diff --git a/platformio/commands/upgrade.py b/platformio/commands/upgrade.py
index d8ba386e6b..73e18982fa 100644
--- a/platformio/commands/upgrade.py
+++ b/platformio/commands/upgrade.py
@@ -111,7 +111,6 @@ def upgrade_pip_dependencies(verbose):
             "pip",
             "install",
             "--upgrade",
-            "pip",
             *get_pip_dependencies(),
         ],
         check=True,
diff --git a/platformio/dependencies.py b/platformio/dependencies.py
index 51e1725d2c..66e3cdb1c4 100644
--- a/platformio/dependencies.py
+++ b/platformio/dependencies.py
@@ -28,6 +28,7 @@ def get_core_dependencies():
 
 def get_pip_dependencies():
     core = [
+        "pip",
         "bottle == 0.13.*",
         "click >=8.0.4, <8.5, !=8.3",  # click 9.0 removes 'protected_args' attribute
         "colorama",
diff --git a/tests/misc/test_dependencies.py b/tests/misc/test_dependencies.py
new file mode 100644
index 0000000000..4854b4d0ce
--- /dev/null
+++ b/tests/misc/test_dependencies.py
@@ -0,0 +1,40 @@
+# Copyright (c) 2014-present PlatformIO <contact@platformio.org>
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#    http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+from platformio.commands import upgrade as cmd_upgrade
+from platformio.dependencies import get_pip_dependencies
+
+
+def test_pip_is_declared_dependency():
+    assert get_pip_dependencies().count("pip") == 1
+
+
+def test_upgrade_pip_dependencies_upgrades_declared_pip_once(monkeypatch):
+    calls = []
+
+    monkeypatch.setattr(cmd_upgrade, "get_pythonexe_path", lambda: "python")
+    monkeypatch.setattr(
+        cmd_upgrade.subprocess,
+        "run",
+        lambda args, **kwargs: calls.append((args, kwargs)),
+    )
+
+    cmd_upgrade.upgrade_pip_dependencies(verbose=False)
+
+    args, kwargs = calls[0]
+    assert args[:5] == ["python", "-m", "pip", "install", "--upgrade"]
+    assert args[5:] == get_pip_dependencies()
+    assert args[5:].count("pip") == 1
+    assert kwargs["check"] is True
+    assert kwargs["stdout"] == cmd_upgrade.subprocess.PIPE