diff --git a/cmd/docker/builder.go b/cmd/docker/builder.go
index 7d463e4a767d..1353694c3284 100644
--- a/cmd/docker/builder.go
+++ b/cmd/docker/builder.go
@@ -86,7 +86,7 @@ func processBuilder(dockerCli command.Cli, cmd *cobra.Command, args, osargs []st
 
 	if useLegacy {
 		// display warning if not wcow and continue
-		if dockerCli.ServerInfo().OSType != "windows" {
+		if dockerCli.ServerInfo().OSType != "" && dockerCli.ServerInfo().OSType != "windows" {
 			_, _ = fmt.Fprintln(dockerCli.Err(), newBuilderError(true, nil))
 		}
 		return args, osargs, nil, nil
diff --git a/cmd/docker/docker.go b/cmd/docker/docker.go
index 0105c7fb5850..c06773195bde 100644
--- a/cmd/docker/docker.go
+++ b/cmd/docker/docker.go
@@ -306,7 +306,7 @@ func hideSubcommandIf(subcmd *cobra.Command, condition func(string) bool, annota
 func hideUnsupportedFeatures(cmd *cobra.Command, details versionDetails) error {
 	var (
 		notExperimental = func(_ string) bool { return !details.ServerInfo().HasExperimental }
-		notOSType       = func(v string) bool { return v != details.ServerInfo().OSType }
+		notOSType       = func(v string) bool { return details.ServerInfo().OSType != "" && v != details.ServerInfo().OSType }
 		notSwarmStatus  = func(v string) bool {
 			s := details.ServerInfo().SwarmStatus
 			if s == nil {
@@ -375,7 +375,7 @@ func findCommand(cmd *cobra.Command, commands []string) bool {
 	return findCommand(cmd.Parent(), commands)
 }
 
-func isSupported(cmd *cobra.Command, details versionDetails) error {
+func isSupported(cmd *cobra.Command, details command.Cli) error {
 	if err := areSubcommandsSupported(cmd, details); err != nil {
 		return err
 	}
@@ -419,10 +419,11 @@ func areSubcommandsSupported(cmd *cobra.Command, details versionDetails) error {
 		if cmdVersion, ok := curr.Annotations["version"]; ok && versions.LessThan(details.CurrentVersion(), cmdVersion) {
 			return fmt.Errorf("%s requires API version %s, but the Docker daemon API version is %s", cmd.CommandPath(), cmdVersion, details.CurrentVersion())
 		}
-		if ost, ok := curr.Annotations["ostype"]; ok && ost != details.ServerInfo().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(), ost, details.ServerInfo().OSType)
+		si := details.ServerInfo()
+		if ost, ok := curr.Annotations["ostype"]; ok && si.OSType != "" && ost != si.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(), ost, si.OSType)
 		}
-		if _, ok := curr.Annotations["experimental"]; ok && !details.ServerInfo().HasExperimental {
+		if _, ok := curr.Annotations["experimental"]; ok && !si.HasExperimental {
 			return fmt.Errorf("%s is only supported on a Docker daemon with experimental features enabled", cmd.CommandPath())
 		}
 	}