diff --git a/server/channels/api4/system.go b/server/channels/api4/system.go
index 9b85abcfb83..c00a0c0a480 100644
--- a/server/channels/api4/system.go
+++ b/server/channels/api4/system.go
@@ -319,7 +319,11 @@ func invalidateCaches(c *Context, w http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	c.App.Srv().InvalidateAllCaches()
+	appErr := c.App.Srv().InvalidateAllCaches()
+	if appErr != nil {
+		c.Err = appErr
+		return
+	}
 
 	auditRec.Success()
 
diff --git a/server/channels/api4/user_test.go b/server/channels/api4/user_test.go
index 6bc2c214b01..e2e65cf7acc 100644
--- a/server/channels/api4/user_test.go
+++ b/server/channels/api4/user_test.go
@@ -3909,7 +3909,8 @@ func TestLoginWithLag(t *testing.T) {
 		_, _, err := th.Client.Login(context.Background(), th.BasicUser.Email, th.BasicUser.Password)
 		require.NoError(t, err)
 
-		th.App.Srv().InvalidateAllCaches()
+		appErr = th.App.Srv().InvalidateAllCaches()
+		require.Nil(t, appErr)
 
 		session, appErr := th.App.GetSession(th.Client.AuthToken)
 		require.Nil(t, appErr)
diff --git a/server/channels/app/admin.go b/server/channels/app/admin.go
index b5ab1a9010f..95afdff8a6a 100644
--- a/server/channels/app/admin.go
+++ b/server/channels/app/admin.go
@@ -137,8 +137,8 @@ func (a *App) GetClusterStatus() []*model.ClusterInfo {
 	return infos
 }
 
-func (s *Server) InvalidateAllCaches() {
-	s.platform.InvalidateAllCaches()
+func (s *Server) InvalidateAllCaches() *model.AppError {
+	return s.platform.InvalidateAllCaches()
 }
 
 func (s *Server) InvalidateAllCachesSkipSend() {
diff --git a/server/channels/app/license.go b/server/channels/app/license.go
index 33efbdd5e3c..c2f879e4758 100644
--- a/server/channels/app/license.go
+++ b/server/channels/app/license.go
@@ -131,6 +131,10 @@ func (s *Server) License() *model.License {
 	return s.platform.License()
 }
 
+func (s *Server) LoadLicense() {
+	s.platform.LoadLicense()
+}
+
 func (s *Server) SaveLicense(licenseBytes []byte) (*model.License, *model.AppError) {
 	return s.platform.SaveLicense(licenseBytes)
 }
diff --git a/server/channels/app/license_test.go b/server/channels/app/license_test.go
new file mode 100644
index 00000000000..26b4b58b70c
--- /dev/null
+++ b/server/channels/app/license_test.go
@@ -0,0 +1,109 @@
+// Copyright (c) 2015-present Mattermost, Inc. All Rights Reserved.
+// See LICENSE.txt for license information.
+
+package app
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+
+	"github.com/mattermost/mattermost/server/public/model"
+)
+
+func TestLoadLicense(t *testing.T) {
+	th := Setup(t)
+	defer th.TearDown()
+
+	th.App.Srv().LoadLicense()
+	require.Nil(t, th.App.Srv().License(), "shouldn't have a valid license")
+}
+
+func TestSaveLicense(t *testing.T) {
+	th := Setup(t)
+	defer th.TearDown()
+
+	b1 := []byte("junk")
+
+	_, err := th.App.Srv().SaveLicense(b1)
+	require.NotNil(t, err, "shouldn't have saved license")
+}
+
+func TestRemoveLicense(t *testing.T) {
+	th := Setup(t)
+	defer th.TearDown()
+
+	err := th.App.Srv().RemoveLicense()
+	require.Nil(t, err, "should have removed license")
+}
+
+func TestSetLicense(t *testing.T) {
+	th := Setup(t)
+	defer th.TearDown()
+
+	l1 := &model.License{}
+	l1.Features = &model.Features{}
+	l1.Customer = &model.Customer{}
+	l1.StartsAt = model.GetMillis() - 1000
+	l1.ExpiresAt = model.GetMillis() + 100000
+	ok := th.App.Srv().SetLicense(l1)
+	require.True(t, ok, "license should have worked")
+
+	l3 := &model.License{}
+	l3.Features = &model.Features{}
+	l3.Customer = &model.Customer{}
+	l3.StartsAt = model.GetMillis() + 10000
+	l3.ExpiresAt = model.GetMillis() + 100000
+	ok = th.App.Srv().SetLicense(l3)
+	require.True(t, ok, "license should have passed")
+}
+
+func TestGetSanitizedClientLicense(t *testing.T) {
+	th := Setup(t)
+	defer th.TearDown()
+
+	setLicense(th, nil)
+
+	m := th.App.Srv().GetSanitizedClientLicense()
+
+	_, ok := m["Name"]
+	assert.False(t, ok)
+	_, ok = m["SkuName"]
+	assert.False(t, ok)
+}
+
+func TestGenerateRenewalToken(t *testing.T) {
+	th := Setup(t)
+	defer th.TearDown()
+
+	t.Run("renewal token generated correctly", func(t *testing.T) {
+		setLicense(th, nil)
+		token, appErr := th.App.Srv().GenerateRenewalToken(JWTDefaultTokenExpiration)
+		require.Nil(t, appErr)
+		require.NotEmpty(t, token)
+	})
+
+	t.Run("return error if there is no active license", func(t *testing.T) {
+		th.App.Srv().SetLicense(nil)
+		_, appErr := th.App.Srv().GenerateRenewalToken(JWTDefaultTokenExpiration)
+		require.NotNil(t, appErr)
+	})
+}
+
+func setLicense(th *TestHelper, customer *model.Customer) {
+	l1 := &model.License{}
+	l1.Features = &model.Features{}
+	if customer != nil {
+		l1.Customer = customer
+	} else {
+		l1.Customer = &model.Customer{}
+		l1.Customer.Name = "TestName"
+		l1.Customer.Email = "test@example.com"
+	}
+	l1.SkuName = "SKU NAME"
+	l1.SkuShortName = "SKU SHORT NAME"
+	l1.StartsAt = model.GetMillis() - 1000
+	l1.ExpiresAt = model.GetMillis() + 100000
+	th.App.Srv().SetLicense(l1)
+}
diff --git a/server/channels/app/notification_test.go b/server/channels/app/notification_test.go
index 9dbf635996a..6b4f638f6dd 100644
--- a/server/channels/app/notification_test.go
+++ b/server/channels/app/notification_test.go
@@ -99,7 +99,8 @@ func TestSendNotifications(t *testing.T) {
 
 	_, appErr = th.App.UpdateActive(th.Context, th.BasicUser2, false)
 	require.Nil(t, appErr)
-	th.App.Srv().InvalidateAllCaches()
+	appErr = th.App.Srv().InvalidateAllCaches()
+	require.Nil(t, appErr)
 
 	post3, appErr := th.App.CreatePostMissingChannel(th.Context, &model.Post{
 		UserId:    th.BasicUser.Id,
diff --git a/server/channels/app/oauth.go b/server/channels/app/oauth.go
index 4c287cd9b2b..1be59084079 100644
--- a/server/channels/app/oauth.go
+++ b/server/channels/app/oauth.go
@@ -113,7 +113,9 @@ func (a *App) DeleteOAuthApp(appID string) *model.AppError {
 		return model.NewAppError("DeleteOAuthApp", "app.oauth.delete_app.app_error", nil, "", http.StatusInternalServerError).Wrap(err)
 	}
 
-	a.Srv().InvalidateAllCaches()
+	if err := a.Srv().InvalidateAllCaches(); err != nil {
+		mlog.Warn("error in invalidating cache", mlog.Err(err))
+	}
 
 	return nil
 }
diff --git a/server/channels/app/platform/cluster_handlers.go b/server/channels/app/platform/cluster_handlers.go
index 2d50fd15165..a45809085b6 100644
--- a/server/channels/app/platform/cluster_handlers.go
+++ b/server/channels/app/platform/cluster_handlers.go
@@ -17,7 +17,6 @@ func (ps *PlatformService) RegisterClusterHandlers() {
 	ps.clusterIFace.RegisterClusterMessageHandler(model.ClusterEventPublish, ps.ClusterPublishHandler)
 	ps.clusterIFace.RegisterClusterMessageHandler(model.ClusterEventUpdateStatus, ps.ClusterUpdateStatusHandler)
 	ps.clusterIFace.RegisterClusterMessageHandler(model.ClusterEventInvalidateAllCaches, ps.ClusterInvalidateAllCachesHandler)
-	ps.clusterIFace.RegisterClusterMessageHandler(model.ClusterEventLoadLicense, ps.LoadLicenseClusterHandler)
 	ps.clusterIFace.RegisterClusterMessageHandler(model.ClusterEventInvalidateCacheForChannelMembersNotifyProps, ps.clusterInvalidateCacheForChannelMembersNotifyPropHandler)
 	ps.clusterIFace.RegisterClusterMessageHandler(model.ClusterEventInvalidateCacheForChannelByName, ps.clusterInvalidateCacheForChannelByNameHandler)
 	ps.clusterIFace.RegisterClusterMessageHandler(model.ClusterEventInvalidateCacheForUser, ps.clusterInvalidateCacheForUserHandler)
@@ -155,27 +154,10 @@ func (ps *PlatformService) InvalidateAllCachesSkipSend() {
 	ps.Store.Webhook().ClearCaches()
 
 	linkCache.Purge()
+	ps.LoadLicense()
 }
 
-func (ps *PlatformService) LoadLicenseClusterHandler(_ *model.ClusterMessage) {
-	ps.loadLicense()
-}
-
-func (ps *PlatformService) TriggerLoadLicense() {
-	ps.loadLicense()
-
-	if ps.clusterIFace != nil {
-		msg := &model.ClusterMessage{
-			Event:            model.ClusterEventLoadLicense,
-			SendType:         model.ClusterSendReliable,
-			WaitForAllToSend: true,
-		}
-
-		ps.clusterIFace.SendClusterMessage(msg)
-	}
-}
-
-func (ps *PlatformService) InvalidateAllCaches() {
+func (ps *PlatformService) InvalidateAllCaches() *model.AppError {
 	ps.InvalidateAllCachesSkipSend()
 
 	if ps.clusterIFace != nil {
@@ -188,4 +170,6 @@ func (ps *PlatformService) InvalidateAllCaches() {
 
 		ps.clusterIFace.SendClusterMessage(msg)
 	}
+
+	return nil
 }
diff --git a/server/channels/app/platform/license.go b/server/channels/app/platform/license.go
index dbe7afb27ff..d3a1b0ecb5c 100644
--- a/server/channels/app/platform/license.go
+++ b/server/channels/app/platform/license.go
@@ -46,7 +46,7 @@ func (ps *PlatformService) License() *model.License {
 	return ps.licenseValue.Load()
 }
 
-func (ps *PlatformService) loadLicense() {
+func (ps *PlatformService) LoadLicense() {
 	// ENV var overrides all other sources of license.
 	licenseStr := os.Getenv(LicenseEnv)
 	if licenseStr != "" {
@@ -326,6 +326,9 @@ func (ps *PlatformService) RequestTrialLicense(trialRequest *model.TrialLicenseR
 		return err
 	}
 
+	ps.ReloadConfig()
+	ps.InvalidateAllCaches()
+
 	return nil
 }
 
diff --git a/server/channels/app/platform/license_test.go b/server/channels/app/platform/license_test.go
index cbc15b507a2..3f1af98ad1d 100644
--- a/server/channels/app/platform/license_test.go
+++ b/server/channels/app/platform/license_test.go
@@ -12,6 +12,14 @@ import (
 	"github.com/mattermost/mattermost/server/public/model"
 )
 
+func TestLoadLicense(t *testing.T) {
+	th := Setup(t)
+	defer th.TearDown()
+
+	th.Service.LoadLicense()
+	require.Nil(t, th.Service.License(), "shouldn't have a valid license")
+}
+
 func TestSaveLicense(t *testing.T) {
 	th := Setup(t)
 	defer th.TearDown()
diff --git a/server/channels/app/platform/service.go b/server/channels/app/platform/service.go
index 9074e5258cf..8869f5ea408 100644
--- a/server/channels/app/platform/service.go
+++ b/server/channels/app/platform/service.go
@@ -292,7 +292,7 @@ func New(sc ServiceConfig, options ...Option) (*PlatformService, error) {
 
 	// Step 7: Init License
 	if model.BuildEnterpriseReady == "true" {
-		ps.TriggerLoadLicense()
+		ps.LoadLicense()
 	}
 
 	// Step 8: Init Metrics Server depends on step 6 (store) and 7 (license)
@@ -353,7 +353,9 @@ func (ps *PlatformService) Start() error {
 		message := model.NewWebSocketEvent(model.WebsocketEventConfigChanged, "", "", "", nil, "")
 
 		message.Add("config", ps.ClientConfigWithComputed())
-		ps.Publish(message)
+		ps.Go(func() {
+			ps.Publish(message)
+		})
 
 		if err := ps.ReconfigureLogger(); err != nil {
 			mlog.Error("Error re-configuring logging after config change", mlog.Err(err))
@@ -366,7 +368,9 @@ func (ps *PlatformService) Start() error {
 
 		message := model.NewWebSocketEvent(model.WebsocketEventLicenseChanged, "", "", "", nil, "")
 		message.Add("license", ps.GetSanitizedClientLicense())
-		ps.Publish(message)
+		ps.Go(func() {
+			ps.Publish(message)
+		})
 
 	})
 	return nil
diff --git a/server/channels/app/server.go b/server/channels/app/server.go
index d59447997f6..a93b79bbcc0 100644
--- a/server/channels/app/server.go
+++ b/server/channels/app/server.go
@@ -209,6 +209,7 @@ func NewServer(options ...Option) (*Server, error) {
 	// Depends on step 1 (s.Platform must be non-nil)
 	s.initEnterprise()
 
+	// Needed to run before loading license.
 	s.userService, err = users.New(users.ServiceConfig{
 		UserStore:    s.Store().User(),
 		SessionStore: s.Store().Session(),
@@ -222,6 +223,11 @@ func NewServer(options ...Option) (*Server, error) {
 		return nil, errors.Wrapf(err, "unable to create users service")
 	}
 
+	if model.BuildEnterpriseReady == "true" {
+		// Dependent on user service
+		s.LoadLicense()
+	}
+
 	s.licenseWrapper = &licenseWrapper{
 		srv: s,
 	}
@@ -1378,6 +1384,8 @@ func (s *Server) sendLicenseUpForRenewalEmail(users map[string]*model.User, lice
 }
 
 func (s *Server) doLicenseExpirationCheck() {
+	s.LoadLicense()
+
 	// This takes care of a rare edge case reported here https://mattermost.atlassian.net/browse/MM-40962
 	// To reproduce that case locally, attach a license to a server that was started with enterprise enabled
 	// Then restart using BUILD_ENTERPRISE=false make restart-server to enter Team Edition
@@ -1387,6 +1395,7 @@ func (s *Server) doLicenseExpirationCheck() {
 	}
 
 	license := s.License()
+
 	if license == nil {
 		mlog.Debug("License cannot be found.")
 		return
diff --git a/server/cmd/mattermost/commands/init.go b/server/cmd/mattermost/commands/init.go
index 5101aa99263..77f40c63868 100644
--- a/server/cmd/mattermost/commands/init.go
+++ b/server/cmd/mattermost/commands/init.go
@@ -49,6 +49,10 @@ func initDBCommandContext(configDSN string, readOnlyConfigStore bool, options ..
 
 	a := app.New(app.ServerConnector(s.Channels()))
 
+	if model.BuildEnterpriseReady == "true" {
+		a.Srv().LoadLicense()
+	}
+
 	return a, nil
 }
 
diff --git a/server/cmd/mattermost/commands/jobserver.go b/server/cmd/mattermost/commands/jobserver.go
index 32895a1492c..18a544b4651 100644
--- a/server/cmd/mattermost/commands/jobserver.go
+++ b/server/cmd/mattermost/commands/jobserver.go
@@ -41,6 +41,8 @@ func jobserverCmdF(command *cobra.Command, args []string) error {
 	}
 	defer a.Srv().Shutdown()
 
+	a.Srv().LoadLicense()
+
 	// Run jobs
 	mlog.Info("Starting Mattermost job server")
 	defer mlog.Info("Stopped Mattermost job server")
diff --git a/server/public/model/cluster_message.go b/server/public/model/cluster_message.go
index 19f5e4079ed..6ff912f9ac8 100644
--- a/server/public/model/cluster_message.go
+++ b/server/public/model/cluster_message.go
@@ -9,7 +9,6 @@ const (
 	ClusterEventPublish                                     ClusterEvent = "publish"
 	ClusterEventUpdateStatus                                ClusterEvent = "update_status"
 	ClusterEventInvalidateAllCaches                         ClusterEvent = "inv_all_caches"
-	ClusterEventLoadLicense                                 ClusterEvent = "load_license"
 	ClusterEventInvalidateCacheForReactions                 ClusterEvent = "inv_reactions"
 	ClusterEventInvalidateCacheForChannelMembersNotifyProps ClusterEvent = "inv_channel_members_notify_props"
 	ClusterEventInvalidateCacheForChannelByName             ClusterEvent = "inv_channel_name"