diff --git a/backend/src/services/integration-auth/integration-sync-secret.ts b/backend/src/services/integration-auth/integration-sync-secret.ts
index 70e3435a2..e693a7fea 100644
--- a/backend/src/services/integration-auth/integration-sync-secret.ts
+++ b/backend/src/services/integration-auth/integration-sync-secret.ts
@@ -257,14 +257,27 @@ const syncSecretsGCPSecretManager = async ({
 const syncSecretsAzureKeyVault = async ({
   integration,
   secrets,
-  accessToken
+  accessToken,
+  createManySecretsRawFn,
+  updateManySecretsRawFn
 }: {
-  integration: TIntegrations;
+  integration: TIntegrations & {
+    projectId: string;
+    environment: {
+      id: string;
+      name: string;
+      slug: string;
+    };
+    secretPath: string;
+  };
   secrets: Record<string, { value: string; comment?: string }>;
   accessToken: string;
+  createManySecretsRawFn: (params: TCreateManySecretsRawFn) => Promise<Array<TSecrets & { _id: string }>>;
+  updateManySecretsRawFn: (params: TUpdateManySecretsRawFn) => Promise<Array<TSecrets & { _id: string }>>;
 }) => {
   interface GetAzureKeyVaultSecret {
     id: string; // secret URI
+    value: string;
     attributes: {
       enabled: true;
       created: number;
@@ -361,6 +374,83 @@ const syncSecretsAzureKeyVault = async ({
     }
   });
 
+  const secretsToAdd: { [key: string]: string } = {};
+  const secretsToUpdate: { [key: string]: string } = {};
+  const secretKeysToRemoveFromDelete = new Set<string>();
+
+  const metadata = IntegrationMetadataSchema.parse(integration.metadata);
+  if (!integration.lastUsed) {
+    Object.keys(res).forEach((key) => {
+      // first time using integration
+      const underscoredKey = key.replace(/-/g, "_");
+
+      // -> apply initial sync behavior
+      switch (metadata.initialSyncBehavior) {
+        case IntegrationInitialSyncBehavior.PREFER_TARGET: {
+          if (!(underscoredKey in secrets)) {
+            secretsToAdd[underscoredKey] = res[key].value;
+            setSecrets.push({
+              key,
+              value: res[key].value
+            });
+          } else if (secrets[underscoredKey]?.value !== res[key].value) {
+            secretsToUpdate[underscoredKey] = res[key].value;
+            const toEditSecretIndex = setSecrets.findIndex((secret) => secret.key === key);
+            if (toEditSecretIndex >= 0) {
+              setSecrets[toEditSecretIndex].value = res[key].value;
+            }
+          }
+
+          secretKeysToRemoveFromDelete.add(key);
+
+          break;
+        }
+        case IntegrationInitialSyncBehavior.PREFER_SOURCE: {
+          if (!(underscoredKey in secrets)) {
+            secretsToAdd[underscoredKey] = res[key].value;
+            setSecrets.push({
+              key,
+              value: res[key].value
+            });
+          }
+
+          secretKeysToRemoveFromDelete.add(key);
+          break;
+        }
+        default:
+          break;
+      }
+    });
+  }
+
+  if (Object.keys(secretsToUpdate).length) {
+    await updateManySecretsRawFn({
+      projectId: integration.projectId,
+      environment: integration.environment.slug,
+      path: integration.secretPath,
+      secrets: Object.keys(secretsToUpdate).map((key) => ({
+        secretName: key,
+        secretValue: secretsToUpdate[key],
+        type: SecretType.Shared,
+        secretComment: ""
+      }))
+    });
+  }
+
+  if (Object.keys(secretsToAdd).length) {
+    await createManySecretsRawFn({
+      projectId: integration.projectId,
+      environment: integration.environment.slug,
+      path: integration.secretPath,
+      secrets: Object.keys(secretsToAdd).map((key) => ({
+        secretName: key,
+        secretValue: secretsToAdd[key],
+        type: SecretType.Shared,
+        secretComment: ""
+      }))
+    });
+  }
+
   const setSecretAzureKeyVault = async ({
     key,
     value,
@@ -428,7 +518,7 @@ const syncSecretsAzureKeyVault = async ({
     });
   }
 
-  for await (const deleteSecret of deleteSecrets) {
+  for await (const deleteSecret of deleteSecrets.filter((secret) => !secretKeysToRemoveFromDelete.has(secret.key))) {
     const { key } = deleteSecret;
     await request.delete(`${integration.app}/secrets/${key}?api-version=7.3`, {
       headers: {
@@ -3512,7 +3602,9 @@ export const syncIntegrationSecrets = async ({
       await syncSecretsAzureKeyVault({
         integration,
         secrets,
-        accessToken
+        accessToken,
+        createManySecretsRawFn,
+        updateManySecretsRawFn
       });
       break;
     case Integrations.AWS_PARAMETER_STORE:
diff --git a/frontend/src/pages/integrations/azure-key-vault/create.tsx b/frontend/src/pages/integrations/azure-key-vault/create.tsx
index acf2c61bd..e6ed57302 100644
--- a/frontend/src/pages/integrations/azure-key-vault/create.tsx
+++ b/frontend/src/pages/integrations/azure-key-vault/create.tsx
@@ -3,6 +3,7 @@ import { useRouter } from "next/router";
 import queryString from "query-string";
 
 import { useCreateIntegration } from "@app/hooks/api";
+import { IntegrationSyncBehavior } from "@app/hooks/api/integrations/types";
 
 import {
   Button,
@@ -16,6 +17,18 @@ import {
 import { useGetIntegrationAuthById } from "../../../hooks/api/integrationAuth";
 import { useGetWorkspaceById } from "../../../hooks/api/workspace";
 
+const initialSyncBehaviors = [
+  {
+    label: "No Import - Overwrite all values in Azure Vault",
+    value: IntegrationSyncBehavior.OVERWRITE_TARGET
+  },
+  {
+    label: "Import - Prefer values from Azure Vault",
+    value: IntegrationSyncBehavior.PREFER_TARGET
+  },
+  { label: "Import - Prefer values from Infisical", value: IntegrationSyncBehavior.PREFER_SOURCE }
+];
+
 export default function AzureKeyVaultCreateIntegrationPage() {
   const router = useRouter();
   const { mutateAsync } = useCreateIntegration();
@@ -30,6 +43,9 @@ export default function AzureKeyVaultCreateIntegrationPage() {
 
   const [vaultBaseUrl, setVaultBaseUrl] = useState("");
   const [vaultBaseUrlErrorText, setVaultBaseUrlErrorText] = useState("");
+  const [initialSyncBehavior, setInitialSyncBehavior] = useState(
+    IntegrationSyncBehavior.PREFER_SOURCE
+  );
 
   const [isLoading, setIsLoading] = useState(false);
 
@@ -59,7 +75,10 @@ export default function AzureKeyVaultCreateIntegrationPage() {
         isActive: true,
         app: vaultBaseUrl,
         sourceEnvironment: selectedSourceEnvironment,
-        secretPath
+        secretPath,
+        metadata: {
+          initialSyncBehavior
+        }
       });
       setIsLoading(false);
 
@@ -107,6 +126,21 @@ export default function AzureKeyVaultCreateIntegrationPage() {
             onChange={(e) => setVaultBaseUrl(e.target.value)}
           />
         </FormControl>
+        <FormControl label="Initial Sync Behavior">
+          <Select
+            value={initialSyncBehavior}
+            onValueChange={(e) => setInitialSyncBehavior(e as IntegrationSyncBehavior)}
+            className="w-full"
+          >
+            {initialSyncBehaviors.map((b) => {
+              return (
+                <SelectItem value={b.value} key={`sync-behavior-${b.value}`}>
+                  {b.label}
+                </SelectItem>
+              );
+            })}
+          </Select>
+        </FormControl>
         <Button
           onClick={handleButtonClick}
           color="mineshaft"