diff --git a/server/channels/app/plugin.go b/server/channels/app/plugin.go
index 51b229f231..952cb5b539 100644
--- a/server/channels/app/plugin.go
+++ b/server/channels/app/plugin.go
@@ -950,7 +950,7 @@ func (ch *Channels) processPrepackagedPlugins(prepackagedPluginsDir string) erro
 	prepackagedPlugins := make([]*plugin.PrepackagedPlugin, 0, len(pluginSignaturePathMap))
 	transitionallyPrepackagedPlugins := make([]*plugin.PrepackagedPlugin, 0)
 	for p := range plugins {
-		if ch.pluginIsTransitionallyPrepackaged(p.Manifest.Id) {
+		if ch.pluginIsTransitionallyPrepackaged(p.Manifest) {
 			if ch.shouldPersistTransitionallyPrepackagedPlugin(availablePluginsMap, p) {
 				transitionallyPrepackagedPlugins = append(transitionallyPrepackagedPlugins, p)
 			}
@@ -1046,13 +1046,18 @@ var transitionallyPrepackagedPlugins = []string{
 	"com.mattermost.plugin-todo",
 	"com.mattermost.welcomebot",
 	"com.mattermost.apps",
+	"playbooks",
 }
 
 // pluginIsTransitionallyPrepackaged identifies plugin ids that are currently prepackaged but
 // slated for future removal.
-func (ch *Channels) pluginIsTransitionallyPrepackaged(pluginID string) bool {
+func (ch *Channels) pluginIsTransitionallyPrepackaged(m *model.Manifest) bool {
 	for _, id := range transitionallyPrepackagedPlugins {
-		if id == pluginID {
+		if id == m.Id {
+			if m.Id == model.PluginIdPlaybooks {
+				return ch.playbooksIsTransitionallyPrepackaged(m)
+			}
+
 			return true
 		}
 	}
@@ -1060,6 +1065,22 @@ func (ch *Channels) pluginIsTransitionallyPrepackaged(pluginID string) bool {
 	return false
 }
 
+// playbooksIsTransitionallyPrepackaged determines if the playbooks plugin is transitionally prepackaged.
+// conditions are:
+// - the server is not enterprise licensed
+// - the playbooks version is <v2
+func (ch *Channels) playbooksIsTransitionallyPrepackaged(m *model.Manifest) bool {
+	license := ch.srv.License()
+	isNotEnterpriseLicensed := !(license != nil && license.IsE20OrEnterprise())
+	version, err := semver.Parse(m.Version)
+	if err != nil {
+		ch.srv.Log().Warn("unable to parse prepackaged playbooks version - not marking it as transitional.", mlog.String("version", m.Version), mlog.Err(err))
+		return false
+	}
+
+	return isNotEnterpriseLicensed && version.LT(SemVerV2)
+}
+
 // shouldPersistTransitionallyPrepackagedPlugin determines if a transitionally prepackaged plugin
 // should be persisted to the filestore, taking into account whether it's already enabled and
 // would improve on what's already in the filestore.