diff --git a/providers/monitor.rb b/providers/monitor.rb
index feb81e2c..a547985e 100644
--- a/providers/monitor.rb
+++ b/providers/monitor.rb
@@ -33,6 +33,10 @@ def whyrun_supported?
 
   service 'datadog-agent' do
     service_name node['datadog']['agent_name']
+    # HACK: the restart can fail when we hit systemd's restart limits (by default, 5 starts every 10 seconds)
+    # To workaround this, retry once after 5 seconds, and a second time after 10 seconds
+    retries 2
+    retry_delay 5
   end
 end
 
diff --git a/recipes/dd-agent.rb b/recipes/dd-agent.rb
index d487527a..8d5877c3 100644
--- a/recipes/dd-agent.rb
+++ b/recipes/dd-agent.rb
@@ -107,6 +107,10 @@ def template_vars # rubocop:disable Metrics/AbcSize
     supports :restart => true, :status => true, :start => true, :stop => true
   end
   subscribes :restart, "template[#{agent_config_file}]", :delayed unless node['datadog']['agent_start'] == false
+  # HACK: the restart can fail when we hit systemd's restart limits (by default, 5 starts every 10 seconds)
+  # To workaround this, retry once after 5 seconds, and a second time after 10 seconds
+  retries 2
+  retry_delay 5
 end
 
 # Install integration packages