[MM-48029] notify admin for plugin install from work templates (#22007)

Co-authored-by: Mattermost Build <build@mattermost.com>
Co-authored-by: Julien Tant <julien@craftyx.fr>

api4/notify_admin.go

@@ -7,10 +7,13 @@ import (
 	"encoding/json"
 	"net/http"
 
+	"github.com/mattermost/mattermost-server/v6/shared/mlog"
+
 	"github.com/mattermost/mattermost-server/v6/model"
 )
 
 func handleNotifyAdmin(c *Context, w http.ResponseWriter, r *http.Request) {
+	mlog.Info("enter handleNotifyAdmin")
 	var notifyAdminRequest *model.NotifyAdminToUpgradeRequest
 	err := json.NewDecoder(r.Body).Decode(&notifyAdminRequest)
 	if err != nil {
@@ -24,11 +27,14 @@ func handleNotifyAdmin(c *Context, w http.ResponseWriter, r *http.Request) {
 		c.Err = appErr
 		return
 	}
+	mlog.Info("exit handleNotifyAdmin")
 
 	ReturnStatusOK(w)
 }
 
 func handleTriggerNotifyAdminPosts(c *Context, w http.ResponseWriter, r *http.Request) {
+	mlog.Info("enter handleTriggerNotifyAdminPosts")
+
 	if !*c.App.Config().ServiceSettings.EnableAPITriggerAdminNotifications {
 		c.Err = model.NewAppError("Api4.handleTriggerNotifyAdminPosts", "api.cloud.app_error", nil, "Manual triggering of notifications not allowed", http.StatusForbidden)
 		return
@@ -53,5 +59,7 @@ func handleTriggerNotifyAdminPosts(c *Context, w http.ResponseWriter, r *http.Re
 		return
 	}
 
+	mlog.Info("exit handleTriggerNotifyAdminPosts")
+
 	ReturnStatusOK(w)
 }

app/app_iface.go

@@ -573,7 +573,7 @@ type AppIface interface {
 	FillInChannelsProps(c request.CTX, channelList model.ChannelList) *model.AppError
 	FilterUsersByVisible(viewer *model.User, otherUsers []*model.User) ([]*model.User, *model.AppError)
 	FindTeamByName(name string) bool
-	FinishSendAdminNotifyPost(trial bool, now int64)
+	FinishSendAdminNotifyPost(trial bool, now int64, pluginBasedData map[string][]*model.NotifyAdminData)
 	GenerateMfaSecret(userID string) (*model.MfaSecret, *model.AppError)
 	GeneratePublicLink(siteURL string, info *model.FileInfo) string
 	GenerateSupportPacket() []model.FileData
@@ -1167,7 +1167,7 @@ type AppIface interface {
 	UpsertGroupMember(groupID string, userID string) (*model.GroupMember, *model.AppError)
 	UpsertGroupMembers(groupID string, userIDs []string) ([]*model.GroupMember, *model.AppError)
 	UpsertGroupSyncable(groupSyncable *model.GroupSyncable) (*model.GroupSyncable, *model.AppError)
-	UserAlreadyNotifiedOnRequiredFeature(user string, feature model.MattermostPaidFeature) bool
+	UserAlreadyNotifiedOnRequiredFeature(user string, feature model.MattermostFeature) bool
 	UserCanSeeOtherUser(userID string, otherUserId string) (bool, *model.AppError)
 	UserIsFirstAdmin(user *model.User) bool
 	VerifyEmailFromToken(c request.CTX, userSuppliedTokenString string) *model.AppError

app/notify_admin.go

@@ -9,6 +9,7 @@ import (
 	"net/http"
 	"os"
 	"strconv"
+	"strings"
 
 	"github.com/mattermost/mattermost-server/v6/app/request"
 	"github.com/mattermost/mattermost-server/v6/model"
@@ -19,14 +20,16 @@ import (
 
 const lastTrialNotificationTimeStamp = "LAST_TRIAL_NOTIFICATION_TIMESTAMP"
 const lastUpgradeNotificationTimeStamp = "LAST_UPGRADE_NOTIFICATION_TIMESTAMP"
-const defaultNotifyAdminCoolOffDays = 14
+const defaultNotifyAdminCoolOffDays = 0.0104166667 // this is a temp change
 
 func (a *App) SaveAdminNotification(userId string, notifyData *model.NotifyAdminToUpgradeRequest) *model.AppError {
 	requiredFeature := notifyData.RequiredFeature
 	requiredPlan := notifyData.RequiredPlan
 	trial := notifyData.TrialNotification
 
-	if a.UserAlreadyNotifiedOnRequiredFeature(userId, requiredFeature) {
+	isUserAlreadyNotified := a.UserAlreadyNotifiedOnRequiredFeature(userId, requiredFeature)
+	mlog.Info("SaveAdminNotification")
+	if isUserAlreadyNotified {
 		return model.NewAppError("app.SaveAdminNotification", "api.cloud.notify_admin_to_upgrade_error.already_notified", nil, "", http.StatusForbidden)
 	}
 
@@ -36,6 +39,7 @@ func (a *App) SaveAdminNotification(userId string, notifyData *model.NotifyAdmin
 		RequiredFeature: requiredFeature,
 		Trial:           trial,
 	})
+
 	if appErr != nil {
 		return appErr
 	}
@@ -57,7 +61,9 @@ func (a *App) DoCheckForAdminNotifications(trial bool) *model.AppError {
 }
 
 func (a *App) SaveAdminNotifyData(data *model.NotifyAdminData) (*model.NotifyAdminData, *model.AppError) {
+	mlog.Info("Trying to save NotifyAdmin data")
 	d, err := a.Srv().Store().NotifyAdmin().Save(data)
+	mlog.Info("NotifyAdmin data saved")
 	if err != nil {
 		var nfErr *store.ErrNotFound
 		switch {
@@ -67,6 +73,7 @@ func (a *App) SaveAdminNotifyData(data *model.NotifyAdminData) (*model.NotifyAdm
 			return nil, model.NewAppError("SaveAdminNotifyData", "app.notify_admin.save.app_error", nil, err.Error(), http.StatusInternalServerError)
 		}
 	}
+	mlog.Info("return from SaveAdminNotifyData")
 
 	return d, nil
 }
@@ -81,6 +88,8 @@ func filterNotificationData(data []*model.NotifyAdminData, test func(*model.Noti
 }
 
 func (a *App) SendNotifyAdminPosts(c *request.Context, workspaceName string, currentSKU string, trial bool) *model.AppError {
+	mlog.Info("enter SendNotifyAdminPosts")
+
 	if !a.CanNotifyAdmin(trial) {
 		return model.NewAppError("SendNotifyAdminPosts", "app.notify_admin.send_notification_post.app_error", nil, "Cannot notify yet", http.StatusForbidden)
 	}
@@ -103,6 +112,8 @@ func (a *App) SendNotifyAdminPosts(c *request.Context, workspaceName string, cur
 	now := model.GetMillis()
 
 	data, err := a.Srv().Store().NotifyAdmin().Get(trial)
+	mlog.Info("SendNotifyAdminPosts")
+
 	if err != nil {
 		return model.NewAppError("SendNotifyAdminPosts", "app.notify_admin.send_notification_post.app_error", nil, err.Error(), http.StatusInternalServerError)
 	}
@@ -110,58 +121,99 @@ func (a *App) SendNotifyAdminPosts(c *request.Context, workspaceName string, cur
 	data = filterNotificationData(data, func(nad *model.NotifyAdminData) bool { return nad.RequiredPlan != currentSKU })
 
 	if len(data) == 0 {
-		mlog.Warn("No notification data available")
+		a.Log().Warn("No notification data available")
 		return nil
 	}
 
-	userBasedData := a.groupNotifyAdminByUser(data)
+	userBasedPaidFeatureData, userBasedPluginData := a.groupNotifyAdminByUser(data)
-	featureBasedData := a.groupNotifyAdminByFeature(data)
+	featureBasedData := a.groupNotifyAdminByPaidFeature(data)
-	props := make(model.StringInterface)
+	pluginBasedData := a.groupNotifyAdminByPlugin(data)
 
 	for _, admin := range sysadmins {
-		T := i18n.GetUserTranslations(admin.Locale)
+		if len(userBasedPaidFeatureData) > 0 && len(featureBasedData) > 0 {
-		message := T("app.cloud.upgrade_plan_bot_message", map[string]interface{}{"UsersNum": len(userBasedData), "WorkspaceName": workspaceName})
+			a.upgradePlanAdminNotifyPost(c, workspaceName, userBasedPaidFeatureData, featureBasedData, systemBot, admin, trial)
-		if len(userBasedData) == 1 {
-			message = T("app.cloud.upgrade_plan_bot_message_single", map[string]interface{}{"UsersNum": len(userBasedData), "WorkspaceName": workspaceName}) // todo (allan): investigate if translations library can do this
-		}
-		if trial {
-			message = T("app.cloud.trial_plan_bot_message", map[string]interface{}{"UsersNum": len(userBasedData), "WorkspaceName": workspaceName})
-			if len(userBasedData) == 1 {
-				message = T("app.cloud.trial_plan_bot_message_single", map[string]interface{}{"UsersNum": len(userBasedData), "WorkspaceName": workspaceName})
-			}
 		}
 
-		channel, appErr := a.GetOrCreateDirectChannel(c, systemBot.UserId, admin.Id)
+		if len(userBasedPluginData) > 0 {
-		if appErr != nil {
+			mlog.Info("SendNotifyAdminPosts", mlog.String("length of user based plugin data", fmt.Sprint(len(userBasedPluginData))))
-			mlog.Warn("Error getting direct channel", mlog.Err(appErr))
-			continue
-		}
 
-		post := &model.Post{
+			a.pluginInstallAdminNotifyPost(c, userBasedPluginData, pluginBasedData, systemBot, admin)
-			Message:   message,
-			UserId:    systemBot.UserId,
-			ChannelId: channel.Id,
-			Type:      fmt.Sprintf("%sup_notification", model.PostCustomTypePrefix), // webapp will have to create renderer for this custom post type
-
-		}
-
-		props["requested_features"] = featureBasedData
-		props["trial"] = trial
-		post.SetProps(props)
-
-		_, appErr = a.CreatePost(c, post, channel, false, true)
-		if appErr != nil {
-			mlog.Warn("Error creating post", mlog.Err(appErr))
-			continue
 		}
 	}
 
-	a.FinishSendAdminNotifyPost(trial, now)
+	a.FinishSendAdminNotifyPost(trial, now, pluginBasedData)
-
 	return nil
 }
 
-func (a *App) UserAlreadyNotifiedOnRequiredFeature(user string, feature model.MattermostPaidFeature) bool {
+func (a *App) pluginInstallAdminNotifyPost(c *request.Context, userBasedData map[string][]*model.NotifyAdminData, pluginBasedPluginData map[string][]*model.NotifyAdminData, systemBot *model.Bot, admin *model.User) {
+	props := make(model.StringInterface)
+
+	channel, appErr := a.GetOrCreateDirectChannel(c, systemBot.UserId, admin.Id)
+	if appErr != nil {
+		a.Log().Warn("Error getting direct channel", mlog.Err(appErr))
+		return
+	}
+
+	post := &model.Post{
+		UserId:    systemBot.UserId,
+		ChannelId: channel.Id,
+		Type:      fmt.Sprintf("%spl_notification", model.PostCustomTypePrefix), // webapp will have to create renderer for this custom post type
+	}
+
+	props["requested_plugins_by_plugin_ids"] = pluginBasedPluginData
+	props["requested_plugins_by_user_ids"] = userBasedData
+	post.SetProps(props)
+	mlog.Info("pluginInstallAdminNotifyPost: send props")
+
+	_, appErr = a.CreatePost(c, post, channel, false, true)
+	mlog.Info("pluginInstallAdminNotifyPost: post created")
+
+	if appErr != nil {
+		a.Log().Warn("Error creating post", mlog.Err(appErr))
+	}
+}
+
+func (a *App) upgradePlanAdminNotifyPost(c *request.Context, workspaceName string, userBasedData map[string][]*model.NotifyAdminData, featureBasedData map[model.MattermostFeature][]*model.NotifyAdminData, systemBot *model.Bot, admin *model.User, trial bool) {
+	props := make(model.StringInterface)
+	T := i18n.GetUserTranslations(admin.Locale)
+
+	message := T("app.cloud.upgrade_plan_bot_message", map[string]interface{}{"UsersNum": len(userBasedData), "WorkspaceName": workspaceName})
+	if len(userBasedData) == 1 {
+		message = T("app.cloud.upgrade_plan_bot_message_single", map[string]interface{}{"UsersNum": len(userBasedData), "WorkspaceName": workspaceName}) // todo (allan): investigate if translations library can do this
+	}
+	if trial {
+		message = T("app.cloud.trial_plan_bot_message", map[string]interface{}{"UsersNum": len(userBasedData), "WorkspaceName": workspaceName})
+		if len(userBasedData) == 1 {
+			message = T("app.cloud.trial_plan_bot_message_single", map[string]interface{}{"UsersNum": len(userBasedData), "WorkspaceName": workspaceName})
+		}
+	}
+
+	channel, appErr := a.GetOrCreateDirectChannel(c, systemBot.UserId, admin.Id)
+	if appErr != nil {
+		a.Log().Warn("Error getting direct channel", mlog.Err(appErr))
+		return
+	}
+
+	post := &model.Post{
+		Message:   message,
+		UserId:    systemBot.UserId,
+		ChannelId: channel.Id,
+		Type:      fmt.Sprintf("%sup_notification", model.PostCustomTypePrefix), // webapp will have to create renderer for this custom post type
+
+	}
+
+	props["requested_features"] = featureBasedData
+	props["trial"] = trial
+	post.SetProps(props)
+
+	_, appErr = a.CreatePost(c, post, channel, false, true)
+
+	if appErr != nil {
+		a.Log().Warn("Error creating post", mlog.Err(appErr))
+	}
+}
+
+func (a *App) UserAlreadyNotifiedOnRequiredFeature(user string, feature model.MattermostFeature) bool {
 	data, err := a.Srv().Store().NotifyAdmin().GetDataByUserIdAndFeature(user, feature)
 	if err != nil {
 		return false
@@ -185,13 +237,13 @@ func (a *App) CanNotifyAdmin(trial bool) bool {
 		if errors.As(sysValErr, &nfErr) { // if no timestamps have been recorded before, system is free to notify
 			return true
 		}
-		mlog.Error("Cannot notify", mlog.Err(sysValErr))
+		a.Log().Error("Cannot notify", mlog.Err(sysValErr))
 		return false
 	}
 
 	lastNotificationTimestamp, err := strconv.ParseFloat(sysVal.Value, 64)
 	if err != nil {
-		mlog.Error("Cannot notify", mlog.Err(err))
+		a.Log().Error("Cannot notify", mlog.Err(err))
 		return false
 	}
 
@@ -205,7 +257,9 @@ func (a *App) CanNotifyAdmin(trial bool) bool {
 	return timeDiff >= int64(daysToMillis)
 }
 
-func (a *App) FinishSendAdminNotifyPost(trial bool, now int64) {
+func (a *App) FinishSendAdminNotifyPost(trial bool, now int64, pluginBasedData map[string][]*model.NotifyAdminData) {
+	mlog.Info("FinishSendAdminNotifyPost")
+
 	systemVarName := lastUpgradeNotificationTimeStamp
 	if trial {
 		systemVarName = lastTrialNotificationTimeStamp
@@ -214,30 +268,64 @@ func (a *App) FinishSendAdminNotifyPost(trial bool, now int64) {
 	val := strconv.FormatInt(model.GetMillis(), 10)
 	sysVar := &model.System{Name: systemVarName, Value: val}
 	if err := a.Srv().Store().System().SaveOrUpdate(sysVar); err != nil {
-		mlog.Error("Unable to finish send admin notify post job", mlog.Err(err))
+		a.Log().Error("Unable to finish send admin notify post job", mlog.Err(err))
+	}
+
+	// All the requested features notifications are now sent in a post and can safely be removed except
+	// the plugin notify admin. We keep it as we do not want the same user to send the notification for the same plugin.
+	// We update the NotifyAdmin SentAt to keep track of it.
+	for pluginId := range pluginBasedData {
+		notifications := pluginBasedData[pluginId]
+		for _, notification := range notifications {
+			requiredFeature := notification.RequiredFeature
+			requiredPlan := notification.RequiredPlan
+			userId := notification.UserId
+			if err := a.Srv().Store().NotifyAdmin().Update(userId, requiredPlan, requiredFeature, now); err != nil {
+				a.Log().Error("Unable to update SentAt for work template feature", mlog.Err(err))
+			}
+		}
 	}
 
-	// all the notifications are now sent in a post and can safely be removed
 	if err := a.Srv().Store().NotifyAdmin().DeleteBefore(trial, now); err != nil {
-		mlog.Error("Unable to finish send admin notify post job", mlog.Err(err))
+		a.Log().Error("Unable to finish send admin notify post job", mlog.Err(err))
 	}
+	mlog.Info("exit FinishSendAdminNotifyPost")
 
 }
 
-func (a *App) groupNotifyAdminByUser(data []*model.NotifyAdminData) map[string][]*model.NotifyAdminData {
+func (a *App) groupNotifyAdminByUser(data []*model.NotifyAdminData) (map[string][]*model.NotifyAdminData, map[string][]*model.NotifyAdminData) {
-	myMap := make(map[string][]*model.NotifyAdminData)
+	userBasedPaidFeatureData := make(map[string][]*model.NotifyAdminData)
+	userBasedPluginData := make(map[string][]*model.NotifyAdminData)
 	for _, d := range data {
-		myMap[d.UserId] = append(myMap[d.UserId], d)
+		if strings.HasPrefix(string(d.RequiredFeature), string(model.PluginFeature)) {
+			userBasedPluginData[d.UserId] = append(userBasedPluginData[d.UserId], d)
+		} else {
+			userBasedPaidFeatureData[d.UserId] = append(userBasedPaidFeatureData[d.UserId], d)
+		}
 	}
-
+	return userBasedPaidFeatureData, userBasedPluginData
-	return myMap
 }
 
-func (a *App) groupNotifyAdminByFeature(data []*model.NotifyAdminData) map[model.MattermostPaidFeature][]*model.NotifyAdminData {
+func (a *App) groupNotifyAdminByPaidFeature(data []*model.NotifyAdminData) map[model.MattermostFeature][]*model.NotifyAdminData {
-	myMap := make(map[model.MattermostPaidFeature][]*model.NotifyAdminData)
+	myMap := make(map[model.MattermostFeature][]*model.NotifyAdminData)
 	for _, d := range data {
+		if strings.HasPrefix(string(d.RequiredFeature), string(model.PluginFeature)) {
+			continue
+		}
 		myMap[d.RequiredFeature] = append(myMap[d.RequiredFeature], d)
 	}
-
+	return myMap
+}
+
+func (a *App) groupNotifyAdminByPlugin(data []*model.NotifyAdminData) map[string][]*model.NotifyAdminData {
+	myMap := make(map[string][]*model.NotifyAdminData)
+	for _, d := range data {
+		if strings.HasPrefix(string(d.RequiredFeature), string(model.PluginFeature)) {
+			plugins := strings.Split(d.RequiredPlan, ",")
+			for _, plugin := range plugins {
+				myMap[plugin] = append(myMap[plugin], d)
+			}
+		}
+	}
 	return myMap
 }

app/notify_admin_test.go

@@ -15,9 +15,11 @@ import (
 	"github.com/stretchr/testify/require"
 )
 
+const PluginIdGithub = "github"
+
 func Test_SendNotifyAdminPosts(t *testing.T) {
 
-	t.Run("no error sending upgrade post when no notifications are available", func(t *testing.T) {
+	t.Run("no error sending non trial upgrade post when no notifications are available", func(t *testing.T) {
 		th := Setup(t).InitBasic()
 		defer th.TearDown()
 
@@ -28,7 +30,7 @@ func Test_SendNotifyAdminPosts(t *testing.T) {
 		require.Nil(t, err)
 	})
 
-	t.Run("no error sending trial post when do notifications are available", func(t *testing.T) {
+	t.Run("no error sending trial upgrade post when no notifications are available", func(t *testing.T) {
 		th := Setup(t).InitBasic()
 		defer th.TearDown()
 
@@ -45,7 +47,7 @@ func Test_SendNotifyAdminPosts(t *testing.T) {
 
 		th.App.Srv().SetLicense(model.NewTestLicense("cloud"))
 
-		// some some notifications
+		// some notifications
 		_, appErr := th.App.SaveAdminNotifyData(&model.NotifyAdminData{
 			UserId:          th.BasicUser.Id,
 			RequiredPlan:    model.LicenseShortSkuProfessional,
@@ -93,13 +95,13 @@ func Test_SendNotifyAdminPosts(t *testing.T) {
 		require.Equal(t, "2 members of the test workspace have requested a workspace upgrade for: ", post.Message)
 	})
 
-	t.Run("successfully send trial notification", func(t *testing.T) {
+	t.Run("successfully send trial upgrade notification", func(t *testing.T) {
 		th := Setup(t).InitBasic()
 		defer th.TearDown()
 
 		th.App.Srv().SetLicense(model.NewTestLicense("cloud"))
 
-		// some some notifications
+		// some notifications
 		_, appErr := th.App.SaveAdminNotifyData(&model.NotifyAdminData{
 			UserId:          th.BasicUser.Id,
 			RequiredPlan:    model.LicenseShortSkuProfessional,
@@ -141,13 +143,128 @@ func Test_SendNotifyAdminPosts(t *testing.T) {
 		require.Equal(t, "1 member of the test workspace has requested starting the Enterprise trial for access to: ", post.Message)
 	})
 
-	t.Run("error when trying to send post before end of cool off period", func(t *testing.T) {
+	t.Run("successfully send install plugin notification", func(t *testing.T) {
+		th := Setup(t).InitBasic()
+		defer th.TearDown()
+
+		// some notifications
+		_, appErr := th.App.SaveAdminNotifyData(&model.NotifyAdminData{
+			UserId:          th.BasicUser.Id,
+			RequiredPlan:    PluginIdGithub,
+			RequiredFeature: model.PluginFeature,
+			Trial:           false,
+		})
+		require.Nil(t, appErr)
+
+		ctx := request.NewContext(context.Background(), model.NewId(), model.NewId(), model.NewId(), model.NewId(), model.NewId(), model.Session{}, nil)
+		appErr = th.App.SendNotifyAdminPosts(ctx, "", "", false)
+		require.Nil(t, appErr)
+
+		bot, appErr := th.App.GetSystemBot()
+		require.Nil(t, appErr)
+
+		var channel *model.Channel
+		var err error
+		var timeout = 5 * time.Second
+		begin := time.Now()
+
+		for {
+			if time.Since(begin) > timeout {
+				break
+			}
+			channel, err = th.App.Srv().Store().Channel().GetByName("", model.GetDMNameFromIds(bot.UserId, th.SystemAdminUser.Id), false)
+			if err == nil && channel != nil {
+				break
+			}
+			time.Sleep(100 * time.Millisecond)
+		}
+		require.NoError(t, err, "Expected message to have been sent within %d seconds", timeout)
+		postList, err := th.App.Srv().Store().Post().GetPosts(model.GetPostsOptions{ChannelId: channel.Id, Page: 0, PerPage: 1}, false, map[string]bool{})
+		require.NoError(t, err)
+
+		post := postList.Posts[postList.Order[0]]
+
+		require.Equal(t, fmt.Sprintf("%spl_notification", model.PostCustomTypePrefix), post.Type)
+		require.Equal(t, bot.UserId, post.UserId)
+	})
+
+	t.Run("persist notify admin data after sending the install plugin notification", func(t *testing.T) {
+		th := Setup(t).InitBasic()
+		defer th.TearDown()
+
+		// some notifications
+		_, appErr := th.App.SaveAdminNotifyData(&model.NotifyAdminData{
+			UserId:          th.BasicUser.Id,
+			RequiredPlan:    PluginIdGithub,
+			RequiredFeature: model.PluginFeature,
+			Trial:           false,
+		})
+		require.Nil(t, appErr)
+
+		ctx := request.NewContext(context.Background(), model.NewId(), model.NewId(), model.NewId(), model.NewId(), model.NewId(), model.Session{}, nil)
+		appErr = th.App.SendNotifyAdminPosts(ctx, "", "", false)
+		require.Nil(t, appErr)
+
+		bot, appErr := th.App.GetSystemBot()
+		require.Nil(t, appErr)
+
+		var channel *model.Channel
+		var err error
+		var timeout = 5 * time.Second
+		begin := time.Now()
+
+		for {
+			if time.Since(begin) > timeout {
+				break
+			}
+			channel, err = th.App.Srv().Store().Channel().GetByName("", model.GetDMNameFromIds(bot.UserId, th.SystemAdminUser.Id), false)
+			if err == nil && channel != nil {
+				break
+			}
+			time.Sleep(100 * time.Millisecond)
+		}
+		require.NoError(t, err, "Expected message to have been sent within %d seconds", timeout)
+		postList, err := th.App.Srv().Store().Post().GetPosts(model.GetPostsOptions{ChannelId: channel.Id, Page: 0, PerPage: 1}, false, map[string]bool{})
+		require.NoError(t, err)
+
+		post := postList.Posts[postList.Order[0]]
+
+		require.Equal(t, fmt.Sprintf("%spl_notification", model.PostCustomTypePrefix), post.Type)
+		require.Equal(t, bot.UserId, post.UserId)
+
+		data, err := th.App.Srv().Store().NotifyAdmin().GetDataByUserIdAndFeature(th.BasicUser.Id, model.PluginFeature)
+		require.NoError(t, err)
+		require.Equal(t, len(data), 1)
+	})
+
+	t.Run("error sending more than one notification to the same user and for the same plugin", func(t *testing.T) {
+		th := Setup(t).InitBasic()
+		defer th.TearDown()
+
+		err := th.App.SaveAdminNotification(th.BasicUser.Id, &model.NotifyAdminToUpgradeRequest{
+			RequiredPlan:      PluginIdGithub,
+			RequiredFeature:   model.PluginFeature,
+			TrialNotification: false,
+		})
+
+		require.Nil(t, err)
+
+		err = th.App.SaveAdminNotification(th.BasicUser.Id, &model.NotifyAdminToUpgradeRequest{
+			RequiredPlan:      PluginIdGithub,
+			RequiredFeature:   model.PluginFeature,
+			TrialNotification: false,
+		})
+
+		require.Equal(t, err.Error(), "app.SaveAdminNotification: Already notified admin")
+	})
+
+	t.Run("error when trying to send upgrade post before end of cool off period", func(t *testing.T) {
 		th := Setup(t).InitBasic()
 		defer th.TearDown()
 
 		th.App.Srv().SetLicense(model.NewTestLicense("cloud"))
 
-		// some some notifications
+		// some notifications
 		_, appErr := th.App.SaveAdminNotifyData(&model.NotifyAdminData{
 			UserId:          th.BasicUser.Id,
 			RequiredPlan:    model.LicenseShortSkuProfessional,
@@ -173,7 +290,7 @@ func Test_SendNotifyAdminPosts(t *testing.T) {
 		require.Equal(t, appErr.Error(), "SendNotifyAdminPosts: Unable to send notification post., Cannot notify yet")
 	})
 
-	t.Run("can send post at the end of cool off period", func(t *testing.T) {
+	t.Run("can send upgrade post at the end of cool off period", func(t *testing.T) {
 		th := Setup(t).InitBasic()
 		defer th.TearDown()
 
@@ -182,7 +299,7 @@ func Test_SendNotifyAdminPosts(t *testing.T) {
 		os.Setenv("MM_NOTIFY_ADMIN_COOL_OFF_DAYS", "0.00003472222222") // set to 3 seconds
 		defer os.Unsetenv("MM_NOTIFY_ADMIN_COOL_OFF_DAYS")
 
-		// some some notifications
+		// some notifications
 		_, appErr := th.App.SaveAdminNotifyData(&model.NotifyAdminData{
 			UserId:          th.BasicUser.Id,
 			RequiredPlan:    model.LicenseShortSkuProfessional,
@@ -215,7 +332,7 @@ func Test_SendNotifyAdminPosts(t *testing.T) {
 
 		th.App.Srv().SetLicense(model.NewTestLicense("cloud"))
 
-		// some some notifications
+		// some notifications
 		_, appErr := th.App.SaveAdminNotifyData(&model.NotifyAdminData{
 			UserId:          th.BasicUser.Id,
 			RequiredPlan:    model.LicenseShortSkuProfessional,
@@ -264,4 +381,68 @@ func Test_SendNotifyAdminPosts(t *testing.T) {
 		require.Equal(t, bot.UserId, post.UserId)
 		require.Equal(t, "1 member of the test workspace has requested a workspace upgrade for: ", post.Message) // expect only one member's notification even though 2 were added
 	})
+
+	t.Run("correctly send upgrade and install plugin post with the correct user request", func(t *testing.T) {
+		th := Setup(t).InitBasic()
+		defer th.TearDown()
+		os.Setenv("MM_NOTIFY_ADMIN_COOL_OFF_DAYS", "0")
+		defer os.Unsetenv("MM_NOTIFY_ADMIN_COOL_OFF_DAYS")
+
+		th.App.Srv().SetLicense(model.NewTestLicense("cloud"))
+
+		ctx := request.NewContext(context.Background(), model.NewId(), model.NewId(), model.NewId(), model.NewId(), model.NewId(), model.Session{}, nil)
+
+		// some notifications
+		_, appErr := th.App.SaveAdminNotifyData(&model.NotifyAdminData{
+			UserId:          th.BasicUser.Id,
+			RequiredPlan:    model.LicenseShortSkuProfessional,
+			RequiredFeature: model.PaidFeatureGuestAccounts,
+			Trial:           false,
+		})
+		require.Nil(t, appErr)
+		appErr = th.App.SendNotifyAdminPosts(ctx, "test", "", false)
+		require.Nil(t, appErr)
+
+		// some notifications
+		_, appErr = th.App.SaveAdminNotifyData(&model.NotifyAdminData{
+			UserId:          th.BasicUser.Id,
+			RequiredPlan:    PluginIdGithub,
+			RequiredFeature: model.PluginFeature,
+			Trial:           false,
+		})
+		require.Nil(t, appErr)
+		appErr = th.App.SendNotifyAdminPosts(ctx, "test", "", false)
+		require.Nil(t, appErr)
+
+		bot, appErr := th.App.GetSystemBot()
+		require.Nil(t, appErr)
+
+		var channel *model.Channel
+		var err error
+		var timeout = 5 * time.Second
+		begin := time.Now()
+
+		for {
+			if time.Since(begin) > timeout {
+				break
+			}
+			channel, err = th.App.Srv().Store().Channel().GetByName("", model.GetDMNameFromIds(bot.UserId, th.SystemAdminUser.Id), false)
+			if err == nil && channel != nil {
+				break
+			}
+			time.Sleep(100 * time.Millisecond)
+		}
+		require.NoError(t, err, "Expected message to have been sent within %d seconds", timeout)
+		postList, err := th.App.Srv().Store().Post().GetPosts(model.GetPostsOptions{ChannelId: channel.Id, Page: 0, PerPage: 2}, false, map[string]bool{})
+		require.NoError(t, err)
+
+		installPluginPost := postList.Posts[postList.Order[0]]
+		require.Equal(t, fmt.Sprintf("%spl_notification", model.PostCustomTypePrefix), installPluginPost.Type)
+		require.Equal(t, bot.UserId, installPluginPost.UserId)
+
+		upgradePost := postList.Posts[postList.Order[1]]
+		require.Equal(t, fmt.Sprintf("%sup_notification", model.PostCustomTypePrefix), upgradePost.Type)
+		require.Equal(t, bot.UserId, upgradePost.UserId)
+		require.Equal(t, "1 member of the test workspace has requested a workspace upgrade for: ", upgradePost.Message)
+	})
 }

app/opentracing/opentracing_layer.go

@@ -4430,7 +4430,7 @@ func (a *OpenTracingAppLayer) FindTeamByName(name string) bool {
 	return resultVar0
 }
 
-func (a *OpenTracingAppLayer) FinishSendAdminNotifyPost(trial bool, now int64) {
+func (a *OpenTracingAppLayer) FinishSendAdminNotifyPost(trial bool, now int64, pluginBasedData map[string][]*model.NotifyAdminData) {
 	origCtx := a.ctx
 	span, newCtx := tracing.StartSpanWithParentByContext(a.ctx, "app.FinishSendAdminNotifyPost")
 
@@ -4442,7 +4442,7 @@ func (a *OpenTracingAppLayer) FinishSendAdminNotifyPost(trial bool, now int64) {
 	}()
 
 	defer span.Finish()
-	a.app.FinishSendAdminNotifyPost(trial, now)
+	a.app.FinishSendAdminNotifyPost(trial, now, pluginBasedData)
 }
 
 func (a *OpenTracingAppLayer) GenerateMfaSecret(userID string) (*model.MfaSecret, *model.AppError) {
@@ -18521,7 +18521,7 @@ func (a *OpenTracingAppLayer) UpsertGroupSyncable(groupSyncable *model.GroupSync
 	return resultVar0, resultVar1
 }
 
-func (a *OpenTracingAppLayer) UserAlreadyNotifiedOnRequiredFeature(user string, feature model.MattermostPaidFeature) bool {
+func (a *OpenTracingAppLayer) UserAlreadyNotifiedOnRequiredFeature(user string, feature model.MattermostFeature) bool {
 	origCtx := a.ctx
 	span, newCtx := tracing.StartSpanWithParentByContext(a.ctx, "app.UserAlreadyNotifiedOnRequiredFeature")
 

app/server.go

@@ -1543,6 +1543,12 @@ func (s *Server) initJobs() {
 		notify_admin.MakeScheduler(s.Jobs, s.License(), model.JobTypeTrialNotifyAdmin),
 	)
 
+	s.Jobs.RegisterJobType(
+		model.JobTypeInstallPluginNotifyAdmin,
+		notify_admin.MakeInstallPluginNotifyWorker(s.Jobs, New(ServerConnector(s.Channels()))),
+		notify_admin.MakeInstallPluginScheduler(s.Jobs, s.License(), model.JobTypeInstallPluginNotifyAdmin),
+	)
+
 	s.Jobs.RegisterJobType(
 		model.JobTypeHostedPurchaseScreening,
 		hosted_purchase_screening.MakeWorker(s.Jobs, s.License(), s.Store().System()),

db/migrations/migrations.list

@@ -204,6 +204,10 @@ db/migrations/mysql/000101_create_true_up_review_history.down.sql
 db/migrations/mysql/000101_create_true_up_review_history.up.sql
 db/migrations/mysql/000102_posts_originalid_index.down.sql
 db/migrations/mysql/000102_posts_originalid_index.up.sql
+db/migrations/mysql/000103_add_sentat_to_notifyadmin.down.sql
+db/migrations/mysql/000103_add_sentat_to_notifyadmin.up.sql
+db/migrations/mysql/000104_upgrade_notifyadmin.down.sql
+db/migrations/mysql/000104_upgrade_notifyadmin.up.sql
 db/migrations/postgres/000001_create_teams.down.sql
 db/migrations/postgres/000001_create_teams.up.sql
 db/migrations/postgres/000002_create_team_members.down.sql
@@ -408,3 +412,7 @@ db/migrations/postgres/000101_create_true_up_review_history.down.sql
 db/migrations/postgres/000101_create_true_up_review_history.up.sql
 db/migrations/postgres/000102_posts_originalid_index.down.sql
 db/migrations/postgres/000102_posts_originalid_index.up.sql
+db/migrations/postgres/000103_add_sentat_to_notifyadmin.down.sql
+db/migrations/postgres/000103_add_sentat_to_notifyadmin.up.sql
+db/migrations/postgres/000104_upgrade_notifyadmin.down.sql
+db/migrations/postgres/000104_upgrade_notifyadmin.up.sql

db/migrations/mysql/000103_add_sentat_to_notifyadmin.down.sql

@@ -0,0 +1,14 @@
+SET @preparedStatement = (SELECT IF(
+    EXISTS(
+        SELECT 1 FROM INFORMATION_SCHEMA.STATISTICS
+        WHERE table_name = 'NotifyAdmin'
+        AND table_schema = DATABASE()
+        AND column_name = 'SentAt'
+    ) > 0,
+    'ALTER TABLE NotifyAdmin DROP COLUMN SentAt;',
+    'SELECT 1;'
+));
+
+PREPARE removeColumnIfExists FROM @preparedStatement;
+EXECUTE removeColumnIfExists;
+DEALLOCATE PREPARE removeColumnIfExists;

db/migrations/mysql/000103_add_sentat_to_notifyadmin.up.sql

@@ -0,0 +1,14 @@
+SET @preparedStatement = (SELECT IF(
+    NOT EXISTS(
+        SELECT 1 FROM INFORMATION_SCHEMA.COLUMNS
+        WHERE table_name = 'NotifyAdmin'
+        AND table_schema = DATABASE()
+        AND column_name = 'SentAt'
+    ),
+    'ALTER TABLE NotifyAdmin ADD COLUMN SentAt bigint DEFAULT NULL;',
+    'SELECT 1;'
+));
+
+PREPARE addColumnIfNotExists FROM @preparedStatement;
+EXECUTE addColumnIfNotExists;
+DEALLOCATE PREPARE addColumnIfNotExists;

db/migrations/mysql/000104_upgrade_notifyadmin.down.sql

@@ -0,0 +1,29 @@
+SET @preparedStatement = (SELECT IF(
+    (
+        SELECT COUNT(*) FROM INFORMATION_SCHEMA.COLUMNS
+        WHERE table_name = 'NotifyAdmin'
+        AND table_schema = DATABASE()
+        AND column_name = 'RequiredFeature'
+        AND column_type != 'varchar(100)'
+    ) > 0,
+    'ALTER TABLE NotifyAdmin MODIFY COLUMN RequiredFeature varchar(100);',
+    'SELECT 1'
+));
+PREPARE alterIfExists FROM @preparedStatement;
+EXECUTE alterIfExists;
+DEALLOCATE PREPARE alterIfExists;
+
+SET @preparedStatement = (SELECT IF(
+    (
+        SELECT COUNT(*) FROM INFORMATION_SCHEMA.COLUMNS
+        WHERE table_name = 'NotifyAdmin'
+        AND table_schema = DATABASE()
+        AND column_name = 'RequiredPlan'
+        AND column_type != 'varchar(26)'
+    ) > 0,
+    'ALTER TABLE NotifyAdmin MODIFY COLUMN RequiredPlan varchar(26);',
+    'SELECT 1'
+));
+PREPARE alterIfExists FROM @preparedStatement;
+EXECUTE alterIfExists;
+DEALLOCATE PREPARE alterIfExists;

db/migrations/mysql/000104_upgrade_notifyadmin.up.sql

@@ -0,0 +1,29 @@
+SET @preparedStatement = (SELECT IF(
+    (
+        SELECT COUNT(*) FROM INFORMATION_SCHEMA.COLUMNS
+        WHERE table_name = 'NotifyAdmin'
+        AND table_schema = DATABASE()
+        AND column_name = 'RequiredFeature'
+        AND column_type != 'varchar(255)'
+    ) > 0,
+    'ALTER TABLE NotifyAdmin MODIFY COLUMN RequiredFeature varchar(255);',
+    'SELECT 1'
+));
+PREPARE alterIfExists FROM @preparedStatement;
+EXECUTE alterIfExists;
+DEALLOCATE PREPARE alterIfExists;
+
+SET @preparedStatement = (SELECT IF(
+    (
+    	SELECT COUNT(*) FROM INFORMATION_SCHEMA.COLUMNS
+        WHERE table_name = 'NotifyAdmin'
+        AND table_schema = DATABASE()
+        AND column_name = 'RequiredPlan'
+        AND column_type != 'varchar(100)'
+    ) > 0,
+    'ALTER TABLE NotifyAdmin MODIFY COLUMN RequiredPlan varchar(100);',
+    'SELECT 1'
+));
+PREPARE alterIfExists FROM @preparedStatement;
+EXECUTE alterIfExists;
+DEALLOCATE PREPARE alterIfExists;

db/migrations/postgres/000103_add_sentat_to_notifyadmin.down.sql

@@ -0,0 +1 @@
+ALTER TABLE NotifyAdmin DROP COLUMN IF EXISTS SentAt;

db/migrations/postgres/000103_add_sentat_to_notifyadmin.up.sql

@@ -0,0 +1 @@
+ALTER TABLE NotifyAdmin ADD COLUMN IF NOT EXISTS SentAt bigint DEFAULT NULL;

db/migrations/postgres/000104_upgrade_notifyadmin.down.sql

@@ -0,0 +1,2 @@
+ALTER TABLE NotifyAdmin ALTER COLUMN RequiredFeature TYPE VARCHAR(100);
+ALTER TABLE NotifyAdmin ALTER COLUMN RequiredPlan TYPE VARCHAR(26);

db/migrations/postgres/000104_upgrade_notifyadmin.up.sql

@@ -0,0 +1,2 @@
+ALTER TABLE NotifyAdmin ALTER COLUMN RequiredFeature TYPE VARCHAR(255);
+ALTER TABLE NotifyAdmin ALTER COLUMN RequiredPlan TYPE VARCHAR(100);

jobs/notify_admin/install_plugin_scheduler.go

@@ -0,0 +1,25 @@
+// Copyright (c) 2015-present Mattermost, Inc. All Rights Reserved.
+// See LICENSE.txt for license information.
+
+package notify_admin
+
+import (
+	"strconv"
+	"time"
+
+	"github.com/mattermost/mattermost-server/v6/jobs"
+	"github.com/mattermost/mattermost-server/v6/model"
+	"github.com/mattermost/mattermost-server/v6/shared/mlog"
+)
+
+const installPluginSchedFreq = 1 * time.Minute
+
+func MakeInstallPluginScheduler(jobServer *jobs.JobServer, license *model.License, jobType string) model.Scheduler {
+	isEnabled := func(cfg *model.Config) bool {
+		enabled := jobType == model.JobTypeInstallPluginNotifyAdmin
+		mlog.Debug("Scheduler: isEnabled: "+strconv.FormatBool(enabled), mlog.String("scheduler", jobType))
+		return enabled
+	}
+	return jobs.NewPeriodicScheduler(jobServer, jobType, installPluginSchedFreq, isEnabled)
+
+}

jobs/notify_admin/worker.go

@@ -11,6 +11,7 @@ import (
 const (
 	UpgradeNotifyJobName = "UpgradeNotifyAdmin"
 	TrialNotifyJobName   = "TrialNotifyAdmin"
+	InstallNotifyJobName = "InstallNotifyAdmin"
 )
 
 type AppIface interface {
@@ -52,3 +53,21 @@ func MakeTrialNotifyWorker(jobServer *jobs.JobServer, license *model.License, ap
 	worker := jobs.NewSimpleWorker(TrialNotifyJobName, jobServer, execute, isEnabled)
 	return worker
 }
+
+func MakeInstallPluginNotifyWorker(jobServer *jobs.JobServer, app AppIface) model.Worker {
+	isEnabled := func(_ *model.Config) bool {
+		return true
+	}
+	execute := func(job *model.Job) error {
+		defer jobServer.HandleJobPanic(job)
+
+		appErr := app.DoCheckForAdminNotifications(false)
+		if appErr != nil {
+			return appErr
+		}
+
+		return nil
+	}
+	worker := jobs.NewSimpleWorker(InstallNotifyJobName, jobServer, execute, isEnabled)
+	return worker
+}

model/job.go

@@ -31,6 +31,7 @@ const (
 	JobTypeLastAccessibleFile           = "last_accessible_file"
 	JobTypeUpgradeNotifyAdmin           = "upgrade_notify_admin"
 	JobTypeTrialNotifyAdmin             = "trial_notify_admin"
+	JobTypeInstallPluginNotifyAdmin     = "install_plugin_notify_admin"
 	JobTypeHostedPurchaseScreening      = "hosted_purchase_screening"
 
 	JobStatusPending         = "pending"

model/notify_admin.go

@@ -4,23 +4,26 @@
 package model
 
 import (
+	"database/sql"
 	"fmt"
 	"net/http"
+	"strings"
 )
 
-type MattermostPaidFeature string
+type MattermostFeature string
 
 const (
-	PaidFeatureGuestAccounts           = MattermostPaidFeature("mattermost.feature.guest_accounts")
+	PaidFeatureGuestAccounts           = MattermostFeature("mattermost.feature.guest_accounts")
-	PaidFeatureCustomUsergroups        = MattermostPaidFeature("mattermost.feature.custom_user_groups")
+	PaidFeatureCustomUsergroups        = MattermostFeature("mattermost.feature.custom_user_groups")
-	PaidFeatureCreateMultipleTeams     = MattermostPaidFeature("mattermost.feature.create_multiple_teams")
+	PaidFeatureCreateMultipleTeams     = MattermostFeature("mattermost.feature.create_multiple_teams")
-	PaidFeatureStartcall               = MattermostPaidFeature("mattermost.feature.start_call")
+	PaidFeatureStartcall               = MattermostFeature("mattermost.feature.start_call")
-	PaidFeaturePlaybooksRetrospective  = MattermostPaidFeature("mattermost.feature.playbooks_retro")
+	PaidFeaturePlaybooksRetrospective  = MattermostFeature("mattermost.feature.playbooks_retro")
-	PaidFeatureUnlimitedMessages       = MattermostPaidFeature("mattermost.feature.unlimited_messages")
+	PaidFeatureUnlimitedMessages       = MattermostFeature("mattermost.feature.unlimited_messages")
-	PaidFeatureUnlimitedFileStorage    = MattermostPaidFeature("mattermost.feature.unlimited_file_storage")
+	PaidFeatureUnlimitedFileStorage    = MattermostFeature("mattermost.feature.unlimited_file_storage")
-	PaidFeatureAllProfessionalfeatures = MattermostPaidFeature("mattermost.feature.all_professional")
+	PaidFeatureAllProfessionalfeatures = MattermostFeature("mattermost.feature.all_professional")
-	PaidFeatureAllEnterprisefeatures   = MattermostPaidFeature("mattermost.feature.all_enterprise")
+	PaidFeatureAllEnterprisefeatures   = MattermostFeature("mattermost.feature.all_enterprise")
-	UpgradeDowngradedWorkspace         = MattermostPaidFeature("mattermost.feature.upgrade_downgraded_workspace")
+	UpgradeDowngradedWorkspace         = MattermostFeature("mattermost.feature.upgrade_downgraded_workspace")
+	PluginFeature                      = MattermostFeature("mattermost.feature.plugin")
 )
 
 var validSKUs map[string]struct{} = map[string]struct{}{
@@ -29,7 +32,7 @@ var validSKUs map[string]struct{} = map[string]struct{}{
 }
 
 // These are the features a non admin would typically ping an admin about
-var paidFeatures map[MattermostPaidFeature]struct{} = map[MattermostPaidFeature]struct{}{
+var paidFeatures map[MattermostFeature]struct{} = map[MattermostFeature]struct{}{
 	PaidFeatureGuestAccounts:           {},
 	PaidFeatureCustomUsergroups:        {},
 	PaidFeatureCreateMultipleTeams:     {},
@@ -43,20 +46,24 @@ var paidFeatures map[MattermostPaidFeature]struct{} = map[MattermostPaidFeature]
 }
 
 type NotifyAdminToUpgradeRequest struct {
-	TrialNotification bool                  `json:"trial_notification"`
+	TrialNotification bool              `json:"trial_notification"`
-	RequiredPlan      string                `json:"required_plan"`
+	RequiredPlan      string            `json:"required_plan"`
-	RequiredFeature   MattermostPaidFeature `json:"required_feature"`
+	RequiredFeature   MattermostFeature `json:"required_feature"`
 }
 
 type NotifyAdminData struct {
-	CreateAt        int64                 `json:"create_at,omitempty"`
+	CreateAt        int64             `json:"create_at,omitempty"`
-	UserId          string                `json:"user_id"`
+	UserId          string            `json:"user_id"`
-	RequiredPlan    string                `json:"required_plan"`
+	RequiredPlan    string            `json:"required_plan"`
-	RequiredFeature MattermostPaidFeature `json:"required_feature"`
+	RequiredFeature MattermostFeature `json:"required_feature"`
-	Trial           bool                  `json:"trial"`
+	Trial           bool              `json:"trial"`
+	SentAt          sql.NullInt64     `json:"sent_at"`
 }
 
 func (nad *NotifyAdminData) IsValid() *AppError {
+	if strings.HasPrefix(string(nad.RequiredFeature), string(PluginFeature)) {
+		return nil
+	}
 	if _, planOk := validSKUs[nad.RequiredPlan]; !planOk {
 		return NewAppError("NotifyAdmin.IsValid", fmt.Sprintf("Invalid plan, %s provided", nad.RequiredPlan), nil, "", http.StatusBadRequest)
 	}

store/opentracinglayer/opentracinglayer.go

@@ -5249,7 +5249,7 @@ func (s *OpenTracingLayerNotifyAdminStore) Get(trial bool) ([]*model.NotifyAdmin
 	return result, err
 }
 
-func (s *OpenTracingLayerNotifyAdminStore) GetDataByUserIdAndFeature(userId string, feature model.MattermostPaidFeature) ([]*model.NotifyAdminData, error) {
+func (s *OpenTracingLayerNotifyAdminStore) GetDataByUserIdAndFeature(userId string, feature model.MattermostFeature) ([]*model.NotifyAdminData, error) {
 	origCtx := s.Root.Store.Context()
 	span, newCtx := tracing.StartSpanWithParentByContext(s.Root.Store.Context(), "NotifyAdminStore.GetDataByUserIdAndFeature")
 	s.Root.Store.SetContext(newCtx)
@@ -5285,6 +5285,24 @@ func (s *OpenTracingLayerNotifyAdminStore) Save(data *model.NotifyAdminData) (*m
 	return result, err
 }
 
+func (s *OpenTracingLayerNotifyAdminStore) Update(userId string, requiredPlan string, requiredFeature model.MattermostFeature, now int64) error {
+	origCtx := s.Root.Store.Context()
+	span, newCtx := tracing.StartSpanWithParentByContext(s.Root.Store.Context(), "NotifyAdminStore.Update")
+	s.Root.Store.SetContext(newCtx)
+	defer func() {
+		s.Root.Store.SetContext(origCtx)
+	}()
+
+	defer span.Finish()
+	err := s.NotifyAdminStore.Update(userId, requiredPlan, requiredFeature, now)
+	if err != nil {
+		span.LogFields(spanlog.Error(err))
+		ext.Error.Set(span, true)
+	}
+
+	return err
+}
+
 func (s *OpenTracingLayerOAuthStore) DeleteApp(id string) error {
 	origCtx := s.Root.Store.Context()
 	span, newCtx := tracing.StartSpanWithParentByContext(s.Root.Store.Context(), "OAuthStore.DeleteApp")

store/retrylayer/retrylayer.go

@@ -5941,7 +5941,7 @@ func (s *RetryLayerNotifyAdminStore) Get(trial bool) ([]*model.NotifyAdminData,
 
 }
 
-func (s *RetryLayerNotifyAdminStore) GetDataByUserIdAndFeature(userId string, feature model.MattermostPaidFeature) ([]*model.NotifyAdminData, error) {
+func (s *RetryLayerNotifyAdminStore) GetDataByUserIdAndFeature(userId string, feature model.MattermostFeature) ([]*model.NotifyAdminData, error) {
 
 	tries := 0
 	for {
@@ -5983,6 +5983,27 @@ func (s *RetryLayerNotifyAdminStore) Save(data *model.NotifyAdminData) (*model.N
 
 }
 
+func (s *RetryLayerNotifyAdminStore) Update(userId string, requiredPlan string, requiredFeature model.MattermostFeature, now int64) error {
+
+	tries := 0
+	for {
+		err := s.NotifyAdminStore.Update(userId, requiredPlan, requiredFeature, now)
+		if err == nil {
+			return nil
+		}
+		if !isRepeatableError(err) {
+			return err
+		}
+		tries++
+		if tries >= 3 {
+			err = errors.Wrap(err, "giving up after 3 consecutive repeatable transaction failures")
+			return err
+		}
+		timepkg.Sleep(100 * timepkg.Millisecond)
+	}
+
+}
+
 func (s *RetryLayerOAuthStore) DeleteApp(id string) error {
 
 	tries := 0

store/sqlstore/notify_admin_store.go

@@ -42,7 +42,7 @@ func (s SqlNotifyAdminStore) Save(data *model.NotifyAdminData) (*model.NotifyAdm
 	return data, nil
 }
 
-func (s SqlNotifyAdminStore) GetDataByUserIdAndFeature(userId string, feature model.MattermostPaidFeature) ([]*model.NotifyAdminData, error) {
+func (s SqlNotifyAdminStore) GetDataByUserIdAndFeature(userId string, feature model.MattermostFeature) ([]*model.NotifyAdminData, error) {
 	data := []*model.NotifyAdminData{}
 	query, args, err := s.getQueryBuilder().
 		Select("*").
@@ -50,7 +50,7 @@ func (s SqlNotifyAdminStore) GetDataByUserIdAndFeature(userId string, feature mo
 		Where(sq.Eq{"UserId": userId, "RequiredFeature": feature}).
 		ToSql()
 	if err != nil {
-		return nil, errors.Wrap(err, "could not build sql query to get all notifcation data by user id and required feature")
+		return nil, errors.Wrap(err, "could not build sql query to get all notification data by user id and required feature")
 	}
 
 	if err := s.GetReplicaX().Select(&data, query, args...); err != nil {
@@ -67,7 +67,8 @@ func (s SqlNotifyAdminStore) Get(trial bool) ([]*model.NotifyAdminData, error) {
 	query, args, err := s.getQueryBuilder().
 		Select("*").
 		From("NotifyAdmin").
-		Where(sq.Eq{"trial": trial}).
+		Where(sq.Eq{"Trial": trial}).
+		Where("(SentAt IS NULL)").
 		ToSql()
 	if err != nil {
 		return nil, errors.Wrap(err, "could not build sql query to get all notifcation data")
@@ -80,8 +81,15 @@ func (s SqlNotifyAdminStore) Get(trial bool) ([]*model.NotifyAdminData, error) {
 }
 
 func (s SqlNotifyAdminStore) DeleteBefore(trial bool, now int64) error {
-	if _, err := s.GetMasterX().Exec("DELETE FROM NotifyAdmin WHERE trial = ? AND createat < ?", trial, now); err != nil {
+	if _, err := s.GetMasterX().Exec("DELETE FROM NotifyAdmin WHERE Trial = ? AND CreateAt < ? AND SentAt IS NULL", trial, now); err != nil {
 		return errors.Wrapf(err, "failed to remove all notification data with trial=%t", trial)
 	}
 	return nil
 }
+
+func (s SqlNotifyAdminStore) Update(userId string, requiredPlan string, requiredFeature model.MattermostFeature, now int64) error {
+	if _, err := s.GetMasterX().Exec("UPDATE NotifyAdmin SET SentAt = ? WHERE UserId = ? AND RequiredPlan = ? AND RequiredFeature = ?", now, userId, requiredPlan, requiredFeature); err != nil {
+		return errors.Wrapf(err, "failed to update SentAt for userId=%s and requiredPlan=%s", userId, requiredPlan)
+	}
+	return nil
+}

store/store.go

@@ -942,9 +942,10 @@ type LinkMetadataStore interface {
 
 type NotifyAdminStore interface {
 	Save(data *model.NotifyAdminData) (*model.NotifyAdminData, error)
-	GetDataByUserIdAndFeature(userId string, feature model.MattermostPaidFeature) ([]*model.NotifyAdminData, error)
+	GetDataByUserIdAndFeature(userId string, feature model.MattermostFeature) ([]*model.NotifyAdminData, error)
 	Get(trial bool) ([]*model.NotifyAdminData, error)
 	DeleteBefore(trial bool, now int64) error
+	Update(userId string, requiredPlan string, requiredFeature model.MattermostFeature, now int64) error
 }
 
 type SharedChannelStore interface {

store/storetest/mocks/NotifyAdminStore.go

@@ -52,11 +52,11 @@ func (_m *NotifyAdminStore) Get(trial bool) ([]*model.NotifyAdminData, error) {
 }
 
 // GetDataByUserIdAndFeature provides a mock function with given fields: userId, feature
-func (_m *NotifyAdminStore) GetDataByUserIdAndFeature(userId string, feature model.MattermostPaidFeature) ([]*model.NotifyAdminData, error) {
+func (_m *NotifyAdminStore) GetDataByUserIdAndFeature(userId string, feature model.MattermostFeature) ([]*model.NotifyAdminData, error) {
 	ret := _m.Called(userId, feature)
 
 	var r0 []*model.NotifyAdminData
-	if rf, ok := ret.Get(0).(func(string, model.MattermostPaidFeature) []*model.NotifyAdminData); ok {
+	if rf, ok := ret.Get(0).(func(string, model.MattermostFeature) []*model.NotifyAdminData); ok {
 		r0 = rf(userId, feature)
 	} else {
 		if ret.Get(0) != nil {
@@ -65,7 +65,7 @@ func (_m *NotifyAdminStore) GetDataByUserIdAndFeature(userId string, feature mod
 	}
 
 	var r1 error
-	if rf, ok := ret.Get(1).(func(string, model.MattermostPaidFeature) error); ok {
+	if rf, ok := ret.Get(1).(func(string, model.MattermostFeature) error); ok {
 		r1 = rf(userId, feature)
 	} else {
 		r1 = ret.Error(1)
@@ -96,3 +96,17 @@ func (_m *NotifyAdminStore) Save(data *model.NotifyAdminData) (*model.NotifyAdmi
 
 	return r0, r1
 }
+
+// Update provides a mock function with given fields: userId, requiredPlan, requiredFeature, now
+func (_m *NotifyAdminStore) Update(userId string, requiredPlan string, requiredFeature model.MattermostFeature, now int64) error {
+	ret := _m.Called(userId, requiredPlan, requiredFeature, now)
+
+	var r0 error
+	if rf, ok := ret.Get(0).(func(string, string, model.MattermostFeature, int64) error); ok {
+		r0 = rf(userId, requiredPlan, requiredFeature, now)
+	} else {
+		r0 = ret.Error(0)
+	}
+
+	return r0
+}

store/storetest/notify_admin_store.go

@@ -4,6 +4,7 @@
 package storetest
 
 import (
+	"database/sql"
 	"testing"
 
 	"github.com/mattermost/mattermost-server/v6/model"
@@ -11,11 +12,14 @@ import (
 	"github.com/stretchr/testify/require"
 )
 
+const PluginIdJenkins = "jenkins"
+
 func TestNotifyAdminStore(t *testing.T, ss store.Store) {
 	t.Run("Save", func(t *testing.T) { testNotifyAdminStoreSave(t, ss) })
 	t.Run("testGetDataByUserIdAndFeature", func(t *testing.T) { testGetDataByUserIdAndFeature(t, ss) })
 	t.Run("testGet", func(t *testing.T) { testGet(t, ss) })
 	t.Run("testDeleteBefore", func(t *testing.T) { testDeleteBefore(t, ss) })
+	t.Run("testUpdate", func(t *testing.T) { testUpdate(t, ss) })
 }
 
 func tearDown(t *testing.T, ss store.Store) {
@@ -145,6 +149,28 @@ func testGetDataByUserIdAndFeature(t *testing.T, ss store.Store) {
 	tearDown(t, ss)
 }
 
+func testUpdate(t *testing.T, ss store.Store) {
+	userId1 := model.NewId()
+	d1 := &model.NotifyAdminData{
+		UserId:          userId1,
+		RequiredPlan:    PluginIdJenkins,
+		RequiredFeature: model.PluginFeature,
+	}
+	_, err := ss.NotifyAdmin().Save(d1)
+	require.NoError(t, err)
+
+	err = ss.NotifyAdmin().Update(d1.UserId, d1.RequiredPlan, d1.RequiredFeature, 100)
+	require.NoError(t, err)
+
+	userRequest, err := ss.NotifyAdmin().GetDataByUserIdAndFeature(d1.UserId, d1.RequiredFeature)
+	require.NoError(t, err)
+
+	require.Equal(t, len(userRequest), 1)
+	require.Equal(t, userRequest[0].SentAt, sql.NullInt64{Int64: 100, Valid: true})
+
+	tearDown(t, ss)
+}
+
 func testDeleteBefore(t *testing.T, ss store.Store) {
 	userId1 := model.NewId()
 	d1 := &model.NotifyAdminData{

store/timerlayer/timerlayer.go

@@ -4764,7 +4764,7 @@ func (s *TimerLayerNotifyAdminStore) Get(trial bool) ([]*model.NotifyAdminData,
 	return result, err
 }
 
-func (s *TimerLayerNotifyAdminStore) GetDataByUserIdAndFeature(userId string, feature model.MattermostPaidFeature) ([]*model.NotifyAdminData, error) {
+func (s *TimerLayerNotifyAdminStore) GetDataByUserIdAndFeature(userId string, feature model.MattermostFeature) ([]*model.NotifyAdminData, error) {
 	start := time.Now()
 
 	result, err := s.NotifyAdminStore.GetDataByUserIdAndFeature(userId, feature)
@@ -4796,6 +4796,22 @@ func (s *TimerLayerNotifyAdminStore) Save(data *model.NotifyAdminData) (*model.N
 	return result, err
 }
 
+func (s *TimerLayerNotifyAdminStore) Update(userId string, requiredPlan string, requiredFeature model.MattermostFeature, now int64) error {
+	start := time.Now()
+
+	err := s.NotifyAdminStore.Update(userId, requiredPlan, requiredFeature, now)
+
+	elapsed := float64(time.Since(start)) / float64(time.Second)
+	if s.Root.Metrics != nil {
+		success := "false"
+		if err == nil {
+			success = "true"
+		}
+		s.Root.Metrics.ObserveStoreMethodDuration("NotifyAdminStore.Update", success, elapsed)
+	}
+	return err
+}
+
 func (s *TimerLayerOAuthStore) DeleteApp(id string) error {
 	start := time.Now()