diff --git a/server/cmd/mmctl/commands/plugin.go b/server/cmd/mmctl/commands/plugin.go
index 1fcb06563d4..ad4e1700631 100644
--- a/server/cmd/mmctl/commands/plugin.go
+++ b/server/cmd/mmctl/commands/plugin.go
@@ -5,6 +5,7 @@ package commands
 
 import (
 	"context"
+	"fmt"
 	"os"
 
 	"github.com/mattermost/mattermost/server/v8/cmd/mmctl/client"
@@ -94,6 +95,7 @@ func init() {
 
 func pluginAddCmdF(c client.Client, cmd *cobra.Command, args []string) error {
 	force, _ := cmd.Flags().GetBool("force")
+	var multiErr *multierror.Error
 
 	for i, plugin := range args {
 		fileReader, err := os.Open(plugin)
@@ -109,13 +111,14 @@ func pluginAddCmdF(c client.Client, cmd *cobra.Command, args []string) error {
 
 		if err != nil {
 			printer.PrintError("Unable to add plugin: " + args[i] + ". Error: " + err.Error())
+			multiErr = multierror.Append(multiErr, err)
 		} else {
 			printer.Print("Added plugin: " + plugin)
 		}
 		fileReader.Close()
 	}
 
-	return nil
+	return multiErr.ErrorOrNil()
 }
 
 func pluginInstallURLCmdF(c client.Client, cmd *cobra.Command, args []string) error {
@@ -136,39 +139,45 @@ func pluginInstallURLCmdF(c client.Client, cmd *cobra.Command, args []string) er
 }
 
 func pluginDeleteCmdF(c client.Client, cmd *cobra.Command, args []string) error {
+	var multiErr *multierror.Error
 	for _, plugin := range args {
 		if _, err := c.RemovePlugin(context.TODO(), plugin); err != nil {
 			printer.PrintError("Unable to delete plugin: " + plugin + ". Error: " + err.Error())
+			multiErr = multierror.Append(multiErr, fmt.Errorf("Unable to delete plugin. %w", err))
 		} else {
 			printer.Print("Deleted plugin: " + plugin)
 		}
 	}
 
-	return nil
+	return multiErr.ErrorOrNil()
 }
 
 func pluginEnableCmdF(c client.Client, cmd *cobra.Command, args []string) error {
+	var multiErr *multierror.Error
 	for _, plugin := range args {
 		if _, err := c.EnablePlugin(context.TODO(), plugin); err != nil {
 			printer.PrintError("Unable to enable plugin: " + plugin + ". Error: " + err.Error())
+			multiErr = multierror.Append(multiErr, err)
 		} else {
 			printer.Print("Enabled plugin: " + plugin)
 		}
 	}
 
-	return nil
+	return multiErr.ErrorOrNil()
 }
 
 func pluginDisableCmdF(c client.Client, cmd *cobra.Command, args []string) error {
+	var multiErr *multierror.Error
 	for _, plugin := range args {
 		if _, err := c.DisablePlugin(context.TODO(), plugin); err != nil {
 			printer.PrintError("Unable to disable plugin: " + plugin + ". Error: " + err.Error())
+			multiErr = multierror.Append(multiErr, err)
 		} else {
 			printer.Print("Disabled plugin: " + plugin)
 		}
 	}
 
-	return nil
+	return multiErr.ErrorOrNil()
 }
 
 func pluginListCmdF(c client.Client, cmd *cobra.Command, args []string) error {
diff --git a/server/cmd/mmctl/commands/plugin_e2e_test.go b/server/cmd/mmctl/commands/plugin_e2e_test.go
index e881a957e04..dee0f8d2cff 100644
--- a/server/cmd/mmctl/commands/plugin_e2e_test.go
+++ b/server/cmd/mmctl/commands/plugin_e2e_test.go
@@ -46,7 +46,7 @@ func (s *MmctlE2ETestSuite) TestPluginAddCmd() {
 		printer.Clean()
 
 		err = pluginAddCmdF(c, &cobra.Command{}, []string{pluginPath})
-		s.Require().Nil(err)
+		s.Require().ErrorContains(err, "Unable to install plugin. A plugin with the same ID is already installed.")
 
 		s.Require().Equal(0, len(printer.GetLines()))
 		s.Require().Equal(1, len(printer.GetErrorLines()))
@@ -108,7 +108,7 @@ func (s *MmctlE2ETestSuite) TestPluginAddCmd() {
 		printer.Clean()
 
 		err := pluginAddCmdF(c, &cobra.Command{}, []string{pluginPath})
-		s.Require().Nil(err)
+		s.Require().ErrorContains(err, "Plugins and/or plugin uploads have been disabled.")
 		s.Require().Equal(1, len(printer.GetErrorLines()))
 		s.Require().Contains(printer.GetErrorLines()[0], "Plugins and/or plugin uploads have been disabled.")
 	})
@@ -156,7 +156,7 @@ func (s *MmctlE2ETestSuite) TestPluginAddCmd() {
 		})
 
 		err := pluginAddCmdF(s.th.Client, &cobra.Command{}, []string{pluginPath})
-		s.Require().Nil(err)
+		s.Require().ErrorContains(err, "You do not have the appropriate permissions")
 		s.Require().Equal(1, len(printer.GetErrorLines()))
 		s.Require().Contains(printer.GetErrorLines()[0], "You do not have the appropriate permissions")
 	})
@@ -201,7 +201,7 @@ func (s *MmctlE2ETestSuite) TestPluginInstallURLCmd() {
 		var expected error
 		expected = multierror.Append(expected, errors.New("You do not have the appropriate permissions.")) //nolint:revive
 		err := pluginInstallURLCmdF(s.th.Client, &cobra.Command{}, []string{jiraURL})
-		s.Require().EqualError(err, expected.Error())
+		s.Require().ErrorContains(err, expected.Error())
 		s.Require().Len(printer.GetLines(), 0)
 		s.Require().Len(printer.GetErrorLines(), 1)
 		s.Require().Contains(printer.GetErrorLines()[0], fmt.Sprintf("Unable to install plugin from URL \"%s\".", jiraURL))
@@ -221,7 +221,7 @@ func (s *MmctlE2ETestSuite) TestPluginInstallURLCmd() {
 		expected = multierror.Append(expected, errors.New("An error occurred while downloading the plugin.")) //nolint:revive
 
 		err := pluginInstallURLCmdF(c, &cobra.Command{}, []string{pluginURL})
-		s.Require().EqualError(err, expected.Error())
+		s.Require().ErrorContains(err, expected.Error())
 		s.Require().Len(printer.GetLines(), 0)
 		s.Require().Len(printer.GetErrorLines(), 1)
 		s.Require().Contains(printer.GetErrorLines()[0], fmt.Sprintf("Unable to install plugin from URL \"%s\".", pluginURL))
@@ -246,7 +246,7 @@ func (s *MmctlE2ETestSuite) TestPluginInstallURLCmd() {
 		var expected error
 		expected = multierror.Append(expected, errors.New("Unable to install plugin. A plugin with the same ID is already installed.")) //nolint:revive
 		err = pluginInstallURLCmdF(c, &cobra.Command{}, []string{jiraURL})
-		s.Require().EqualError(err, expected.Error())
+		s.Require().ErrorContains(err, expected.Error())
 		s.Require().Len(printer.GetLines(), 1)
 		s.Require().Len(printer.GetErrorLines(), 1)
 		s.Require().Contains(printer.GetErrorLines()[0], fmt.Sprintf("Unable to install plugin from URL \"%s\".", jiraURL))
@@ -329,7 +329,7 @@ func (s *MmctlE2ETestSuite) TestPluginDeleteCmd() {
 		printer.Clean()
 
 		err := pluginDeleteCmdF(c, &cobra.Command{}, []string{dummyPluginID})
-		s.Require().Nil(err)
+		s.Require().ErrorContains(err, "Plugins have been disabled.")
 		s.Require().Len(printer.GetLines(), 0)
 		s.Require().Len(printer.GetErrorLines(), 1)
 		s.Require().Contains(printer.GetErrorLines()[0], fmt.Sprintf("Unable to delete plugin: %s.", dummyPluginID))
@@ -367,7 +367,7 @@ func (s *MmctlE2ETestSuite) TestPluginDeleteCmd() {
 
 		// Delete Test
 		err := pluginDeleteCmdF(s.th.Client, &cobra.Command{}, []string{jiraPluginID})
-		s.Require().Nil(err)
+		s.Require().ErrorContains(err, "You do not have the appropriate permissions.")
 		s.Require().Len(printer.GetLines(), 1)
 		s.Require().Len(printer.GetErrorLines(), 1)
 		s.Require().Contains(printer.GetErrorLines()[0], fmt.Sprintf("Unable to delete plugin: %s.", jiraPluginID))
diff --git a/server/cmd/mmctl/commands/plugin_marketplace_e2e_test.go b/server/cmd/mmctl/commands/plugin_marketplace_e2e_test.go
index 6806e64f5c0..db9bb2999cb 100644
--- a/server/cmd/mmctl/commands/plugin_marketplace_e2e_test.go
+++ b/server/cmd/mmctl/commands/plugin_marketplace_e2e_test.go
@@ -94,7 +94,7 @@ func (s *MmctlE2ETestSuite) TestPluginMarketplaceInstallCmd() {
 func removePluginIfInstalled(c client.Client, s *MmctlE2ETestSuite, pluginID string) {
 	appErr := pluginDeleteCmdF(c, &cobra.Command{}, []string{pluginID})
 	if appErr != nil {
-		s.Require().Contains(appErr.Error(), "Plugin is not installed.")
+		s.Require().Contains(appErr.Error(), "Unable to delete plugin.")
 	}
 }
 
diff --git a/server/cmd/mmctl/commands/plugin_test.go b/server/cmd/mmctl/commands/plugin_test.go
index 37df9b377a3..7ef03818596 100644
--- a/server/cmd/mmctl/commands/plugin_test.go
+++ b/server/cmd/mmctl/commands/plugin_test.go
@@ -10,7 +10,6 @@ import (
 	"strings"
 
 	"github.com/golang/mock/gomock"
-	"github.com/hashicorp/go-multierror"
 	"github.com/mattermost/mattermost/server/public/model"
 	"github.com/pkg/errors"
 
@@ -86,7 +85,7 @@ func (s *MmctlUnitTestSuite) TestPluginAddCmd() {
 			Times(1)
 
 		err = pluginAddCmdF(s.client, &cobra.Command{}, []string{pluginName})
-		s.Require().NoError(err)
+		s.Require().ErrorContains(err, "plugin add error")
 		s.Require().Len(printer.GetErrorLines(), 1)
 		s.Require().Equal(printer.GetErrorLines()[0], "Unable to add plugin: "+pluginName+". Error: "+mockError.Error())
 	})
@@ -117,7 +116,7 @@ func (s *MmctlUnitTestSuite) TestPluginAddCmd() {
 		}
 
 		err := pluginAddCmdF(s.client, &cobra.Command{}, args)
-		s.Require().NoError(err)
+		s.Require().ErrorContains(err, "plugin add error")
 		s.Require().Len(printer.GetLines(), 1)
 		s.Require().Equal(printer.GetLines()[0], "Added plugin: "+args[1])
 		s.Require().Len(printer.GetErrorLines(), 2)
@@ -198,11 +197,8 @@ func (s *MmctlUnitTestSuite) TestPluginInstallUrlCmd() {
 			Return(nil, &model.Response{}, errors.New("mock error")).
 			Times(1)
 
-		var expected error
-		expected = multierror.Append(expected, errors.New("mock error"))
-
 		err := pluginInstallURLCmdF(s.client, &cobra.Command{}, args)
-		s.Require().EqualError(err, expected.Error())
+		s.Require().ErrorContains(err, "mock error")
 		s.Require().Len(printer.GetErrorLines(), 1)
 		s.Require().Equal("Unable to install plugin from URL \"https://example.com/plugin2.tar.gz\". Error: mock error", printer.GetErrorLines()[0])
 		s.Require().Len(printer.GetLines(), 1)
@@ -240,7 +236,7 @@ func (s *MmctlUnitTestSuite) TestPluginDisableCmd() {
 			Times(1)
 
 		err := pluginDisableCmdF(s.client, &cobra.Command{}, []string{arg})
-		s.Require().Nil(err)
+		s.Require().ErrorContains(err, "mock error")
 		s.Require().Len(printer.GetLines(), 0)
 		s.Require().Len(printer.GetErrorLines(), 1)
 		s.Require().Equal(printer.GetErrorLines()[0], "Unable to disable plugin: "+arg+". Error: "+mockError.Error())
@@ -268,7 +264,7 @@ func (s *MmctlUnitTestSuite) TestPluginDisableCmd() {
 		}
 
 		err := pluginDisableCmdF(s.client, &cobra.Command{}, args)
-		s.Require().Nil(err)
+		s.Require().ErrorContains(err, "mock error")
 		s.Require().Len(printer.GetLines(), 2)
 		s.Require().Equal(printer.GetLines()[0], "Disabled plugin: "+args[1])
 		s.Require().Equal(printer.GetLines()[1], "Disabled plugin: "+args[2])
@@ -329,7 +325,7 @@ func (s *MmctlUnitTestSuite) TestPluginEnableCmd() {
 			Times(1)
 
 		err := pluginEnableCmdF(s.client, &cobra.Command{}, []string{pluginArg})
-		s.Require().Nil(err)
+		s.Require().ErrorContains(err, "mock error")
 		s.Require().Len(printer.GetLines(), 0)
 		s.Require().Len(printer.GetErrorLines(), 1)
 		s.Require().Equal(printer.GetErrorLines()[0], "Unable to enable plugin: "+pluginArg+". Error: "+mockErr.Error())
@@ -361,7 +357,7 @@ func (s *MmctlUnitTestSuite) TestPluginEnableCmd() {
 		}
 
 		err := pluginEnableCmdF(s.client, &cobra.Command{}, allPlugins)
-		s.Require().Nil(err)
+		s.Require().ErrorContains(err, "mock error")
 		s.Require().Len(printer.GetLines(), 2)
 		s.Require().Equal(printer.GetLines()[0], "Enabled plugin: "+okPlugins[0])
 		s.Require().Equal(printer.GetLines()[1], "Enabled plugin: "+okPlugins[1])
@@ -533,6 +529,7 @@ func (s *MmctlUnitTestSuite) TestPluginListCmd() {
 
 		err := pluginListCmdF(s.client, &cobra.Command{}, nil)
 		s.Require().NotNil(err)
+		s.Require().Len(printer.GetLines(), 0)
 		s.Require().EqualError(err, "Unable to list plugins. Error: "+mockError.Error())
 	})
 }
@@ -550,7 +547,7 @@ func (s *MmctlUnitTestSuite) TestPluginDeleteCmd() {
 			Times(1)
 
 		err := pluginDeleteCmdF(s.client, &cobra.Command{}, []string{args})
-		s.Require().NoError(err)
+		s.Require().ErrorContains(err, "mock error")
 		s.Require().Len(printer.GetLines(), 0)
 		s.Require().Len(printer.GetErrorLines(), 1)
 		s.Require().Equal("Unable to delete plugin: "+args+". Error: "+mockError.Error(), printer.GetErrorLines()[0])
@@ -611,7 +608,7 @@ func (s *MmctlUnitTestSuite) TestPluginDeleteCmd() {
 			Times(1)
 
 		err := pluginDeleteCmdF(s.client, &cobra.Command{}, args)
-		s.Require().NoError(err)
+		s.Require().ErrorContains(err, "mock error")
 		s.Require().Len(printer.GetLines(), 2)
 		s.Require().Equal("Deleted plugin: "+args[0], printer.GetLines()[0])
 		s.Require().Equal("Deleted plugin: "+args[3], printer.GetLines()[1])