diff --git a/src/server/lib/nativeHelm/__tests__/helm.test.ts b/src/server/lib/nativeHelm/__tests__/helm.test.ts
index eb069be..4f89f6a 100644
--- a/src/server/lib/nativeHelm/__tests__/helm.test.ts
+++ b/src/server/lib/nativeHelm/__tests__/helm.test.ts
@@ -483,6 +483,38 @@ describe('Native Helm', () => {
       expect(result).not.toContain('--version');
     });
 
+    it('should preserve inner double quotes in --set keys for annotation paths', () => {
+      const result = constructHelmCommand(
+        'upgrade --install',
+        'my-chart',
+        'my-release',
+        'my-namespace',
+        ['ingress.extraAnnotations."app\\.kubernetes\\.io/name"=my-app'],
+        [],
+        ChartType.PUBLIC,
+        undefined,
+        'https://example.com/charts'
+      );
+
+      expect(result).toContain('--set "ingress.extraAnnotations.\\"app\\.kubernetes\\.io/name\\"=my-app"');
+    });
+
+    it('should escape inner double quotes in --set values', () => {
+      const result = constructHelmCommand(
+        'upgrade --install',
+        'my-chart',
+        'my-release',
+        'my-namespace',
+        ['deployment.env.MSG="hello world"'],
+        [],
+        ChartType.PUBLIC,
+        undefined,
+        'https://example.com/charts'
+      );
+
+      expect(result).toContain('--set "deployment.env.MSG=\\"hello world\\""');
+    });
+
     it('should not add chart version for PUBLIC charts when version is not specified', () => {
       const result = constructHelmCommand(
         'upgrade --install',
diff --git a/src/server/lib/nativeHelm/utils.ts b/src/server/lib/nativeHelm/utils.ts
index 7ea2de1..d722c68 100644
--- a/src/server/lib/nativeHelm/utils.ts
+++ b/src/server/lib/nativeHelm/utils.ts
@@ -93,12 +93,12 @@ export function constructHelmCommand(
   customValues.forEach((value) => {
     const equalIndex = value.indexOf('=');
     if (equalIndex > -1) {
-      const key = value.substring(0, equalIndex);
+      const key = value.substring(0, equalIndex).replace(/"/g, '\\"');
       const val = value.substring(equalIndex + 1);
-      const escapedVal = escapeHelmValue(val);
+      const escapedVal = escapeHelmValue(val).replace(/"/g, '\\"');
       command += ` --set "${key}=${escapedVal}"`;
     } else {
-      command += ` --set "${value}"`;
+      command += ` --set "${value.replace(/"/g, '\\"')}"`;
     }
   });