diff --git a/kasa/cli/discover.py b/kasa/cli/discover.py
index af367e32b..4ee01d3ee 100644
--- a/kasa/cli/discover.py
+++ b/kasa/cli/discover.py
@@ -29,6 +29,7 @@
 from kasa.protocols.iotprotocol import REDACTORS as IOT_REDACTORS
 from kasa.protocols.protocol import redact_data
 
+from ..exceptions import UnsupportedAuthenticationError
 from ..json import dumps as json_dumps
 from .common import echo, error
 
@@ -70,14 +71,16 @@ async def detail(ctx: click.Context) -> DeviceDict:
     async def print_unsupported(unsupported_exception: UnsupportedDeviceError) -> None:
         unsupported.append(unsupported_exception)
         async with sem:
+            echo("== Unsupported device ==")
+            echo(f"\t{unsupported_exception}")
+            echo()
+
             if unsupported_exception.discovery_result:
-                echo("== Unsupported device ==")
                 _echo_discovery_info(unsupported_exception.discovery_result)
                 echo()
-            else:
-                echo("== Unsupported device ==")
-                echo(f"\t{unsupported_exception}")
-                echo()
+                if isinstance(unsupported_exception, UnsupportedAuthenticationError):
+                    echo("\t[red bold]Provisioned using unsupported 'tss'.[/red bold]")
+                    echo("\tTo fix, reset and provision manually.")
 
     from .device import state
 
diff --git a/kasa/discover.py b/kasa/discover.py
index 8e2b981af..22aaa1afb 100755
--- a/kasa/discover.py
+++ b/kasa/discover.py
@@ -123,6 +123,7 @@
 from kasa.exceptions import (
     KasaException,
     TimeoutError,
+    UnsupportedAuthenticationError,
     UnsupportedDeviceError,
 )
 from kasa.iot.iotdevice import IotDevice, _extract_sys_info
@@ -805,6 +806,13 @@ def _get_connection_parameters(
         discovery_result: DiscoveryResult,
     ) -> DeviceConnectionParameters:
         """Get connection parameters from the discovery result."""
+        # Raise specific exception for unsupported authentication source
+        if getattr(discovery_result, "obd_src", None) == "tss":
+            raise UnsupportedAuthenticationError(
+                f"Device at {discovery_result.ip} uses unsupported onboarding 'tss'.",
+                discovery_result=discovery_result.to_dict(),
+                host=discovery_result.ip,
+            )
         type_ = discovery_result.device_type
         if (encrypt_schm := discovery_result.mgt_encrypt_schm) is None:
             raise UnsupportedDeviceError(
@@ -885,7 +893,7 @@ def _get_device_instance(
             conn_params = Discover._get_connection_parameters(discovery_result)
             config.connection_type = conn_params
         except KasaException as ex:
-            if isinstance(ex, UnsupportedDeviceError):
+            if isinstance(ex, UnsupportedDeviceError | UnsupportedAuthenticationError):
                 raise
             raise UnsupportedDeviceError(
                 f"Unsupported device {config.host} of type {type_} "
diff --git a/kasa/exceptions.py b/kasa/exceptions.py
index 1c764ad7a..5115dabce 100644
--- a/kasa/exceptions.py
+++ b/kasa/exceptions.py
@@ -200,3 +200,11 @@ def from_int(value: int) -> SmartErrorCode:
     SmartErrorCode.TRANSPORT_UNKNOWN_CREDENTIALS_ERROR,
     SmartErrorCode.HOMEKIT_LOGIN_FAIL,
 ]
+
+
+class UnsupportedAuthenticationError(UnsupportedDeviceError, AuthenticationError):
+    """Raised when authentication fails with unsupported provisioning method.
+
+    This can be used to display a more helpful message to the user when their devices
+    have been provisioned using the tplink simple setup (tss).
+    """
diff --git a/tests/discovery_fixtures.py b/tests/discovery_fixtures.py
index 3cf726f48..939709048 100644
--- a/tests/discovery_fixtures.py
+++ b/tests/discovery_fixtures.py
@@ -399,3 +399,21 @@ async def mock_discover(self):
     mocker.patch("kasa.discover._DiscoverProtocol.do_discover", mock_discover)
 
     return discovery_data
+
+
+def test_unsupported_authentication_exception_for_tss():
+    from kasa.discover import Discover, DiscoveryResult
+    from kasa.exceptions import UnsupportedAuthenticationError
+
+    # Create a mock discovery result with obd_src='tss'
+    dr = DiscoveryResult(
+        device_type="SomeType",
+        device_model="SomeModel",
+        device_id="SomeID",
+        ip="127.0.0.2",
+        mac="00:11:22:33:44:55",
+        obd_src="tss",
+    )
+    with pytest.raises(UnsupportedAuthenticationError) as excinfo:
+        Discover._get_connection_parameters(dr)
+    assert "obd_src='tss'" in str(excinfo.value)