diff --git a/jupyterhub/app.py b/jupyterhub/app.py
index 41abcf4c..22e7bb53 100644
--- a/jupyterhub/app.py
+++ b/jupyterhub/app.py
@@ -2013,12 +2013,19 @@ class JupyterHub(Application):
         # parallelize checks for running Spawners
         # run query on extant Server objects
         # so this is O(running servers) not O(total users)
+        # Server objects can be associated with either a Spawner or a Service,
+        # we are only interested in the ones associated with a Spawner
         check_futures = []
         for orm_server in db.query(orm.Server):
-            orm_spawners = orm_server.spawner
-            if not orm_spawners:
+            orm_spawner = orm_server.spawner
+            if not orm_spawner:
+                # sanity check for orphaned Server rows
+                # this shouldn't happen if we've got our sqlachemy right
+                if not orm_server.service:
+                    self.log.warning("deleting orphaned server %s", orm_server)
+                    self.db.delete(orm_server)
+                    self.db.commit()
                 continue
-            orm_spawner = orm_spawners[0]
             # instantiate Spawner wrapper and check if it's still alive
             # spawner should be running
             user = self.users[orm_spawner.user]
diff --git a/jupyterhub/orm.py b/jupyterhub/orm.py
index 4e151092..81c01dd3 100644
--- a/jupyterhub/orm.py
+++ b/jupyterhub/orm.py
@@ -26,6 +26,7 @@ from sqlalchemy import select
 from sqlalchemy import Table
 from sqlalchemy import Unicode
 from sqlalchemy.ext.declarative import declarative_base
+from sqlalchemy.orm import backref
 from sqlalchemy.orm import interfaces
 from sqlalchemy.orm import object_session
 from sqlalchemy.orm import relationship
@@ -230,7 +231,12 @@ class Spawner(Base):
     user_id = Column(Integer, ForeignKey('users.id', ondelete='CASCADE'))
 
     server_id = Column(Integer, ForeignKey('servers.id', ondelete='SET NULL'))
-    server = relationship(Server, backref='spawner', cascade="all")
+    server = relationship(
+        Server,
+        backref=backref('spawner', uselist=False),
+        single_parent=True,
+        cascade="all, delete-orphan",
+    )
 
     state = Column(JSONDict)
     name = Column(Unicode(255))
@@ -282,7 +288,12 @@ class Service(Base):
 
     # service-specific interface
     _server_id = Column(Integer, ForeignKey('servers.id', ondelete='SET NULL'))
-    server = relationship(Server, backref='service', cascade='all')
+    server = relationship(
+        Server,
+        backref=backref('service', uselist=False),
+        single_parent=True,
+        cascade="all, delete-orphan",
+    )
     pid = Column(Integer)
 
     def new_api_token(self, token=None, **kwargs):