diff --git a/llm_be/chat_backend/consumers.py b/llm_be/chat_backend/consumers.py
index 20f3328..6346478 100644
--- a/llm_be/chat_backend/consumers.py
+++ b/llm_be/chat_backend/consumers.py
@@ -143,7 +143,10 @@ def get_messages(conversation_id, prompt, file_string: str = None, file_type: st
             prompt_instance.file_type = file_type
             prompt_instance.save()
 
-    for prompt_obj in Prompt.objects.filter(conversation__id=conversation_id):
+    for prompt_obj in (
+        Prompt.objects.filter(conversation__id=conversation_id)
+        .order_by("created", "id")
+    ):
         messages.append(
             {
                 "content": prompt_obj.message,
diff --git a/llm_be/chat_backend/consumers_graph.py b/llm_be/chat_backend/consumers_graph.py
index 90e4fec..b261689 100644
--- a/llm_be/chat_backend/consumers_graph.py
+++ b/llm_be/chat_backend/consumers_graph.py
@@ -126,7 +126,10 @@ def get_messages(conversation_id, prompt, file_string: str = None, file_type: st
             prompt_instance.file_type = file_type
             prompt_instance.save()
 
-    for prompt_obj in Prompt.objects.filter(conversation__id=conversation_id):
+    for prompt_obj in (
+        Prompt.objects.filter(conversation__id=conversation_id)
+        .order_by("created", "id")
+    ):
         messages.append(
             {
                 "content": prompt_obj.message,
diff --git a/llm_be/chat_backend/migrations/0036_enable_conversation_context.py b/llm_be/chat_backend/migrations/0036_enable_conversation_context.py
new file mode 100644
index 0000000..eba3a0a
--- /dev/null
+++ b/llm_be/chat_backend/migrations/0036_enable_conversation_context.py
@@ -0,0 +1,36 @@
+from django.db import migrations, models
+
+
+def enable_same_chat_history(apps, schema_editor):
+    """Turn on thread history for accounts still on the old default (#84).
+
+    The column defaulted to false, so an explicit opt-out cannot be told apart
+    from "never touched". Follow-ups were ignoring the open chat. Accounts that
+    still want one-shot answers can turn the setting off again.
+    """
+    CustomUser = apps.get_model("chat_backend", "CustomUser")
+    CustomUser.objects.filter(use_conversation_context=False).update(
+        use_conversation_context=True
+    )
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ("chat_backend", "0035_waitlistentry"),
+    ]
+
+    operations = [
+        migrations.AlterField(
+            model_name="customuser",
+            name="use_conversation_context",
+            field=models.BooleanField(
+                default=True,
+                help_text=(
+                    "When enabled, earlier turns in the open chat are included "
+                    "when answering a follow-up. Turn off to answer each message alone."
+                ),
+            ),
+        ),
+        migrations.RunPython(enable_same_chat_history, migrations.RunPython.noop),
+    ]
diff --git a/llm_be/chat_backend/models.py b/llm_be/chat_backend/models.py
index f2ace53..cc0c335 100644
--- a/llm_be/chat_backend/models.py
+++ b/llm_be/chat_backend/models.py
@@ -74,10 +74,10 @@ class CustomUser(AbstractUser):
         default=True, help_text="How the conversations should display"
     )
     use_conversation_context = models.BooleanField(
-        default=False,
+        default=True,
         help_text=(
-            "When enabled, prior turns in the conversation are used as "
-            "LLM/RAG context for a more tailored experience"
+            "When enabled, earlier turns in the open chat are included "
+            "when answering a follow-up. Turn off to answer each message alone."
         ),
     )
 
@@ -525,9 +525,7 @@ class DriveConnection(TimeInfoBase):
         help_text="Required for company connections; optional for personal (#55).",
     )
     provider = models.CharField(max_length=32, choices=Provider.choices)
-    kind = models.CharField(
-        max_length=16, choices=Kind.choices, default=Kind.PERSONAL
-    )
+    kind = models.CharField(max_length=16, choices=Kind.choices, default=Kind.PERSONAL)
     access_token = models.TextField(blank=True, default="")
     refresh_token = models.TextField(blank=True, default="")
     token_expires_at = models.DateTimeField(null=True, blank=True)
diff --git a/llm_be/chat_backend/services/assistant_identity.py b/llm_be/chat_backend/services/assistant_identity.py
index 2196dc9..5ac324d 100644
--- a/llm_be/chat_backend/services/assistant_identity.py
+++ b/llm_be/chat_backend/services/assistant_identity.py
@@ -13,12 +13,18 @@ ASSISTANT_SYSTEM_PROMPT = (
 )
 
 GROUNDED_ANSWER_INSTRUCTIONS = (
-    "You have been given numbered live sources. Answer ONLY from those sources. "
-    "Cite source indexes inline like [1] or [2]. "
-    "If the sources do not settle the question, say so explicitly — do not fill "
-    "gaps from memory or training data. "
+    "You may have numbered live sources and the conversation so far. "
+    "Use the conversation for follow-ups: explain a previous answer, reformat it "
+    "(including a table of items already named), and reply to lines such as "
+    '"I don\'t know, why?". Do not say that list or answer is missing when it '
+    "is already in the conversation. "
+    "Cite source indexes inline like [1] or [2] only for facts taken from live sources. "
+    "If a new external fact (price, rating, date, news) is in neither the conversation "
+    "nor the sources, say that specific fact is unavailable, and still complete the "
+    "part the conversation already answers. "
     "When sources conflict, prefer the most recent dated source. "
-    "Never state a date, number, name, or event that does not appear in the sources."
+    "Never invent a date, number, name, or event that is in neither the conversation "
+    "nor the sources."
 )
 
 RETRIEVAL_FAILED_MESSAGE = (
diff --git a/llm_be/chat_backend/services/grounded_chat.py b/llm_be/chat_backend/services/grounded_chat.py
index 0c5718b..603c59c 100644
--- a/llm_be/chat_backend/services/grounded_chat.py
+++ b/llm_be/chat_backend/services/grounded_chat.py
@@ -88,8 +88,8 @@ async def prepare_grounded_chat(
     ``on_status(stage, detail)`` emits live activity frames (#96) when provided;
     otherwise uses the context-bound emitter from :mod:`status_context`.
 
-    ``use_conversation_context`` gates prior-turn history in the LLM prompt
-    (#33); default off (opt-in).
+    ``use_conversation_context`` gates prior-turn history in the LLM prompt.
+    The account setting defaults on so follow-ups see this chat (#84).
     """
     gen_kwargs = {"use_conversation_context": use_conversation_context}
     internet = getattr(settings, "ALLOW_INTERNET_ACCESS", False)
@@ -104,7 +104,9 @@ async def prepare_grounded_chat(
         )
 
     await _emit(on_status, "evaluating")
-    decision = await grounding_decider.decide_async(message)
+    # Prior turns exist once the current user message is not the only row.
+    has_history = bool(use_conversation_context) and len(messages) > 1
+    decision = await grounding_decider.decide_async(message, has_history=has_history)
 
     if not decision.needs_retrieval:
         await _emit(on_status, "refining")
diff --git a/llm_be/chat_backend/services/grounding_decider.py b/llm_be/chat_backend/services/grounding_decider.py
index 00fabe3..1512397 100644
--- a/llm_be/chat_backend/services/grounding_decider.py
+++ b/llm_be/chat_backend/services/grounding_decider.py
@@ -43,6 +43,28 @@ _TEMPORAL_PATTERNS = (
 _TEMPORAL_RE = re.compile("|".join(_TEMPORAL_PATTERNS), re.IGNORECASE)
 _YEAR_RE = re.compile(r"\b((?:19|20)\d{2})\b")
 
+# Pure follow-ups should reuse the open chat, not a fresh web search (#84).
+_PURE_FOLLOWUP_RE = re.compile(
+    r"("
+    r"\bi don'?t know\b"
+    r"|^\s*why\b"
+    r"|\bwhy\s*\??\s*$"
+    r"|\bwhat do you mean\b"
+    r"|\bexplain\b"
+    r"|\b(that|this|the|your) (list|joke|answer|setup|punchline)\b"
+    r"|\bmake (that|this|it|them)\b"
+    r"|\bput (that|this|it|them)\b"
+    r"|\bin a table\b"
+    r"|\binto a table\b"
+    r")",
+    re.IGNORECASE,
+)
+# These still need live sources even when the sentence points at earlier turns.
+_NEW_EXTERNAL_FACT_RE = re.compile(
+    r"\b(price|prices|rating|ratings|cost|costs|review|reviews|cheapest)\b",
+    re.IGNORECASE,
+)
+
 
 @dataclass
 class GroundingDecision:
@@ -107,6 +129,28 @@ message). Example: "did Taylor Swift get married" →
             source="prepass",
         )
 
+    def followup_prepass(
+        self, prompt: str, *, has_history: bool
+    ) -> GroundingDecision | None:
+        """Skip web search when the line only continues the open chat (#84)."""
+        if not has_history:
+            return None
+        text = (prompt or "").strip()
+        if not text or not _PURE_FOLLOWUP_RE.search(text):
+            return None
+        if _NEW_EXTERNAL_FACT_RE.search(text):
+            return None
+        temporal = self.temporal_prepass(text)
+        if temporal is not None and temporal.needs_retrieval:
+            return None
+        return GroundingDecision(
+            needs_retrieval=False,
+            reason="follow-up on the current conversation",
+            queries=[],
+            temporal=False,
+            source="prepass",
+        )
+
     def _parse(self, raw: str, fallback_query: str) -> GroundingDecision:
         text = (raw or "").strip()
         # Strip markdown fences if the small model wraps JSON.
@@ -144,7 +188,12 @@ message). Example: "did Taylor Swift get married" →
             source="model",
         )
 
-    async def decide_async(self, prompt: str) -> GroundingDecision:
+    async def decide_async(
+        self, prompt: str, *, has_history: bool = False
+    ) -> GroundingDecision:
+        follow = self.followup_prepass(prompt, has_history=has_history)
+        if follow is not None:
+            return follow
         pre = self.temporal_prepass(prompt)
         # Even on temporal prepass, ask the model for better queries when possible.
         try:
@@ -173,7 +222,10 @@ message). Example: "did Taylor Swift get married" →
             )
         return decision
 
-    def decide(self, prompt: str) -> GroundingDecision:
+    def decide(self, prompt: str, *, has_history: bool = False) -> GroundingDecision:
+        follow = self.followup_prepass(prompt, has_history=has_history)
+        if follow is not None:
+            return follow
         pre = self.temporal_prepass(prompt)
         try:
             raw = self.chain.invoke({"prompt": prompt})
diff --git a/llm_be/chat_backend/services/llm_service.py b/llm_be/chat_backend/services/llm_service.py
index c473a38..9a8cf24 100644
--- a/llm_be/chat_backend/services/llm_service.py
+++ b/llm_be/chat_backend/services/llm_service.py
@@ -173,16 +173,12 @@ Response:"""
         block (when grounded) is never trimmed.
         """
         sources = self.sources_block or kwargs.get("sources_block", "") or ""
-        use_conversation_context = bool(
-            kwargs.get("use_conversation_context", False)
-        )
+        use_conversation_context = bool(kwargs.get("use_conversation_context", False))
         history_text = ""
         if use_conversation_context:
             reserved = (
                 estimate_tokens(ASSISTANT_SYSTEM_PROMPT)
-                + estimate_tokens(
-                    GROUNDED_ANSWER_INSTRUCTIONS if self.grounded else ""
-                )
+                + estimate_tokens(GROUNDED_ANSWER_INSTRUCTIONS if self.grounded else "")
                 + estimate_tokens(sources)
                 + estimate_tokens(query)
                 + 256  # response headroom / instructions
@@ -203,8 +199,9 @@ Response:"""
                     and str(getattr(m, "content", "")).startswith("Live sources:")
                 )
             ]
-            # Exclude the latest user turn from history (it's in {query}).
-            prior = clean[:-1] if clean else []
+            # Current user turn is passed as {query}. Drop that text, not
+            # whichever row happens to be last.
+            prior = prior_turns(clean, query)
             windowed = window_history(
                 prior, budget_tokens=history_budget, reserved_tokens=0
             )
@@ -220,6 +217,33 @@ Response:"""
             yield chunk
 
 
+def message_text(message) -> str:
+    text = getattr(message, "content", "") or ""
+    if not isinstance(text, str):
+        text = str(text)
+    return text
+
+
+def prior_turns(messages, query: str) -> list:
+    """Drop the current user turn from history.
+
+    Match the query text, newest hit first, so an unordered transcript cannot
+    drop a different turn just because it sits at the end of the list (#84).
+    If the query is not in the list, keep every turn.
+    """
+    if not messages:
+        return []
+    needle = (query or "").strip()
+    for index in range(len(messages) - 1, -1, -1):
+        message = messages[index]
+        if (
+            getattr(message, "type", "") == "human"
+            and message_text(message).strip() == needle
+        ):
+            return list(messages[:index]) + list(messages[index + 1 :])
+    return list(messages)
+
+
 def build_chat_service(
     *,
     model_name: str | None,
diff --git a/llm_be/chat_backend/tests/test_consumers.py b/llm_be/chat_backend/tests/test_consumers.py
index b5cf827..8e1d1cc 100644
--- a/llm_be/chat_backend/tests/test_consumers.py
+++ b/llm_be/chat_backend/tests/test_consumers.py
@@ -1,9 +1,11 @@
-from unittest import mock
 import json
+from datetime import timedelta
+from unittest import mock
 
 from asgiref.sync import sync_to_async
 from channels.testing import WebsocketCommunicator
 from django.test import TestCase, TransactionTestCase, override_settings
+from django.utils import timezone
 from langchain_core.messages import AIMessage, HumanMessage
 from parameterized import parameterized
 
@@ -47,9 +49,7 @@ class DatabaseHelperTestCase(TransactionTestCase):
 
     @parameterized.expand([("websocket", consumers), ("langgraph", consumers_graph)])
     async def test_get_workspace(self, _name, module):
-        workspace = await module.get_workspace(
-            self.conversation.id, user=self.user
-        )
+        workspace = await module.get_workspace(self.conversation.id, user=self.user)
 
         self.assertEqual(workspace.id, self.workspace.id)
 
@@ -99,6 +99,29 @@ class DatabaseHelperTestCase(TransactionTestCase):
             [type(message) for message in messages], [AIMessage, HumanMessage]
         )
 
+    @parameterized.expand([("websocket", consumers), ("langgraph", consumers_graph)])
+    async def test_get_messages_orders_by_created_not_insert_order(self, _name, module):
+        now = timezone.now()
+        await sync_to_async(Prompt.objects.create)(
+            conversation=self.conversation,
+            message="newer answer",
+            user_created=False,
+            created=now,
+        )
+        await sync_to_async(Prompt.objects.create)(
+            conversation=self.conversation,
+            message="older question",
+            user_created=True,
+            created=now - timedelta(minutes=5),
+        )
+
+        messages, _prompt = await module.get_messages(self.conversation.id, "follow up")
+
+        self.assertEqual(
+            [message.content for message in messages],
+            ["older question", "newer answer", "follow up"],
+        )
+
     async def test_get_messages_stores_attachment_and_inlines_csv(self):
         messages, prompt_instance = await consumers.get_messages(
             self.conversation.id, "analyze this", b"name,sales\nalice,10\n", "csv"
@@ -587,13 +610,16 @@ class WebSocketReceiveGuardTestCase(TransactionTestCase):
         connected, _ = await communicator.connect()
         self.assertTrue(connected)
 
-        with mock.patch(
-            "chat_backend.consumers.title_generator.generate_async",
-            new_callable=mock.AsyncMock,
-        ) as title_chat, mock.patch(
-            "chat_backend.consumers_graph.title_generator.generate_async",
-            new_callable=mock.AsyncMock,
-        ) as title_graph:
+        with (
+            mock.patch(
+                "chat_backend.consumers.title_generator.generate_async",
+                new_callable=mock.AsyncMock,
+            ) as title_chat,
+            mock.patch(
+                "chat_backend.consumers_graph.title_generator.generate_async",
+                new_callable=mock.AsyncMock,
+            ) as title_graph,
+        ):
             await communicator.send_json_to({"type": "ping", "email": "a@b.com"})
             # No reply expected; give the event loop a tick.
             self.assertTrue(await communicator.receive_nothing(timeout=0.2))
@@ -612,13 +638,16 @@ class WebSocketReceiveGuardTestCase(TransactionTestCase):
         connected, _ = await communicator.connect()
         self.assertTrue(connected)
 
-        with mock.patch(
-            "chat_backend.consumers.title_generator.generate_async",
-            new_callable=mock.AsyncMock,
-        ) as title_chat, mock.patch(
-            "chat_backend.consumers_graph.title_generator.generate_async",
-            new_callable=mock.AsyncMock,
-        ) as title_graph:
+        with (
+            mock.patch(
+                "chat_backend.consumers.title_generator.generate_async",
+                new_callable=mock.AsyncMock,
+            ) as title_chat,
+            mock.patch(
+                "chat_backend.consumers_graph.title_generator.generate_async",
+                new_callable=mock.AsyncMock,
+            ) as title_graph,
+        ):
             await communicator.send_json_to(
                 {"message": "   ", "email": "a@b.com", "conversation_id": None}
             )
diff --git a/llm_be/chat_backend/tests/test_grounding_search.py b/llm_be/chat_backend/tests/test_grounding_search.py
index 2ef46e5..aff8e5c 100644
--- a/llm_be/chat_backend/tests/test_grounding_search.py
+++ b/llm_be/chat_backend/tests/test_grounding_search.py
@@ -86,6 +86,25 @@ class GroundingPrepassTestCase(SimpleTestCase):
         self.assertEqual(decision.source, "fail_open")
         self.assertEqual(decision.queries, ["fallback query"])
 
+    def test_pure_followup_skips_retrieval_without_calling_model(self):
+        self.decider.chain = mock.Mock()
+        decision = self.decider.decide("I don't know. Why?", has_history=True)
+        self.assertFalse(decision.needs_retrieval)
+        self.assertEqual(decision.reason, "follow-up on the current conversation")
+        self.decider.chain.invoke.assert_not_called()
+
+    def test_followup_without_history_does_not_short_circuit(self):
+        self.assertIsNone(
+            self.decider.followup_prepass("I don't know. Why?", has_history=False)
+        )
+
+    def test_price_followup_still_allows_retrieval(self):
+        decision = self.decider.followup_prepass(
+            "Can you make that list for me and add the prices and ratings in a table",
+            has_history=True,
+        )
+        self.assertIsNone(decision)
+
     def test_decide_fail_open_on_llm_error(self):
         self.decider.chain = mock.Mock()
         self.decider.chain.invoke.side_effect = RuntimeError("ollama down")
diff --git a/llm_be/chat_backend/tests/test_migration_graph.py b/llm_be/chat_backend/tests/test_migration_graph.py
index 5b9092c..6e52cae 100644
--- a/llm_be/chat_backend/tests/test_migration_graph.py
+++ b/llm_be/chat_backend/tests/test_migration_graph.py
@@ -6,9 +6,11 @@ from django.test import TestCase
 class MigrationGraphTests(TestCase):
     def test_chat_backend_has_a_single_leaf(self):
         loader = MigrationLoader(connection, ignore_no_migrations=True)
-        leaves = [name for app, name in loader.graph.leaf_nodes() if app == "chat_backend"]
-        self.assertEqual(leaves, ["0035_waitlistentry"])
+        leaves = [
+            name for app, name in loader.graph.leaf_nodes() if app == "chat_backend"
+        ]
+        self.assertEqual(leaves, ["0036_enable_conversation_context"])
 
-        node = loader.graph.nodes[("chat_backend", "0035_waitlistentry")]
+        node = loader.graph.nodes[("chat_backend", "0036_enable_conversation_context")]
         parents = [name for app, name in node.dependencies if app == "chat_backend"]
-        self.assertEqual(parents, ["0034_customuser_use_conversation_context"])
+        self.assertEqual(parents, ["0035_waitlistentry"])
diff --git a/llm_be/chat_backend/tests/test_models.py b/llm_be/chat_backend/tests/test_models.py
index eef159d..7e4a498 100644
--- a/llm_be/chat_backend/tests/test_models.py
+++ b/llm_be/chat_backend/tests/test_models.py
@@ -81,7 +81,7 @@ class CompanyAndUserTestCase(TestCase):
         self.assertFalse(user.deleted)
         self.assertFalse(user.has_signed_tos)
         self.assertTrue(user.conversation_order)
-        self.assertFalse(user.use_conversation_context)
+        self.assertTrue(user.use_conversation_context)
 
 
 class ConversationAndPromptTestCase(TestCase):
diff --git a/llm_be/chat_backend/tests/test_services_llm.py b/llm_be/chat_backend/tests/test_services_llm.py
index d085ff9..98b009a 100644
--- a/llm_be/chat_backend/tests/test_services_llm.py
+++ b/llm_be/chat_backend/tests/test_services_llm.py
@@ -1,7 +1,12 @@
 from django.test import SimpleTestCase
 from langchain_core.messages import AIMessage, HumanMessage
 
-from chat_backend.services.llm_service import AsyncLLMService, SyncLLMService
+from chat_backend.services.assistant_identity import GROUNDED_ANSWER_INSTRUCTIONS
+from chat_backend.services.llm_service import (
+    AsyncLLMService,
+    SyncLLMService,
+    prior_turns,
+)
 from chat_backend.services.prompt_budget import format_history, window_history
 
 from .fakes import FakeChain
@@ -36,7 +41,7 @@ class AsyncLLMServiceTestCase(SimpleTestCase):
 
     async def test_generate_response_sends_single_history_window(self):
         self.service.conversation_chain = FakeChain(chunks=["ok"])
-        messages = conversation(4)  # 8 messages
+        messages = conversation(4) + [HumanMessage(content="latest")]
 
         async for _ in self.service.generate_response(
             messages, "latest", 1, use_conversation_context=True
@@ -47,10 +52,33 @@ class AsyncLLMServiceTestCase(SimpleTestCase):
         self.assertEqual(payload["query"], "latest")
         # Latest user turn is in {query}; history is prior turns only, once.
         self.assertIn("history", payload)
+        self.assertNotIn("User: latest", payload["history"])
+        self.assertIn("AI: answer 3", payload["history"])
         self.assertNotIn("recent_conversation", payload)
         self.assertNotIn("conversation", payload)
-        # 8 messages → drop last (query) → 7 prior lines max in window.
-        self.assertLessEqual(len(payload["history"].splitlines()), 7)
+        self.assertLessEqual(len(payload["history"].splitlines()), 8)
+
+    async def test_history_drops_matching_turn_even_if_it_is_not_last(self):
+        self.service.conversation_chain = FakeChain(chunks=["ok"])
+        # Unordered transcript: current question is first, older turns follow.
+        messages = [
+            HumanMessage(content="I don't know. Why?"),
+            AIMessage(content="Why did the meditation instructor bring a ladder?"),
+            HumanMessage(content="Tell me a joke"),
+        ]
+
+        async for _ in self.service.generate_response(
+            messages,
+            "I don't know. Why?",
+            1,
+            use_conversation_context=True,
+        ):
+            pass
+
+        history = self.service.conversation_chain.calls[0]["history"]
+        self.assertNotIn("I don't know", history)
+        self.assertIn("Tell me a joke", history)
+        self.assertIn("meditation instructor", history)
 
     async def test_generate_response_skips_history_when_context_disabled(self):
         self.service.conversation_chain = FakeChain(chunks=["ok"])
@@ -73,7 +101,9 @@ class AsyncLLMServiceTestCase(SimpleTestCase):
         self.assertEqual(self.service.conversation_chain.calls[0]["history"], "")
 
     async def test_grounded_service_includes_sources(self):
-        service = AsyncLLMService(grounded=True, sources_block='[1] "T" — x.com — undated')
+        service = AsyncLLMService(
+            grounded=True, sources_block='[1] "T" — x.com — undated'
+        )
         service.conversation_chain = FakeChain(chunks=["ok"])
 
         async for _ in service.generate_response(
@@ -90,6 +120,24 @@ class SyncLLMServiceTestCase(SimpleTestCase):
         self.assertIsNotNone(SyncLLMService())
 
 
+class PriorTurnsTestCase(SimpleTestCase):
+    def test_grounded_instructions_keep_the_conversation(self):
+        self.assertIn("conversation", GROUNDED_ANSWER_INSTRUCTIONS.lower())
+        self.assertNotIn("Answer ONLY from those sources", GROUNDED_ANSWER_INSTRUCTIONS)
+
+    def test_prior_turns_drops_newest_matching_user_text(self):
+        messages = [
+            HumanMessage(content="I don't know. Why?"),
+            AIMessage(content="the joke"),
+            HumanMessage(content="Tell me a joke"),
+        ]
+        kept = prior_turns(messages, "I don't know. Why?")
+        self.assertEqual(
+            [message.content for message in kept],
+            ["the joke", "Tell me a joke"],
+        )
+
+
 class PromptBudgetTestCase(SimpleTestCase):
     def test_window_history_drops_oldest_first(self):
         messages = [HumanMessage(content="x" * 40) for _ in range(10)]
@@ -99,7 +147,5 @@ class PromptBudgetTestCase(SimpleTestCase):
         self.assertEqual(kept[-1].content, messages[-1].content)
 
     def test_format_history_labels_speakers(self):
-        text = format_history(
-            [HumanMessage(content="hello"), AIMessage(content="hi")]
-        )
+        text = format_history([HumanMessage(content="hello"), AIMessage(content="hi")])
         self.assertEqual(text, "User: hello\nAI: hi")
diff --git a/llm_be/chat_backend/tests/test_views_conversations.py b/llm_be/chat_backend/tests/test_views_conversations.py
index 90708ac..8612d18 100644
--- a/llm_be/chat_backend/tests/test_views_conversations.py
+++ b/llm_be/chat_backend/tests/test_views_conversations.py
@@ -1,4 +1,7 @@
+from datetime import timedelta
+
 from django.urls import reverse
+from django.utils import timezone
 from rest_framework import status
 from rest_framework.test import APITestCase
 
@@ -57,7 +60,7 @@ class ConversationPreferencesTestCase(APITestCase):
 
         self.assertEqual(response.status_code, status.HTTP_200_OK)
         self.assertTrue(response.data["order"])
-        self.assertFalse(response.data["use_conversation_context"])
+        self.assertTrue(response.data["use_conversation_context"])
 
     def test_post_toggles_and_persists_order(self):
         response = self.client.post(self.url)
@@ -115,8 +118,33 @@ class ConversationDetailViewTestCase(APITestCase):
             [("hello", True), ("hi there", False)],
         )
 
+    def test_get_returns_prompts_oldest_first_even_if_inserted_newest_first(self):
+        now = timezone.now()
+        make_prompt(
+            self.conversation,
+            message="later",
+            user_created=False,
+            created=now,
+        )
+        make_prompt(
+            self.conversation,
+            message="earlier",
+            user_created=True,
+            created=now - timedelta(minutes=5),
+        )
+
+        response = self.client.get(self.url, {"conversation_id": self.conversation.id})
+
+        self.assertEqual(response.status_code, status.HTTP_200_OK)
+        self.assertEqual(
+            [item["message"] for item in response.data],
+            ["earlier", "later"],
+        )
+
     def test_get_rejects_other_users_conversation(self):
-        other = make_user(email="other-tenant@example.com", company=make_company("Other"))
+        other = make_user(
+            email="other-tenant@example.com", company=make_company("Other")
+        )
         foreign = make_conversation(user=other)
         make_prompt(foreign, message="secret")
 
diff --git a/llm_be/chat_backend/views.py b/llm_be/chat_backend/views.py
index 9fc21f2..2a98f6c 100644
--- a/llm_be/chat_backend/views.py
+++ b/llm_be/chat_backend/views.py
@@ -680,7 +680,7 @@ class ConversationDetailView(APIView):
         prompts = list(
             Prompt.objects.filter(
                 conversation__id=conversation_id, conversation__user=request.user
-            )
+            ).order_by("created", "id")
         )
         serializer = PromptSerializer(
             prompts,
@@ -734,7 +734,7 @@ class ConversationDetailView(APIView):
                 messages = []
                 for prompt_obj in Prompt.objects.filter(
                     conversation__id=conversation_id
-                ):
+                ).order_by("created", "id"):
                     messages.append(
                         {
                             "content": prompt_obj.message,