diff --git a/api4/cloud.go b/api4/cloud.go
index 9c23f30fca..f9d1aa3c32 100644
--- a/api4/cloud.go
+++ b/api4/cloud.go
@@ -48,6 +48,25 @@ func (api *API) InitCloud() {
 
 	// POST /api/v4/cloud/webhook
 	api.BaseRoutes.Cloud.Handle("/webhook", api.CloudAPIKeyRequired(handleCWSWebhook)).Methods("POST")
+
+	api.BaseRoutes.Cloud.Handle("/notify-admin-to-upgrade", api.APISessionRequired(handleNotifyAdminToUpgrade)).Methods("POST")
+}
+
+func handleNotifyAdminToUpgrade(c *Context, w http.ResponseWriter, r *http.Request) {
+	var notifyAdminRequest *model.NotifyAdminToUpgradeRequest
+	err := json.NewDecoder(r.Body).Decode(&notifyAdminRequest)
+	if err != nil {
+		c.SetInvalidParam("notifyAdminRequest")
+		return
+	}
+
+	appErr := c.App.NotifySystemAdminsToUpgrade(c.AppContext, notifyAdminRequest.CurrentTeamId)
+	if appErr != nil {
+		c.Err = appErr
+		return
+	}
+
+	ReturnStatusOK(w)
 }
 
 func getSubscription(c *Context, w http.ResponseWriter, r *http.Request) {
diff --git a/api4/cloud_test.go b/api4/cloud_test.go
index 48d3555478..4d77d9089d 100644
--- a/api4/cloud_test.go
+++ b/api4/cloud_test.go
@@ -5,9 +5,12 @@ package api4
 
 import (
 	"errors"
+	"fmt"
 	"net/http"
 	"net/http/httptest"
+	"os"
 	"testing"
+	"time"
 
 	"github.com/stretchr/testify/mock"
 	"github.com/stretchr/testify/require"
@@ -295,6 +298,108 @@ func Test_requestTrial(t *testing.T) {
 	})
 }
 
+func TestNotifyAdminToUpgrade(t *testing.T) {
+	t.Run("user can only notify admin once in cool off period", func(t *testing.T) {
+		th := Setup(t).InitBasic().InitLogin()
+		defer th.TearDown()
+
+		statusCode := th.Client.NotifyAdmin(&model.NotifyAdminToUpgradeRequest{
+			CurrentTeamId: th.BasicTeam.Id,
+		})
+
+		bot, appErr := th.App.GetSystemBot()
+		require.Nil(t, appErr)
+
+		// message sending is async, wait time for it
+		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)
+
+		require.Equal(t, len(postList.Order), 1)
+
+		post := postList.Posts[postList.Order[0]]
+
+		require.Equal(t, fmt.Sprintf("%sup_notification", model.PostCustomTypePrefix), post.Type)
+		require.Equal(t, bot.UserId, post.UserId)
+		require.Equal(t, fmt.Sprintf("A member of %s has notified you to upgrade this workspace.", th.BasicTeam.Name), post.Message)
+
+		require.Equal(t, http.StatusOK, statusCode)
+
+		// second time trying to call notify endpoint by same user is forbidden
+		statusCode = th.Client.NotifyAdmin(&model.NotifyAdminToUpgradeRequest{
+			CurrentTeamId: th.BasicTeam.Id,
+		})
+		require.Equal(t, http.StatusForbidden, statusCode)
+	})
+
+	t.Run("user can only notify admin after cool off period", func(t *testing.T) {
+		th := Setup(t).InitBasic().InitLogin()
+		defer th.TearDown()
+
+		os.Setenv("MM_CLOUD_NOTIFY_ADMIN_COOL_OFF_DAYS", "0.00003472222222") // set to 3 seconds
+		defer os.Unsetenv("MM_CLOUD_NOTIFY_ADMIN_COOL_OFF_DAYS")
+
+		statusCode := th.Client.NotifyAdmin(&model.NotifyAdminToUpgradeRequest{
+			CurrentTeamId: th.BasicTeam.Id,
+		})
+
+		bot, appErr := th.App.GetSystemBot()
+		require.Nil(t, appErr)
+
+		channel, err := th.App.Srv().Store.Channel().GetByName("", model.GetDMNameFromIds(bot.UserId, th.SystemAdminUser.Id), false)
+		require.NoError(t, err)
+
+		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)
+
+		require.Equal(t, len(postList.Order), 1)
+
+		post := postList.Posts[postList.Order[0]]
+
+		require.Equal(t, fmt.Sprintf("%sup_notification", model.PostCustomTypePrefix), post.Type)
+		require.Equal(t, bot.UserId, post.UserId)
+		require.Equal(t, fmt.Sprintf("A member of %s has notified you to upgrade this workspace.", th.BasicTeam.Name), post.Message)
+
+		require.Equal(t, http.StatusOK, statusCode)
+
+		time.Sleep(5 * time.Second)
+
+		// second time trying to call notify endpoint by same user is NOT forbidden because it is after cool off period set to 3 seconds
+		statusCode = th.Client.NotifyAdmin(&model.NotifyAdminToUpgradeRequest{
+			CurrentTeamId: th.BasicTeam.Id,
+		})
+
+		require.Equal(t, http.StatusOK, statusCode)
+	})
+
+	t.Run("can cloud/model.Notify", func(t *testing.T) {
+
+		os.Setenv("MM_CLOUD_NOTIFY_ADMIN_COOL_OFF_DAYS", "10") // set to 10 days
+		canNotify := model.CanNotify(model.GetMillis())
+		require.Equal(t, false, canNotify)
+
+		os.Setenv("MM_CLOUD_NOTIFY_ADMIN_COOL_OFF_DAYS", "0.00003472222222") // set to 3 seconds
+		canNotify = model.CanNotify(model.GetMillis())
+		time.Sleep(5 * time.Second)
+		require.Equal(t, false, canNotify)
+		os.Unsetenv("MM_CLOUD_NOTIFY_ADMIN_COOL_OFF_DAYS")
+	})
+}
 func Test_validateBusinessEmail(t *testing.T) {
 	t.Run("Initial request has invalid email", func(t *testing.T) {
 		th := Setup(t).InitBasic()
diff --git a/app/app_iface.go b/app/app_iface.go
index c80b3df099..c75fad5249 100644
--- a/app/app_iface.go
+++ b/app/app_iface.go
@@ -890,6 +890,7 @@ type AppIface interface {
 	NotificationsLog() *mlog.Logger
 	NotifyAndSetWarnMetricAck(warnMetricId string, sender *model.User, forceAck bool, isBot bool) *model.AppError
 	NotifySharedChannelUserUpdate(user *model.User)
+	NotifySystemAdminsToUpgrade(c *request.Context, currentUserTeamID string) *model.AppError
 	OpenInteractiveDialog(request model.OpenDialogRequest) *model.AppError
 	OriginChecker() func(*http.Request) bool
 	PatchChannel(c *request.Context, channel *model.Channel, patch *model.ChannelPatch, userID string) (*model.Channel, *model.AppError)
diff --git a/app/cloud.go b/app/cloud.go
index 7b23f469b5..4b2fbb93d3 100644
--- a/app/cloud.go
+++ b/app/cloud.go
@@ -4,15 +4,108 @@
 package app
 
 import (
+	"encoding/json"
 	"fmt"
 	"net/http"
+	"strings"
 	"time"
 
+	"github.com/mattermost/mattermost-server/v6/app/request"
 	"github.com/mattermost/mattermost-server/v6/einterfaces"
 	"github.com/mattermost/mattermost-server/v6/model"
+	"github.com/mattermost/mattermost-server/v6/shared/i18n"
 	"github.com/mattermost/mattermost-server/v6/shared/mlog"
 )
 
+func (a *App) NotifySystemAdminsToUpgrade(c *request.Context, currentUserTeamID string) *model.AppError {
+	userId := c.Session().Id
+
+	fakeId := strings.ReplaceAll(model.CloudNotifyAdminInfo, "_", "") + "123456"
+
+	// check if already notified
+	notificationPref, err := a.Srv().Store.Preference().Get(fakeId, model.PreferenceCloudUserEphemeralInfo, model.CloudNotifyAdminInfo)
+	if err != nil {
+		mlog.Warn("Unable to get preference cloud_user_ephemeral_info", mlog.Err(err))
+	}
+
+	if notificationPref != nil {
+		info := &model.AdminNotificationUserInfo{}
+		err = json.Unmarshal([]byte(notificationPref.Value), info)
+		if err != nil {
+			mlog.Warn("Unable to Unmarshal", mlog.Err(err))
+		}
+
+		if !model.CanNotify(info.LastNotificationTimestamp) {
+			return model.NewAppError("app.NotifySystemAdminsToUpgrade", "api.cloud.notify_admin_to_upgrade_error.already_notified", nil, "", http.StatusForbidden)
+		}
+	}
+
+	team, appErr := a.GetTeam(currentUserTeamID)
+	if appErr != nil {
+		return appErr
+	}
+
+	sysadmins, appErr := a.GetUsersFromProfiles(&model.UserGetOptions{
+		Page:     0,
+		PerPage:  100,
+		Role:     model.SystemAdminRoleId,
+		Inactive: false,
+	})
+
+	if appErr != nil {
+		return appErr
+	}
+
+	systemBot, appErr := a.GetSystemBot()
+	if appErr != nil {
+		return appErr
+	}
+
+	for _, admin := range sysadmins {
+		T := i18n.GetUserTranslations(admin.Locale)
+		channel, appErr := a.GetOrCreateDirectChannel(c, systemBot.UserId, admin.Id)
+		if appErr != nil {
+			mlog.Warn("Error getting direct channel", mlog.Err(appErr))
+			continue
+		}
+
+		post := &model.Post{
+			Message:   T("api.cloud.upgrade_plan_bot_message", map[string]interface{}{"TeamName": team.Name}),
+			UserId:    systemBot.UserId,
+			ChannelId: channel.Id,
+			Type:      fmt.Sprintf("%sup_notification", model.PostCustomTypePrefix), // webapp will have to create renderer for this custom post type
+		}
+
+		_, appErr = a.CreatePost(c, post, channel, false, true)
+		if appErr != nil {
+			mlog.Warn("Error creating post", mlog.Err(appErr))
+			continue
+		}
+	}
+
+	// mark as done for current user until end of cool off period
+	out, err := json.Marshal(&model.AdminNotificationUserInfo{
+		LastUserIDToNotify:        userId,
+		LastNotificationTimestamp: model.GetMillis(),
+	})
+	if err != nil {
+		mlog.Warn("Unable to Marshal", mlog.Err(err))
+	}
+
+	pref := model.Preference{
+		UserId:   fakeId, // to only have one preference for now and not a preference per user
+		Category: model.PreferenceCloudUserEphemeralInfo,
+		Name:     model.CloudNotifyAdminInfo,
+		Value:    string(out),
+	}
+
+	if err := a.Srv().Store.Preference().Save(model.Preferences{pref}); err != nil {
+		mlog.Warn("Encountered error saving cloud_user_ephemeral_info preference", mlog.Err(err))
+	}
+
+	return nil
+}
+
 type cloudWrapper struct {
 	cloud einterfaces.CloudInterface
 }
diff --git a/app/opentracing/opentracing_layer.go b/app/opentracing/opentracing_layer.go
index db76b6626b..a824fef3f1 100644
--- a/app/opentracing/opentracing_layer.go
+++ b/app/opentracing/opentracing_layer.go
@@ -12280,6 +12280,28 @@ func (a *OpenTracingAppLayer) NotifySharedChannelUserUpdate(user *model.User) {
 	a.app.NotifySharedChannelUserUpdate(user)
 }
 
+func (a *OpenTracingAppLayer) NotifySystemAdminsToUpgrade(c *request.Context, currentUserTeamID string) *model.AppError {
+	origCtx := a.ctx
+	span, newCtx := tracing.StartSpanWithParentByContext(a.ctx, "app.NotifySystemAdminsToUpgrade")
+
+	a.ctx = newCtx
+	a.app.Srv().Store.SetContext(newCtx)
+	defer func() {
+		a.app.Srv().Store.SetContext(origCtx)
+		a.ctx = origCtx
+	}()
+
+	defer span.Finish()
+	resultVar0 := a.app.NotifySystemAdminsToUpgrade(c, currentUserTeamID)
+
+	if resultVar0 != nil {
+		span.LogFields(spanlog.Error(resultVar0))
+		ext.Error.Set(span, true)
+	}
+
+	return resultVar0
+}
+
 func (a *OpenTracingAppLayer) OpenInteractiveDialog(request model.OpenDialogRequest) *model.AppError {
 	origCtx := a.ctx
 	span, newCtx := tracing.StartSpanWithParentByContext(a.ctx, "app.OpenInteractiveDialog")
diff --git a/i18n/en.json b/i18n/en.json
index 05fe271ff8..9185c4ebe3 100644
--- a/i18n/en.json
+++ b/i18n/en.json
@@ -475,6 +475,10 @@
     "id": "api.cloud.license_error",
     "translation": "Your license does not support cloud requests."
   },
+  {
+    "id": "api.cloud.notify_admin_to_upgrade_error.already_notified",
+    "translation": "Already notified admin"
+  },
   {
     "id": "api.cloud.request_error",
     "translation": "Error processing request to CWS."
@@ -491,6 +495,10 @@
     "id": "api.cloud.teams_limit_reached.restore",
     "translation": "Unable to restore team because teams limit has been reached"
   },
+  {
+    "id": "api.cloud.upgrade_plan_bot_message",
+    "translation": "A member of {{.TeamName}} has notified you to upgrade this workspace."
+  },
   {
     "id": "api.command.admin_only.app_error",
     "translation": "Integrations have been limited to admins only."
diff --git a/model/client4.go b/model/client4.go
index 5e3f61e910..8a4ac768b4 100644
--- a/model/client4.go
+++ b/model/client4.go
@@ -7915,6 +7915,22 @@ func (c *Client4) RequestCloudTrial(email *StartCloudTrialRequest) (*Subscriptio
 	return subscription, BuildResponse(r), nil
 }
 
+func (c *Client4) NotifyAdmin(nr *NotifyAdminToUpgradeRequest) int {
+	nrJSON, jsonErr := json.Marshal(nr)
+	if jsonErr != nil {
+		return 0
+	}
+
+	r, err := c.DoAPIPost(c.cloudRoute()+"/notify-admin-to-upgrade", string(nrJSON))
+	if err != nil {
+		return r.StatusCode
+	}
+
+	closeBody(r)
+
+	return r.StatusCode
+}
+
 func (c *Client4) ValidateBusinessEmail(email *ValidateBusinessEmailRequest) (*Response, error) {
 	payload, _ := json.Marshal(email)
 	r, err := c.DoAPIPostBytes(c.cloudRoute()+"/validate-business-email", payload)
diff --git a/model/cloud.go b/model/cloud.go
index 92645a4cee..7a1a39be15 100644
--- a/model/cloud.go
+++ b/model/cloud.go
@@ -3,7 +3,11 @@
 
 package model
 
-import "strings"
+import (
+	"os"
+	"strconv"
+	"strings"
+)
 
 const (
 	EventTypeFailedPayment                = "failed-payment"
@@ -37,6 +41,9 @@ const (
 	SubscriptionFamilyOnPrem = SubscriptionFamily("on-prem")
 )
 
+const defaultCloudNotifyAdminCoolOffDays = 30
+const CloudNotifyAdminInfo = "cloud_notify_admin_info"
+
 // Product model represents a product on the cloud system.
 type Product struct {
 	ID                string             `json:"id"`
@@ -228,3 +235,23 @@ type ProductLimits struct {
 	Messages     *MessagesLimits     `json:"messages,omitempty"`
 	Teams        *TeamsLimits        `json:"teams,omitempty"`
 }
+
+type NotifyAdminToUpgradeRequest struct {
+	CurrentTeamId string `json:"current_team_id"`
+}
+
+type AdminNotificationUserInfo struct {
+	LastUserIDToNotify        string
+	LastNotificationTimestamp int64
+}
+
+func CanNotify(lastNotificationTimestamp int64) bool {
+	coolOffPeriodDaysEnv := os.Getenv("MM_CLOUD_NOTIFY_ADMIN_COOL_OFF_DAYS")
+	coolOffPeriodDays, parseError := strconv.ParseFloat(coolOffPeriodDaysEnv, 64)
+	if parseError != nil {
+		coolOffPeriodDays = defaultCloudNotifyAdminCoolOffDays
+	}
+	daysToMillis := coolOffPeriodDays * 24 * 60 * 60 * 1000
+	timeDiff := GetMillis() - lastNotificationTimestamp
+	return timeDiff >= int64(daysToMillis)
+}
diff --git a/model/preference.go b/model/preference.go
index 9f06580c10..6ce93be67a 100644
--- a/model/preference.go
+++ b/model/preference.go
@@ -59,6 +59,7 @@ const (
 	PreferenceEmailIntervalFifteenAsSeconds  = "900"
 	PreferenceEmailIntervalHour              = "hour"
 	PreferenceEmailIntervalHourAsSeconds     = "3600"
+	PreferenceCloudUserEphemeralInfo         = "cloud_user_ephemeral_info"
 )
 
 type Preference struct {