diff --git a/platformio/commands/upgrade.py b/platformio/commands/upgrade.py
index ba26b844..df9fc0ee 100644
--- a/platformio/commands/upgrade.py
+++ b/platformio/commands/upgrade.py
@@ -18,11 +18,15 @@ import click
 import requests
 
 from platformio import VERSION, __version__, exception, util
+from platformio.managers.core import update_core_packages
 
 
 @click.command(
     "upgrade", short_help="Upgrade PlatformIO to the latest version")
 def cli():
+    # Update PlatformIO's Core packages
+    update_core_packages(silent=True)
+
     latest = get_latest_version()
     if __version__ == latest:
         return click.secho(
diff --git a/platformio/maintenance.py b/platformio/maintenance.py
index b9d245da..3e198f08 100644
--- a/platformio/maintenance.py
+++ b/platformio/maintenance.py
@@ -234,6 +234,9 @@ def check_platformio_upgrade():
     if (time() - interval) < last_check.get("platformio_upgrade", 0):
         return
 
+    # Update PlatformIO's Core packages
+    update_core_packages(silent=True)
+
     last_check['platformio_upgrade'] = int(time())
     app.set_state_item("last_check", last_check)