diff --git a/crates/cli/src/file_watcher.rs b/crates/cli/src/file_watcher.rs
index ca0156a..c6bfc3d 100644
--- a/crates/cli/src/file_watcher.rs
+++ b/crates/cli/src/file_watcher.rs
@@ -2,6 +2,7 @@
 use actix::prelude::*;
 
 use actix::Recipient;
+use anyhow::{Context, Result};
 use notify::event::ModifyKind;
 use notify::Watcher;
 use tracing::error;
@@ -19,15 +20,13 @@ pub enum Error {
     #[error("io")]
     Io(#[from] std::io::Error),
 }
-pub async fn watch_file(path: PathBuf, recipient: Recipient<FileUpdated>) {
+pub async fn watch_file(path: PathBuf, recipient: Recipient<FileUpdated>) -> Result<()> {
     let (tx, rx) = std::sync::mpsc::channel();
 
-    #[allow(clippy::expect_used)]
-    let mut handler = notify::recommended_watcher(tx).expect("file watcher");
-    #[allow(clippy::expect_used)]
+    let mut handler = notify::recommended_watcher(tx).context("file watcher")?;
     handler
         .watch(&path, notify::RecursiveMode::NonRecursive)
-        .expect("watch file");
+        .with_context(|| format!("Watch file: {path:?}"))?;
     info!("Watching: {:?}", path);
     async move {
         loop {
@@ -55,4 +54,5 @@ pub async fn watch_file(path: PathBuf, recipient: Recipient<FileUpdated>) {
         }
     }
     .await;
+    Ok(())
 }
diff --git a/crates/cli/src/server/actor/handlers/file_updated.rs b/crates/cli/src/server/actor/handlers/file_updated.rs
index 7aa6d49..fb49d35 100644
--- a/crates/cli/src/server/actor/handlers/file_updated.rs
+++ b/crates/cli/src/server/actor/handlers/file_updated.rs
@@ -12,13 +12,13 @@ impl Handler<FileUpdated> for ServerActor {
     type Result = ();
 
     fn handle(&mut self, _msg: FileUpdated, ctx: &mut Self::Context) -> Self::Result {
-        let server_config = match ServerConfig::load(&self.fs) {
-            Ok(server_config) => server_config,
+        match ServerConfig::load(&self.fs) {
+            Ok(server_config) => {
+                self.do_send(ReceiveServerConfig::new(server_config), ctx);
+            }
             Err(err) => {
-                tracing::error!("Failed to load config file. Error: {}", err);
-                return;
+                self.abort(ctx, format!("Failed to load config file. Error: {}", err));
             }
         };
-        self.do_send(ReceiveServerConfig::new(server_config), ctx);
     }
 }
diff --git a/crates/cli/src/server/actor/handlers/receive_server_config.rs b/crates/cli/src/server/actor/handlers/receive_server_config.rs
index 889f5ed..121a4ae 100644
--- a/crates/cli/src/server/actor/handlers/receive_server_config.rs
+++ b/crates/cli/src/server/actor/handlers/receive_server_config.rs
@@ -12,18 +12,15 @@ impl Handler<ReceiveServerConfig> for ServerActor {
     fn handle(&mut self, msg: ReceiveServerConfig, ctx: &mut Self::Context) -> Self::Result {
         tracing::info!("recieved server config");
         let Ok(socket_addr) = msg.http() else {
-            tracing::error!("Unable to parse http.addr");
-            return;
+            self.abort(ctx, "Unable to parse http.addr");
         };
 
         let Some(server_storage) = self.server_storage(&msg) else {
-            tracing::error!("Server storage not available");
-            return;
+            self.abort(ctx, "Server storage not available");
         };
 
         if msg.inbound_webhook().base_url().ends_with('/') {
-            tracing::error!("webhook.url must not end with a '/'");
-            return;
+            self.abort(ctx, "webhook.url must not end with a '/'");
         }
 
         self.do_send(
diff --git a/crates/cli/src/server/actor/mod.rs b/crates/cli/src/server/actor/mod.rs
index dd4e717..763d79e 100644
--- a/crates/cli/src/server/actor/mod.rs
+++ b/crates/cli/src/server/actor/mod.rs
@@ -229,6 +229,19 @@ impl ServerActor {
         Some(server_storage)
     }
 
+    /// Attempts to gracefully shutdown the server before terminating the process.
+    fn abort(
+        &mut self,
+        ctx: &mut <Self as actix::Actor>::Context,
+        message: impl Into<String>,
+    ) -> ! {
+        tracing::error!("Aborting: {}", message.into());
+        self.do_send(crate::server::actor::messages::Shutdown, ctx);
+        std::thread::sleep(std::time::Duration::from_millis(200));
+        System::current().stop();
+        std::process::exit(-1);
+    }
+
     fn do_send<M>(&mut self, msg: M, _ctx: &mut <Self as actix::Actor>::Context)
     where
         M: actix::Message + Send + 'static + std::fmt::Debug,
diff --git a/crates/cli/src/server/mod.rs b/crates/cli/src/server/mod.rs
index 2ec68d4..f2b9673 100644
--- a/crates/cli/src/server/mod.rs
+++ b/crates/cli/src/server/mod.rs
@@ -46,7 +46,10 @@ pub fn start(
         server.do_send(FileUpdated);
 
         info!("Starting File Watcher...");
-        watch_file("git-next-server.toml".into(), server.clone().recipient()).await;
+        #[allow(clippy::expect_used)]
+        watch_file("git-next-server.toml".into(), server.clone().recipient())
+            .await
+            .expect("file watcher");
 
         info!("Server running - Press Ctrl-C to stop...");
         let _ = actix_rt::signal::ctrl_c().await;