diff --git a/tests/test_auth.py b/tests/test_auth.py
index 7ff63ec..a06117a 100644
--- a/tests/test_auth.py
+++ b/tests/test_auth.py
@@ -293,3 +293,54 @@ def test_clear_credentials_removes_config_keys(self):
         assert "YOUTRACK_VERIFY_SSL" not in config_values
         assert "YOUTRACK_API_KEY" not in config_values
         assert config_values.get("OTHER_CONFIG") == "should_remain"
+
+
+@pytest.mark.unit
+class TestCredentialsStoredButUnreadable:
+    """Issue #746: distinguish 'no credentials' from 'stored but unreadable'.
+
+    After an upgrade/move relocates the CLI binary, the OS keychain can deny the
+    new binary access to the saved token, so load_credentials() returns None even
+    though a keyring-backed login is recorded in the config file.
+    """
+
+    def _manager(self, tmp_path, env_lines):
+        from youtrack_cli.security import SecurityConfig
+
+        cfg = tmp_path / ".env"
+        cfg.write_text("\n".join(env_lines) + "\n")
+        return AuthManager(str(cfg), security_config=SecurityConfig(enable_credential_encryption=True))
+
+    def test_flags_placeholder_with_unreadable_token(self, tmp_path, monkeypatch):
+        monkeypatch.delenv("YOUTRACK_TOKEN", raising=False)
+        mgr = self._manager(
+            tmp_path,
+            ["YOUTRACK_BASE_URL=https://yt.example.com", "YOUTRACK_API_KEY=[Stored in keyring]"],
+        )
+        # Keyring cannot return the token (simulates the post-upgrade ACL denial).
+        mgr.credential_manager.retrieve_credential = MagicMock(return_value=None)
+        assert mgr.load_credentials() is None
+        assert mgr.credentials_stored_but_unreadable() is True
+
+    def test_not_flagged_when_token_is_readable(self, tmp_path, monkeypatch):
+        monkeypatch.delenv("YOUTRACK_TOKEN", raising=False)
+        mgr = self._manager(
+            tmp_path,
+            ["YOUTRACK_BASE_URL=https://yt.example.com", "YOUTRACK_API_KEY=[Stored in keyring]"],
+        )
+        stored = {
+            "youtrack_base_url": "https://yt.example.com",
+            "youtrack_token": "perm:REAL-TOKEN",
+            "youtrack_username": "ryan",
+        }
+        mgr.credential_manager.retrieve_credential = MagicMock(side_effect=lambda key: stored.get(key))
+        assert mgr.load_credentials() is not None
+        assert mgr.credentials_stored_but_unreadable() is False
+
+    def test_not_flagged_when_nothing_configured(self, tmp_path, monkeypatch):
+        monkeypatch.delenv("YOUTRACK_TOKEN", raising=False)
+        monkeypatch.delenv("YOUTRACK_BASE_URL", raising=False)
+        mgr = self._manager(tmp_path, ["# no credentials configured"])
+        mgr.credential_manager.retrieve_credential = MagicMock(return_value=None)
+        assert mgr.load_credentials() is None
+        assert mgr.credentials_stored_but_unreadable() is False
diff --git a/youtrack_cli/auth.py b/youtrack_cli/auth.py
index 8ee2ec6..d0218a9 100644
--- a/youtrack_cli/auth.py
+++ b/youtrack_cli/auth.py
@@ -18,7 +18,7 @@
 from urllib.parse import urlparse
 
 import httpx
-from dotenv import load_dotenv
+from dotenv import dotenv_values, load_dotenv
 from pydantic import BaseModel, Field, ValidationError
 
 from .client import reset_client_manager_sync
@@ -256,6 +256,27 @@ def load_credentials(self) -> AuthConfig | None:
         except ValidationError:
             return None
 
+    def credentials_stored_but_unreadable(self) -> bool:
+        """Report whether keyring-backed credentials exist on record but can't be read.
+
+        Distinguishes "never logged in" from "logged in previously, but the token
+        is no longer readable". The config file records a keyring-backed login as
+        ``YOUTRACK_API_KEY=[Stored in keyring]`` alongside the base URL, while the
+        real token lives in the system keyring. If that placeholder is present but
+        :meth:`load_credentials` returns ``None``, the keyring entry has become
+        unreadable — e.g. after an upgrade or move relocated the CLI binary and the
+        OS keychain no longer grants the new binary access. Re-running
+        ``yt auth login`` re-stores the credential and fixes it.
+
+        Returns:
+            True if a keyring-backed credential is on record but currently
+            unreadable; False otherwise (including when credentials load fine).
+        """
+        if self.load_credentials() is not None:
+            return False
+        values = dotenv_values(self.config_path)
+        return bool(values.get("YOUTRACK_BASE_URL")) and values.get("YOUTRACK_API_KEY") == "[Stored in keyring]"
+
     def clear_credentials(self) -> None:
         """Clear saved authentication credentials from both keyring and file."""
         # Clear from keyring
diff --git a/youtrack_cli/main.py b/youtrack_cli/main.py
index edae877..41d1500 100644
--- a/youtrack_cli/main.py
+++ b/youtrack_cli/main.py
@@ -1398,6 +1398,18 @@ def status(ctx: click.Context) -> None:
     try:
         credentials = auth_manager.load_credentials()
         if not credentials:
+            if auth_manager.credentials_stored_but_unreadable():
+                console.print(
+                    "⚠ Credentials are stored in the system keyring but can't be read.",
+                    style="yellow",
+                )
+                console.print(
+                    "This can happen after upgrading or moving the CLI — the OS keychain "
+                    "may no longer grant the new binary access to the saved token.",
+                    style="yellow",
+                )
+                console.print("Run 'yt auth login' to re-store your credentials.", style="blue")
+                return
             format_and_print_error(CommonErrors.no_credentials())
             console.print("Run 'yt auth login' to authenticate first.", style="blue")
             return