diff --git a/src/octoprint/plugins/pluginmanager/__init__.py b/src/octoprint/plugins/pluginmanager/__init__.py
index bcd70bb4..0b3e4fe1 100644
--- a/src/octoprint/plugins/pluginmanager/__init__.py
+++ b/src/octoprint/plugins/pluginmanager/__init__.py
@@ -667,6 +667,9 @@ class PluginManagerPlugin(octoprint.plugin.SimpleApiPlugin,
 			octoprint_version_string = octoprint_version_string[:octoprint_version_string.find("-")]
 
 		octoprint_version = pkg_resources.parse_version(octoprint_version_string)
+		# A leading v is common in github release tags and old setuptools doesn't remove it.
+		if octoprint_version and isinstance(octoprint_version, tuple) and octoprint_version[0].lower() == "*v":
+			octoprint_version = octoprint_version[1:]
 		if base:
 			if isinstance(octoprint_version, tuple):
 				# old setuptools
diff --git a/src/octoprint/plugins/softwareupdate/version_checks/github_release.py b/src/octoprint/plugins/softwareupdate/version_checks/github_release.py
index a8867105..494bf025 100644
--- a/src/octoprint/plugins/softwareupdate/version_checks/github_release.py
+++ b/src/octoprint/plugins/softwareupdate/version_checks/github_release.py
@@ -150,6 +150,9 @@ def _get_comparable_version_pkg_resources(version_string, force_base=True):
 
 	version = pkg_resources.parse_version(version_string)
 
+	# A leading v is common in github release tags and old setuptools doesn't remove it.
+	if version and isinstance(version, tuple) and version[0].lower() == "*v":
+		version = version[1:]
 	if force_base:
 		if isinstance(version, tuple):
 			# old setuptools