diff --git a/ragna/deploy/_api/database.py b/ragna/deploy/_api/database.py
index ae0bccb0..cbf388e2 100644
--- a/ragna/deploy/_api/database.py
+++ b/ragna/deploy/_api/database.py
@@ -6,7 +6,7 @@
 from urllib.parse import urlsplit
 
 from sqlalchemy import create_engine, select
-from sqlalchemy.orm import Session
+from sqlalchemy.orm import Session, joinedload
 from sqlalchemy.orm import sessionmaker as _sessionmaker
 
 from ragna.core import RagnaException
@@ -136,30 +136,49 @@ def _orm_to_schema_chat(chat: orm.Chat) -> schemas.Chat:
     )
 
 
+def _select_chat(*, eager: bool = False) -> Any:
+    selector = select(orm.Chat)
+    if eager:
+        selector = selector.options(  # type: ignore[attr-defined]
+            joinedload(orm.Chat.messages).joinedload(orm.Message.sources),
+            joinedload(orm.Chat.documents),
+        )
+    return selector
+
+
 def get_chats(session: Session, *, user: str) -> list[schemas.Chat]:
     return [
         _orm_to_schema_chat(chat)
         for chat in session.execute(
-            select(orm.Chat).where(orm.Chat.user_id == _get_user_id(session, user))
+            _select_chat(eager=True).where(
+                orm.Chat.user_id == _get_user_id(session, user)
+            )
         )
         .scalars()
+        .unique()
         .all()
     ]
 
 
-def _get_orm_chat(session: Session, *, user: str, id: uuid.UUID) -> orm.Chat:
-    chat: Optional[orm.Chat] = session.execute(
-        select(orm.Chat).where(
-            (orm.Chat.id == id) & (orm.Chat.user_id == _get_user_id(session, user))
+def _get_orm_chat(
+    session: Session, *, user: str, id: uuid.UUID, eager: bool = False
+) -> orm.Chat:
+    chat: Optional[orm.Chat] = (
+        session.execute(
+            _select_chat(eager=eager).where(
+                (orm.Chat.id == id) & (orm.Chat.user_id == _get_user_id(session, user))
+            )
         )
-    ).scalar_one_or_none()
+        .unique()
+        .scalar_one_or_none()
+    )
     if chat is None:
         raise RagnaException()
     return chat
 
 
 def get_chat(session: Session, *, user: str, id: uuid.UUID) -> schemas.Chat:
-    return _orm_to_schema_chat(_get_orm_chat(session, user=user, id=id))
+    return _orm_to_schema_chat(_get_orm_chat(session, user=user, id=id, eager=True))
 
 
 def _schema_to_orm_source(session: Session, source: schemas.Source) -> orm.Source:
diff --git a/ragna/deploy/_api/orm.py b/ragna/deploy/_api/orm.py
index 7e3f8c8e..033d4b4e 100644
--- a/ragna/deploy/_api/orm.py
+++ b/ragna/deploy/_api/orm.py
@@ -86,7 +86,9 @@ class Chat(Base):
     source_storage = Column(types.String)
     assistant = Column(types.String)
     params = Column(Json)
-    messages = relationship("Message", cascade="all, delete")
+    messages = relationship(
+        "Message", cascade="all, delete", order_by="Message.timestamp"
+    )
     prepared = Column(types.Boolean)
 
 
diff --git a/ragna/deploy/_api/schemas.py b/ragna/deploy/_api/schemas.py
index 7439f0d5..53957a74 100644
--- a/ragna/deploy/_api/schemas.py
+++ b/ragna/deploy/_api/schemas.py
@@ -56,9 +56,7 @@ class Message(BaseModel):
     content: str
     role: ragna.core.MessageRole
     sources: list[Source] = Field(default_factory=list)
-    timestamp: datetime.datetime = Field(
-        default_factory=lambda: datetime.datetime.utcnow()
-    )
+    timestamp: datetime.datetime = Field(default_factory=datetime.datetime.utcnow)
 
     @classmethod
     def from_core(cls, message: ragna.core.Message) -> Message:
diff --git a/tests/deploy/api/test_e2e.py b/tests/deploy/api/test_e2e.py
index 0efa0014..41b154db 100644
--- a/tests/deploy/api/test_e2e.py
+++ b/tests/deploy/api/test_e2e.py
@@ -1,4 +1,5 @@
 import json
+import time
 
 import pytest
 from fastapi.testclient import TestClient
@@ -12,6 +13,10 @@
 
 class TestAssistant(RagnaDemoAssistant):
     def answer(self, prompt, sources, *, multiple_answer_chunks: bool):
+        # Simulate a "real" assistant through a small delay. See
+        # https://github.com/Quansight/ragna/pull/401#issuecomment-2095851440
+        # for why this is needed.
+        time.sleep(1e-3)
         content = next(super().answer(prompt, sources))
 
         if multiple_answer_chunks: