diff --git a/src/tests/test_legacy_migration_second_session.py b/src/tests/test_legacy_migration_second_session.py
new file mode 100644
index 0000000..e83db3a
--- /dev/null
+++ b/src/tests/test_legacy_migration_second_session.py
@@ -0,0 +1,62 @@
+import json
+import hashlib
+from pathlib import Path
+from types import SimpleNamespace
+
+from cryptography.fernet import Fernet
+
+from helpers import create_vault, TEST_SEED, TEST_PASSWORD
+from seedpass.core.manager import PasswordManager, EncryptionMode
+from seedpass.core.vault import Vault
+from seedpass.core.encryption import EncryptionManager
+from utils.key_derivation import derive_index_key
+from utils.fingerprint import generate_fingerprint
+
+
+def test_legacy_migration_second_session(monkeypatch, tmp_path: Path) -> None:
+    fingerprint = generate_fingerprint(TEST_SEED)
+    fp_dir = tmp_path / fingerprint
+    fp_dir.mkdir()
+    vault, _ = create_vault(fp_dir, TEST_SEED, TEST_PASSWORD)
+
+    key = derive_index_key(TEST_SEED)
+    data = {"schema_version": 4, "entries": {}}
+    enc = Fernet(key).encrypt(json.dumps(data).encode())
+    legacy_file = fp_dir / "seedpass_passwords_db.json.enc"
+    legacy_file.write_bytes(enc)
+    (fp_dir / "seedpass_passwords_db_checksum.txt").write_text(
+        hashlib.sha256(enc).hexdigest()
+    )
+
+    monkeypatch.setattr(
+        "seedpass.core.encryption.prompt_existing_password", lambda *_: TEST_PASSWORD
+    )
+    monkeypatch.setattr("builtins.input", lambda *_a, **_k: "y")
+    vault.load_index()
+    new_file = fp_dir / "seedpass_entries_db.json.enc"
+    assert new_file.read_bytes().startswith(b"V2:")
+
+    new_enc_mgr = EncryptionManager(key, fp_dir)
+    new_vault = Vault(new_enc_mgr, fp_dir)
+    pm = PasswordManager.__new__(PasswordManager)
+    pm.encryption_mode = EncryptionMode.SEED_ONLY
+    pm.encryption_manager = new_enc_mgr
+    pm.vault = new_vault
+    pm.parent_seed = TEST_SEED
+    pm.fingerprint_dir = fp_dir
+    pm.current_fingerprint = fp_dir.name
+    pm.bip85 = SimpleNamespace()
+    monkeypatch.setattr(
+        "seedpass.core.manager.NostrClient", lambda *a, **k: SimpleNamespace()
+    )
+
+    def fail_prompt(*_a, **_k):  # pragma: no cover - ensures no prompts occur
+        raise AssertionError("Prompt should not be called")
+
+    monkeypatch.setattr("builtins.input", fail_prompt)
+    monkeypatch.setattr(
+        "seedpass.core.encryption.prompt_existing_password", fail_prompt
+    )
+
+    pm.initialize_managers()
+    assert new_file.read_bytes().startswith(b"V2:")