diff --git a/cmdfactory/builder.go b/cmdfactory/builder.go
index 10ddd3be7..6d4570ac4 100644
--- a/cmdfactory/builder.go
+++ b/cmdfactory/builder.go
@@ -20,8 +20,6 @@ import (
 
 	"github.com/spf13/cobra"
 	"github.com/spf13/pflag"
-
-	"kraftkit.sh/internal/set"
 )
 
 var (
@@ -93,8 +91,12 @@ func expandRegisteredFlags(cmd *cobra.Command) {
 			continue
 		}
 
-		for _, flag := range flags {
-			subCmd.Flags().AddFlag(flag)
+		if subCmd != nil && subCmd.Flags() != nil {
+			for _, flag := range flags {
+				if subCmd.Flags().Lookup(flag.Name) == nil {
+					subCmd.Flags().AddFlag(flag)
+				}
+			}
 		}
 	}
 }
@@ -106,9 +108,9 @@ func filterOutRegisteredFlags(cmd *cobra.Command, args []string) (filteredArgs [
 			continue
 		}
 
-		registeredFlagsNames := set.NewStringSet()
+		registeredFlagsNames := map[string]*pflag.Flag{}
 		for _, flag := range flags {
-			registeredFlagsNames.Add(flag.Name)
+			registeredFlagsNames[flag.Name] = flag
 		}
 
 		for len(args) > 0 {
@@ -125,8 +127,8 @@ func filterOutRegisteredFlags(cmd *cobra.Command, args []string) (filteredArgs [
 				subs := strings.SplitN(arg, "=", 2)
 
 				flagName := strings.TrimPrefix(subs[0], "--")
-				if registeredFlagsNames.ContainsExactly(flagName) {
-					if len(subs) == 1 {
+				if flag, ok := registeredFlagsNames[flagName]; ok {
+					if flag.Value.Type() != "bool" && len(subs) == 1 {
 						args = args[1:]
 					}
 					continue
@@ -139,7 +141,7 @@ func filterOutRegisteredFlags(cmd *cobra.Command, args []string) (filteredArgs [
 				subs := strings.SplitN(arg, "=", 2)
 
 				flagName := strings.TrimPrefix(subs[0], "-")
-				if registeredFlagsNames.ContainsExactly(flagName) {
+				if _, ok := registeredFlagsNames[flagName]; ok {
 					if len(subs) == 1 {
 						args = args[1:]
 					}
@@ -461,9 +463,9 @@ func AttributeFlags(c *cobra.Command, obj any, args ...string) error {
 
 	// If any arguments are passed, parse them immediately
 	if len(args) > 0 {
-		// Some kraft commands accept flags which registration is delayed using
-		// RegisterFlag. Parsing these here would result in a failure.
-		args = filterOutRegisteredFlags(c, args)
+		// Expand all registered flags pre-emptively such that they can be correctly
+		// parsed.
+		expandRegisteredFlags(c)
 
 		if err := c.ParseFlags(args); err != nil && !errors.Is(err, pflag.ErrHelp) {
 			return err