diff --git a/base/fill/path_value.go b/base/fill/path_value.go
index eb243f6f0..f9f95f1a5 100644
--- a/base/fill/path_value.go
+++ b/base/fill/path_value.go
@@ -37,7 +37,7 @@ func SetPathValue(path string, val interface{}, output interface{}) error {
 	target, field, err := findTargetAtPath(steps, target)
 	if err != nil {
 		if err == ErrNotFound {
-			return fmt.Errorf("at \"%s\": path not found", path)
+			return fmt.Errorf("at %q: %w", path, ErrNotFound)
 		}
 		collector.Add(err)
 		return collector.AsSingleError()
@@ -65,22 +65,22 @@ func GetPathValue(path string, input interface{}) (interface{}, error) {
 	// Find target place to assign to, field is a non-empty string only if target is a map.
 	target, field, err := findTargetAtPath(steps, target)
 	if err != nil {
-		if err == ErrNotFound {
-			return nil, fmt.Errorf("at \"%s\": path not found", path)
-		}
-		return nil, fmt.Errorf("at \"%s\": %s", path, err)
+		return nil, fmt.Errorf("at %q: %w", path, err)
 	}
+	// If all steps completed, resolve the target to a real value.
 	if field == "" {
 		return target.Interface(), nil
 	}
-
-	lookup := target.MapIndex(reflect.ValueOf(field))
-	if lookup.IsValid() {
+	// Otherwise, one step is left, look it up using case-insensitive comparison.
+	if lookup := mapLookupCaseInsensitive(target, field); lookup != nil {
 		return lookup.Interface(), nil
 	}
-	return nil, fmt.Errorf("at \"%s\": invalid path", path)
+	return nil, fmt.Errorf("at %q: %w", path, ErrNotFound)
 }
 
+// Recursively look up the first step in place, until there are no steps left. If place is ever
+// a map with one step left, return that map and final step - this is done in order to enable
+// assignment to that map.
 func findTargetAtPath(steps []string, place reflect.Value) (reflect.Value, string, error) {
 	if len(steps) == 0 {
 		return place, "", nil
@@ -94,6 +94,16 @@ func findTargetAtPath(steps []string, place reflect.Value) (reflect.Value, strin
 			return place, "", ErrNotFound
 		}
 		return findTargetAtPath(rest, field)
+	} else if place.Kind() == reflect.Interface {
+		var inner reflect.Value
+		if place.IsNil() {
+			alloc := reflect.New(place.Type().Elem())
+			place.Set(alloc)
+			inner = alloc.Elem()
+		} else {
+			inner = place.Elem()
+		}
+		return findTargetAtPath(steps, inner)
 	} else if place.Kind() == reflect.Ptr {
 		var inner reflect.Value
 		if place.IsNil() {
@@ -108,9 +118,14 @@ func findTargetAtPath(steps []string, place reflect.Value) (reflect.Value, strin
 		if place.IsNil() {
 			place.Set(reflect.MakeMap(place.Type()))
 		}
-		// TODO: Handle case where `rest` has more steps and `val` is a struct: more
-		// recursive is needed.
-		return place, s, nil
+		if len(steps) == 1 {
+			return place, s, nil
+		}
+		found := mapLookupCaseInsensitive(place, s)
+		if found == nil {
+			return place, "", ErrNotFound
+		}
+		return findTargetAtPath(rest, *found)
 	} else if place.Kind() == reflect.Slice {
 		num, err := coerceToInt(s)
 		if err != nil {
@@ -126,6 +141,36 @@ func findTargetAtPath(steps []string, place reflect.Value) (reflect.Value, strin
 	}
 }
 
+// Look up value in the map, using case-insensitive string comparison. Return nil if not found
+func mapLookupCaseInsensitive(mapValue reflect.Value, k string) *reflect.Value {
+	// Try looking up the value without changing the string case
+	key := reflect.ValueOf(k)
+	result := mapValue.MapIndex(key)
+	if result.IsValid() {
+		return &result
+	}
+	// Try lower-casing the key and looking that up
+	klower := strings.ToLower(k)
+	key = reflect.ValueOf(klower)
+	result = mapValue.MapIndex(key)
+	if result.IsValid() {
+		return &result
+	}
+	// Iterate over the map keys, compare each, using case-insensitive matching
+	mapKeys := mapValue.MapKeys()
+	for _, mk := range mapKeys {
+		mstr := mk.String()
+		if strings.ToLower(mstr) == klower {
+			result = mapValue.MapIndex(mk)
+			if result.IsValid() {
+				return &result
+			}
+		}
+	}
+	// Not found, return nil
+	return nil
+}
+
 func coerceToTargetType(val interface{}, place reflect.Value) (interface{}, error) {
 	switch place.Kind() {
 	case reflect.Bool:
diff --git a/base/fill/path_value_test.go b/base/fill/path_value_test.go
index e60a667e4..e43d27351 100644
--- a/base/fill/path_value_test.go
+++ b/base/fill/path_value_test.go
@@ -106,8 +106,8 @@ func TestFillPathValue(t *testing.T) {
 	}
 
 	c = Collection{}
-	err = SetPathValue("not_found", "missing", &c)
-	expect = `at "not_found": path not found`
+	err = SetPathValue("non_existent", "missing", &c)
+	expect = `at "non_existent": not found`
 	if err == nil {
 		t.Fatalf("expected: error \"%s\", got no error", expect)
 	}
@@ -208,6 +208,10 @@ func TestGetPathValue(t *testing.T) {
 			"extra": "misc",
 		},
 		List: []string{"cat", "dog", "eel"},
+		Sub: SubElement {
+			Num: 7,
+			Text: "sandwich",
+		},
 	}
 
 	val, err := GetPathValue("name", &c)
@@ -226,8 +230,24 @@ func TestGetPathValue(t *testing.T) {
 		t.Errorf("expected: val should be \"misc\"")
 	}
 
-	val, err = GetPathValue("not_found", &c)
-	expect := `at "not_found": path not found`
+	val, err = GetPathValue("sub.num", &c)
+	if err != nil {
+		panic(err)
+	}
+	if val != 7 {
+		t.Errorf("expected: val should be 7, got %v", val)
+	}
+
+	val, err = GetPathValue("sub.text", &c)
+	if err != nil {
+		panic(err)
+	}
+	if val != "sandwich" {
+		t.Errorf("expected: val should be \"sandwich\", got %v", val)
+	}
+
+	val, err = GetPathValue("non_existent", &c)
+	expect := `at "non_existent": not found`
 	if err == nil {
 		t.Fatalf("expected: error \"%s\", got no error", expect)
 	}
@@ -236,7 +256,7 @@ func TestGetPathValue(t *testing.T) {
 	}
 
 	val, err = GetPathValue("dict.missing_key", &c)
-	expect = `at "dict.missing_key": invalid path`
+	expect = `at "dict.missing_key": not found`
 	if err == nil {
 		t.Fatalf("expected: error \"%s\", got no error", expect)
 	}
@@ -262,3 +282,64 @@ func TestGetPathValue(t *testing.T) {
 	}
 
 }
+
+func TestDictKeysCaseInsenstive(t *testing.T) {
+	obj := map[string]interface{}{
+		"Parent": map[string]interface{}{
+			"Child": "ok",
+		},
+		"First": map[string]interface{}{
+			"Second": map[string]interface{}{
+				"Third": "alright",
+			},
+		},
+	}
+
+	val, err := GetPathValue("parent.child", obj)
+	if err != nil {
+		panic(err)
+	}
+	if val != "ok" {
+		t.Errorf("expected: val should be \"ok\"")
+	}
+
+	val, err = GetPathValue("parent.Child", obj)
+	if err != nil {
+		panic(err)
+	}
+	if val != "ok" {
+		t.Errorf("expected: val should be \"ok\"")
+	}
+
+	val, err = GetPathValue("parent.CHILD", obj)
+	if err != nil {
+		panic(err)
+	}
+	if val != "ok" {
+		t.Errorf("expected: val should be \"ok\"")
+	}
+
+	val, err = GetPathValue("Parent.Child", obj)
+	if err != nil {
+		panic(err)
+	}
+	if val != "ok" {
+		t.Errorf("expected: val should be \"ok\"")
+	}
+
+	val, err = GetPathValue("first.second.third", obj)
+	if err != nil {
+		panic(err)
+	}
+	if val != "alright" {
+		t.Errorf("expected: val should be \"alright\"")
+	}
+
+	val, err = GetPathValue("FIRST.SECOND.THIRD", obj)
+	if err != nil {
+		panic(err)
+	}
+	if val != "alright" {
+		t.Errorf("expected: val should be \"alright\"")
+	}
+}
diff --git a/base/fill/struct_test.go b/base/fill/struct_test.go
index 889084a89..8faa77f30 100644
--- a/base/fill/struct_test.go
+++ b/base/fill/struct_test.go
@@ -258,6 +258,7 @@ type SubElement struct {
 	Num    int
 	Things *map[string]string
 	Any    interface{}
+	Text   string
 }
 
 func (c *Collection) SetArbitrary(key string, val interface{}) error {