diff --git a/tool/teleport/common/teleport.go b/tool/teleport/common/teleport.go
index ae39e3d9c86ba..08a3fb74fcf51 100644
--- a/tool/teleport/common/teleport.go
+++ b/tool/teleport/common/teleport.go
@@ -300,7 +300,7 @@ func Run(options Options) (app *kingpin.Application, executedCommand string, con
 	dbConfigureCreate.Flag("gcp-instance-id", "(Only for Cloud SQL) GCP Cloud SQL instance identifier.").StringVar(&dbConfigCreateFlags.DatabaseGCPInstanceID)
 	dbConfigureCreate.Flag("ca-cert-file", "Database CA certificate path.").StringVar(&dbConfigCreateFlags.DatabaseCACertFile)
 	dbConfigureCreate.Flag("output",
-		"Write to stdout with -o=stdout, default config file with -o=file or custom path with -o=file:///path").Short('o').Default(
+		`Write to stdout with "--output=stdout", default config file with "--output=file" or custom path with --output=file:///path`).Short('o').Default(
 		teleport.SchemeStdout).StringVar(&dbConfigCreateFlags.output)
 	dbConfigureCreate.Flag("dynamic-resources-labels", "Comma-separated list(s) of labels to match dynamic resources, for example env=dev,dept=it. Required to enable dynamic resources matching.").StringsVar(&dbConfigCreateFlags.DynamicResourcesRawLabels)
 	dbConfigureCreate.Alias(dbCreateConfigExamples) // We're using "alias" section to display usage examples.
@@ -367,7 +367,7 @@ func Run(options Options) (app *kingpin.Application, executedCommand string, con
 	systemdInstall.Flag("pid-file", "Full path to the PID file.").Default(config.SystemdDefaultPIDFile).StringVar(&systemdInstallFlags.PIDFile)
 	systemdInstall.Flag("fd-limit", "Maximum number of open file descriptors.").Default(fmt.Sprintf("%v", config.SystemdDefaultFileDescriptorLimit)).IntVar(&systemdInstallFlags.FileDescriptorLimit)
 	systemdInstall.Flag("teleport-path", "Full path to the Teleport binary.").StringVar(&systemdInstallFlags.TeleportInstallationFile)
-	systemdInstall.Flag("output", "Write to stdout with -o=stdout or custom path with -o=file:///path").Short('o').Default(teleport.SchemeStdout).StringVar(&systemdInstallFlags.output)
+	systemdInstall.Flag("output", `Write to stdout with "--output=stdout" or custom path with --output=file:///path`).Short('o').Default(teleport.SchemeStdout).StringVar(&systemdInstallFlags.output)
 	systemdInstall.Alias(systemdInstallExamples) // We're using "alias" section to display usage examples.
 
 	// define a hidden 'scp' command (it implements server-side implementation of handling
@@ -386,7 +386,7 @@ func Run(options Options) (app *kingpin.Application, executedCommand string, con
 	dump.Flag("cluster-name",
 		"Unique cluster name, e.g. example.com.").StringVar(&dumpFlags.ClusterName)
 	dump.Flag("output",
-		"Write to stdout with -o=stdout, default config file with -o=file or custom path with -o=file:///path").Short('o').Default(
+		`Write to stdout with "--output=stdout", default config file with "--output=file" or custom path with --output=file:///path`).Short('o').Default(
 		teleport.SchemeStdout).StringVar(&dumpFlags.output)
 	dump.Flag("acme",
 		"Get automatic certificate from Letsencrypt.org using ACME.").BoolVar(&dumpFlags.ACMEEnabled)
@@ -414,7 +414,7 @@ func Run(options Options) (app *kingpin.Application, executedCommand string, con
 	dumpNodeConfigure.Flag("cluster-name",
 		"Unique cluster name, e.g. example.com.").StringVar(&dumpFlags.ClusterName)
 	dumpNodeConfigure.Flag("output",
-		"Write to stdout with -o=stdout, default config file with -o=file or custom path with -o=file:///path").Short('o').Default(
+		`Write to stdout with "--output=stdout", default config file with "--output=file" or custom path with --output=file:///path`).Short('o').Default(
 		teleport.SchemeStdout).StringVar(&dumpFlags.output)
 	dumpNodeConfigure.Flag("version", "Teleport configuration version.").Default(defaults.TeleportConfigVersionV3).StringVar(&dumpFlags.Version)
 	dumpNodeConfigure.Flag("public-addr", "The hostport that the node advertises for the SSH endpoint.").StringVar(&dumpFlags.PublicAddr)