diff --git a/hospexplorer/ask/admin.py b/hospexplorer/ask/admin.py
index 8c38f3f..3910bbc 100644
--- a/hospexplorer/ask/admin.py
+++ b/hospexplorer/ask/admin.py
@@ -1,3 +1,16 @@
 from django.contrib import admin
+from ask.models import QARecord
 
-# Register your models here.
+
+@admin.register(QARecord)
+class QARecordAdmin(admin.ModelAdmin):
+    list_display = ["id", "user", "truncated_question", "question_timestamp", "answer_timestamp"]
+    list_filter = ["question_timestamp", "user"]
+    search_fields = ["question_text", "answer_text", "user__username"]
+    readonly_fields = ["question_timestamp", "answer_timestamp", "answer_raw_response"]
+    raw_id_fields = ["user"]
+    date_hierarchy = "question_timestamp"
+
+    def truncated_question(self, obj):
+        return obj.question_text[:75] + "..." if len(obj.question_text) > 75 else obj.question_text
+    truncated_question.short_description = "Question"
diff --git a/hospexplorer/ask/migrations/0001_initial.py b/hospexplorer/ask/migrations/0001_initial.py
new file mode 100644
index 0000000..98d680a
--- /dev/null
+++ b/hospexplorer/ask/migrations/0001_initial.py
@@ -0,0 +1,35 @@
+# Generated by Django 6.0.1 on 2026-01-30 19:36
+
+import django.db.models.deletion
+from django.conf import settings
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+
+    initial = True
+
+    dependencies = [
+        migrations.swappable_dependency(settings.AUTH_USER_MODEL),
+    ]
+
+    operations = [
+        migrations.CreateModel(
+            name='QARecord',
+            fields=[
+                ('id', models.BigAutoField(auto_created=True, primary_key=True, serialize=False, verbose_name='ID')),
+                ('question_text', models.TextField()),
+                ('question_timestamp', models.DateTimeField(auto_now_add=True)),
+                ('answer_text', models.TextField(blank=True, default='')),
+                ('answer_raw_response', models.JSONField(default=dict)),
+                ('answer_timestamp', models.DateTimeField(blank=True, null=True)),
+                ('user', models.ForeignKey(on_delete=django.db.models.deletion.CASCADE, related_name='qa_records', to=settings.AUTH_USER_MODEL)),
+            ],
+            options={
+                'verbose_name': 'Q&A Record',
+                'verbose_name_plural': 'Q&A Records',
+                'ordering': ['-question_timestamp'],
+                'indexes': [models.Index(fields=['user', '-question_timestamp'], name='ask_qarecor_user_id_f4353f_idx')],
+            },
+        ),
+    ]
diff --git a/hospexplorer/ask/migrations/0002_qarecord_is_error.py b/hospexplorer/ask/migrations/0002_qarecord_is_error.py
new file mode 100644
index 0000000..10ddcac
--- /dev/null
+++ b/hospexplorer/ask/migrations/0002_qarecord_is_error.py
@@ -0,0 +1,18 @@
+# Generated by Django 6.0.1 on 2026-02-04 23:32
+
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ('ask', '0001_initial'),
+    ]
+
+    operations = [
+        migrations.AddField(
+            model_name='qarecord',
+            name='is_error',
+            field=models.BooleanField(default=False),
+        ),
+    ]
diff --git a/hospexplorer/ask/models.py b/hospexplorer/ask/models.py
index 71a8362..aa69d52 100644
--- a/hospexplorer/ask/models.py
+++ b/hospexplorer/ask/models.py
@@ -1,3 +1,32 @@
 from django.db import models
+from django.conf import settings
 
-# Create your models here.
+
+class QARecord(models.Model):
+    """
+    Stores a question-answer pair from user interactions with the LLM.
+    """
+    # Question fields
+    question_text = models.TextField()
+    question_timestamp = models.DateTimeField(auto_now_add=True)
+
+    # Answer fields
+    answer_text = models.TextField(blank=True, default="")
+    answer_raw_response = models.JSONField(default=dict)
+    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")
+
+    class Meta:
+        ordering = ["-question_timestamp"]
+        verbose_name = "Q&A Record"
+        verbose_name_plural = "Q&A Records"
+        indexes = [
+            models.Index(fields=["user", "-question_timestamp"]),
+        ]
+
+    def __str__(self):
+        truncated = self.question_text[:50]
+        suffix = "..." if len(self.question_text) > 50 else ""
+        return f"{self.user.username}: {truncated}{suffix}"
diff --git a/hospexplorer/ask/static/css/styles.css b/hospexplorer/ask/static/css/styles.css
index 07c61b4..42db981 100644
--- a/hospexplorer/ask/static/css/styles.css
+++ b/hospexplorer/ask/static/css/styles.css
@@ -10870,3 +10870,36 @@ body.sb-sidenav-toggled #wrapper #sidebar-wrapper {
     margin-left: -15rem;
   }
 }
+
+/* Recent Questions Sidebar Styles */
+#sidebar-wrapper {
+  display: flex;
+  flex-direction: column;
+}
+
+#sidebar-wrapper .list-group {
+  flex: 1;
+  overflow-y: auto;
+  max-height: calc(100vh - 180px);
+}
+
+#sidebar-wrapper .question-item {
+  font-size: 0.875rem;
+  white-space: nowrap;
+  overflow: hidden;
+  text-overflow: ellipsis;
+  border-left: 3px solid transparent;
+  transition: border-color 0.2s, background-color 0.2s;
+}
+
+#sidebar-wrapper .question-item:hover {
+  border-left-color: #0d6efd;
+  background-color: #f8f9fa;
+}
+
+#sidebar-wrapper .sidebar-section-heading {
+  font-weight: 600;
+  text-transform: uppercase;
+  letter-spacing: 0.05em;
+  font-size: 0.75rem;
+}
diff --git a/hospexplorer/ask/static/js/scripts.js b/hospexplorer/ask/static/js/scripts.js
index 81efcaa..92acbb1 100644
--- a/hospexplorer/ask/static/js/scripts.js
+++ b/hospexplorer/ask/static/js/scripts.js
@@ -10,17 +10,19 @@
 window.addEventListener('DOMContentLoaded', event => {
 
     // Toggle the side navigation
-    const sidebarToggle = document.body.querySelector('#sidebarToggle');
-    if (sidebarToggle) {
-        // Uncomment Below to persist sidebar toggle between refreshes
-        // if (localStorage.getItem('sb|sidebar-toggle') === 'true') {
-        //     document.body.classList.toggle('sb-sidenav-toggled');
-        // }
-        sidebarToggle.addEventListener('click', event => {
+    const sidebarToggles = document.body.querySelectorAll('#sidebarToggle');
+
+    // Restore sidebar state from localStorage
+    if (localStorage.getItem('sb|sidebar-toggle') === 'true') {
+        document.body.classList.add('sb-sidenav-toggled');
+    }
+
+    sidebarToggles.forEach(toggle => {
+        toggle.addEventListener('click', event => {
             event.preventDefault();
             document.body.classList.toggle('sb-sidenav-toggled');
             localStorage.setItem('sb|sidebar-toggle', document.body.classList.contains('sb-sidenav-toggled'));
         });
-    }
+    });
 
 });
diff --git a/hospexplorer/ask/templates/_base.html b/hospexplorer/ask/templates/_base.html
index 6665c53..9af7852 100644
--- a/hospexplorer/ask/templates/_base.html
+++ b/hospexplorer/ask/templates/_base.html
@@ -17,14 +17,30 @@
     <body>
         <div class="d-flex" id="wrapper">
             <!-- Sidebar-->
-            <div class="border-end bg-white" id="sidebar-wrapper">
+            <div class="border-end bg-white" id="sidebar-wrapper"
+                 x-data="sidebarQuestions()"
+                 @question-asked.window="addQuestion($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 -->
+                    <div class="sidebar-section-heading small text-muted px-3 py-2 border-bottom bg-light">
+                        Recent Questions
+                    </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)">
+                        </a>
+                    </template>
+                    <div x-show="questions.length === 0" class="text-muted small px-3 py-2">
+                        No questions yet
+                    </div>
+
                     {% if user.is_authenticated %}
-                    <div class="p-3 border-top">
+                    <div class="p-3 border-top mt-auto">
                         <div class="small text-muted mb-2">Signed in as <strong>{{ user.username }}</strong></div>
                         <a href="{% url 'account_logout' %}" class="btn btn-outline-secondary btn-sm w-100">Sign Out</a>
                     </div>
@@ -33,32 +49,18 @@
             </div>
             <!-- Page content wrapper-->
             <div id="page-content-wrapper">
-                <!-- Top navigation-->
-                <!--<nav class="navbar navbar-expand-lg navbar-light bg-white border-bottom">
+                <!-- Top navigation with toggle -->
+                <nav class="navbar navbar-light bg-white border-bottom">
                     <div class="container-fluid">
-                        <button class="btn btn-primary" id="sidebarToggle">Toggle Menu</button>
-                        <button class="navbar-toggler" type="button" data-bs-toggle="collapse" data-bs-target="#navbarSupportedContent" aria-controls="navbarSupportedContent" aria-expanded="false" aria-label="Toggle navigation"><span class="navbar-toggler-icon"></span></button>
-                        <div class="collapse navbar-collapse" id="navbarSupportedContent">
-                            <ul class="navbar-nav ms-auto mt-2 mt-lg-0">
-                                <li class="nav-item active"><a class="nav-link" href="#!">Home</a></li>
-                                <li class="nav-item"><a class="nav-link" href="#!">Link</a></li>
-                                <li class="nav-item dropdown">
-                                    <a class="nav-link dropdown-toggle" id="navbarDropdown" href="#" role="button" data-bs-toggle="dropdown" aria-haspopup="true" aria-expanded="false">Dropdown</a>
-                                    <div class="dropdown-menu dropdown-menu-end" aria-labelledby="navbarDropdown">
-                                        <a class="dropdown-item" href="#!">Action</a>
-                                        <a class="dropdown-item" href="#!">Another action</a>
-                                        <div class="dropdown-divider"></div>
-                                        <a class="dropdown-item" href="#!">Something else here</a>
-                                    </div>
-                                </li>
-                            </ul>
-                        </div>
+                        <button class="btn btn-outline-secondary btn-sm" id="sidebarToggle">
+                            &#9776; Menu
+                        </button>
                     </div>
-                </nav>-->
+                </nav>
                 <!-- Page content-->
                 <div class="container-fluid">
                     {% block content %}{% endblock %}
-                
+
                 </div>
             </div>
         </div>
@@ -66,5 +68,32 @@
         <script src="https://cdn.jsdelivr.net/npm/bootstrap@5.2.3/dist/js/bootstrap.bundle.min.js"></script>
         <!-- Core theme JS-->
         <script src="{% static 'js/scripts.js' %}"></script>
+        <!-- Sidebar Questions Component -->
+        <script>
+            window.initialQuestions = {{ recent_questions_json|safe|default:"[]" }};
+
+            function sidebarQuestions() {
+                return {
+                    questions: window.initialQuestions || [],
+
+                    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);
+                        }
+                    },
+
+                    truncate(text, length) {
+                        if (!text) return '';
+                        if (text.length <= length) return text;
+                        return text.substring(0, length) + '...';
+                    }
+                };
+            }
+        </script>
     </body>
 </html>
diff --git a/hospexplorer/ask/templates/index.html b/hospexplorer/ask/templates/index.html
index c015a36..8138d81 100644
--- a/hospexplorer/ask/templates/index.html
+++ b/hospexplorer/ask/templates/index.html
@@ -19,9 +19,16 @@ <h1 class="mt-4">Hopper</h1>
             isLoading: false,
 
             async getAnswer() {
+                if (!this.userQuery.trim()) return;
+
+                const questionText = this.userQuery;
                 this.isLoading = true;
+
+                // Dispatch event to update sidebar
+                $dispatch('question-asked', { text: questionText });
+
                 try {
-                    const response = await fetch('{% url 'ask:query-llm' %}?query=' + encodeURIComponent(this.userQuery));
+                    const response = await fetch('{% url 'ask:query-llm' %}?query=' + encodeURIComponent(questionText));
                     const data = await response.json();
                     if (!response.ok || data.error) {
                         this.answers.push('Something went wrong. Please try again.');
@@ -31,6 +38,7 @@ <h1 class="mt-4">Hopper</h1>
                 } catch (error) {
                     this.answers.push('Something went wrong. Please try again.');
                 }
+                this.userQuery = '';
                 this.isLoading = false;
             }
         }">
diff --git a/hospexplorer/ask/views.py b/hospexplorer/ask/views.py
index b948680..a1ace15 100644
--- a/hospexplorer/ask/views.py
+++ b/hospexplorer/ask/views.py
@@ -1,28 +1,67 @@
+import logging
 from django.shortcuts import render
 from django.http import JsonResponse
 from django.conf import settings
 from django.contrib.auth.decorators import login_required
+from django.utils import timezone
+import json
 import ask.llm_connector
+from ask.models import QARecord
 
+logger = logging.getLogger(__name__)
 
 @login_required
 def index(request):
-    return render(request, "index.html", {})
+    recent_questions = list(
+        QARecord.objects.filter(user=request.user).values('id', 'question_text')[:10]
+    )
+    return render(request, "index.html", {
+        'recent_questions_json': json.dumps(recent_questions, default=str)
+    })
 
 
 @login_required
 def mock_response(request):
+    """Returns a mock LLM response in the same format as the real server."""
     return JsonResponse({
-        "message": "Okay, the user wants a three-sentence bedtime story about a unicorn. Let's start by thinking about the key elements of a good bedtime story. They usually have a peaceful setting, a gentle conflict or quest, and a happy ending.\n\nFirst sentence needs to set the scene. Maybe a magical forest with a unicorn. Luna is a common unicorn name, sounds soft. Moonlight and stars could add a calming effect.\n\nSecond sentence should introduce a small problem or something the unicorn does. Healing powers are typical for unicorns. Maybe she finds an injured animal, like a fox. Using her horn to heal adds magic.\n\nThird sentence wraps it up with a happy ending. The fox recovers, they become friends, and the forest is peaceful. Emphasize safety and dreams to make it soothing for bedtime.\n\nCheck if it's exactly three sentences. Yes. Language is simple and comforting, suitable for a child. Avoid any scary elements. Make sure it flows smoothly and conveys warmth.\n</think>\n\nUnder the shimmering moonlit sky, a silver-maned unicorn named Luna trotted through the enchanted forest, her hooves leaving trails of stardust. When she discovered a wounded fox whimpering beneath an ancient oak, she touched her glowing horn to its paw, weaving magic that healed the hurt. With the fox curled beside her, Luna rested on a bed of moss, her heart full as the forest whispered lullabies, ensuring all creatures drifted into dreams of peace."
+        "choices": [{
+            "message": {
+                "content": "Under the shimmering moonlit sky, a silver-maned unicorn named Luna trotted through the enchanted forest, her hooves leaving trails of stardust. When she discovered a wounded fox whimpering beneath an ancient oak, she touched her glowing horn to its paw, weaving magic that healed the hurt. With the fox curled beside her, Luna rested on a bed of moss, her heart full as the forest whispered lullabies, ensuring all creatures drifted into dreams of peace."
+            }
+        }]
     })
 
 @login_required
 def query(request):
+    query_text = request.GET.get("query", "")
+    record = QARecord.objects.create(
+        question_text=query_text,
+        user=request.user,
+    )
     try:
-        llm_response = ask.llm_connector.query_llm(request.GET["query"])
-        content = llm_response["choices"][0]["message"]["content"]
-        return JsonResponse({"message": content})
-    except (KeyError, IndexError, TypeError) as e:
-        return JsonResponse({"error": f"Unexpected response from server: {e}"}, status=500)
+        llm_response = ask.llm_connector.query_llm(query_text)
+
+        # Mock and real LLM use the same response format
+        if "choices" not in llm_response or not llm_response["choices"]:
+            raise ValueError("LLM response is missing structure")
+        answer_text = llm_response["choices"][0].get("message", {}).get("content", "")
+
+        record.answer_text = answer_text
+        record.answer_raw_response = llm_response
+        record.answer_timestamp = timezone.now()
+        record.save()
+
+        return JsonResponse({"message": answer_text})
+    except (KeyError, IndexError, TypeError, ValueError) as e:
+        logger.exception("Unexpected response from server")
+        error_msg = f"Unexpected response from server: {e}"
     except Exception as e:
-        return JsonResponse({"error": f"Failed to connect to server: {e}"}, status=500)
\ No newline at end of file
+        logger.exception("Failed to connect to server")
+        error_msg = f"Failed to connect to server: {e}"
+
+    # The try block returns on success, so this only runs on error.
+    record.is_error = True
+    record.answer_text = error_msg
+    record.answer_timestamp = timezone.now()
+    record.save()
+    return JsonResponse({"error": error_msg}, status=500)
diff --git a/mockoon/llm-mock.json b/mockoon/llm-mock.json
index f52caae..b31015a 100644
--- a/mockoon/llm-mock.json
+++ b/mockoon/llm-mock.json
@@ -17,7 +17,7 @@
       "responses": [
         {
           "uuid": "chat-completions-response",
-          "body": "{\n  \"message\": \"This is a mock response from the local mockserver. Your query was received successfully.\"\n}",
+          "body": "{\n  \"choices\": [{\n    \"message\": {\n      \"content\": \"Under the shimmering moonlit sky, a silver-maned unicorn named Luna trotted through the enchanted forest, her hooves leaving trails of stardust. When she discovered a wounded fox whimpering beneath an ancient oak, she touched her glowing horn to its paw, weaving magic that healed the hurt. With the fox curled beside her, Luna rested on a bed of moss, her heart full as the forest whispered lullabies, ensuring all creatures drifted into dreams of peace.\"\n    }\n  }]\n}",
           "latency": 0,
           "statusCode": 200,
           "label": "Success response",