diff --git a/options/locale/locale_en-US.ini b/options/locale/locale_en-US.ini
index 035dc9b9e3..de25392d88 100644
--- a/options/locale/locale_en-US.ini
+++ b/options/locale/locale_en-US.ini
@@ -2133,12 +2133,14 @@ settings.webhook_deletion_desc = Removing a webhook deletes its settings and del
 settings.webhook_deletion_success = The webhook has been removed.
 settings.webhook.test_delivery = Test Delivery
 settings.webhook.test_delivery_desc = Test this webhook with a fake event.
+settings.webhook.test_delivery_desc_disabled = To test this webhook with a fake event, activate it.
 settings.webhook.request = Request
 settings.webhook.response = Response
 settings.webhook.headers = Headers
 settings.webhook.payload = Content
 settings.webhook.body = Body
 settings.webhook.replay.description = Replay this webhook.
+settings.webhook.replay.description_disabled = To replay this webhook, activate it.
 settings.webhook.delivery.success = An event has been added to the delivery queue. It may take few seconds before it shows up in the delivery history.
 settings.githooks_desc = "Git Hooks are powered by Git itself. You can edit hook files below to set up custom operations."
 settings.githook_edit_desc = If the hook is inactive, sample content will be presented. Leaving content to an empty value will disable this hook.
diff --git a/templates/repo/settings/webhook/history.tmpl b/templates/repo/settings/webhook/history.tmpl
index 07d6f4bede..69e50989e6 100644
--- a/templates/repo/settings/webhook/history.tmpl
+++ b/templates/repo/settings/webhook/history.tmpl
@@ -1,9 +1,13 @@
+{{$isNew:=or .PageIsSettingsHooksNew .PageIsAdminDefaultHooksNew .PageIsAdminSystemHooksNew}}
 {{if .PageIsSettingsHooksEdit}}
 	<h4 class="ui top attached header">
 		{{.locale.Tr "repo.settings.recent_deliveries"}}
 		{{if .Permission.IsAdmin}}
 			<div class="ui right">
-				<button class="ui teal tiny button" id="test-delivery" data-tooltip-content="{{.locale.Tr "repo.settings.webhook.test_delivery_desc"}}" data-link="{{.Link}}/test" data-redirect="{{.Link}}">{{.locale.Tr "repo.settings.webhook.test_delivery"}}</button>
+				<!-- the button is wrapped with a span because the tooltip doesn't show on hover if we put data-tooltip-content directly on the button -->
+				<span data-tooltip-content="{{if or $isNew .Webhook.IsActive}}{{.locale.Tr "repo.settings.webhook.test_delivery_desc"}}{{else}}{{.locale.Tr "repo.settings.webhook.test_delivery_desc_disabled"}}{{end}}">
+					<button class="ui teal tiny button{{if not (or $isNew .Webhook.IsActive)}} disabled{{end}}" id="test-delivery" data-link="{{.Link}}/test" data-redirect="{{.Link}}">{{.locale.Tr "repo.settings.webhook.test_delivery"}}</button>
+			</span>
 			</div>
 		{{end}}
 	</h4>
@@ -43,7 +47,9 @@
 							<div class="right menu">
 								<form class="item" action="{{$.Link}}/replay/{{.UUID}}" method="post">
 									{{$.CsrfTokenHtml}}
-									<button class="ui tiny button" data-tooltip-content="{{$.locale.Tr "repo.settings.webhook.replay.description"}}">{{svg "octicon-sync"}}</button>
+									<span data-tooltip-content="{{if $.Webhook.IsActive}}{{$.locale.Tr "repo.settings.webhook.replay.description"}}{{else}}{{$.locale.Tr "repo.settings.webhook.replay.description_disabled"}}{{end}}">
+										<button class="ui tiny button{{if not $.Webhook.IsActive}} disabled{{end}}">{{svg "octicon-sync"}}</button>
+									</span>
 								</form>
 							</div>
 							{{end}}