.1
diff --git a/src/flask/cli.py b/src/flask/cli.py
index 972698dfa1..36c4f1b6dc 100644
--- a/src/flask/cli.py
+++ b/src/flask/cli.py
@@ -763,7 +763,10 @@ def convert(self, value, param, ctx):
 @click.option("--host", "-h", default="127.0.0.1", help="The interface to bind to.")
 @click.option("--port", "-p", default=5000, help="The port to bind to.")
 @click.option(
-    "--cert", type=CertParamType(), help="Specify a certificate file to use HTTPS."
+    "--cert",
+    type=CertParamType(),
+    help="Specify a certificate file to use HTTPS.",
+    is_eager=True,
 )
 @click.option(
     "--key",
diff --git a/tests/test_cli.py b/tests/test_cli.py
index 6271c72a59..f9f3673a67 100644
--- a/tests/test_cli.py
+++ b/tests/test_cli.py
@@ -553,9 +553,14 @@ def test_run_cert_path():
     with pytest.raises(click.BadParameter):
         run_command.make_context("run", ["--key", __file__])
 
+    # cert specified first
     ctx = run_command.make_context("run", ["--cert", __file__, "--key", __file__])
     assert ctx.params["cert"] == (__file__, __file__)
 
+    # key specified first
+    ctx = run_command.make_context("run", ["--key", __file__, "--cert", __file__])
+    assert ctx.params["cert"] == (__file__, __file__)
+
 
 def test_run_cert_adhoc(monkeypatch):
     monkeypatch.setitem(sys.modules, "cryptography", None)