diff --git a/src/main.rs b/src/main.rs
index 957f9c8..59e5eed 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -268,6 +268,14 @@ async fn check_hold_support(plugin: Plugin<PluginState>) -> Result<(), anyhow::E
         cert_dir.to_str().unwrap()
     );
 
+    let max_retries = 10;
+    let mut retries = 0;
+    while retries < max_retries && !do_certificates_exist(&cert_dir) {
+        log::debug!("Hold certificates incomplete. Waiting...");
+        time::sleep(Duration::from_millis(500)).await;
+        retries += 1;
+    }
+
     let ca_cert = tokio::fs::read(cert_dir.join("ca.pem")).await?;
     let client_cert = tokio::fs::read(cert_dir.join("client.pem")).await?;
     let client_key = tokio::fs::read(cert_dir.join("client-key.pem")).await?;
@@ -289,3 +297,12 @@ async fn check_hold_support(plugin: Plugin<PluginState>) -> Result<(), anyhow::E
 
     Ok(())
 }
+
+fn do_certificates_exist(cert_dir: &Path) -> bool {
+    let required_files = ["client.pem", "client-key.pem", "ca.pem"];
+
+    required_files.iter().all(|file| {
+        let path = cert_dir.join(file);
+        path.exists() && path.metadata().map(|m| m.len() > 0).unwrap_or(false)
+    })
+}