diff --git a/server/Makefile b/server/Makefile
index df9418ef3c..fa10189b22 100644
--- a/server/Makefile
+++ b/server/Makefile
@@ -148,7 +148,9 @@ PLUGIN_PACKAGES += mattermost-plugin-calls-v0.29.1
 PLUGIN_PACKAGES += mattermost-plugin-github-v2.3.0
 PLUGIN_PACKAGES += mattermost-plugin-gitlab-v1.9.1
 PLUGIN_PACKAGES += mattermost-plugin-jira-v4.1.1
+# We need to prepackage both versions of playbooks and install the correct one based on the server license. See MM-60025.
 PLUGIN_PACKAGES += mattermost-plugin-playbooks-v1.39.3
+PLUGIN_PACKAGES += mattermost-plugin-playbooks-v2.0.0
 PLUGIN_PACKAGES += mattermost-plugin-nps-v1.3.3
 PLUGIN_PACKAGES += mattermost-plugin-servicenow-v2.3.4
 PLUGIN_PACKAGES += mattermost-plugin-zoom-v1.8.0
diff --git a/server/channels/app/plugin.go b/server/channels/app/plugin.go
index 03a55b363f..51b229f231 100644
--- a/server/channels/app/plugin.go
+++ b/server/channels/app/plugin.go
@@ -997,13 +997,19 @@ func (ch *Channels) processPrepackagedPlugin(pluginPath *pluginSignaturePath) (*
 		if err != nil {
 			return nil, errors.Wrapf(err, "Unable to verify prepackaged playbooks version")
 		}
-		if version.GTE(SemVerV2) {
-			license := ch.License()
-			canUsePlaybookv2 := license != nil && license.IsE20OrEnterprise()
-			if !canUsePlaybookv2 {
-				logger.Info("Skip installing prepackaged playbooks because the license does not allow it")
-				return plugin, nil
-			}
+		license := ch.License()
+		hasEnterpriseLicense := license != nil && license.IsE20OrEnterprise()
+
+		// Do not install playbooks >=v2 if we do not have an enterprise license
+		if version.GTE(SemVerV2) && !hasEnterpriseLicense {
+			logger.Info("Skip installing prepackaged playbooks >=v2 because the license does not allow it")
+			return plugin, nil
+		}
+
+		// Do not install playbooks <v2 if we have an enterprise license
+		if version.LT(SemVerV2) && hasEnterpriseLicense {
+			logger.Info("Skip installing prepackaged playbooks <v2 because the license allows v2")
+			return plugin, nil
 		}
 	}