diff --git a/app/app.go b/app/app.go
index c3e66c9923..0051aaca5b 100644
--- a/app/app.go
+++ b/app/app.go
@@ -142,6 +142,18 @@ func (a *App) getSystemInstallDate() (int64, *model.AppError) {
 	return value, nil
 }
 
+func (a *App) getFirstServerRunTimestamp() (int64, *model.AppError) {
+	systemData, appErr := a.Srv().Store.System().GetByName(model.SYSTEM_FIRST_SERVER_RUN_TIMESTAMP_KEY)
+	if appErr != nil {
+		return 0, appErr
+	}
+	value, err := strconv.ParseInt(systemData.Value, 10, 64)
+	if err != nil {
+		return 0, model.NewAppError("getFirstServerRunTimestamp", "app.system_install_date.parse_int.app_error", nil, err.Error(), http.StatusInternalServerError)
+	}
+	return value, nil
+}
+
 func (a *App) Srv() *Server {
 	return a.srv
 }
diff --git a/app/app_test.go b/app/app_test.go
index e19a1bc249..0d2bbb013a 100644
--- a/app/app_test.go
+++ b/app/app_test.go
@@ -39,6 +39,7 @@ func TestUnitUpdateConfig(t *testing.T) {
 	mockPostStore.On("GetMaxPostSize").Return(65535, nil)
 	mockSystemStore := mocks.SystemStore{}
 	mockSystemStore.On("GetByName", "InstallationDate").Return(&model.System{Name: "InstallationDate", Value: "10"}, nil)
+	mockSystemStore.On("GetByName", "FirstServerRunTimestamp").Return(&model.System{Name: "FirstServerRunTimestamp", Value: "10"}, nil)
 	mockStore.On("User").Return(&mockUserStore)
 	mockStore.On("Post").Return(&mockPostStore)
 	mockStore.On("System").Return(&mockSystemStore)
diff --git a/app/config.go b/app/config.go
index 4130ecfefe..183f6d09a1 100644
--- a/app/config.go
+++ b/app/config.go
@@ -265,6 +265,22 @@ func (a *App) ensureInstallationDate() error {
 	return nil
 }
 
+func (a *App) ensureFirstServerRunTimestamp() error {
+	_, err := a.getFirstServerRunTimestamp()
+	if err == nil {
+		return nil
+	}
+
+	err = a.Srv().Store.System().SaveOrUpdate(&model.System{
+		Name:  model.SYSTEM_FIRST_SERVER_RUN_TIMESTAMP_KEY,
+		Value: strconv.FormatInt(utils.MillisFromTime(time.Now()), 10),
+	})
+	if err != nil {
+		return err
+	}
+	return nil
+}
+
 // AsymmetricSigningKey will return a private key that can be used for asymmetric signing.
 func (s *Server) AsymmetricSigningKey() *ecdsa.PrivateKey {
 	return s.asymmetricSigningKey
diff --git a/app/enterprise_test.go b/app/enterprise_test.go
index 9c770d0645..4cd3e041c9 100644
--- a/app/enterprise_test.go
+++ b/app/enterprise_test.go
@@ -105,6 +105,8 @@ func TestSAMLSettings(t *testing.T) {
 			mockPostStore.On("GetMaxPostSize").Return(65535, nil)
 			mockSystemStore := storemocks.SystemStore{}
 			mockSystemStore.On("GetByName", "InstallationDate").Return(&model.System{Name: "InstallationDate", Value: "10"}, nil)
+			mockSystemStore.On("GetByName", "FirstServerRunTimestamp").Return(&model.System{Name: "FirstServerRunTimestamp", Value: "10"}, nil)
+
 			mockStore.On("User").Return(&mockUserStore)
 			mockStore.On("Post").Return(&mockPostStore)
 			mockStore.On("System").Return(&mockSystemStore)
diff --git a/app/notification_push_test.go b/app/notification_push_test.go
index bbd4e29658..727548fb9e 100644
--- a/app/notification_push_test.go
+++ b/app/notification_push_test.go
@@ -555,6 +555,8 @@ func TestGetPushNotificationMessage(t *testing.T) {
 	mockPostStore.On("GetMaxPostSize").Return(65535, nil)
 	mockSystemStore := mocks.SystemStore{}
 	mockSystemStore.On("GetByName", "InstallationDate").Return(&model.System{Name: "InstallationDate", Value: "10"}, nil)
+	mockSystemStore.On("GetByName", "FirstServerRunTimestamp").Return(&model.System{Name: "FirstServerRunTimestamp", Value: "10"}, nil)
+
 	mockStore.On("User").Return(&mockUserStore)
 	mockStore.On("Post").Return(&mockPostStore)
 	mockStore.On("System").Return(&mockSystemStore)
@@ -1125,6 +1127,8 @@ func TestClearPushNotificationSync(t *testing.T) {
 	mockPostStore.On("GetMaxPostSize").Return(65535, nil)
 	mockSystemStore := mocks.SystemStore{}
 	mockSystemStore.On("GetByName", "InstallationDate").Return(&model.System{Name: "InstallationDate", Value: "10"}, nil)
+	mockSystemStore.On("GetByName", "FirstServerRunTimestamp").Return(&model.System{Name: "FirstServerRunTimestamp", Value: "10"}, nil)
+
 	mockSessionStore := mocks.SessionStore{}
 	mockSessionStore.On("GetSessionsWithActiveDeviceIds", mock.AnythingOfType("string")).Return([]*model.Session{sess1, sess2}, nil)
 	mockSessionStore.On("UpdateDeviceId", mock.AnythingOfType("string"), mock.AnythingOfType("string"), mock.AnythingOfType("int64")).Return("testdeviceID", nil)
@@ -1177,6 +1181,8 @@ func TestUpdateMobileAppBadgeSync(t *testing.T) {
 	mockPostStore.On("GetMaxPostSize").Return(65535, nil)
 	mockSystemStore := mocks.SystemStore{}
 	mockSystemStore.On("GetByName", "InstallationDate").Return(&model.System{Name: "InstallationDate", Value: "10"}, nil)
+	mockSystemStore.On("GetByName", "FirstServerRunTimestamp").Return(&model.System{Name: "FirstServerRunTimestamp", Value: "10"}, nil)
+
 	mockSessionStore := mocks.SessionStore{}
 	mockSessionStore.On("GetSessionsWithActiveDeviceIds", mock.AnythingOfType("string")).Return([]*model.Session{sess1, sess2}, nil)
 	mockSessionStore.On("UpdateDeviceId", mock.AnythingOfType("string"), mock.AnythingOfType("string"), mock.AnythingOfType("int64")).Return("testdeviceID", nil)
@@ -1217,6 +1223,8 @@ func TestSendAckToPushProxy(t *testing.T) {
 	mockPostStore.On("GetMaxPostSize").Return(65535, nil)
 	mockSystemStore := mocks.SystemStore{}
 	mockSystemStore.On("GetByName", "InstallationDate").Return(&model.System{Name: "InstallationDate", Value: "10"}, nil)
+	mockSystemStore.On("GetByName", "FirstServerRunTimestamp").Return(&model.System{Name: "FirstServerRunTimestamp", Value: "10"}, nil)
+
 	mockStore.On("User").Return(&mockUserStore)
 	mockStore.On("Post").Return(&mockPostStore)
 	mockStore.On("System").Return(&mockSystemStore)
@@ -1371,6 +1379,8 @@ func BenchmarkPushNotificationThroughput(b *testing.B) {
 	mockPostStore.On("GetMaxPostSize").Return(65535, nil)
 	mockSystemStore := mocks.SystemStore{}
 	mockSystemStore.On("GetByName", "InstallationDate").Return(&model.System{Name: "InstallationDate", Value: "10"}, nil)
+	mockSystemStore.On("GetByName", "FirstServerRunTimestamp").Return(&model.System{Name: "FirstServerRunTimestamp", Value: "10"}, nil)
+
 	mockSessionStore := mocks.SessionStore{}
 	mockPreferenceStore := mocks.PreferenceStore{}
 	mockPreferenceStore.On("Get", mock.AnythingOfType("string"), mock.AnythingOfType("string"), mock.AnythingOfType("string")).Return(&model.Preference{Value: "test"}, nil)
diff --git a/app/plugin_signature_test.go b/app/plugin_signature_test.go
index 9eb5806253..862caecdbe 100644
--- a/app/plugin_signature_test.go
+++ b/app/plugin_signature_test.go
@@ -27,6 +27,8 @@ func TestPluginPublicKeys(t *testing.T) {
 	mockPostStore.On("GetMaxPostSize").Return(65535, nil)
 	mockSystemStore := mocks.SystemStore{}
 	mockSystemStore.On("GetByName", "InstallationDate").Return(&model.System{Name: "InstallationDate", Value: "10"}, nil)
+	mockSystemStore.On("GetByName", "FirstServerRunTimestamp").Return(&model.System{Name: "FirstServerRunTimestamp", Value: "10"}, nil)
+
 	mockStore.On("User").Return(&mockUserStore)
 	mockStore.On("Post").Return(&mockPostStore)
 	mockStore.On("System").Return(&mockSystemStore)
diff --git a/app/post_test.go b/app/post_test.go
index aaf8d54285..c675098b6c 100644
--- a/app/post_test.go
+++ b/app/post_test.go
@@ -460,6 +460,8 @@ func TestImageProxy(t *testing.T) {
 	mockPostStore.On("GetMaxPostSize").Return(65535, nil)
 	mockSystemStore := storemocks.SystemStore{}
 	mockSystemStore.On("GetByName", "InstallationDate").Return(&model.System{Name: "InstallationDate", Value: "10"}, nil)
+	mockSystemStore.On("GetByName", "FirstServerRunTimestamp").Return(&model.System{Name: "FirstServerRunTimestamp", Value: "10"}, nil)
+
 	mockStore.On("User").Return(&mockUserStore)
 	mockStore.On("Post").Return(&mockPostStore)
 	mockStore.On("System").Return(&mockSystemStore)
diff --git a/app/server.go b/app/server.go
index 83f8465a9b..43e8564763 100644
--- a/app/server.go
+++ b/app/server.go
@@ -146,7 +146,8 @@ type Server struct {
 
 	CacheProvider cache.Provider
 
-	tracer *tracing.Tracer
+	tracer                      *tracing.Tracer
+	timestampLastDiagnosticSent time.Time
 }
 
 func NewServer(options ...Option) (*Server, error) {
@@ -727,11 +728,32 @@ func runSecurityJob(s *Server) {
 	}, time.Hour*4)
 }
 
-func runDiagnosticsJob(s *Server) {
-	doDiagnostics(s)
-	model.CreateRecurringTask("Diagnostics", func() {
+func doDiagnosticsIfNeeded(s *Server, firstRun time.Time) {
+	hoursSinceFirstServerRun := time.Since(firstRun).Hours()
+	// Send once every 10 minutes for the first hour
+	// Send once every hour thereafter for the first 12 hours
+	// Send at the 24 hour mark and every 24 hours after
+	if hoursSinceFirstServerRun < 1 {
 		doDiagnostics(s)
-	}, time.Hour*24)
+	} else if hoursSinceFirstServerRun <= 12 && time.Since(s.timestampLastDiagnosticSent) >= time.Hour {
+		doDiagnostics(s)
+	} else if hoursSinceFirstServerRun > 12 && time.Since(s.timestampLastDiagnosticSent) >= 24*time.Hour {
+		doDiagnostics(s)
+	}
+}
+
+func runDiagnosticsJob(s *Server) {
+	// Send on boot
+	doDiagnostics(s)
+	firstRun, err := s.FakeApp().getFirstServerRunTimestamp()
+	if err != nil {
+		mlog.Warn("Fetching time of first server run failed. Setting to 'now'.")
+		s.FakeApp().ensureFirstServerRunTimestamp()
+		firstRun = utils.MillisFromTime(time.Now())
+	}
+	model.CreateRecurringTask("Diagnostics", func() {
+		doDiagnosticsIfNeeded(s, utils.TimeFromMillis(firstRun))
+	}, time.Minute*10)
 }
 
 func runTokenCleanupJob(s *Server) {
@@ -761,6 +783,7 @@ func doSecurity(s *Server) {
 
 func doDiagnostics(s *Server) {
 	if *s.Config().LogSettings.EnableDiagnostics {
+		s.timestampLastDiagnosticSent = time.Now()
 		s.FakeApp().SendDailyDiagnostics()
 	}
 }
diff --git a/app/server_app_adapters.go b/app/server_app_adapters.go
index 555ec2b584..eb3252757c 100644
--- a/app/server_app_adapters.go
+++ b/app/server_app_adapters.go
@@ -97,6 +97,10 @@ func (s *Server) RunOldAppInitialization() error {
 		return errors.Wrapf(err, "unable to ensure installation date")
 	}
 
+	if err := s.FakeApp().ensureFirstServerRunTimestamp(); err != nil {
+		return errors.Wrapf(err, "unable to ensure first run timestamp")
+	}
+
 	s.ensureDiagnosticId()
 	s.FakeApp().regenerateClientConfig()
 
diff --git a/model/system.go b/model/system.go
index 473292a876..4c3132e2be 100644
--- a/model/system.go
+++ b/model/system.go
@@ -10,14 +10,15 @@ import (
 )
 
 const (
-	SYSTEM_DIAGNOSTIC_ID             = "DiagnosticId"
-	SYSTEM_RAN_UNIT_TESTS            = "RanUnitTests"
-	SYSTEM_LAST_SECURITY_TIME        = "LastSecurityTime"
-	SYSTEM_ACTIVE_LICENSE_ID         = "ActiveLicenseId"
-	SYSTEM_LAST_COMPLIANCE_TIME      = "LastComplianceTime"
-	SYSTEM_ASYMMETRIC_SIGNING_KEY    = "AsymmetricSigningKey"
-	SYSTEM_POST_ACTION_COOKIE_SECRET = "PostActionCookieSecret"
-	SYSTEM_INSTALLATION_DATE_KEY     = "InstallationDate"
+	SYSTEM_DIAGNOSTIC_ID                  = "DiagnosticId"
+	SYSTEM_RAN_UNIT_TESTS                 = "RanUnitTests"
+	SYSTEM_LAST_SECURITY_TIME             = "LastSecurityTime"
+	SYSTEM_ACTIVE_LICENSE_ID              = "ActiveLicenseId"
+	SYSTEM_LAST_COMPLIANCE_TIME           = "LastComplianceTime"
+	SYSTEM_ASYMMETRIC_SIGNING_KEY         = "AsymmetricSigningKey"
+	SYSTEM_POST_ACTION_COOKIE_SECRET      = "PostActionCookieSecret"
+	SYSTEM_INSTALLATION_DATE_KEY          = "InstallationDate"
+	SYSTEM_FIRST_SERVER_RUN_TIMESTAMP_KEY = "FirstServerRunTimestamp"
 )
 
 type System struct {
diff --git a/testlib/store.go b/testlib/store.go
index c5cfeefebe..94a6bfa4fb 100644
--- a/testlib/store.go
+++ b/testlib/store.go
@@ -27,6 +27,7 @@ func GetMockStoreForSetupFunctions() *mocks.Store {
 	systemStore.On("GetByName", "AsymmetricSigningKey").Return(nil, model.NewAppError("FakeError", "store.sql_system.get_by_name.app_error", nil, "", http.StatusInternalServerError))
 	systemStore.On("GetByName", "PostActionCookieSecret").Return(nil, model.NewAppError("FakeError", "store.sql_system.get_by_name.app_error", nil, "", http.StatusInternalServerError))
 	systemStore.On("GetByName", "InstallationDate").Return(&model.System{Name: "InstallationDate", Value: strconv.FormatInt(model.GetMillis(), 10)}, nil)
+	systemStore.On("GetByName", "FirstServerRunTimestamp").Return(&model.System{Name: "FirstServerRunTimestamp", Value: "10"}, nil)
 	systemStore.On("GetByName", "AdvancedPermissionsMigrationComplete").Return(&model.System{Name: "AdvancedPermissionsMigrationComplete", Value: "true"}, nil)
 	systemStore.On("GetByName", "EmojisPermissionsMigrationComplete").Return(&model.System{Name: "EmojisPermissionsMigrationComplete", Value: "true"}, nil)
 	systemStore.On("GetByName", "GuestRolesCreationMigrationComplete").Return(&model.System{Name: "GuestRolesCreationMigrationComplete", Value: "true"}, nil)
diff --git a/web/handlers_test.go b/web/handlers_test.go
index 670b5439b1..c4fc13472e 100644
--- a/web/handlers_test.go
+++ b/web/handlers_test.go
@@ -71,6 +71,8 @@ func TestHandlerServeHTTPSecureTransport(t *testing.T) {
 	mockPostStore.On("GetMaxPostSize").Return(65535, nil)
 	mockSystemStore := mocks.SystemStore{}
 	mockSystemStore.On("GetByName", "InstallationDate").Return(&model.System{Name: "InstallationDate", Value: "10"}, nil)
+	mockSystemStore.On("GetByName", "FirstServerRunTimestamp").Return(&model.System{Name: "FirstServerRunTimestamp", Value: "10"}, nil)
+
 	mockStore.On("User").Return(&mockUserStore)
 	mockStore.On("Post").Return(&mockPostStore)
 	mockStore.On("System").Return(&mockSystemStore)
@@ -310,6 +312,8 @@ func TestHandlerServeCSPHeader(t *testing.T) {
 		mockPostStore.On("GetMaxPostSize").Return(65535, nil)
 		mockSystemStore := mocks.SystemStore{}
 		mockSystemStore.On("GetByName", "InstallationDate").Return(&model.System{Name: "InstallationDate", Value: "10"}, nil)
+		mockSystemStore.On("GetByName", "FirstServerRunTimestamp").Return(&model.System{Name: "FirstServerRunTimestamp", Value: "10"}, nil)
+
 		mockStore.On("User").Return(&mockUserStore)
 		mockStore.On("Post").Return(&mockPostStore)
 		mockStore.On("System").Return(&mockSystemStore)
@@ -474,6 +478,8 @@ func TestCheckCSRFToken(t *testing.T) {
 		mockPostStore.On("GetMaxPostSize").Return(65535, nil)
 		mockSystemStore := mocks.SystemStore{}
 		mockSystemStore.On("GetByName", "InstallationDate").Return(&model.System{Name: "InstallationDate", Value: "10"}, nil)
+		mockSystemStore.On("GetByName", "FirstServerRunTimestamp").Return(&model.System{Name: "FirstServerRunTimestamp", Value: "10"}, nil)
+
 		mockStore.On("User").Return(&mockUserStore)
 		mockStore.On("Post").Return(&mockPostStore)
 		mockStore.On("System").Return(&mockSystemStore)