diff --git a/supervisor/core.py b/supervisor/core.py
index 6f3cfd79cca..6cb299ee60d 100644
--- a/supervisor/core.py
+++ b/supervisor/core.py
@@ -28,7 +28,7 @@
 from .resolution.const import ContextType, IssueType, SuggestionType, UnhealthyReason
 from .utils.dt import utcnow
 from .utils.sentry import capture_exception
-from .utils.whoami import retrieve_whoami
+from .utils.whoami import WhoamiData, retrieve_whoami
 
 _LOGGER: logging.Logger = logging.getLogger(__name__)
 
@@ -363,6 +363,13 @@ def _update_last_boot(self):
         self.sys_config.last_boot = self.sys_hardware.helper.last_boot
         self.sys_config.save_data()
 
+    async def _retrieve_whoami(self, with_ssl: bool) -> WhoamiData | None:
+        try:
+            return await retrieve_whoami(self.sys_websession, with_ssl)
+        except WhoamiSSLError:
+            _LOGGER.info("Whoami service SSL error")
+            return None
+
     async def _adjust_system_datetime(self):
         """Adjust system time/date on startup."""
         # If no timezone is detect or set
@@ -375,21 +382,15 @@ async def _adjust_system_datetime(self):
 
         # Get Timezone data
         try:
-            data = await retrieve_whoami(self.sys_websession)
-        except WhoamiSSLError:
-            pass
+            data = await self._retrieve_whoami(True)
+
+            # SSL Date Issue & possible time drift
+            if not data:
+                data = await self._retrieve_whoami(False)
         except WhoamiError as err:
             _LOGGER.warning("Can't adjust Time/Date settings: %s", err)
             return
 
-        # SSL Date Issue & possible time drift
-        if not data:
-            try:
-                data = await retrieve_whoami(self.sys_websession, with_ssl=False)
-            except WhoamiError as err:
-                _LOGGER.error("Can't adjust Time/Date settings: %s", err)
-                return
-
         self.sys_config.timezone = self.sys_config.timezone or data.timezone
 
         # Calculate if system time is out of sync
diff --git a/tests/test_core.py b/tests/test_core.py
index eaf55957942..08a044b6d5c 100644
--- a/tests/test_core.py
+++ b/tests/test_core.py
@@ -1,7 +1,15 @@
 """Testing handling with CoreState."""
+# pylint: disable=W0212
+import datetime
+from unittest.mock import AsyncMock, PropertyMock, patch
 
 from supervisor.const import CoreState
 from supervisor.coresys import CoreSys
+from supervisor.exceptions import WhoamiSSLError
+from supervisor.host.control import SystemControl
+from supervisor.host.info import InfoCenter
+from supervisor.supervisor import Supervisor
+from supervisor.utils.whoami import WhoamiData
 
 
 def test_write_state(run_dir, coresys: CoreSys):
@@ -14,3 +22,58 @@ def test_write_state(run_dir, coresys: CoreSys):
     coresys.core.state = CoreState.SHUTDOWN
 
     assert run_dir.read_text() == CoreState.SHUTDOWN
+
+
+async def test_adjust_system_datetime(coresys: CoreSys):
+    """Test _adjust_system_datetime method with successful retrieve_whoami."""
+    utc_ts = datetime.datetime.now().replace(tzinfo=datetime.UTC)
+    with patch(
+        "supervisor.core.retrieve_whoami",
+        new_callable=AsyncMock,
+        side_effect=[WhoamiData("Europe/Zurich", utc_ts)],
+    ) as mock_retrieve_whoami:
+        await coresys.core._adjust_system_datetime()
+        mock_retrieve_whoami.assert_called_once()
+        assert coresys.core.sys_config.timezone == "Europe/Zurich"
+
+        # Validate we don't retrieve whoami once timezone has been set
+        mock_retrieve_whoami.reset_mock()
+        await coresys.core._adjust_system_datetime()
+        mock_retrieve_whoami.assert_not_called()
+
+
+async def test_adjust_system_datetime_without_ssl(coresys: CoreSys):
+    """Test _adjust_system_datetime method when retrieve_whoami raises WhoamiSSLError."""
+    utc_ts = datetime.datetime.now().replace(tzinfo=datetime.UTC)
+    with patch(
+        "supervisor.core.retrieve_whoami",
+        new_callable=AsyncMock,
+        side_effect=[WhoamiSSLError("SSL error"), WhoamiData("Europe/Zurich", utc_ts)],
+    ) as mock_retrieve_whoami:
+        await coresys.core._adjust_system_datetime()
+        assert mock_retrieve_whoami.call_count == 2
+        assert mock_retrieve_whoami.call_args_list[0].args[1]
+        assert not mock_retrieve_whoami.call_args_list[1].args[1]
+        assert coresys.core.sys_config.timezone == "Europe/Zurich"
+
+
+async def test_adjust_system_datetime_if_time_behind(coresys: CoreSys):
+    """Test _adjust_system_datetime method when current time is ahead more than 3 days."""
+    utc_ts = datetime.datetime.now().replace(tzinfo=datetime.UTC) + datetime.timedelta(
+        days=4
+    )
+    with patch(
+        "supervisor.core.retrieve_whoami",
+        new_callable=AsyncMock,
+        side_effect=[WhoamiData("Europe/Zurich", utc_ts)],
+    ) as mock_retrieve_whoami, patch.object(
+        SystemControl, "set_datetime"
+    ) as mock_set_datetime, patch.object(
+        InfoCenter, "dt_synchronized", new=PropertyMock(return_value=False)
+    ), patch.object(
+        Supervisor, "check_connectivity"
+    ) as mock_check_connectivity:
+        await coresys.core._adjust_system_datetime()
+        mock_retrieve_whoami.assert_called_once()
+        mock_set_datetime.assert_called_once()
+        mock_check_connectivity.assert_called_once()