diff --git a/services/server/config/config.go b/services/server/config/config.go
index 794e25c145..9b4b0460fb 100644
--- a/services/server/config/config.go
+++ b/services/server/config/config.go
@@ -253,13 +253,18 @@ func loadConfigFile(path string) (*Config, error) {
 }
 
 // resolveImports resolves import strings list to absolute paths list:
-// - If path contains *, glob pattern matching applied
 // - Non abs path is relative to parent config file directory
+// - If path contains *, glob pattern matching applied
 // - Abs paths returned as is
 func resolveImports(parent string, imports []string) ([]string, error) {
 	var out []string
 
 	for _, path := range imports {
+		path := filepath.Clean(path)
+		if !filepath.IsAbs(path) {
+			path = filepath.Join(filepath.Dir(parent), path)
+		}
+
 		if strings.Contains(path, "*") {
 			matches, err := filepath.Glob(path)
 			if err != nil {
@@ -268,11 +273,6 @@ func resolveImports(parent string, imports []string) ([]string, error) {
 
 			out = append(out, matches...)
 		} else {
-			path = filepath.Clean(path)
-			if !filepath.IsAbs(path) {
-				path = filepath.Join(filepath.Dir(parent), path)
-			}
-
 			out = append(out, path)
 		}
 	}
diff --git a/services/server/config/config_test.go b/services/server/config/config_test.go
index a589ecc4c9..18da5a3d2b 100644
--- a/services/server/config/config_test.go
+++ b/services/server/config/config_test.go
@@ -96,6 +96,17 @@ func TestResolveImports(t *testing.T) {
 		filepath.Join(tempDir, "test.toml"),
 		filepath.Join(tempDir, "current.toml"),
 	})
+
+	t.Run("GlobRelativePath", func(t *testing.T) {
+		imports, err := resolveImports(filepath.Join(tempDir, "root.toml"), []string{
+			"config_*.toml", // Glob files from working dir
+		})
+		assert.NoError(t, err)
+		assert.Equal(t, imports, []string{
+			filepath.Join(tempDir, "config_1.toml"),
+			filepath.Join(tempDir, "config_2.toml"),
+		})
+	})
 }
 
 func TestLoadSingleConfig(t *testing.T) {