diff --git a/flytecopilot/cmd/sidecar.go b/flytecopilot/cmd/sidecar.go
index 09abdb31e5c..2f597565bac 100644
--- a/flytecopilot/cmd/sidecar.go
+++ b/flytecopilot/cmd/sidecar.go
@@ -2,6 +2,7 @@ package cmd
 
 import (
 	"context"
+	stderrors "errors"
 	"fmt"
 	"time"
 
@@ -144,10 +145,14 @@ func (u *UploadOptions) Sidecar(ctx context.Context) error {
 
 	if err := u.uploader(ctx); err != nil {
 		logger.Errorf(ctx, "Uploading failed, err %s", err)
-		if err := u.UploadError(ctx, "OutputUploadFailed", err, storage.DataReference(u.remoteOutputsPrefix)); err != nil {
-			logger.Errorf(ctx, "Failed to write error document, err :%s", err)
-			return err
+		if uerr := u.UploadError(ctx, "OutputUploadFailed", err, storage.DataReference(u.remoteOutputsPrefix)); uerr != nil {
+			logger.Errorf(ctx, "Failed to write error document, err :%s", uerr)
+			return stderrors.Join(uerr, err)
 		}
+
+		// failure to upload should still return err exit code from process
+		logger.Error(ctx, "Setting sidecar command error return value")
+		return err
 	}
 	return nil
 }
@@ -164,7 +169,10 @@ func NewUploadCommand(opts *RootOptions) *cobra.Command {
 		Short: "uploads flyteData from the localpath to a remote dir.",
 		Long:  `Currently it looks at the outputs.pb and creates one file per variable.`,
 		RunE: func(cmd *cobra.Command, args []string) error {
-			return uploadOptions.Sidecar(context.Background())
+			err := uploadOptions.Sidecar(context.Background())
+			// failure to upload should still return err exit code from process
+			logger.Error(cmd.Context(), "NewUploadCommand returning failure through RunE, err %s", err)
+			return err
 		},
 	}