diff --git a/app/buck2_client_ctx/src/daemon/client/connect.rs b/app/buck2_client_ctx/src/daemon/client/connect.rs
index 631a936265570..9e5f272ce1cb4 100644
--- a/app/buck2_client_ctx/src/daemon/client/connect.rs
+++ b/app/buck2_client_ctx/src/daemon/client/connect.rs
@@ -639,7 +639,7 @@ impl<'a> BuckdConnectOptions<'a> {
         {
             Ok(client) => Ok(client.with_subscribers(self.subscribers)),
             Err(e) => {
-                handle.await.unwrap()?;
+                handle.await.unwrap().context("Daemon Failed to Connect")?;
                 self.subscribers.handle_daemon_connection_failure(&e);
                 Err(e.into())
             }
diff --git a/app/buck2_file_watcher/src/watchman/core.rs b/app/buck2_file_watcher/src/watchman/core.rs
index ef169fc1987ed..e2bdb4b73ccad 100644
--- a/app/buck2_file_watcher/src/watchman/core.rs
+++ b/app/buck2_file_watcher/src/watchman/core.rs
@@ -152,11 +152,11 @@ async fn with_timeout<R>(
     match tokio::time::timeout(Duration::from_secs(timeout), fut).await {
         Ok(Ok(res)) => Ok(res),
         Ok(Err(e)) => {
-            validate_certs().await?;
+            validate_certs().await.context("Watchman Request Failed")?;
             Err(WatchmanClientError::RequestFailed(e).into())
         }
         Err(_) => {
-            validate_certs().await?;
+            validate_certs().await.context("Watchman Timed Out")?;
             Err(WatchmanClientError::Timeout(timeout).into())
         }
     }