diff --git a/src/crypto/keychainManager.ts b/src/crypto/keychainManager.ts
index 9f8d140b..748941bd 100644
--- a/src/crypto/keychainManager.ts
+++ b/src/crypto/keychainManager.ts
@@ -15,19 +15,25 @@ import { perform2FAVerification } from '../middleware/perform2FAVerification';
 
 const SERVICE = 'dashlane-cli';
 
-export const setLocalKey = (login: string, shouldNotSaveMasterPassword: boolean, localKey?: Buffer): Buffer => {
+export const generateLocalKey = (): Buffer => {
+    const localKey = crypto.randomBytes(32);
     if (!localKey) {
-        localKey = crypto.randomBytes(32);
-        if (!localKey) {
-            throw new Error('Unable to generate AES local key');
-        }
+        throw new Error('Unable to generate AES local key');
     }
+    return localKey;
+};
 
-    if (!shouldNotSaveMasterPassword) {
+export const setLocalKey = (login: string, localKey: Buffer, callbackOnError: (errorMessage: string) => void) => {
+    try {
         const entry = new Entry(SERVICE, login);
         entry.setPassword(localKey.toString('base64'));
+    } catch (error) {
+        let errorMessage = 'unknown error';
+        if (error instanceof Error) {
+            errorMessage = error.message;
+        }
+        callbackOnError(errorMessage);
     }
-    return localKey;
 };
 
 const getLocalKey = (login: string): Buffer | undefined => {
@@ -77,19 +83,7 @@ const getSecretsWithoutDB = async (
     login: string,
     shouldNotSaveMasterPassword: boolean
 ): Promise<Secrets> => {
-    let localKey: Buffer;
-    try {
-        localKey = setLocalKey(login, shouldNotSaveMasterPassword);
-    } catch (error) {
-        let errorMessage = 'unknown error';
-        if (error instanceof Error) {
-            errorMessage = error.message;
-        }
-        winston.debug(`Unable to reach OS keychain: ${errorMessage}`);
-        throw new Error(
-            'Your OS keychain is probably unreachable. Install it or disable its usage via `dcli configure save-master-password false`'
-        );
-    }
+    const localKey = generateLocalKey();
 
     // Register the user's device
     const { deviceAccessKey, deviceSecretKey, serverKey } = await registerDevice({ login });
@@ -115,6 +109,13 @@ const getSecretsWithoutDB = async (
     const masterPasswordEncrypted = encryptAES(localKey, Buffer.from(masterPassword));
     const localKeyEncrypted = encryptAES(derivate, localKey);
 
+    if (!shouldNotSaveMasterPassword) {
+        setLocalKey(login, localKey, (errorMessage) => {
+            warnUnreachableKeychainDisabled(errorMessage);
+            shouldNotSaveMasterPassword = true;
+        });
+    }
+
     db.prepare('REPLACE INTO device VALUES (?, ?, ?, ?, ?, ?, ?, ?, ?, ?)')
         .bind(
             login,
@@ -163,7 +164,12 @@ const getSecretsWithoutKeychain = async (login: string, deviceConfiguration: Dev
         await decrypt(deviceConfiguration.secretKeyEncrypted, { type: 'alreadyComputed', symmetricKey: localKey })
     ).toString('hex');
 
-    setLocalKey(login, deviceConfiguration.shouldNotSaveMasterPassword, localKey);
+    if (!deviceConfiguration.shouldNotSaveMasterPassword) {
+        setLocalKey(login, localKey, (errorMessage) => {
+            winston.warn(`Unable to reach OS keychain because of error: "${errorMessage}". \
+Install it or disable its usage via \`dcli configure save-master-password false\`.`);
+        });
+    }
 
     return {
         login,
@@ -270,3 +276,9 @@ export const getSecrets = async (
         secretKey,
     };
 };
+
+export const warnUnreachableKeychainDisabled = (errorMessage: string) => {
+    winston.warn(`Unable to reach OS keychain because of error: "${errorMessage}", so its use has been disabled. \
+To retry using it, please execute \`dcli configure save-master-password true\`. \
+Until then, you will have to retype your master password each time you run the CLI.`);
+};
diff --git a/src/middleware/configure.ts b/src/middleware/configure.ts
index e74f2dc2..2a5c6449 100644
--- a/src/middleware/configure.ts
+++ b/src/middleware/configure.ts
@@ -1,7 +1,7 @@
 import Database from 'better-sqlite3';
 import winston from 'winston';
 import { encryptAES } from '../crypto/encrypt';
-import { deleteLocalKey, setLocalKey } from '../crypto/keychainManager';
+import { deleteLocalKey, setLocalKey, warnUnreachableKeychainDisabled } from '../crypto/keychainManager';
 import { Secrets } from '../types';
 
 interface ConfigureSaveMasterPassword {
@@ -17,7 +17,8 @@ interface ConfigureDisableAutoSync {
 }
 
 export const configureSaveMasterPassword = (params: ConfigureSaveMasterPassword) => {
-    const { db, secrets, shouldNotSaveMasterPassword } = params;
+    const { db, secrets } = params;
+    let shouldNotSaveMasterPassword = params.shouldNotSaveMasterPassword;
 
     if (shouldNotSaveMasterPassword) {
         // Forget the local key stored in the OS keychain because the master password and the DB are enough to retrieve the
@@ -30,7 +31,7 @@ export const configureSaveMasterPassword = (params: ConfigureSaveMasterPassword)
             if (error instanceof Error) {
                 errorMessage = error.message;
             }
-            winston.debug(`Unable to delete the local key from the keychain: ${errorMessage}`);
+            winston.warn(`Unable to delete the local key from the keychain: ${errorMessage}`);
         }
     }
 
@@ -41,8 +42,13 @@ export const configureSaveMasterPassword = (params: ConfigureSaveMasterPassword)
         // Set encrypted master password in the DB
         masterPasswordEncrypted = encryptAES(secrets.localKey, Buffer.from(secrets.masterPassword));
 
-        // Set local key in the OS keychain
-        setLocalKey(secrets.login, shouldNotSaveMasterPassword, secrets.localKey);
+        if (!shouldNotSaveMasterPassword) {
+            // Set local key in the OS keychain
+            setLocalKey(secrets.login, secrets.localKey, (errorMessage: string) => {
+                warnUnreachableKeychainDisabled(errorMessage);
+                shouldNotSaveMasterPassword = true;
+            });
+        }
     }
 
     db.prepare('UPDATE device SET masterPasswordEncrypted = ?, shouldNotSaveMasterPassword = ? WHERE login = ?')