diff --git a/src/worker/deploy/caddy.rs b/src/worker/deploy/caddy.rs
index 9f9c098..b69f1b6 100644
--- a/src/worker/deploy/caddy.rs
+++ b/src/worker/deploy/caddy.rs
@@ -1,6 +1,55 @@
 use anyhow::{Context, Result};
 use serde::{Deserialize, Serialize};
 use std::path::Path;
+use std::time::Duration;
+
+const CADDY_READY_TIMEOUT: Duration = Duration::from_secs(60);
+const CADDY_READY_INTERVAL: Duration = Duration::from_millis(500);
+
+/// Wait for Caddy admin API to be ready
+///
+/// Polls the Caddy admin API until it responds or timeout is reached.
+/// This should be called before attempting to restore routes on startup.
+pub async fn wait_for_caddy_ready(
+    http_client: &reqwest::Client,
+    caddy_admin_api: &str,
+) -> Result<()> {
+    let start = std::time::Instant::now();
+    let url = format!("{}/config/", caddy_admin_api);
+
+    tracing::info!(
+        caddy_admin_api = caddy_admin_api,
+        timeout_secs = CADDY_READY_TIMEOUT.as_secs(),
+        "Waiting for Caddy to be ready"
+    );
+
+    loop {
+        match http_client.get(&url).send().await {
+            Ok(response) if response.status().is_success() => {
+                tracing::info!(
+                    elapsed_ms = start.elapsed().as_millis() as u64,
+                    "Caddy admin API is ready"
+                );
+                return Ok(());
+            }
+            Ok(response) => {
+                tracing::debug!(
+                    status = %response.status(),
+                    "Caddy not ready yet (unexpected status)"
+                );
+            }
+            Err(e) => {
+                tracing::debug!(error = %e, "Caddy not ready yet");
+            }
+        }
+
+        if start.elapsed() >= CADDY_READY_TIMEOUT {
+            anyhow::bail!("Caddy admin API not ready after {:?}", CADDY_READY_TIMEOUT);
+        }
+
+        tokio::time::sleep(CADDY_READY_INTERVAL).await;
+    }
+}
 
 /// Configure a Caddy route for a deployment via the admin API
 ///
diff --git a/src/worker/deploy/mod.rs b/src/worker/deploy/mod.rs
index 7ec6796..e5e491c 100644
--- a/src/worker/deploy/mod.rs
+++ b/src/worker/deploy/mod.rs
@@ -2,6 +2,6 @@ pub mod caddy;
 pub mod cloudflare;
 pub mod sites;
 
-pub use caddy::{configure_caddy_route, remove_caddy_route};
+pub use caddy::{configure_caddy_route, remove_caddy_route, wait_for_caddy_ready};
 pub use cloudflare::{CloudflareClient, CloudflareConfig};
 pub use sites::{SiteMetadata, restore_all_routes, write_site_metadata};
diff --git a/src/worker/server.rs b/src/worker/server.rs
index 07ad29c..637e5ab 100644
--- a/src/worker/server.rs
+++ b/src/worker/server.rs
@@ -8,7 +8,9 @@ use axum::{
 use tower_http::trace::TraceLayer;
 
 use crate::config::WorkerConfig;
-use crate::worker::deploy::{CloudflareClient, CloudflareConfig, restore_all_routes};
+use crate::worker::deploy::{
+    CloudflareClient, CloudflareConfig, restore_all_routes, wait_for_caddy_ready,
+};
 use crate::worker::handlers::{handle_build, handle_cleanup};
 
 /// Shared application state
@@ -45,15 +47,20 @@ pub async fn run(config: WorkerConfig) -> Result<()> {
         cloudflare,
     };
 
-    // Restore Caddy routes for existing site deployments
-    match restore_all_routes(&http_client, &config.caddy_admin_api, &config.sites_dir).await {
-        Ok(count) => {
-            if count > 0 {
-                tracing::info!(count, "Restored Caddy routes for existing sites");
+    // Wait for Caddy admin API to be ready before restoring routes
+    if let Err(e) = wait_for_caddy_ready(&http_client, &config.caddy_admin_api).await {
+        tracing::error!(error = %e, "Caddy admin API not available, skipping route restoration");
+    } else {
+        // Restore Caddy routes for existing site deployments
+        match restore_all_routes(&http_client, &config.caddy_admin_api, &config.sites_dir).await {
+            Ok(count) => {
+                if count > 0 {
+                    tracing::info!(count, "Restored Caddy routes for existing sites");
+                }
+            }
+            Err(e) => {
+                tracing::error!(error = %e, "Failed to restore Caddy routes");
             }
-        }
-        Err(e) => {
-            tracing::error!(error = %e, "Failed to restore Caddy routes");
         }
     }