diff --git a/cmd/nvidia-ctk/runtime/configure/configure_test.go b/cmd/nvidia-ctk/runtime/configure/configure_test.go
index 32b5419e9..305d24686 100644
--- a/cmd/nvidia-ctk/runtime/configure/configure_test.go
+++ b/cmd/nvidia-ctk/runtime/configure/configure_test.go
@@ -43,6 +43,36 @@ func TestConfigureLifecycle(t *testing.T) {
 		assertConditions   func(*testing.T, string) error
 	}{
 		// Containerd v2 test cases
+		{
+			description: "containerd: config exists with imports",
+			args: []string{
+				"--runtime", "containerd",
+				"--config", "{{ .testRoot }}/etc/containerd/config.toml",
+				"--drop-in-config", "{{ .testRoot }}/etc/containerd/conf.d/99-nvidia.toml",
+			},
+			prepareEnvironment: func(t *testing.T, testRoot string) error {
+				configPath := filepath.Join(testRoot, "etc/containerd/config.toml")
+				require.NoError(t, os.MkdirAll(filepath.Dir(configPath), 0755))
+
+				initialConfig := `version = 2
+imports = ["/foo/bar/*.toml"]
+`
+				return os.WriteFile(configPath, []byte(initialConfig), 0600)
+			},
+			assertConditions: func(t *testing.T, testRoot string) error {
+				mainConfig := filepath.Join(testRoot, "etc/containerd/config.toml")
+				content, err := os.ReadFile(mainConfig)
+				require.NoError(t, err)
+
+				expectedTemplate := `imports = ["/foo/bar/*.toml", "{{ .testRoot }}/etc/containerd/conf.d/*.toml"]
+version = 2
+`
+				expected := strings.ReplaceAll(expectedTemplate, "{{ .testRoot }}", testRoot)
+
+				require.Equal(t, expected, string(content))
+				return nil
+			},
+		},
 		{
 			description: "containerd: v2 config does not exist with drop-in",
 			args: []string{
diff --git a/pkg/config/engine/containerd/config_drop_in.go b/pkg/config/engine/containerd/config_drop_in.go
index 8264523e4..0f16dc8de 100644
--- a/pkg/config/engine/containerd/config_drop_in.go
+++ b/pkg/config/engine/containerd/config_drop_in.go
@@ -173,12 +173,35 @@ func (c *topLevelConfig) removeVersion() {
 	c.config.Delete("version")
 }
 
+func (c *topLevelConfig) getCurrentImports() []string {
+	rawImports := c.config.Get("imports")
+	if rawImports == nil {
+		return nil
+	}
+
+	if importsStringSlice, ok := rawImports.([]string); ok {
+		return importsStringSlice
+	}
+
+	importsAnySlice, ok := rawImports.([]any)
+	if !ok {
+		return nil
+	}
+	var importsStringSlice []string
+	for _, importAny := range importsAnySlice {
+		importString, ok := importAny.(string)
+		if !ok {
+			continue
+		}
+		importsStringSlice = append(importsStringSlice, importString)
+	}
+
+	return importsStringSlice
+}
+
 func (c *topLevelConfig) ensureImports(dropInFilename string) {
 	config := c.config.Tree
-	var currentImports []string
-	if ci, ok := c.config.Get("imports").([]string); ok {
-		currentImports = ci
-	}
+	currentImports := c.getCurrentImports()
 
 	requiredImport := c.importPattern(dropInFilename)
 	for _, currentImport := range currentImports {
diff --git a/pkg/config/engine/containerd/config_drop_in_test.go b/pkg/config/engine/containerd/config_drop_in_test.go
new file mode 100644
index 000000000..fe597ed8c
--- /dev/null
+++ b/pkg/config/engine/containerd/config_drop_in_test.go
@@ -0,0 +1,74 @@
+/**
+# SPDX-FileCopyrightText: Copyright (c) 2025 NVIDIA CORPORATION & AFFILIATES. All rights reserved.
+# SPDX-License-Identifier: Apache-2.0
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+**/
+
+package containerd
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/require"
+
+	"github.com/NVIDIA/nvidia-container-toolkit/pkg/config/toml"
+)
+
+func TestEnsureImports(t *testing.T) {
+	testCases := []struct {
+		description     string
+		configMap       map[string]any
+		path            string
+		expectedImports []string
+	}{
+		{
+			description:     "empty",
+			path:            "/another/path/file.toml",
+			expectedImports: []string{"/another/path/*.toml"},
+		},
+		{
+			description: "existing imports as string slice",
+			configMap: map[string]any{
+				"imports": []string{"/foo/bar/*.toml"},
+			},
+			path:            "/another/path/file.toml",
+			expectedImports: []string{"/foo/bar/*.toml", "/another/path/*.toml"},
+		},
+		{
+			description: "existing imports as any slice",
+			configMap: map[string]any{
+				"imports": []any{"/foo/bar/*.toml"},
+			},
+			path:            "/another/path/file.toml",
+			expectedImports: []string{"/foo/bar/*.toml", "/another/path/*.toml"},
+		},
+	}
+
+	for _, tc := range testCases {
+		t.Run(tc.description, func(t *testing.T) {
+			cut := topLevelConfig{
+				config: &Config{
+					Tree: func() *toml.Tree {
+						t, _ := toml.FromMap(tc.configMap).Load()
+						return t
+					}(),
+				},
+			}
+
+			cut.ensureImports("/another/path/file.toml")
+			require.EqualValues(t, tc.expectedImports, cut.config.Get("imports"))
+		})
+	}
+
+}