diff --git a/app/plugin.go b/app/plugin.go
index e9d70a5d77..789ebe2364 100644
--- a/app/plugin.go
+++ b/app/plugin.go
@@ -180,6 +180,7 @@ func (s *Server) initPlugins(c *request.Context, pluginDir, webappPluginDir stri
 	s.PluginsLock.RUnlock()
 	if pluginsEnvironment != nil || !*s.Config().PluginSettings.Enable {
 		s.syncPluginsActiveState()
+		pluginsEnvironment.TogglePluginHealthCheckJob(*s.Config().PluginSettings.EnableHealthCheck)
 		return
 	}
 
@@ -208,6 +209,8 @@ func (s *Server) initPlugins(c *request.Context, pluginDir, webappPluginDir stri
 	s.PluginsEnvironment = env
 	s.PluginsLock.Unlock()
 
+	s.PluginsEnvironment.TogglePluginHealthCheckJob(*s.Config().PluginSettings.EnableHealthCheck)
+
 	if err := s.syncPlugins(); err != nil {
 		mlog.Error("Failed to sync plugins from the file store", mlog.Err(err))
 	}
@@ -327,7 +330,10 @@ func (s *Server) syncPlugins() *model.AppError {
 }
 
 func (s *Server) ShutDownPlugins() {
-	pluginsEnvironment := s.GetPluginsEnvironment()
+	// Acquiring lock manually, as plugins might be disabled. See GetPluginsEnvironment.
+	s.PluginsLock.RLock()
+	pluginsEnvironment := s.PluginsEnvironment
+	s.PluginsLock.RUnlock()
 	if pluginsEnvironment == nil {
 		return
 	}
diff --git a/app/server.go b/app/server.go
index 2e961188e5..b973e0cc42 100644
--- a/app/server.go
+++ b/app/server.go
@@ -571,20 +571,6 @@ func NewServer(options ...Option) (*Server, error) {
 		s.EmailService.InitEmailBatching()
 	})
 
-	// Start plugin health check job
-	pluginsEnvironment := s.PluginsEnvironment
-	if pluginsEnvironment != nil {
-		pluginsEnvironment.InitPluginHealthCheckJob(*s.Config().PluginSettings.Enable && *s.Config().PluginSettings.EnableHealthCheck)
-	}
-	s.AddConfigListener(func(_, c *model.Config) {
-		s.PluginsLock.RLock()
-		pluginsEnvironment := s.PluginsEnvironment
-		s.PluginsLock.RUnlock()
-		if pluginsEnvironment != nil {
-			pluginsEnvironment.InitPluginHealthCheckJob(*s.Config().PluginSettings.Enable && *c.PluginSettings.EnableHealthCheck)
-		}
-	})
-
 	logCurrentVersion := fmt.Sprintf("Current version is %v (%v/%v/%v/%v)", model.CurrentVersion, model.BuildNumber, model.BuildDate, model.BuildHash, model.BuildHashEnterprise)
 	mlog.Info(
 		logCurrentVersion,
diff --git a/plugin/environment.go b/plugin/environment.go
index 1071e735af..70c738733a 100644
--- a/plugin/environment.go
+++ b/plugin/environment.go
@@ -332,9 +332,7 @@ func (env *Environment) RestartPlugin(id string) error {
 
 // Shutdown deactivates all plugins and gracefully shuts down the environment.
 func (env *Environment) Shutdown() {
-	if env.pluginHealthCheckJob != nil {
-		env.pluginHealthCheckJob.Cancel()
-	}
+	env.TogglePluginHealthCheckJob(false)
 
 	var wg sync.WaitGroup
 	env.registeredPlugins.Range(func(key, value interface{}) bool {
@@ -507,8 +505,8 @@ func newRegisteredPlugin(bundle *model.BundleInfo) registeredPlugin {
 	return registeredPlugin{State: state, BundleInfo: bundle}
 }
 
-// InitPluginHealthCheckJob starts a new job if one is not running and is set to enabled, or kills an existing one if set to disabled.
-func (env *Environment) InitPluginHealthCheckJob(enable bool) {
+// TogglePluginHealthCheckJob starts a new job if one is not running and is set to enabled, or kills an existing one if set to disabled.
+func (env *Environment) TogglePluginHealthCheckJob(enable bool) {
 	// Config is set to enable. No job exists, start a new job.
 	if enable && env.pluginHealthCheckJob == nil {
 		mlog.Debug("Enabling plugin health check job", mlog.Duration("interval_s", HealthCheckInterval))