diff --git a/internal/status/checksum.go b/internal/status/checksum.go
index 653a8e35..572d4650 100644
--- a/internal/status/checksum.go
+++ b/internal/status/checksum.go
@@ -45,13 +45,16 @@ func (c *Checksum) IsUpToDate() (bool, error) {
 		}
 	}
 
-	if len(c.Generates) != 0 {
-		// For each specified 'generates' field, check whether the files actually exist.
+	if len(c.Generates) > 0 {
+		// For each specified 'generates' field, check whether the files actually exist
 		for _, g := range c.Generates {
 			generates, err := glob(c.Dir, g)
-			if err != nil {
+			if os.IsNotExist(err) {
 				return false, nil
 			}
+			if err != nil {
+				return false, err
+			}
 			if len(generates) == 0 {
 				return false, nil
 			}
diff --git a/internal/status/glob.go b/internal/status/glob.go
index b46f7616..a70f663d 100644
--- a/internal/status/glob.go
+++ b/internal/status/glob.go
@@ -10,7 +10,7 @@ import (
 	"github.com/mattn/go-zglob"
 )
 
-func globs(dir string, globs []string) ([]string, error){
+func globs(dir string, globs []string) ([]string, error) {
 	files := make([]string, 0)
 	for _, g := range globs {
 		f, err := glob(dir, g)
@@ -39,13 +39,12 @@ func glob(dir string, g string) ([]string, error) {
 	for _, f := range fs {
 		info, err := os.Stat(f)
 		if err != nil {
-			continue
+			return nil, err
 		}
 		if info.IsDir() {
 			continue
 		}
 		files = append(files, f)
 	}
-	sort.Strings(files)
 	return files, nil
 }