diff --git a/lib/utils/cli.go b/lib/utils/cli.go
index 75e4f7167a9..1b2e685cb7a 100644
--- a/lib/utils/cli.go
+++ b/lib/utils/cli.go
@@ -292,7 +292,55 @@ func InitCLIParser(appName, appHelp string) (app *kingpin.Application) {
 	app.HelpFlag.NoEnvar()
 
 	// set our own help template
-	return app.UsageTemplate(defaultUsageTemplate)
+	return app.UsageTemplate(createUsageTemplate())
+}
+
+// createUsageTemplate creates an usage template for kingpin applications.
+func createUsageTemplate(opts ...func(*usageTemplateOptions)) string {
+	opt := &usageTemplateOptions{
+		commandPrintfWidth: defaultCommandPrintfWidth,
+	}
+
+	for _, optFunc := range opts {
+		optFunc(opt)
+	}
+	return fmt.Sprintf(defaultUsageTemplate, opt.commandPrintfWidth)
+}
+
+// UpdateAppUsageTemplate updates usage template for kingpin applications by
+// pre-parsing the arguments then applying any changes to the usage template if
+// necessary.
+func UpdateAppUsageTemplate(app *kingpin.Application, args []string) {
+	// If ParseContext fails, kingpin will not show usage so there is no need
+	// to update anything here. See app.Parse for more details.
+	context, err := app.ParseContext(args)
+	if err != nil {
+		return
+	}
+
+	app.UsageTemplate(createUsageTemplate(
+		withCommandPrintfWidth(app, context),
+	))
+}
+
+// withCommandPrintfWidth returns an usage template option that
+// updates command printf width if longer than default.
+func withCommandPrintfWidth(app *kingpin.Application, context *kingpin.ParseContext) func(*usageTemplateOptions) {
+	return func(opt *usageTemplateOptions) {
+		var commands []*kingpin.CmdModel
+		if context.SelectedCommand != nil {
+			commands = context.SelectedCommand.Model().FlattenedCommands()
+		} else {
+			commands = app.Model().FlattenedCommands()
+		}
+
+		for _, command := range commands {
+			if !command.Hidden && len(command.FullCommand) > opt.commandPrintfWidth {
+				opt.commandPrintfWidth = len(command.FullCommand)
+			}
+		}
+
+	}
 }
 
 // SplitIdentifiers splits list of identifiers by commas/spaces/newlines.  Helpful when
@@ -380,8 +428,19 @@ func needsQuoting(text string) bool {
 	return false
 }
 
-// Usage template with compactly formatted commands.
-var defaultUsageTemplate = `{{define "FormatCommand"}}\
+// usageTemplateOptions defines options to format the usage template.
+type usageTemplateOptions struct {
+	// commandPrintfWidth is the width of the command name with padding, for
+	//   {{.FullCommand | printf "%%-%ds"}}
+	commandPrintfWidth int
+}
+
+// defaultCommandPrintfWidth is the default command printf width.
+const defaultCommandPrintfWidth = 12
+
+// defaultUsageTemplate is a fmt format that defines the usage template with
+// compactly formatted commands. Should be only used in createUsageTemplate.
+const defaultUsageTemplate = `{{define "FormatCommand"}}\
 {{if .FlagSummary}} {{.FlagSummary}}{{end}}\
 {{range .Args}} {{if not .Required}}[{{end}}<{{.Name}}>{{if .Value|IsCumulative}}...{{end}}{{if not .Required}}]{{end}}{{end}}\
 {{end}}\
@@ -389,7 +448,7 @@ var defaultUsageTemplate = `{{define "FormatCommand"}}\
 {{define "FormatCommands"}}\
 {{range .FlattenedCommands}}\
 {{if not .Hidden}}\
-  {{.FullCommand | printf "%-12s" }}{{if .Default}} (Default){{end}} {{ .Help }}
+  {{.FullCommand | printf "%%-%ds"}}{{if .Default}} (Default){{end}} {{ .Help }}
 {{end}}\
 {{end}}\
 {{end}}\
diff --git a/tool/tbot/main.go b/tool/tbot/main.go
index c38b0e525c8..484a73f97ca 100644
--- a/tool/tbot/main.go
+++ b/tool/tbot/main.go
@@ -71,6 +71,7 @@ func Run(args []string) error {
 	app := utils.InitCLIParser("tbot", "tbot: Teleport Machine ID").Interspersed(false)
 	app.Flag("debug", "Verbose logging to stdout").Short('d').BoolVar(&cf.Debug)
 	app.Flag("config", "Path to a configuration file. Defaults to `/etc/tbot.yaml` if unspecified.").Short('c').StringVar(&cf.ConfigPath)
+	app.HelpFlag.Short('h')
 
 	versionCmd := app.Command("version", "Print the version")
 
@@ -97,6 +98,7 @@ func Run(args []string) error {
 
 	watchCmd := app.Command("watch", "Watch a destination directory for changes.").Hidden()
 
+	utils.UpdateAppUsageTemplate(app, args)
 	command, err := app.Parse(args)
 	if err != nil {
 		app.Usage(args)
diff --git a/tool/tctl/common/tctl.go b/tool/tctl/common/tctl.go
index ea7c8855eeb..12010a012cd 100644
--- a/tool/tctl/common/tctl.go
+++ b/tool/tctl/common/tctl.go
@@ -137,6 +137,7 @@ func Run(commands []CLICommand) {
 	app.HelpFlag.Short('h')
 
 	// parse CLI commands+flags:
+	utils.UpdateAppUsageTemplate(app, os.Args[1:])
 	selectedCmd, err := app.Parse(os.Args[1:])
 	if err != nil {
 		app.Usage(os.Args[1:])
diff --git a/tool/teleport/common/teleport.go b/tool/teleport/common/teleport.go
index 6128d732587..8bd6bc0a2b0 100644
--- a/tool/teleport/common/teleport.go
+++ b/tool/teleport/common/teleport.go
@@ -294,6 +294,7 @@ func Run(options Options) (app *kingpin.Application, executedCommand string, con
 	dump.Flag("key-file", "Path to a TLS key file for the proxy.").ExistingFileVar(&dumpFlags.KeyFile)
 
 	// parse CLI commands+flags:
+	utils.UpdateAppUsageTemplate(app, options.Args)
 	command, err := app.Parse(options.Args)
 	if err != nil {
 		app.Usage(options.Args)
diff --git a/tool/tsh/tsh.go b/tool/tsh/tsh.go
index d24e890d6fd..0e5285d080b 100644
--- a/tool/tsh/tsh.go
+++ b/tool/tsh/tsh.go
@@ -638,6 +638,7 @@ func Run(args []string, opts ...cliOption) error {
 	}
 
 	// parse CLI commands+flags:
+	utils.UpdateAppUsageTemplate(app, args)
 	command, err := app.Parse(args)
 	if err != nil {
 		app.Usage(args)