diff --git a/internal/pkg/cli/exec.go b/internal/pkg/cli/exec.go
index e428dcba436..41a9553e7a7 100644
--- a/internal/pkg/cli/exec.go
+++ b/internal/pkg/cli/exec.go
@@ -14,5 +14,5 @@ type execVars struct {
 	command          string
 	taskID           string
 	containerName    string
-	skipConfirmation bool
+	skipConfirmation *bool // If nil, we will prompt to upgrade the ssm plugin.
 }
diff --git a/internal/pkg/cli/flag.go b/internal/pkg/cli/flag.go
index 15341fc11fb..3c3ea7d10b8 100644
--- a/internal/pkg/cli/flag.go
+++ b/internal/pkg/cli/flag.go
@@ -155,6 +155,7 @@ const (
 	pipelineFlagDescription = "Name of the pipeline."
 	profileFlagDescription  = "Name of the profile."
 	yesFlagDescription      = "Skips confirmation prompt."
+	execYesFlagDescription  = "Optional. Whether to update the Session Manager Plugin."
 	jsonFlagDescription     = "Optional. Outputs in JSON format."
 
 	imageTagFlagDescription     = `Optional. The container image tag.`
diff --git a/internal/pkg/cli/svc_exec.go b/internal/pkg/cli/svc_exec.go
index cd05efd3f46..0d6e44ebae0 100644
--- a/internal/pkg/cli/svc_exec.go
+++ b/internal/pkg/cli/svc_exec.go
@@ -207,7 +207,10 @@ func (o *svcExecOpts) selectContainer() string {
 	return o.name
 }
 
-func validateSSMBinary(prompt prompter, manager ssmPluginManager, skipConfirmation bool) error {
+func validateSSMBinary(prompt prompter, manager ssmPluginManager, skipConfirmation *bool) error {
+	if skipConfirmation != nil && !aws.BoolValue(skipConfirmation) {
+		return nil
+	}
 	err := manager.ValidateBinary()
 	if err == nil {
 		return nil
@@ -215,7 +218,7 @@ func validateSSMBinary(prompt prompter, manager ssmPluginManager, skipConfirmati
 	switch v := err.(type) {
 	case *exec.ErrSSMPluginNotExist:
 		// If ssm plugin is not install, prompt users to install the plugin.
-		if !skipConfirmation {
+		if skipConfirmation == nil {
 			confirmInstall, err := prompt.Confirm(ssmPluginInstallPrompt, ssmPluginInstallPromptHelp)
 			if err != nil {
 				return fmt.Errorf("prompt to confirm installing the plugin: %w", err)
@@ -230,7 +233,7 @@ func validateSSMBinary(prompt prompter, manager ssmPluginManager, skipConfirmati
 		return nil
 	case *exec.ErrOutdatedSSMPlugin:
 		// If ssm plugin is not up to date, prompt users to update the plugin.
-		if !skipConfirmation {
+		if skipConfirmation == nil {
 			confirmUpdate, err := prompt.Confirm(
 				fmt.Sprintf(ssmPluginUpdatePrompt, v.CurrentVersion, v.LatestVersion), "")
 			if err != nil {
@@ -258,6 +261,7 @@ https://docs.aws.amazon.com/systems-manager/latest/userguide/session-manager-wor
 // buildSvcExecCmd builds the command for execute a running container in a service.
 func buildSvcExecCmd() *cobra.Command {
 	vars := execVars{}
+	var skipPrompt bool
 	cmd := &cobra.Command{
 		Use:   "exec",
 		Short: "Execute a command in a running container part of a service.",
@@ -271,6 +275,12 @@ func buildSvcExecCmd() *cobra.Command {
 			if err != nil {
 				return err
 			}
+			if cmd.Flags().Changed(yesFlag) {
+				opts.skipConfirmation = aws.Bool(false)
+				if skipPrompt {
+					opts.skipConfirmation = aws.Bool(true)
+				}
+			}
 			if err := opts.Validate(); err != nil {
 				return err
 			}
@@ -286,7 +296,7 @@ func buildSvcExecCmd() *cobra.Command {
 	cmd.Flags().StringVarP(&vars.command, commandFlag, commandFlagShort, defaultCommand, execCommandFlagDescription)
 	cmd.Flags().StringVar(&vars.taskID, taskIDFlag, "", taskIDFlagDescription)
 	cmd.Flags().StringVar(&vars.containerName, containerFlag, "", containerFlagDescription)
-	cmd.Flags().BoolVar(&vars.skipConfirmation, yesFlag, false, yesFlagDescription)
+	cmd.Flags().BoolVar(&skipPrompt, yesFlag, false, execYesFlagDescription)
 
 	cmd.SetUsageTemplate(template.Usage)
 	return cmd
diff --git a/internal/pkg/cli/svc_exec_test.go b/internal/pkg/cli/svc_exec_test.go
index 5689d299a03..dd270784183 100644
--- a/internal/pkg/cli/svc_exec_test.go
+++ b/internal/pkg/cli/svc_exec_test.go
@@ -37,7 +37,7 @@ func TestSvcExec_Validate(t *testing.T) {
 	)
 	mockErr := errors.New("some error")
 	testCases := map[string]struct {
-		skipConfirmation bool
+		skipConfirmation *bool
 		setupMocks       func(mocks execSvcMocks)
 
 		wantedError error
@@ -76,6 +76,20 @@ func TestSvcExec_Validate(t *testing.T) {
 
 			wantedError: fmt.Errorf("some error"),
 		},
+		"skip without installing/updating if yes flag is set to be false": {
+			skipConfirmation: aws.Bool(false),
+			setupMocks: func(m execSvcMocks) {
+				gomock.InOrder(
+					m.storeSvc.EXPECT().GetApplication("my-app").Return(&config.Application{
+						Name: "my-app",
+					}, nil),
+					m.storeSvc.EXPECT().GetEnvironment("my-app", "my-env").Return(&config.Environment{
+						Name: "my-env",
+					}, nil),
+					m.storeSvc.EXPECT().GetService("my-app", "my-svc").Return(&config.Workload{}, nil),
+				)
+			},
+		},
 		"should bubble error if cannot validate ssm plugin": {
 			setupMocks: func(m execSvcMocks) {
 				gomock.InOrder(
@@ -251,8 +265,8 @@ func TestSvcExec_Validate(t *testing.T) {
 
 			wantedError: nil,
 		},
-		"valid case with ssm plugin updating and skip confirming": {
-			skipConfirmation: true,
+		"valid case with ssm plugin updating and skip confirming to install": {
+			skipConfirmation: aws.Bool(true),
 			setupMocks: func(m execSvcMocks) {
 				gomock.InOrder(
 					m.storeSvc.EXPECT().GetApplication("my-app").Return(&config.Application{
diff --git a/internal/pkg/cli/task_exec.go b/internal/pkg/cli/task_exec.go
index 6e0ef92b7c8..fcfc064a28d 100644
--- a/internal/pkg/cli/task_exec.go
+++ b/internal/pkg/cli/task_exec.go
@@ -192,6 +192,7 @@ func (o *taskExecOpts) configSession() (*session.Session, error) {
 
 // buildTaskExecCmd builds the command for execute a running container in a one-off task.
 func buildTaskExecCmd() *cobra.Command {
+	var skipPrompt bool
 	vars := taskExecVars{}
 	cmd := &cobra.Command{
 		Use:   "exec",
@@ -208,6 +209,12 @@ func buildTaskExecCmd() *cobra.Command {
 			if err != nil {
 				return err
 			}
+			if cmd.Flags().Changed(yesFlag) {
+				opts.skipConfirmation = aws.Bool(false)
+				if skipPrompt {
+					opts.skipConfirmation = aws.Bool(true)
+				}
+			}
 			if err := opts.Validate(); err != nil {
 				return err
 			}
@@ -223,7 +230,7 @@ func buildTaskExecCmd() *cobra.Command {
 	cmd.Flags().StringVarP(&vars.command, commandFlag, commandFlagShort, defaultCommand, execCommandFlagDescription)
 	cmd.Flags().StringVar(&vars.taskID, taskIDFlag, "", taskIDFlagDescription)
 	cmd.Flags().BoolVar(&vars.useDefault, taskDefaultFlag, false, taskExecDefaultFlagDescription)
-	cmd.Flags().BoolVar(&vars.skipConfirmation, yesFlag, false, yesFlagDescription)
+	cmd.Flags().BoolVar(&skipPrompt, yesFlag, false, execYesFlagDescription)
 
 	cmd.SetUsageTemplate(template.Usage)
 	return cmd