diff --git a/Makefile b/Makefile
index bf2345c..bbe032d 100644
--- a/Makefile
+++ b/Makefile
@@ -145,7 +145,10 @@ deploy: dist
 ## or copying the files directly to a sibling mattermost-server directory.
 ifneq ($(and $(MM_SERVICESETTINGS_SITEURL),$(MM_ADMIN_USERNAME),$(MM_ADMIN_PASSWORD),$(CURL)),)
 	@echo "Installing plugin via API"
-	$(eval TOKEN := $(shell curl -i --post301 --location $(MM_SERVICESETTINGS_SITEURL) -X POST $(MM_SERVICESETTINGS_SITEURL)/api/v4/users/login -d '{"login_id": "$(MM_ADMIN_USERNAME)", "password": "$(MM_ADMIN_PASSWORD)"}' | grep Token | cut -f2 -d' ' 2> /dev/null))
+	$(eval TOKEN := $(shell curl -i --fail --post301 --location $(MM_SERVICESETTINGS_SITEURL) -X POST $(MM_SERVICESETTINGS_SITEURL)/api/v4/users/login -d '{"login_id": "$(MM_ADMIN_USERNAME)", "password": "$(MM_ADMIN_PASSWORD)"}' | grep Token | cut -f2 -d' ' 2> /dev/null))
+	@if [$(TOKEN) == '']; then\
+		$(error Failed to authenticate and extract token using $(MM_ADMIN_USERNAME): check server logs.)\
+	fi
 	@curl -s --post301 --location $(MM_SERVICESETTINGS_SITEURL) -H "Authorization: Bearer $(TOKEN)" -X POST $(MM_SERVICESETTINGS_SITEURL)/api/v4/plugins -F "plugin=@dist/$(BUNDLE_NAME)" -F "force=true" > /dev/null && \
 		curl -s --post301 --location $(MM_SERVICESETTINGS_SITEURL) -H "Authorization: Bearer $(TOKEN)" -X POST $(MM_SERVICESETTINGS_SITEURL)/api/v4/plugins/$(PLUGIN_ID)/enable > /dev/null && \
 		echo "OK." || echo "Sorry, something went wrong."