diff --git a/backend/app_mixins/chat.py b/backend/app_mixins/chat.py
index 23fe801..51054c6 100644
--- a/backend/app_mixins/chat.py
+++ b/backend/app_mixins/chat.py
@@ -39,6 +39,7 @@ class ChatMixin:
         with self.sql_session() as session:
             session.execute(db.Membership.__table__.delete().where(db.Membership.chat_id == chat_id))
             session.execute(db.Chat.__table__.delete().where(db.Chat.id == chat_id))
+            # TODO: Delete messages from the chat
             session.commit()
             print(f"Deleted chat #{chat_id} and its memberships.")
 
@@ -103,9 +104,8 @@ class ChatMixin:
             session.refresh(message)
 
         # Notify chat owner
-        if sender != 'user':
-            chat_owner = session.execute(select(db.Chat.user_id).where(db.Chat.id == chat_id)).scalar()
-            self.notify_message_to_user(chat_owner, message)
+        chat_owner = session.execute(select(db.Chat.user_id).where(db.Chat.id == chat_id)).scalar()
+        self.notify_message_to_user(chat_owner, message)
 
         # Notify participant agents
         agent_ids = session.execute(select(db.Membership.agent_id).where(db.Membership.chat_id == chat_id)).scalars().all()
diff --git a/backend/database.py b/backend/database.py
index a62fe0d..7bfb3a9 100644
--- a/backend/database.py
+++ b/backend/database.py
@@ -82,7 +82,7 @@ class Message(Base):
 
     # Identifier of the sender: user / system / user-$ID / agent-$ID
     sender: Mapped[str]
-    # Timestamp of this message
+    # Timestamp when this message was sent
     time: Mapped[int]
     # Timestamp of this message's last edit
     #last_edit: Mapped[int]
diff --git a/frontend-vue/src/App.vue b/frontend-vue/src/App.vue
index 753729d..4679cf8 100644
--- a/frontend-vue/src/App.vue
+++ b/frontend-vue/src/App.vue
@@ -1,9 +1,9 @@
 <script setup>
 import { ref } from 'vue';
 import { RouterLink, RouterView } from 'vue-router'
-import HelloWorld from './components/HelloWorld.vue'
-import Alerts from './components/main/Alerts.vue'
 import Sidebar from './components/main/Sidebar.vue'
+import Alerts from './components/main/Alerts.vue'
+import ContextMenu from './components/main/ContextMenu.vue'
 
 import * as ui from './ui';
 import * as backend from './backend';
@@ -47,6 +47,7 @@ backend.authResult().then(handleAuthResult);
 
 <template>
   <Alerts />
+  <ContextMenu />
 
   <div class="container" v-if="loginState=='loading'">
     <div class="content">
diff --git a/frontend-vue/src/components/main/ContextMenu.vue b/frontend-vue/src/components/main/ContextMenu.vue
new file mode 100644
index 0000000..c95c685
--- /dev/null
+++ b/frontend-vue/src/components/main/ContextMenu.vue
@@ -0,0 +1,153 @@
+<!--
+How to use: import ui, then call like this:
+
+let selectedValue = await ui.contextMenu([
+  {value: 'this-entry-value', icon: 'fa-symbol', title: "Name displayed"},
+  {title: "Entry with children (no value)", entries: [
+    {value: 'inner-entry', title: "Entry inside the group"}
+  ]},
+]);
+
+And to trigger it from a document interaction, add this attribute:
+
+<div @contextmenu.prevent="customContextMenu()"></div>
+-->
+<script setup lang="ts">
+  import { ref, onMounted, onUnmounted } from 'vue';
+  import * as ui from '../../ui';
+
+  const entries = ref(null);
+  const menuElem = ref(null);
+  const menuStyle = ref({});
+
+  let callback = null;
+
+  const mousePos = {x: null, y: null};
+  const screenSize = {x: null, y: null};
+
+  function returnValue (value) {
+    entries.value = null;
+    // Send result back in two frames
+    requestAnimationFrame(() => {
+      requestAnimationFrame(() => {
+        callback(value);
+      });
+    });
+  }
+
+  function onMouseMove (event) {
+    mousePos.x = event.clientX;
+    mousePos.y = event.clientY;
+  }
+
+  function onMouseDown (event) {
+    // missfire
+    if (!menuElem.value) return;
+
+    if (!menuElem.value.contains(event.target)) {
+      returnValue(null);
+    }
+  }
+
+  ui.listen('context-menu', ev => {
+    if (!ev.entries || ev.entries.length == 0) {
+      ev.callback(null);
+      return;
+    }
+
+    entries.value = ev.entries;
+    callback = ev.callback;
+
+    screenSize.x = window.innerWidth;
+    screenSize.y = window.innerHeight;
+
+    computeStyle();
+  });
+
+  onMounted(() => {
+    window.addEventListener('mousemove', onMouseMove);
+    window.addEventListener('mousedown', onMouseDown);
+  });
+
+  onUnmounted(() => {
+    window.removeEventListener('mousemove', onMouseMove);
+    window.removeEventListener('mousedown', onMouseDown);
+  });
+
+  function selectEntry (entry) {
+    if (entry.value != null) {
+      returnValue(entry.value);
+    }
+
+    if (entry.entries) {
+      let newEntries = Array.from(entry.entries);
+
+      if (!entry.backButton) {
+        newEntries.unshift({
+          title: 'Back',
+          icon: 'fa-caret-left',
+          entries: entries.value,
+          backButton: true,
+        });
+      }
+
+      entries.value = newEntries;
+    }
+  }
+
+  function computeStyle () {
+    let w = screenSize.x;
+    let h = screenSize.y;
+
+    let style = {};
+
+    if (mousePos.x < w/2) {
+      style.left = mousePos.x + 'px';
+    } else {
+      style.right = w-mousePos.x + 'px';
+    }
+
+    if (mousePos.y < h/2) {
+      style.top = mousePos.y + 'px';
+    } else {
+      style.bottom = h-mousePos.y + 'px';
+    }
+
+    menuStyle.value = style;
+  }
+</script>
+
+<template>
+  <div v-if="entries" ref="menuElem" class="context-menu" :style="menuStyle">
+    <div v-for="entry in entries" class="entry" @click.prevent="selectEntry(entry)">
+      <i v-if="typeof entry.icon == 'string' && entry.icon.startsWith('fa-')" :class="['fa-solid', entry.icon]"></i>
+      {{entry.title}}
+
+      <i v-if="entry.entries && !entry.backButton" class="fa-solid fa-angle-right" style="font-size: 70%; float: right; opacity: 50%; line-height: 200%;"></i>
+    </div>
+  </div>
+</template>
+
+<style scoped>
+  .context-menu {
+    position: absolute;
+    min-width: 10em;
+    background-color: var(--color-background);
+    border: 1px solid var(--color-border);
+    z-index: 500;
+  }
+
+  .entry {
+    padding: 0.2em 0.4em;
+  }
+
+  .entry:hover {
+    background-color: var(--color-green-dark);
+  }
+
+  i {
+    width: 1em;
+    text-align: center;
+    margin-right: 0.3em;
+  }
+</style>
diff --git a/frontend-vue/src/views/Chat.vue b/frontend-vue/src/views/Chat.vue
index 77e05e2..d6fd74b 100644
--- a/frontend-vue/src/views/Chat.vue
+++ b/frontend-vue/src/views/Chat.vue
@@ -20,9 +20,10 @@
   // Chat State
   const chat = ref({});
   const messages = ref([]);
+  const unsentMessages = ref([]);
   const currentThreadId = ref(null);
   const chatEntries = computed(() => {
-    return computeChatEntries(messages.value);
+    return computeChatEntries(messages.value.concat(unsentMessages.value));
   });
 
   // UI State
@@ -30,6 +31,20 @@
   const editingMessageId = ref(null);
   const noteMode = ref(false);
 
+  const editInfo = computed(() => {
+    if (editingMessageId.value != null) {
+      if (noteMode.value) {
+        return `Editing Note ${editingMessageId.value}`;
+      } else {
+        return `Editing ${editingMessageId.value}`;
+      }
+    } else if (noteMode.value) {
+      return 'Editing Note';
+    } else {
+      return null;
+    }
+  });
+
   let _isMounted = false;
   let unsubscribeChat = null;
 
@@ -59,7 +74,19 @@
     });
 
     unsubscribeChat = backend.onChatMessages(chatId, it => {
-      if (it.sender == 'user') return;
+      if (it.sender == 'user') {
+        let unsent = unsentMessages.value.shift();
+        if (unsent) {
+          if (unsent.content == it.content) {
+            unsent.id = it.id;
+            addMessage(unsent);
+            return;
+          } else {
+            // Remove from unsent list and add message as received
+            ui.alert("Unsent messages received differently");
+          }
+        }
+      }
 
       addMessage({
         id: it.id,
@@ -133,10 +160,13 @@
   const inputFieldElem = ref(null);
   const chatContainerElem = ref(null);
 
-  function addMessage (message) {
+  function addMessage (message, options={}) {
     requestRescroll();
-    message.id = _messageNonce++;
-    messages.value.push(message);
+    if (options.unsent) {
+      unsentMessages.value.push(message);
+    } else {
+      messages.value.push(message);
+    }
   }
 
   async function sendMessage () {
@@ -167,9 +197,9 @@
         content,
         threadId,
       };
-      addMessage(newMessage);
+      addMessage(newMessage, {unsent: true});
     } else {
-      const messageRef = messages.firstWhere((element) => element.id == messageId);
+      const messageRef = messages.value.find((it) => it.id == messageId);
 
       backend.sendAction("update-chat-message", {
         messageId, content,
@@ -270,9 +300,51 @@
     }
   }
 
+  function editMessage (message) {
+    let elem = inputFieldElem.value;
+    if (message) {
+      editingMessageId.value = message.id;
+      elem.innerText = message.content;
+    } else {
+      editingMessageId.value = null;
+      elem.innerText = "";
+    }
+  }
+
 
   // === UI Helper Functions === //
 
+  async function chatEntryContextMenu (message) {
+    let selected = await ui.contextMenu([
+      {value: 'pin', title: "Pin message"},
+      {value: 'edit', title: "Edit message"},
+      {value: 'start-thread', title: "Start thread from here"},
+      {value: 'delete', icon: 'fa-trash', title: "Delete message"},
+    ]);
+
+    switch (selected) {
+      case 'pin': {
+        alert("Pin Message (TODO)");
+        break;
+      }
+      case 'edit': {
+        editMessage(message);
+        break;
+      }
+      case 'start-thread': {
+        alert("Start Thread (TODO)");
+        break;
+      }
+      case 'delete': {
+        if (confirm("Are you sure you want to delete this message?")) {
+          alert("Delete Message (TODO)");
+        }
+        break;
+      }
+
+    }
+  }
+
   function requestRescroll ({forceBottom=false, bottomRelative=false}={}) {
     const elem = chatContainerElem.value;
 
@@ -319,7 +391,7 @@
     <h1>{{ chat.name || 'Chat #' + chat.id }}</h1>
 
     <div class="messages-container" ref="chatContainerElem">
-      <div v-for="msg in chatEntries" :class="chatEntryClass(msg)">
+      <div v-for="msg in chatEntries" :class="chatEntryClass(msg)" @contextmenu.prevent="chatEntryContextMenu(msg)">
         <template v-if="msg.type == 'message' || msg.type == null">
           <div v-if="msg.sender != 'user'" class="sender">{{msg.sender}}</div>
           <div class="content">{{msg.content}}</div>
@@ -342,8 +414,8 @@
     </div>
 
     <div class="input-container">
-      <div v-if="noteMode" style="font-size: 75%; margin-bottom: 0.7em;">
-        Editing Note
+      <div v-if="editInfo" style="font-size: 75%; margin-bottom: 0.7em;">
+        {{editInfo}}
       </div>
 
       <div class="input-field" ref="inputFieldElem" @keydown="inputKeyDown($event)" contenteditable></div>
@@ -355,6 +427,9 @@
         <button @click="noteMode=!noteMode">
           {{noteMode ? 'Cancel Note' : 'Make Note'}}
         </button>
+        <button v-if="editingMessageId != null" @click="editMessage(null)">
+          Cancel Edit
+        </button>
         <button id="send-button" @click="sendMessage()">
           Send
           <span style="font-size: 66%;">(Ctrl+Enter)</span>