diff --git a/src/core/bootstrap/mod.rs b/src/core/bootstrap/mod.rs
index 35f8d8925..758756641 100644
--- a/src/core/bootstrap/mod.rs
+++ b/src/core/bootstrap/mod.rs
@@ -512,6 +512,8 @@ impl BootstrapManager {
     }
 
     pub async fn bootstrap(&mut self) -> Result<()> {
+        info!("=== BOOTSTRAP STARTING ===");
+
         // Generate certificates first (including for Vault)
         info!("Generating TLS certificates...");
         if let Err(e) = self.generate_certificates().await {
@@ -552,13 +554,20 @@ impl BootstrapManager {
 
         for component in required_components {
             // For vault, also check if it needs initialization
+            let is_installed = pm.is_installed(component);
             let needs_install = if component == "vault" {
-                !pm.is_installed(component) || vault_needs_setup
+                !is_installed || vault_needs_setup
             } else {
-                !pm.is_installed(component)
+                !is_installed
             };
 
+            info!(
+                "Component {}: installed={}, needs_install={}, vault_needs_setup={}",
+                component, is_installed, needs_install, vault_needs_setup
+            );
+
             if needs_install {
+                info!("Installing/configuring component: {}", component);
                 // Quick check if component might be running - don't hang on this
                 let bin_path = pm.base_path.join("bin").join(component);
                 let binary_name = pm
@@ -630,6 +639,7 @@ impl BootstrapManager {
 
                 // After Vault is installed, START the server then initialize it
                 if component == "vault" {
+                    info!("=== VAULT SETUP BLOCK ENTERED ===");
                     info!("Starting Vault server...");
                     match pm.start("vault") {
                         Ok(_) => {
@@ -697,6 +707,7 @@ impl BootstrapManager {
                 }
             }
         }
+        info!("=== BOOTSTRAP COMPLETED SUCCESSFULLY ===");
         Ok(())
     }
 
diff --git a/src/main.rs b/src/main.rs
index df92f4dbc..04e3222bc 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -303,15 +303,28 @@ async fn main() -> std::io::Result<()> {
     // Load .env for VAULT_* variables only (all other secrets come from Vault)
     dotenvy::dotenv().ok();
 
-    // Initialize SecretsManager early - this connects to Vault if configured
-    // Only VAULT_ADDR, VAULT_TOKEN, and VAULT_SKIP_VERIFY should be in .env
-    if let Err(e) = crate::shared::utils::init_secrets_manager().await {
-        warn!(
-            "Failed to initialize SecretsManager: {}. Falling back to env vars.",
-            e
-        );
+    // Check if bootstrap is complete BEFORE trying to init SecretsManager
+    let env_path_early = std::path::Path::new("./.env");
+    let vault_init_path_early = std::path::Path::new("./botserver-stack/conf/vault/init.json");
+    let bootstrap_ready = env_path_early.exists() && vault_init_path_early.exists() && {
+        std::fs::read_to_string(env_path_early)
+            .map(|content| content.contains("VAULT_TOKEN="))
+            .unwrap_or(false)
+    };
+
+    // Only initialize SecretsManager early if bootstrap is complete
+    // Otherwise, bootstrap will handle it
+    if bootstrap_ready {
+        if let Err(e) = crate::shared::utils::init_secrets_manager().await {
+            warn!(
+                "Failed to initialize SecretsManager: {}. Falling back to env vars.",
+                e
+            );
+        } else {
+            info!("SecretsManager initialized - fetching secrets from Vault");
+        }
     } else {
-        info!("SecretsManager initialized - fetching secrets from Vault");
+        trace!("Bootstrap not complete - skipping early SecretsManager init");
     }
 
     // Initialize logger early to capture all logs with filters for noisy libraries
@@ -508,8 +521,15 @@ async fn main() -> std::io::Result<()> {
                 }
             }
         } else {
+            info!("Bootstrap not complete - running full bootstrap...");
             trace!(".env file not found, running bootstrap.bootstrap()...");
-            _ = bootstrap.bootstrap().await;
+            if let Err(e) = bootstrap.bootstrap().await {
+                error!("Bootstrap failed: {}", e);
+                return Err(std::io::Error::new(
+                    std::io::ErrorKind::Other,
+                    format!("Bootstrap failed: {}", e),
+                ));
+            }
             trace!("bootstrap.bootstrap() completed");
             progress_tx_clone
                 .send(BootstrapProgress::StartingComponent(