From a8425e8d9342c112ba387ec735ce169ca4645d3a Mon Sep 17 00:00:00 2001
From: Ryan VanGundy <ryan.vangundy+rmvangun@gmail.com>
Date: Sat, 19 Jul 2025 10:22:27 -0400
Subject: [PATCH] fix(config): Fixes error when running --set to a boolean
 value

When running things like `windsor init --set dns.enabled=false`, we were seeing type errors using a string as a bool. This likely emerged in the recent pipeline refactor. Performs additional internal casting to accommodate.
---
 pkg/config/yaml_config_handler.go      | 13 ++++++++---
 pkg/config/yaml_config_handler_test.go | 30 ++++++++++++++++++++++++++
 2 files changed, 40 insertions(+), 3 deletions(-)

diff --git a/pkg/config/yaml_config_handler.go b/pkg/config/yaml_config_handler.go
index 5fc1b69ce..e632341eb 100644
--- a/pkg/config/yaml_config_handler.go
+++ b/pkg/config/yaml_config_handler.go
@@ -480,7 +480,9 @@ func setValueByPath(currValue reflect.Value, pathKeys []string, value any, fullP
 	return nil
 }
 
-// assignValue assigns a value to a field, converting types if necessary.
+// assignValue assigns a value to a struct field, performing type conversion if necessary.
+// It supports string-to-type conversion, pointer assignment, and type compatibility checks.
+// Returns a reflect.Value suitable for assignment or an error if conversion is not possible.
 func assignValue(fieldValue reflect.Value, value any) (reflect.Value, error) {
 	if !fieldValue.CanSet() {
 		return reflect.Value{}, fmt.Errorf("cannot set field")
@@ -489,17 +491,22 @@ func assignValue(fieldValue reflect.Value, value any) (reflect.Value, error) {
 	fieldType := fieldValue.Type()
 	valueType := reflect.TypeOf(value)
 
+	if strValue, ok := value.(string); ok {
+		convertedValue, err := convertValue(strValue, fieldType)
+		if err == nil {
+			return reflect.ValueOf(convertedValue), nil
+		}
+	}
+
 	if fieldType.Kind() == reflect.Ptr {
 		elemType := fieldType.Elem()
 		newValue := reflect.New(elemType)
 		val := reflect.ValueOf(value)
 
-		// If the value is already a pointer of the correct type, use it directly
 		if valueType.AssignableTo(fieldType) {
 			return val, nil
 		}
 
-		// If the value is convertible to the element type, convert and wrap in pointer
 		if val.Type().ConvertibleTo(elemType) {
 			val = val.Convert(elemType)
 			newValue.Elem().Set(val)
diff --git a/pkg/config/yaml_config_handler_test.go b/pkg/config/yaml_config_handler_test.go
index 1467c19b5..57fc4ccd8 100644
--- a/pkg/config/yaml_config_handler_test.go
+++ b/pkg/config/yaml_config_handler_test.go
@@ -2004,6 +2004,36 @@ func TestYamlConfigHandler_SetContextValue(t *testing.T) {
 			t.Errorf("Expected 6.28, got %v", val)
 		}
 	})
+
+	t.Run("ConvertStringToBoolPointer", func(t *testing.T) {
+		// Given a handler with a default context
+		handler, _ := setup(t)
+		handler.context = "default"
+		handler.config.Contexts = map[string]*v1alpha1.Context{
+			"default": {},
+		}
+
+		// When setting a string "false" to a bool pointer field (dns.enabled)
+		if err := handler.SetContextValue("dns.enabled", "false"); err != nil {
+			t.Fatalf("Failed to set dns.enabled=false from string: %v", err)
+		}
+
+		// Then the value should be correctly set as a boolean
+		config := handler.GetConfig()
+		if config.DNS == nil || config.DNS.Enabled == nil || *config.DNS.Enabled != false {
+			t.Errorf("Expected dns.enabled to be false, got %v", config.DNS.Enabled)
+		}
+
+		// And when setting "true" as well
+		if err := handler.SetContextValue("dns.enabled", "true"); err != nil {
+			t.Fatalf("Failed to set dns.enabled=true from string: %v", err)
+		}
+
+		config = handler.GetConfig()
+		if config.DNS == nil || config.DNS.Enabled == nil || *config.DNS.Enabled != true {
+			t.Errorf("Expected dns.enabled to be true, got %v", config.DNS.Enabled)
+		}
+	})
 }
 
 func TestYamlConfigHandler_LoadConfigString(t *testing.T) {