diff --git a/app/Actions/SendMessageAction.php b/app/Actions/SendMessageAction.php
index d270013..c9a8ad1 100644
--- a/app/Actions/SendMessageAction.php
+++ b/app/Actions/SendMessageAction.php
@@ -3,7 +3,9 @@
 namespace App\Actions;
 
 use App\Events\MessageSent;
+use App\Exceptions\MessageNotSendException;
 use App\Models\User;
+use DB;
 
 final readonly class SendMessageAction
 {
@@ -14,18 +16,30 @@ public function __construct(private CreateOrGetInboxAction $inboxAction) {}
      */
     public function execute(User $sender, User $recipient, array $data): void
     {
-        // find the inbox between the two users
-        \DB::beginTransaction();
-        $inbox = $this->inboxAction->execute($recipient, $sender);
-        $inbox->last_message = $data['message'];
-        $inbox->last_user_id = $sender->id;
-        $inbox->save();
-        $message = $inbox->messages()->create([
-            'message' => $data['message'],
-            'user_id' => $sender->id,
-        ]);
+        try {
 
-        broadcast(new MessageSent($message))->toOthers();
-        \DB::commit();
+            // find the inbox between the two users
+            DB::beginTransaction();
+            $inbox = $this->inboxAction->execute($recipient, $sender);
+
+            // update the inbox with the last message and last user as current user
+            $inbox->last_message = $data['message'];
+            $inbox->last_user_id = $sender->id;
+            $inbox->save();
+
+            // create a new message in the inbox
+            $message = $inbox->messages()->create([
+                'message' => $data['message'],
+                'user_id' => $sender->id,
+            ]);
+
+            // Send the message to all other users in the inbox
+            broadcast(new MessageSent($message))->toOthers();
+
+            DB::commit();
+        } catch (\Throwable $e) {
+            DB::rollBack();
+            throw new MessageNotSendException('Message not sent.', previous: $e);
+        }
     }
 }
diff --git a/app/Exceptions/MessageNotSendException.php b/app/Exceptions/MessageNotSendException.php
new file mode 100644
index 0000000..8c82fd1
--- /dev/null
+++ b/app/Exceptions/MessageNotSendException.php
@@ -0,0 +1,7 @@
+<?php
+
+namespace App\Exceptions;
+
+use Exception;
+
+class MessageNotSendException extends Exception {}
diff --git a/app/Http/Controllers/ChatController.php b/app/Http/Controllers/ChatController.php
index 88b38f6..f60af60 100644
--- a/app/Http/Controllers/ChatController.php
+++ b/app/Http/Controllers/ChatController.php
@@ -4,9 +4,12 @@
 
 use App\Actions\CreateOrGetInboxAction;
 use App\Actions\SendMessageAction;
+use App\Exceptions\MessageNotSendException;
 use App\Http\Requests\SendMessageRequest;
 use App\Models\User;
 use Illuminate\Container\Attributes\CurrentUser;
+use Log;
+use Throwable;
 
 class ChatController extends Controller
 {
@@ -21,8 +24,8 @@ public function show(#[CurrentUser] User $sender, User $recipient, CreateOrGetIn
     {
         try {
             $inbox = $action->execute($recipient, $sender);
-        } catch (\Throwable $e) {
-            \Log::error('Inbox instantiation Failed: ', [$e->getMessage()]);
+        } catch (Throwable $e) {
+            Log::error('Inbox instantiation Failed: ', [$e->getMessage()]);
             abort(500);
         }
 
@@ -33,7 +36,7 @@ public function show(#[CurrentUser] User $sender, User $recipient, CreateOrGetIn
     }
 
     /**
-     * @throws \Throwable
+     * @throws Throwable
      */
     public function store(
         #[CurrentUser] User $sender,
@@ -41,8 +44,16 @@ public function store(
         SendMessageRequest $request,
         SendMessageAction $action
     ) {
-        $action->execute($sender, $recipient, $request->validated());
+        try {
+            $action->execute($sender, $recipient, $request->validated());
 
-        response()->json(['message' => 'Message sent successfully.']);
+            return response()->json(['message' => 'Message sent successfully.']);
+
+        } catch (MessageNotSendException $e) {
+
+            Log::error('Message send failed', [$e->getMessage()]);
+
+            return response()->json(['message' => 'Message sent failed.'], 500);
+        }
     }
 }
diff --git a/app/Models/Message.php b/app/Models/Message.php
index ad41f43..98af994 100644
--- a/app/Models/Message.php
+++ b/app/Models/Message.php
@@ -2,8 +2,11 @@
 
 namespace App\Models;
 
+use Eloquent;
+use Illuminate\Database\Eloquent\Builder;
 use Illuminate\Database\Eloquent\Model;
 use Illuminate\Database\Eloquent\Relations\BelongsTo;
+use Illuminate\Support\Carbon;
 
 /**
  * @property int $id
@@ -14,24 +17,24 @@
  * @property string|null $delivered_at
  * @property string|null $deleted_at
  * @property string|null $failed_at
- * @property \Illuminate\Support\Carbon $created_at
- * @property-read \App\Models\Inbox|null $inbox
- * @property-read \App\Models\User|null $user
+ * @property Carbon $created_at
+ * @property-read Inbox|null $inbox
+ * @property-read User|null $user
  *
- * @method static \Illuminate\Database\Eloquent\Builder<static>|Message newModelQuery()
- * @method static \Illuminate\Database\Eloquent\Builder<static>|Message newQuery()
- * @method static \Illuminate\Database\Eloquent\Builder<static>|Message query()
- * @method static \Illuminate\Database\Eloquent\Builder<static>|Message whereCreatedAt($value)
- * @method static \Illuminate\Database\Eloquent\Builder<static>|Message whereDeletedAt($value)
- * @method static \Illuminate\Database\Eloquent\Builder<static>|Message whereDeliveredAt($value)
- * @method static \Illuminate\Database\Eloquent\Builder<static>|Message whereFailedAt($value)
- * @method static \Illuminate\Database\Eloquent\Builder<static>|Message whereId($value)
- * @method static \Illuminate\Database\Eloquent\Builder<static>|Message whereInboxId($value)
- * @method static \Illuminate\Database\Eloquent\Builder<static>|Message whereMessage($value)
- * @method static \Illuminate\Database\Eloquent\Builder<static>|Message whereReadAt($value)
- * @method static \Illuminate\Database\Eloquent\Builder<static>|Message whereUserId($value)
+ * @method static Builder<static>|Message newModelQuery()
+ * @method static Builder<static>|Message newQuery()
+ * @method static Builder<static>|Message query()
+ * @method static Builder<static>|Message whereCreatedAt($value)
+ * @method static Builder<static>|Message whereDeletedAt($value)
+ * @method static Builder<static>|Message whereDeliveredAt($value)
+ * @method static Builder<static>|Message whereFailedAt($value)
+ * @method static Builder<static>|Message whereId($value)
+ * @method static Builder<static>|Message whereInboxId($value)
+ * @method static Builder<static>|Message whereMessage($value)
+ * @method static Builder<static>|Message whereReadAt($value)
+ * @method static Builder<static>|Message whereUserId($value)
  *
- * @mixin \Eloquent
+ * @mixin Eloquent
  */
 class Message extends Model
 {
@@ -43,6 +46,10 @@ class Message extends Model
         'created_at', 'delivered_at',
     ];
 
+    protected $casts = [
+        'created_at' => 'datetime',
+    ];
+
     public function inbox(): BelongsTo
     {
         return $this->belongsTo(Inbox::class);
diff --git a/resources/js/message.js b/resources/js/message.js
index 4f9eda1..19940e7 100644
--- a/resources/js/message.js
+++ b/resources/js/message.js
@@ -1,34 +1,51 @@
+import {showToast} from "./toast.js";
+
 export const sendMessage = async (element, event) => {
-    event.preventDefault()
+    event.preventDefault();
     const messageInput = element.querySelector('[name="message"]');
-    if (!messageInput.value) return;
+    const message = messageInput.value;
+    if (!message) return;
 
     const recipentId = element.dataset.recipientId;
-    const message = messageInput.value;
     messageInput.value = '';
 
-    addMessageToChat({message: message}, true);
+    // Capture the ID of the UI element we just added
+    const tempMessageId = addMessageToChat({message: message}, true);
 
-    const response = await axios.post(`/api/chat/${recipentId}/message`, {message: message});
+    try {
+        await axios.post(`/api/chat/${recipentId}/message`, {message: message});
+    } catch (e) {
+        console.error(e);
+        showToast('Message could not be sent.');
+
+        const failedMessage = document.getElementById(tempMessageId);
+        if (failedMessage) {
+            failedMessage.remove();
+        }
+
+        messageInput.value = message;
+    }
 }
 
 export const addMessageToChat = (message, right = false) => {
     const chatContainer = document.getElementById('chat-container');
     if (!chatContainer) return;
 
+    const tempId = 'msg-' + Date.now();
+
     const placeholder = chatContainer.querySelector('#no-messages-placeholder');
-    if (placeholder) {
-        placeholder.remove();
-    }
+    if (placeholder) placeholder.remove();
 
     const messagePlaceholder = `
-        <div class="grid px-4 my-1 w-full ${right ? 'place-items-end' : 'place-items-start'}">
-            <div class="max-w-[40vw] py-2 px-4 rounded-2xl  bg-gray-200">
+        <div id="${tempId}" class="grid px-4 my-1 w-full ${right ? 'place-items-end' : 'place-items-start'}">
+            <div class="max-w-[40vw] py-2 px-4 rounded-full ${right ? 'rounded-br-none' : 'rounded-tl-none'} bg-gray-200">
                 ${message.message}
             </div>
         </div>`;
 
     chatContainer.insertAdjacentHTML('afterbegin', messagePlaceholder);
-
     chatContainer.scrollTop = 0;
+
+    // Return the ID so the caller can find this specific message later
+    return tempId;
 }
diff --git a/resources/views/components/chat/message-box.blade.php b/resources/views/components/chat/message-box.blade.php
index 6679e01..bcb08a5 100644
--- a/resources/views/components/chat/message-box.blade.php
+++ b/resources/views/components/chat/message-box.blade.php
@@ -1,14 +1,32 @@
 @props(['recipient', 'messages' => []])
+@php
+    $groupedMessages = $messages->groupBy(function($msg) {
+        return $msg->created_at->format('M j, Y');
+    });
+@endphp
+
 <x-dashboard.page-heading class="m-0 mb-0.5" :title="$recipient->name" description="offline"/>
 <div class="bg-gray-50 h-full overflow-hidden flex-shrink-0">
     <div id="chat-container" data-auth-id="{{ auth()->id() }}" data-partner-id="{{ $recipient->id }}"
          class="text-sm flex flex-col-reverse overflow-y-scroll h-full max-h-screen pb-50 scroll-snap-y-container">
-        @forelse($messages as $message)
-            <x-chat.message :right="$message->user_id === auth()->user()->id">{{$message->message}}</x-chat.message>
-        @empty
-            <div id="no-messages-placeholder" class="grid px-4 my-1 w-full h-full place-items-center ">
-                <p class="text-gray-600">No Messages Found!</p>
+        @forelse($groupedMessages as $date => $dayMessages)
+            @foreach($dayMessages as $message)
+                <x-chat.message :right="$message->user_id === auth()->id()">
+                    <p>{{ $message->message }}</p>
+                    <span class="text-[10px] opacity-70 block text-right mt-1">
+                    {{ $message->created_at->format('g:i A') }}
+                </span>
+                </x-chat.message>
+            @endforeach
+
+            {{-- The Date Divider --}}
+            <div class="flex justify-center my-4 top-0">
+            <span class="bg-gray-200 text-gray-600 text-xs px-3 py-1 rounded-full shadow-sm">
+                {{ $date }}
+            </span>
             </div>
+        @empty
+            <div id="no-messages-placeholder">No Messages Found !</div>
         @endforelse
     </div>
     <x-chat.message-input :recipient_id="$recipient->id"/>
diff --git a/resources/views/components/chat/message.blade.php b/resources/views/components/chat/message.blade.php
index 4ba36dd..3a0c52c 100644
--- a/resources/views/components/chat/message.blade.php
+++ b/resources/views/components/chat/message.blade.php
@@ -1,7 +1,11 @@
 @props(['right' => false])
 <div class="grid px-4 my-1 w-full @if($right) place-items-end @else place-items-start @endif">
-    <div class="max-w-[40vw] py-2 px-4 @if($right) rounded-l-xl rounded-br-xl @else rounded-r-xl rounded-bl-xl @endif bg-gray-200">
-        {{ $slot }}
-
+    <div class="max-w-[70vw] md:max-w-[40vw] py-2 px-4 bg-gray-200 rounded-3xl
+        @if($right)
+            rounded-br-none
+        @else
+            rounded-tl-none
+        @endif">
+        {{$slot}}
     </div>
 </div>
diff --git a/resources/views/components/explore/profile-menu.blade.php b/resources/views/components/explore/profile-menu.blade.php
index b563fa6..fcbf2b6 100644
--- a/resources/views/components/explore/profile-menu.blade.php
+++ b/resources/views/components/explore/profile-menu.blade.php
@@ -1,27 +1,30 @@
+@php use App\Enums\UserTypes; @endphp
 @props(['profileLink' => ''])
 <div class="flex items-center">
     @auth
-    <div class="relative group">
-        <x-ui.button icon="user-circle" class="cursor-pointer" onclick="showMenu(this)"></x-ui.button>
-        <ul class="menu opacity-0 z-10 scale-10 group-hover:scale-100 group-hover:opacity-100 transition-all duration-300 ease-in-out w-48 absolute right-0  bg-white border border-gray-300 rounded-md shadow-xl py-2 text-accent-600">
-            <li class="py-2 px-4 hover:bg-gray-100 hover:text-gray-900 hover:cursor-pointer hover:font-bold">
-                <a href="{{$profileLink}}" class="flex space-x-4">
-                    <div class="p-1 bg-gray-200 rounded-xl text-gray-900">
-                        <x-heroicon-o-user class="w-4"/>
-                    </div>
-                    <p>Profile</p>
-                </a>
-            </li>
-
-            @if(auth()->check() && auth()->user()->role === \App\Enums\UserTypes::Broker->value)
+        <div class="relative group">
+            <x-ui.button icon="user-circle" class="cursor-pointer" onclick="showMenu(this)"></x-ui.button>
+            <ul class="menu opacity-0 z-10 scale-10 group-hover:scale-100 group-hover:opacity-100 transition-all duration-300 ease-in-out w-48 absolute right-0  bg-white border border-gray-300 rounded-md shadow-xl py-2 text-accent-600">
                 <li class="py-2 px-4 hover:bg-gray-100 hover:text-gray-900 hover:cursor-pointer hover:font-bold">
-                    <a href="{{route('broker.dashboard')}}" class="flex space-x-4">
+                    <a href="{{$profileLink}}" class="flex space-x-4">
                         <div class="p-1 bg-gray-200 rounded-xl text-gray-900">
-                            <x-heroicon-o-adjustments-horizontal class="w-4"/>
+                            <x-heroicon-o-user class="w-4"/>
                         </div>
-                        <p>Control Panel</p>
+                        <p>Profile</p>
                     </a>
                 </li>
+
+                @if(auth()->check() && auth()->user()->role === UserTypes::Broker->value)
+                    <li class="py-2 px-4 hover:bg-gray-100 hover:text-gray-900 hover:cursor-pointer hover:font-bold">
+                        <a href="{{route('broker.dashboard')}}" class="flex space-x-4">
+                            <div class="p-1 bg-gray-200 rounded-xl text-gray-900">
+                                <x-heroicon-o-adjustments-horizontal class="w-4"/>
+                            </div>
+                            <p>Control Panel</p>
+                        </a>
+                    </li>
+                @endif
+
                 <li class="py-2 px-4 hover:bg-gray-100 hover:text-gray-900 hover:cursor-pointer hover:font-bold">
                     <a href="{{route('chat')}}" class="flex space-x-4">
                         <div class="p-1 bg-gray-200 rounded-xl text-gray-900">
@@ -30,10 +33,8 @@
                         <p>Chat</p>
                     </a>
                 </li>
-            @endif
-
-        </ul>
-    </div>
+            </ul>
+        </div>
     @endauth
     @guest
         <x-ui.button variant="neutral" link="{{route('login.create')}}">
diff --git a/resources/views/dashboards/user/chat.blade.php b/resources/views/dashboards/user/chat.blade.php
index c1358cd..7539428 100644
--- a/resources/views/dashboards/user/chat.blade.php
+++ b/resources/views/dashboards/user/chat.blade.php
@@ -1,10 +1,11 @@
+@php use App\Services\ProfileInitialsService; @endphp
 <x-chat.layout>
     <x-slot:sidebarItems>
         @forelse($inboxes as $inbox)
             <x-chat.sidebar-item
                 :name="$inbox->recipient->name"
                 :link="route('chat.show', $inbox->recipient->id)"
-                :avatar="(new \App\Services\ProfileInitialsService)->create($inbox->recipient->name)"
+                :avatar="(new ProfileInitialsService)->create($inbox->recipient->name)"
                 :message="$inbox->last_message"/>
         @empty
             No chats found !
@@ -20,4 +21,5 @@
             </div>
         @endif
     </div>
+    <x-ui.toast/>
 </x-chat.layout>