diff --git a/src/middlewared/middlewared/api/v25_04_0/iscsi_target.py b/src/middlewared/middlewared/api/v25_04_0/iscsi_target.py
index 5a9bab136c064..c5ede91e1020e 100644
--- a/src/middlewared/middlewared/api/v25_04_0/iscsi_target.py
+++ b/src/middlewared/middlewared/api/v25_04_0/iscsi_target.py
@@ -86,6 +86,7 @@ class IscsiTargetUpdateResult(BaseModel):
 class IscsiTargetDeleteArgs(BaseModel):
     id: int
     force: bool = False
+    delete_extents: bool = False
 
 
 class IscsiTargetDeleteResult(BaseModel):
diff --git a/src/middlewared/middlewared/plugins/iscsi_/targets.py b/src/middlewared/middlewared/plugins/iscsi_/targets.py
index 8741b53e196e7..62ed2c9a6da9a 100644
--- a/src/middlewared/middlewared/plugins/iscsi_/targets.py
+++ b/src/middlewared/middlewared/plugins/iscsi_/targets.py
@@ -334,7 +334,7 @@ async def do_update(self, audit_callback, id_, data):
         audit='Delete iSCSI target',
         audit_callback=True
     )
-    async def do_delete(self, audit_callback, id_, force):
+    async def do_delete(self, audit_callback, id_, force, delete_extents):
         """
         Delete iSCSI Target of `id`.
 
@@ -350,6 +350,8 @@ async def do_delete(self, audit_callback, id_, force):
                 raise CallError(f'Target {target["name"]} is in use.')
         for target_to_extent in await self.middleware.call('iscsi.targetextent.query', [['target', '=', id_]]):
             await self.middleware.call('iscsi.targetextent.delete', target_to_extent['id'], force)
+            if delete_extents:
+                await self.middleware.call('iscsi.extent.delete', target_to_extent['extent'], False, force)
 
         await self.middleware.call(
             'datastore.delete', 'services.iscsitargetgroups', [['iscsi_target', '=', id_]]
diff --git a/tests/api2/assets/websocket/iscsi.py b/tests/api2/assets/websocket/iscsi.py
index 85a3c3b5dfbaa..6d31e3f78fe63 100644
--- a/tests/api2/assets/websocket/iscsi.py
+++ b/tests/api2/assets/websocket/iscsi.py
@@ -72,7 +72,8 @@ def target(target_name, groups, alias=None):
     try:
         yield target_config
     finally:
-        call('iscsi.target.delete', target_config['id'], True)
+        if call('iscsi.target.query', [['id', '=', target_config['id']]]):
+            call('iscsi.target.delete', target_config['id'], True)
 
 
 @contextlib.contextmanager
@@ -86,7 +87,8 @@ def zvol_extent(zvol, extent_name):
     try:
         yield config
     finally:
-        call('iscsi.extent.delete', config['id'], True, True)
+        if call('iscsi.extent.query', [['id', '=', config['id']]]):
+            call('iscsi.extent.delete', config['id'], True, True)
 
 
 @contextlib.contextmanager
@@ -105,7 +107,9 @@ def target_extent_associate(target_id, extent_id, lun_id=0):
     try:
         yield associate_config
     finally:
-        call('iscsi.targetextent.delete', associate_config['id'], True)
+        # We may have deleted the association
+        if call('iscsi.targetextent.query', [['id', '=', associate_config['id']]]):
+            call('iscsi.targetextent.delete', associate_config['id'], True)
     if alua_enabled:
         sleep(2)
 
diff --git a/tests/api2/test_261_iscsi_cmd.py b/tests/api2/test_261_iscsi_cmd.py
index 3f6ec516252ca..212e6eafe0d36 100644
--- a/tests/api2/test_261_iscsi_cmd.py
+++ b/tests/api2/test_261_iscsi_cmd.py
@@ -23,7 +23,7 @@
 from pyscsi.pyscsi.scsi_sense import sense_ascq_dict, sense_key_dict
 from pytest_dependency import depends
 
-from middlewared.service_exception import InstanceNotFound, ValidationError, ValidationErrors
+from middlewared.service_exception import CallError, InstanceNotFound, ValidationError, ValidationErrors
 from middlewared.test.integration.assets.iscsi import target_login_test
 from middlewared.test.integration.assets.pool import dataset, snapshot
 from middlewared.test.integration.utils import call, ssh
@@ -2950,3 +2950,47 @@ def check_readonly_state(zvolid, extentid, readonly):
                 read_lbas(s, True)
                 write_lbas(s)
                 read_lbas(s)
+
+
+def test__target_delete_extents(iscsi_running):
+    """Validate that we can delete a target and its extents."""
+    name1 = f"{target_name}x1"
+    name2 = f"{target_name}x2"
+    name3 = f"{target_name}x3"
+    iqn1 = f'{basename}:{name1}'
+    iqn2 = f'{basename}:{name2}'
+
+    with initiator_portal() as config:
+        with configured_target(config, name1, 'VOLUME') as target1_config:
+            with iscsi_scsi_connection(truenas_server.ip, iqn1):
+                # Without force we cannot delete a target that is logged into
+                with pytest.raises(CallError) as ve:
+                    call('iscsi.target.delete', target1_config['target']['id'])
+                assert f'Target {name1} is in use' in ve.value.errmsg
+
+                # Force the target delete, but do NOT remove the associated
+                # extents
+                call('iscsi.target.delete', target1_config['target']['id'], True)
+
+                # Ensure the extent still exists
+                extents = call('iscsi.extent.query', [['id', '=', target1_config['extent']['id']]])
+                assert len(extents) == 1, extents
+
+        with configured_target(config, name2, 'VOLUME') as target2_config:
+            with iscsi_scsi_connection(truenas_server.ip, iqn2):
+                # Force the target delete, and DO remove the associated
+                # extents
+                call('iscsi.target.delete', target2_config['target']['id'], True, True)
+
+                # Ensure the extent does not exist
+                extents = call('iscsi.extent.query', [['id', '=', target2_config['extent']['id']]])
+                assert len(extents) == 0, extents
+
+        with configured_target(config, name3, 'VOLUME') as target3_config:
+            # Force the target delete, and DO remove the associated
+            # extents. but no force necessary
+            call('iscsi.target.delete', target3_config['target']['id'], False, True)
+
+            # Ensure the extent does not exist
+            extents = call('iscsi.extent.query', [['id', '=', target3_config['extent']['id']]])
+            assert len(extents) == 0, extents