diff --git a/hospexplorer/ask/admin.py b/hospexplorer/ask/admin.py
index 3910bbc..d221989 100644
--- a/hospexplorer/ask/admin.py
+++ b/hospexplorer/ask/admin.py
@@ -1,14 +1,29 @@
 from django.contrib import admin
-from ask.models import QARecord
+from ask.models import Conversation, QARecord
+
+
+class QARecordInline(admin.TabularInline):
+    model = QARecord
+    extra = 0
+    readonly_fields = ("question_text", "question_timestamp", "answer_text", "answer_timestamp", "is_error")
+    fields = ("question_text", "question_timestamp", "answer_text", "answer_timestamp", "is_error")
+
+
+@admin.register(Conversation)
+class ConversationAdmin(admin.ModelAdmin):
+    list_display = ("id", "title", "user", "created_at", "updated_at")
+    list_filter = ("user",)
+    search_fields = ("title", "user__username")
+    inlines = [QARecordInline]
 
 
 @admin.register(QARecord)
 class QARecordAdmin(admin.ModelAdmin):
-    list_display = ["id", "user", "truncated_question", "question_timestamp", "answer_timestamp"]
-    list_filter = ["question_timestamp", "user"]
+    list_display = ["id", "user", "conversation", "truncated_question", "question_timestamp", "answer_timestamp", "is_error"]
+    list_filter = ["question_timestamp", "user", "is_error"]
     search_fields = ["question_text", "answer_text", "user__username"]
     readonly_fields = ["question_timestamp", "answer_timestamp", "answer_raw_response"]
-    raw_id_fields = ["user"]
+    raw_id_fields = ["user", "conversation"]
     date_hierarchy = "question_timestamp"
 
     def truncated_question(self, obj):
diff --git a/hospexplorer/ask/context_processors.py b/hospexplorer/ask/context_processors.py
new file mode 100644
index 0000000..8dfd5cc
--- /dev/null
+++ b/hospexplorer/ask/context_processors.py
@@ -0,0 +1,26 @@
+from django.conf import settings
+from django.urls import reverse
+from ask.models import Conversation
+
+
+def sidebar_conversations(request):
+    if request.user.is_authenticated:
+        limit = getattr(settings, "SIDEBAR_CONVERSATIONS_LIMIT", 10)
+        conversations = Conversation.objects.filter(
+            user=request.user
+        )[:limit]
+
+        sidebar_items = []
+        for conv in conversations:
+            label = conv.title if conv.title else conv.created_at.strftime("%b %d, %Y %I:%M %p")
+            sidebar_items.append({
+                "id": conv.id,
+                "label": label,
+                "url": reverse("ask:conversation", kwargs={"conversation_id": conv.id}),
+                "updated_at": conv.updated_at.isoformat(),
+            })
+        return {
+            "sidebar_conversations": sidebar_items,
+            "sidebar_conversations_limit": limit,
+        }
+    return {"sidebar_conversations": [], "sidebar_conversations_limit": 0}
diff --git a/hospexplorer/ask/migrations/0001_initial.py b/hospexplorer/ask/migrations/0001_initial.py
index 98d680a..9738a6a 100644
--- a/hospexplorer/ask/migrations/0001_initial.py
+++ b/hospexplorer/ask/migrations/0001_initial.py
@@ -1,4 +1,4 @@
-# Generated by Django 6.0.1 on 2026-01-30 19:36
+# Generated by Django 6.0.1 on 2026-02-20 21:44
 
 import django.db.models.deletion
 from django.conf import settings
@@ -14,6 +14,18 @@ class Migration(migrations.Migration):
     ]
 
     operations = [
+        migrations.CreateModel(
+            name='Conversation',
+            fields=[
+                ('id', models.BigAutoField(auto_created=True, primary_key=True, serialize=False, verbose_name='ID')),
+                ('created_at', models.DateTimeField(auto_now_add=True)),
+                ('updated_at', models.DateTimeField(auto_now=True)),
+                ('user', models.ForeignKey(on_delete=django.db.models.deletion.CASCADE, related_name='conversations', to=settings.AUTH_USER_MODEL)),
+            ],
+            options={
+                'ordering': ['-updated_at'],
+            },
+        ),
         migrations.CreateModel(
             name='QARecord',
             fields=[
@@ -23,6 +35,8 @@ class Migration(migrations.Migration):
                 ('answer_text', models.TextField(blank=True, default='')),
                 ('answer_raw_response', models.JSONField(default=dict)),
                 ('answer_timestamp', models.DateTimeField(blank=True, null=True)),
+                ('is_error', models.BooleanField(default=False)),
+                ('conversation', models.ForeignKey(on_delete=django.db.models.deletion.CASCADE, related_name='qa_records', to='ask.conversation')),
                 ('user', models.ForeignKey(on_delete=django.db.models.deletion.CASCADE, related_name='qa_records', to=settings.AUTH_USER_MODEL)),
             ],
             options={
diff --git a/hospexplorer/ask/migrations/0002_qarecord_is_error.py b/hospexplorer/ask/migrations/0002_conversation_title.py
similarity index 52%
rename from hospexplorer/ask/migrations/0002_qarecord_is_error.py
rename to hospexplorer/ask/migrations/0002_conversation_title.py
index 10ddcac..bbdc0e3 100644
--- a/hospexplorer/ask/migrations/0002_qarecord_is_error.py
+++ b/hospexplorer/ask/migrations/0002_conversation_title.py
@@ -1,4 +1,4 @@
-# Generated by Django 6.0.1 on 2026-02-04 23:32
+# Generated by Django 6.0.1 on 2026-02-25 22:44
 
 from django.db import migrations, models
 
@@ -11,8 +11,8 @@ class Migration(migrations.Migration):
 
     operations = [
         migrations.AddField(
-            model_name='qarecord',
-            name='is_error',
-            field=models.BooleanField(default=False),
+            model_name='conversation',
+            name='title',
+            field=models.CharField(blank=True, default='', max_length=200),
         ),
     ]
diff --git a/hospexplorer/ask/models.py b/hospexplorer/ask/models.py
index aa69d52..76e8364 100644
--- a/hospexplorer/ask/models.py
+++ b/hospexplorer/ask/models.py
@@ -2,10 +2,37 @@
 from django.conf import settings
 
 
+class Conversation(models.Model):
+    user = models.ForeignKey(
+        settings.AUTH_USER_MODEL,
+        on_delete=models.CASCADE,
+        related_name="conversations",
+    )
+    title = models.CharField(max_length=200, blank=True, default="")
+    created_at = models.DateTimeField(auto_now_add=True)
+    updated_at = models.DateTimeField(auto_now=True)
+
+    class Meta:
+        ordering = ["-updated_at"]
+
+    def __str__(self):
+        if self.title:
+            truncated = self.title[:50]
+            suffix = "..." if len(self.title) > 50 else ""
+            return f"Conversation {self.id}: {truncated}{suffix}"
+        return f"Conversation {self.id} ({self.user.username})"
+
+
 class QARecord(models.Model):
     """
     Stores a question-answer pair from user interactions with the LLM.
     """
+    conversation = models.ForeignKey(
+        Conversation,
+        on_delete=models.CASCADE,
+        related_name="qa_records",
+    )
+
     # Question fields
     question_text = models.TextField()
     question_timestamp = models.DateTimeField(auto_now_add=True)
@@ -16,7 +43,11 @@ class QARecord(models.Model):
     answer_timestamp = models.DateTimeField(null=True, blank=True)
     is_error = models.BooleanField(default=False)
 
-    user = models.ForeignKey(settings.AUTH_USER_MODEL, on_delete=models.CASCADE, related_name="qa_records")
+    user = models.ForeignKey(
+        settings.AUTH_USER_MODEL,
+        on_delete=models.CASCADE,
+        related_name="qa_records",
+    )
 
     class Meta:
         ordering = ["-question_timestamp"]
diff --git a/hospexplorer/ask/static/css/ask.css b/hospexplorer/ask/static/css/ask.css
index 37f72d1..23e60a7 100644
--- a/hospexplorer/ask/static/css/ask.css
+++ b/hospexplorer/ask/static/css/ask.css
@@ -358,4 +358,5 @@
     .chat-input-bar {
         padding: 0.5rem 1rem;
     }
+
 }
diff --git a/hospexplorer/ask/static/css/styles.css b/hospexplorer/ask/static/css/styles.css
index 9967a22..53d956c 100644
--- a/hospexplorer/ask/static/css/styles.css
+++ b/hospexplorer/ask/static/css/styles.css
@@ -10894,10 +10894,19 @@ body.sb-sidenav-toggled #wrapper #sidebar-wrapper {
 }
 
 #sidebar-wrapper .question-item:hover {
-  border-left-color: #0d6efd;
+  border-left-color: #8c1d40;
   background-color: #f8f9fa;
 }
 
+#sidebar-wrapper .question-item.active {
+  border-left-color: #8c1d40;
+  background-color: rgba(140, 29, 64, 0.1);
+  color: #8c1d40;
+  font-weight: 600;
+  border-color: transparent;
+  border-left: 3px solid #8c1d40;
+}
+
 #sidebar-wrapper .sidebar-section-heading {
   font-weight: 600;
   text-transform: uppercase;
diff --git a/hospexplorer/ask/templates/_base.html b/hospexplorer/ask/templates/_base.html
index 6fdaca8..2619e7e 100644
--- a/hospexplorer/ask/templates/_base.html
+++ b/hospexplorer/ask/templates/_base.html
@@ -18,31 +18,41 @@
         <div class="d-flex" id="wrapper">
             <!-- Sidebar-->
             <div class="border-end bg-white" id="sidebar-wrapper"
-                 x-data="sidebarQuestions()"
-                 @question-asked.window="addQuestion($event.detail)">
+                 x-data="sidebarConversations()"
+                 @conversation-updated.window="upsertConversation($event.detail)">
                 <div class="sidebar-heading border-bottom bg-white">
                     <img width="50" src="{% static 'assets/asu.png' %}">
                     Hopper
                 </div>
                 <div class="list-group list-group-flush">
-                    <!-- Recent Questions Section -->
+                    {% if user.is_authenticated %}
                     <div class="sidebar-section-heading small text-muted px-3 py-2 border-bottom bg-light">
-                        Recent Questions
+                        Conversations
+                    </div>
+                    <div class="p-3">
+                        <form method="post" action="{% url 'ask:new-conversation' %}">
+                            {% csrf_token %}
+                            <button type="submit" class="btn btn-outline-secondary btn-sm w-100">New Chat +</button>
+                        </form>
                     </div>
-                    <template x-for="question in questions" :key="question.id">
-                        <a href="#" class="list-group-item list-group-item-action py-2 px-3 question-item"
-                           :title="question.question_text"
-                           x-text="truncate(question.question_text, 35)">
+                    {% endif %}
+                    <!-- Conversations Section -->
+
+                    <template x-for="conv in conversations" :key="conv.id">
+                        <a :href="conv.url" class="list-group-item list-group-item-action py-2 px-3 question-item"
+                           :class="{ 'active': conv.id === activeConversationId }"
+                           :title="conv.label"
+                           x-text="conv.label">
                         </a>
                     </template>
-                    <div x-show="questions.length === 0" class="text-muted small px-3 py-2">
-                        No questions yet
+                    <div x-show="conversations.length === 0" class="text-muted small px-3 py-2">
+                        No conversations yet
                     </div>
 
                     {% if user.is_authenticated %}
                     <div class="p-3 border-top mt-auto">
                         <div class="small text-muted mb-2">Signed in as <strong>{{ user.username }}</strong></div>
-                        <button type="button" class="btn btn-outline-secondary btn-sm w-100 mb-2" data-bs-toggle="modal" data-bs-target="#deleteHistoryModal">Delete Question History</button>
+                        <button type="button" class="btn btn-outline-secondary btn-sm w-100 mb-2" data-bs-toggle="modal" data-bs-target="#deleteHistoryModal">Delete All Conversations</button>
                         <a href="{% url 'account_logout' %}" class="btn btn-outline-secondary btn-sm w-100">Sign Out</a>
                     </div>
                     {% endif %}
@@ -70,11 +80,11 @@
             <div class="modal-dialog">
                 <div class="modal-content">
                     <div class="modal-header">
-                        <h5 class="modal-title" id="deleteHistoryModalLabel">Delete Question History</h5>
+                        <h5 class="modal-title" id="deleteHistoryModalLabel">Delete All Conversations</h5>
                         <button type="button" class="btn-close" data-bs-dismiss="modal" aria-label="Close"></button>
                     </div>
                     <div class="modal-body">
-                        Are you sure you want to delete your question history? This action is irreversible.
+                        Are you sure you want to delete all your conversations? This action is irreversible.
                     </div>
                     <div class="modal-footer">
                         <button type="button" class="btn btn-secondary" data-bs-dismiss="modal">No</button>
@@ -116,29 +126,31 @@ <h5 class="modal-title" id="deleteHistoryModalLabel">Delete Question History</h5
                 }
             });
         </script>
-        <!-- Sidebar Questions Component -->
+        <!-- Sidebar Conversations Component -->
+        {{ sidebar_conversations|json_script:"sidebar-conversations-data" }}
         <script>
-            window.initialQuestions = {{ recent_questions_json|safe|default:"[]" }};
+            window.initialConversations = JSON.parse(
+                document.getElementById('sidebar-conversations-data').textContent
+            );
 
-            function sidebarQuestions() {
+            function sidebarConversations() {
                 return {
-                    questions: window.initialQuestions || [],
+                    conversations: window.initialConversations || [],
+                    activeConversationId: {{ conversation.id|default:"null" }},
+                    maxItems: {{ sidebar_conversations_limit|default:"10" }},
 
-                    addQuestion(detail) {
-                        const newQuestion = {
-                            id: Date.now(),
-                            question_text: detail.text
-                        };
-                        this.questions.unshift(newQuestion);
-                        if (this.questions.length > 10) {
-                            this.questions = this.questions.slice(0, 10);
+                    upsertConversation(detail) {
+                        this.conversations = this.conversations.filter(c => c.id !== detail.id);
+                        this.conversations.unshift({
+                            id: detail.id,
+                            label: detail.label,
+                            url: detail.url,
+                        });
+                        // 10 conversations shown in the sidebar
+                        if (this.conversations.length > this.maxItems) {
+                            this.conversations = this.conversations.slice(0, this.maxItems);
                         }
-                    },
-
-                    truncate(text, length) {
-                        if (!text) return '';
-                        if (text.length <= length) return text;
-                        return text.substring(0, length) + '...';
+                        this.activeConversationId = detail.id;
                     }
                 };
             }
diff --git a/hospexplorer/ask/templates/index.html b/hospexplorer/ask/templates/index.html
index a73e510..97e868c 100644
--- a/hospexplorer/ask/templates/index.html
+++ b/hospexplorer/ask/templates/index.html
@@ -6,7 +6,17 @@
     <div
         x-data="{
             userQuery: '',
-            messages: [], // in-memory only; resets on page refresh (not persisted to localStorage, session, or DB)
+            messages: [
+                {% if conversation %}
+                    {% for qa in conversation.qa_records.all reversed %}
+                        { role: 'user', content: '{{ qa.question_text|escapejs }}' },
+                        {% if qa.answer_text %}
+                            { role: 'assistant', content: '{{ qa.answer_text|escapejs }}' },
+                        {% endif %}
+                    {% endfor %}
+                {% endif %}
+            ],
+            conversationId: '{{ conversation.id|default_if_none:'' }}',
             isLoading: false,
             showScrollBtn: false,
 
@@ -21,12 +31,26 @@
 
                 this.isLoading = true;
 
-                // Dispatch event to update sidebar
-                $dispatch('question-asked', { text: question });
-
                 try {
-                    const response = await fetch('{% url 'ask:query-llm' %}?query=' + encodeURIComponent(question));
+                    let url = '{% url 'ask:query-llm' %}?query=' + encodeURIComponent(question);
+                    if (this.conversationId) {
+                        url += '&conversation_id=' + encodeURIComponent(this.conversationId);
+                    }
+                    const response = await fetch(url);
                     const data = await response.json();
+                    // Update conversation ID and URL on first response
+                    if (data.conversation_id && !this.conversationId) {
+                        this.conversationId = data.conversation_id;
+                        history.pushState({}, '', '{% url "ask:index" %}c/' + data.conversation_id + '/');
+                    }
+                    // Update sidebar with this conversation
+                    if (data.conversation_id) {
+                        $dispatch('conversation-updated', {
+                            id: data.conversation_id,
+                            label: data.conversation_title || question,
+                            url: '{% url "ask:index" %}c/' + data.conversation_id + '/',
+                        });
+                    }
                     if (!response.ok || data.error) {
                         this.messages.push({ role: 'assistant', content: 'Something went wrong. Please try again.' });
                     } else {
@@ -35,7 +59,6 @@
                 } catch (error) {
                     this.messages.push({ role: 'assistant', content: 'Something went wrong. Please try again.' });
                 }
-                this.userQuery = '';
                 this.isLoading = false;
                 this.$nextTick(() => this.scrollToBottom());
             },
diff --git a/hospexplorer/ask/urls.py b/hospexplorer/ask/urls.py
index ca35af5..f48d2ef 100644
--- a/hospexplorer/ask/urls.py
+++ b/hospexplorer/ask/urls.py
@@ -1,11 +1,13 @@
-from django.urls import re_path
+from django.urls import path, re_path
 from ask import views
 
 app_name = "ask"
 
 urlpatterns = [
-    re_path(r"^$", views.index, name="index"),
+    path("", views.index, name="index"),
+    path("new/", views.new_conversation, name="new-conversation"),
+    path("c/<int:conversation_id>/", views.conversation_detail, name="conversation"),
+    path("query/", views.query, name="query-llm"),
     re_path(r"^mock$", views.mock_response, name="mock-response"),
-    re_path(r"^query$", views.query, name="query-llm"),
     re_path(r"^history/delete$", views.delete_history, name="delete-history"),
-]
\ No newline at end of file
+]
diff --git a/hospexplorer/ask/views.py b/hospexplorer/ask/views.py
index 2fdb540..8b9c5e5 100644
--- a/hospexplorer/ask/views.py
+++ b/hospexplorer/ask/views.py
@@ -1,25 +1,37 @@
 import logging
-from django.shortcuts import render
-from django.views.decorators.http import require_http_methods
+from django.shortcuts import render, redirect, get_object_or_404
 from django.http import JsonResponse
-from django.conf import settings
 from django.contrib.auth.decorators import login_required
+from django.views.decorators.http import require_POST, require_http_methods
 from django.utils import timezone
-import json
+
 import ask.llm_connector
-from ask.models import QARecord
+from ask.models import Conversation, QARecord
 
 logger = logging.getLogger(__name__)
 
+
 @login_required
 def index(request):
-    recent_questions = list(
-        QARecord.objects.filter(user=request.user)
-        .order_by('-question_timestamp')
-        .values('id', 'question_text')[:settings.RECENT_QUESTIONS_LIMIT]
+    return render(request, "index.html")
+
+
+@login_required
+@require_POST
+def new_conversation(request):
+    """Create a new blank conversation and redirect to it."""
+    conversation = Conversation.objects.create(user=request.user)
+    return redirect("ask:conversation", conversation_id=conversation.id)
+
+
+@login_required
+def conversation_detail(request, conversation_id):
+    """Display an existing conversation with all its QA records."""
+    conversation = get_object_or_404(
+        Conversation, id=conversation_id, user=request.user
     )
     return render(request, "index.html", {
-        'recent_questions_json': json.dumps(recent_questions, default=str)
+        "conversation": conversation,
     })
 
 
@@ -33,13 +45,38 @@ def mock_response(request):
         }
     })
 
+
 @login_required
 def query(request):
+    """
+    Accept a user query via GET, save it and the LLM response as a QARecord.
+    Uses the conversation specified by conversation_id, or the most recent one,
+    or creates a new one if none exist.
+    """
     query_text = request.GET.get("query", "")
+    if not query_text:
+        return JsonResponse({"error": "No query provided."}, status=400)
+
+    conversation_id = request.GET.get("conversation_id")
+    if conversation_id:
+        conversation = get_object_or_404(
+            Conversation, id=conversation_id, user=request.user
+        )
+    else:
+        conversation = Conversation.objects.filter(user=request.user).first()
+        if not conversation:
+            conversation = Conversation.objects.create(user=request.user)
+
     record = QARecord.objects.create(
+        conversation=conversation,
         question_text=query_text,
         user=request.user,
     )
+
+    # conversation title is set from the first question
+    if not conversation.title:
+        conversation.title = query_text[:200]
+
     try:
         llm_response = ask.llm_connector.query_llm(query_text)
 
@@ -54,13 +91,15 @@ def query(request):
         record.answer_timestamp = timezone.now()
         record.save()
 
-        return JsonResponse({"message": answer_text})
+        # Touch updated_at so this conversation stays as the most recent
+        conversation.save()
+
+        return JsonResponse({"message": answer_text, "conversation_id": conversation.id, "conversation_title": conversation.title})
     except (KeyError, IndexError, TypeError, ValueError) as e:
-        # logger.exception() logs the exception and the stack trace
-        logger.exception(f"Unexpected response from server {e}")
+        logger.exception("Unexpected response from server: %s", e)
         error_msg = f"Unexpected response from server: {e}"
     except Exception as e:
-        logger.exception(f"Failed to connect to server {e}")
+        logger.exception("Failed to connect to server: %s", e)
         error_msg = f"Failed to connect to server: {e}"
 
     # The try block returns on success, so this only runs on error.
@@ -68,10 +107,11 @@ def query(request):
     record.answer_text = error_msg
     record.answer_timestamp = timezone.now()
     record.save()
-    return JsonResponse({"error": error_msg}, status=500)
+    return JsonResponse({"error": error_msg, "conversation_id": conversation.id, "conversation_title": conversation.title}, status=500)
+
 
 @login_required
 @require_http_methods(["DELETE"])
 def delete_history(request):
-    request.user.qa_records.all().delete()
-    return JsonResponse({"message": "Question history deleted successfully!"})
+    request.user.conversations.all().delete()
+    return JsonResponse({"message": "All conversations deleted successfully!"})
diff --git a/hospexplorer/hospexplorer/settings.py b/hospexplorer/hospexplorer/settings.py
index 2522e13..cf93a9e 100644
--- a/hospexplorer/hospexplorer/settings.py
+++ b/hospexplorer/hospexplorer/settings.py
@@ -79,6 +79,7 @@
                 "django.template.context_processors.request",
                 "django.contrib.auth.context_processors.auth",
                 "django.contrib.messages.context_processors.messages",
+                "ask.context_processors.sidebar_conversations",
             ],
         },
     },
@@ -150,8 +151,8 @@
 LLM_QUERY_ENDPOINT = os.getenv("LLM_QUERY_ENDPOINT", "v1/chat/completions")
 LLM_MAX_TOKENS = int(os.getenv("LLM_MAX_TOKENS", "4096"))
 
-# User question history limit
-RECENT_QUESTIONS_LIMIT = 10
+# Sidebar conversations limit
+SIDEBAR_CONVERSATIONS_LIMIT = 10
 
 # Django-Allauth Configuration
 LOGIN_REDIRECT_URL = "/" + APP_ROOT + "ask/"