diff --git a/proxy/src/context/parquet.rs b/proxy/src/context/parquet.rs
index d7ffff0483..4f1dd39d92 100644
--- a/proxy/src/context/parquet.rs
+++ b/proxy/src/context/parquet.rs
@@ -423,11 +423,11 @@ async fn upload_parquet(
     .await
     .ok_or_else(|| anyhow::Error::new(TimeoutOrCancel::Cancel))
     .and_then(|x| x)
-    .context("request_data_upload")
+    .with_context(|| format!("request_data_upload: path={path}"))
     .err();
 
     if let Some(err) = maybe_err {
-        tracing::error!(%id, error = ?err, "failed to upload request data");
+        tracing::error!(%id, %path, error = ?err, "failed to upload request data");
     }
 
     Ok(buffer.writer())
diff --git a/proxy/src/usage_metrics.rs b/proxy/src/usage_metrics.rs
index 487504d709..e1cc7e87b4 100644
--- a/proxy/src/usage_metrics.rs
+++ b/proxy/src/usage_metrics.rs
@@ -396,13 +396,13 @@ async fn upload_backup_events(
         TimeoutOrCancel::caused_by_cancel,
         FAILED_UPLOAD_WARN_THRESHOLD,
         FAILED_UPLOAD_MAX_RETRIES,
-        "request_data_upload",
+        "usage_metrics_upload",
         cancel,
     )
     .await
     .ok_or_else(|| anyhow::Error::new(TimeoutOrCancel::Cancel))
     .and_then(|x| x)
-    .context("request_data_upload")?;
+    .with_context(|| format!("usage_metrics_upload: path={remote_path}"))?;
     Ok(())
 }