diff --git a/cli/command/checkpoint/cmd.go b/cli/command/checkpoint/cmd.go
index 097d4dbf90..2a698e74e5 100644
--- a/cli/command/checkpoint/cmd.go
+++ b/cli/command/checkpoint/cmd.go
@@ -9,11 +9,15 @@ import (
 // NewCheckpointCommand returns the `checkpoint` subcommand (only in experimental)
 func NewCheckpointCommand(dockerCli command.Cli) *cobra.Command {
 	cmd := &cobra.Command{
-		Use:         "checkpoint",
-		Short:       "Manage checkpoints",
-		Args:        cli.NoArgs,
-		RunE:        command.ShowHelp(dockerCli.Err()),
-		Annotations: map[string]string{"experimental": "", "version": "1.25"},
+		Use:   "checkpoint",
+		Short: "Manage checkpoints",
+		Args:  cli.NoArgs,
+		RunE:  command.ShowHelp(dockerCli.Err()),
+		Annotations: map[string]string{
+			"experimental": "",
+			"ostype":       "linux",
+			"version":      "1.25",
+		},
 	}
 	cmd.AddCommand(
 		newCreateCommand(dockerCli),
diff --git a/cli/command/container/start.go b/cli/command/container/start.go
index 243097c0cd..e388302841 100644
--- a/cli/command/container/start.go
+++ b/cli/command/container/start.go
@@ -47,8 +47,10 @@ func NewStartCommand(dockerCli command.Cli) *cobra.Command {
 
 	flags.StringVar(&opts.checkpoint, "checkpoint", "", "Restore from this checkpoint")
 	flags.SetAnnotation("checkpoint", "experimental", nil)
+	flags.SetAnnotation("checkpoint", "ostype", []string{"linux"})
 	flags.StringVar(&opts.checkpointDir, "checkpoint-dir", "", "Use a custom checkpoint storage directory")
 	flags.SetAnnotation("checkpoint-dir", "experimental", nil)
+	flags.SetAnnotation("checkpoint-dir", "ostype", []string{"linux"})
 	return cmd
 }
 
diff --git a/cmd/docker/docker.go b/cmd/docker/docker.go
index f20530dac5..4fe8bf738e 100644
--- a/cmd/docker/docker.go
+++ b/cmd/docker/docker.go
@@ -256,6 +256,9 @@ func hideUnsupportedFeatures(cmd *cobra.Command, details versionDetails) {
 		if subcmdVersion, ok := subcmd.Annotations["version"]; ok && versions.LessThan(clientVersion, subcmdVersion) {
 			subcmd.Hidden = true
 		}
+		if v, ok := subcmd.Annotations["ostype"]; ok && v != osType {
+			subcmd.Hidden = true
+		}
 	}
 }
 
@@ -282,14 +285,14 @@ func areFlagsSupported(cmd *cobra.Command, details versionDetails) error {
 				return
 			}
 			if !isOSTypeSupported(f, osType) {
-				errs = append(errs, fmt.Sprintf("\"--%s\" requires the Docker daemon to run on %s, but the Docker daemon is running on %s", f.Name, getFlagAnnotation(f, "ostype"), osType))
+				errs = append(errs, fmt.Sprintf("\"--%s\" is only supported on a Docker daemon running on %s, but the Docker daemon is running on %s", f.Name, getFlagAnnotation(f, "ostype"), osType))
 				return
 			}
 			if _, ok := f.Annotations["experimental"]; ok && !hasExperimental {
 				errs = append(errs, fmt.Sprintf("\"--%s\" is only supported on a Docker daemon with experimental features enabled", f.Name))
 			}
 			if _, ok := f.Annotations["experimentalCLI"]; ok && !hasExperimentalCLI {
-				errs = append(errs, fmt.Sprintf("\"--%s\" is only supported when experimental cli features are enabled", f.Name))
+				errs = append(errs, fmt.Sprintf("\"--%s\" is on a Docker cli with experimental cli features enabled", f.Name))
 			}
 			_, isKubernetesAnnotated := f.Annotations["kubernetes"]
 			_, isSwarmAnnotated := f.Annotations["swarm"]
@@ -310,6 +313,7 @@ func areFlagsSupported(cmd *cobra.Command, details versionDetails) error {
 // Check recursively so that, e.g., `docker stack ls` returns the same output as `docker stack`
 func areSubcommandsSupported(cmd *cobra.Command, details versionDetails) error {
 	clientVersion := details.Client().ClientVersion()
+	osType := details.ServerInfo().OSType
 	hasExperimental := details.ServerInfo().HasExperimental
 	hasExperimentalCLI := details.ClientInfo().HasExperimental
 	hasKubernetes := details.ClientInfo().HasKubernetes()
@@ -319,11 +323,14 @@ func areSubcommandsSupported(cmd *cobra.Command, details versionDetails) error {
 		if cmdVersion, ok := curr.Annotations["version"]; ok && versions.LessThan(clientVersion, cmdVersion) {
 			return fmt.Errorf("%s requires API version %s, but the Docker daemon API version is %s", cmd.CommandPath(), cmdVersion, clientVersion)
 		}
+		if os, ok := curr.Annotations["ostype"]; ok && os != osType {
+			return fmt.Errorf("%s is only supported on a Docker daemon running on %s, but the Docker daemon is running on %s", cmd.CommandPath(), os, osType)
+		}
 		if _, ok := curr.Annotations["experimental"]; ok && !hasExperimental {
 			return fmt.Errorf("%s is only supported on a Docker daemon with experimental features enabled", cmd.CommandPath())
 		}
 		if _, ok := curr.Annotations["experimentalCLI"]; ok && !hasExperimentalCLI {
-			return fmt.Errorf("%s is only supported when experimental cli features are enabled", cmd.CommandPath())
+			return fmt.Errorf("%s is only supported on a Docker cli with experimental cli features enabled", cmd.CommandPath())
 		}
 		_, isKubernetesAnnotated := curr.Annotations["kubernetes"]
 		_, isSwarmAnnotated := curr.Annotations["swarm"]