diff --git a/cmd/containerd/server/config/config.go b/cmd/containerd/server/config/config.go
index ad23c51ac..5979ddcd5 100644
--- a/cmd/containerd/server/config/config.go
+++ b/cmd/containerd/server/config/config.go
@@ -373,6 +373,11 @@ 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 {
@@ -381,11 +386,6 @@ 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/cmd/containerd/server/config/config_test.go b/cmd/containerd/server/config/config_test.go
index de916f661..8240aad01 100644
--- a/cmd/containerd/server/config/config_test.go
+++ b/cmd/containerd/server/config/config_test.go
@@ -105,6 +105,17 @@ 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) {