diff --git a/pkg/cmd/grafana-cli/commands/commands.go b/pkg/cmd/grafana-cli/commands/commands.go
index 2099a576647..b301924d956 100644
--- a/pkg/cmd/grafana-cli/commands/commands.go
+++ b/pkg/cmd/grafana-cli/commands/commands.go
@@ -14,7 +14,7 @@ func runCommand(command func(commandLine CommandLine) error) func(context *cli.C
 		cmd := &contextCommandLine{context}
 		if err := command(cmd); err != nil {
 			logger.Errorf("\n%s: ", color.RedString("Error"))
-			logger.Errorf("%s\n\n", err)
+			logger.Errorf("%s %s\n\n", color.RedString("✗"), err)
 
 			cmd.ShowHelp()
 			os.Exit(1)
diff --git a/pkg/cmd/grafana-cli/commands/upgrade_all_command.go b/pkg/cmd/grafana-cli/commands/upgrade_all_command.go
index 1a6df719053..636292cce11 100644
--- a/pkg/cmd/grafana-cli/commands/upgrade_all_command.go
+++ b/pkg/cmd/grafana-cli/commands/upgrade_all_command.go
@@ -53,8 +53,16 @@ func upgradeAllCommand(c CommandLine) error {
 	for _, p := range pluginsToUpgrade {
 		logger.Infof("Updating %v \n", p.Id)
 
-		s.RemoveInstalledPlugin(pluginsDir, p.Id)
-		InstallPlugin(p.Id, "", c)
+		var err error
+		err = s.RemoveInstalledPlugin(pluginsDir, p.Id)
+		if err != nil {
+			return err
+		}
+
+		err = InstallPlugin(p.Id, "", c)
+		if err != nil {
+			return err
+		}
 	}
 
 	return nil