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..2bb1fb5 100644
--- a/hospexplorer/ask/static/js/scripts.js
+++ b/hospexplorer/ask/static/js/scripts.js
@@ -3,9 +3,9 @@
 * Copyright 2013-2023 Start Bootstrap
 * Licensed under MIT (https://github.com/StartBootstrap/startbootstrap-simple-sidebar/blob/master/LICENSE)
 */
-// 
+//
 // Scripts
-// 
+//
 
 window.addEventListener('DOMContentLoaded', event => {
 
diff --git a/hospexplorer/ask/templates/_base.html b/hospexplorer/ask/templates/_base.html
index 6665c53..91c7a7c 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 +49,10 @@
             </div>
             <!-- Page content wrapper-->
             <div id="page-content-wrapper">
-                <!-- Top navigation-->
-                <!--<nav class="navbar navbar-expand-lg 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>
-                    </div>
-                </nav>-->
                 <!-- Page content-->
                 <div class="container-fluid">
                     {% block content %}{% endblock %}
-                
+
                 </div>
             </div>
         </div>
@@ -66,5 +60,32 @@
         <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 3b75de4..d6fdf0c 100644
--- a/hospexplorer/ask/views.py
+++ b/hospexplorer/ask/views.py
@@ -4,6 +4,7 @@
 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
 
@@ -11,7 +12,14 @@
 
 @login_required
 def index(request):
-    return render(request, "index.html", {})
+    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", {
+        'recent_questions_json': json.dumps(recent_questions, default=str)
+    })
 
 
 @login_required
diff --git a/hospexplorer/hospexplorer/settings.py b/hospexplorer/hospexplorer/settings.py
index 62eb38e..2522e13 100644
--- a/hospexplorer/hospexplorer/settings.py
+++ b/hospexplorer/hospexplorer/settings.py
@@ -150,6 +150,8 @@
 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
 
 # Django-Allauth Configuration
 LOGIN_REDIRECT_URL = "/" + APP_ROOT + "ask/"
