diff --git a/cmd/draft.go b/cmd/draft.go
index 4da164dc..25207328 100644
--- a/cmd/draft.go
+++ b/cmd/draft.go
@@ -1,6 +1,7 @@
 package main
 
 import (
+	"encoding/json"
 	"strings"
 
 	amodels "github.com/abhinavxd/libredesk/internal/auth/models"
@@ -10,7 +11,8 @@ import (
 )
 
 type draftReq struct {
-	Content string `json:"content"`
+	Content string          `json:"content"`
+	Meta    json.RawMessage `json:"meta"`
 }
 
 // handleUpsertConversationDraft saves or updates a draft for a conversation.
@@ -43,7 +45,7 @@ func handleUpsertConversationDraft(r *fastglue.Request) error {
 		return r.SendErrorEnvelope(fasthttp.StatusBadRequest, app.i18n.Ts("globals.messages.invalid", "name", "content"), nil, envelope.InputError)
 	}
 
-	draft, err := app.conversation.UpsertConversationDraft(conv.ID, user.ID, req.Content)
+	draft, err := app.conversation.UpsertConversationDraft(conv.ID, user.ID, req.Content, req.Meta)
 	if err != nil {
 		return sendErrorEnvelope(r, err)
 	}
diff --git a/config.sample.toml b/config.sample.toml
index 284736de..ae06134b 100644
--- a/config.sample.toml
+++ b/config.sample.toml
@@ -118,7 +118,7 @@ timeout = "15s"
 [conversation]
 # How often to check for conversations to unsnooze
 unsnooze_interval = "5m"
-# How long to keep drafts before deleting them (e.g., "720h", "48h")
+# How long to keep drafts before deleting them from the database. (e.g. "720h", "48h")
 draft_retention_period = "720h"
 
 [sla]
diff --git a/frontend/src/components/editor/TextEditor.vue b/frontend/src/components/editor/TextEditor.vue
index 9090fb59..f8e87f37 100644
--- a/frontend/src/components/editor/TextEditor.vue
+++ b/frontend/src/components/editor/TextEditor.vue
@@ -243,18 +243,17 @@ const editor = useEditor({
   }
 })
 
-// Watch htmlContent for external changes (like draft loading)
-watch(htmlContent, (newContent) => {
-  if (!isInternalUpdate.value && editor.value) {
-    const editorHTML = editor.value.getHTML()
-    
-    // Only update if content is actually different
-    if (newContent !== editorHTML) {
+watch(
+  htmlContent,
+  (newContent) => {
+    if (!isInternalUpdate.value && editor.value && newContent !== editor.value.getHTML()) {
       editor.value.commands.setContent(newContent || '', false)
       textContent.value = editor.value.getText()
+      editor.value.commands.focus()
     }
-  }
-})
+  },
+  { immediate: true }
+)
 
 // Insert content at cursor position when insertContent prop changes.
 watch(
diff --git a/frontend/src/composables/useDraftManager.js b/frontend/src/composables/useDraftManager.js
index 81baee67..e11aafa6 100644
--- a/frontend/src/composables/useDraftManager.js
+++ b/frontend/src/composables/useDraftManager.js
@@ -1,51 +1,101 @@
 import { ref, watch } from 'vue'
 import { watchDebounced } from '@vueuse/core'
 import { useDraftStore } from '@/stores/draftStore'
+import { useConversationStore } from '@/stores/conversation'
+import { MACRO_CONTEXT } from '@/constants/conversation'
 
 /**
  * Composable for managing draft state and persistence
  * @param key - Reactive reference to current draft key
+ * @param uploadedFiles - Optional reactive reference to uploaded files array
  */
-export function useDraftManager (key) {
+export function useDraftManager (key, uploadedFiles = null) {
   const draftStore = useDraftStore()
+  const conversationStore = useConversationStore()
   const htmlContent = ref('')
   const textContent = ref('')
-  const isLoadingDraft = ref(false)
+  const meta = ref({})
+  const isLoading = ref(false)
   const isDirty = ref(false)
+  const loadedAttachments = ref([])
+
+  /**
+   * Reset all draft state to initial values
+   */
+  const resetState = () => {
+    htmlContent.value = ''
+    textContent.value = ''
+    meta.value = {}
+    isLoading.value = false
+    isDirty.value = false
+    loadedAttachments.value = []
+  }
 
   /**
    * Load draft from backend for a given key
    */
   const loadDraft = async (key) => {
     if (!key) return
-    isLoadingDraft.value = true
-    const draft = await draftStore.getDraft(key)
-    htmlContent.value = draft.htmlContent
-    textContent.value = draft.textContent
+    isLoading.value = true
     isDirty.value = false
-    isLoadingDraft.value = false
+    try {
+      const draft = await draftStore.getDraft(key)
+      console.log("Loaded draft:", draft)
+      htmlContent.value = draft.htmlContent
+      textContent.value = draft.textContent
+      meta.value = draft.meta || {}
+      loadedAttachments.value = draft.meta?.attachments || []
+    } catch (error) {
+      resetState()
+    } finally {
+      isLoading.value = false
+    }
   }
 
   /**
    * Save draft to store
    */
   const saveDraft = async (key) => {
-    if (!key || isLoadingDraft.value) return
-    await draftStore.setDraft(key, htmlContent.value, textContent.value)
-    isDirty.value = false
+    if (!key || isLoading.value) return
+    if (!isDirty.value) return
+    try {
+      const macroActions = getCurrentMacroActions()
+      let meta = {}
+      if (macroActions.length > 0) {
+        meta.macro_actions = macroActions
+      }
+      if (uploadedFiles && uploadedFiles.value && uploadedFiles.value.length > 0) {
+        meta.attachments = uploadedFiles.value
+      }
+      await draftStore.setDraft(key, htmlContent.value, textContent.value, meta)
+      isDirty.value = false
+    } catch (error) {
+      // pass
+    }
   }
 
   /**
    * Clear draft and local state
    */
-  const clearDraft = (key) => {
+  const clearDraft = async (key) => {
     if (!key) return
-    isLoadingDraft.value = true
-    draftStore.clearDraft(key)
-    htmlContent.value = ''
-    textContent.value = ''
-    isDirty.value = false
-    isLoadingDraft.value = false
+    isLoading.value = true
+    try {
+      await draftStore.clearDraft(key)
+      resetState()
+    } catch (error) {
+      // pass
+    } finally {
+      isLoading.value = false
+    }
+  }
+
+  /**
+   * Returns current set macro ID from draft meta
+   */
+  const getCurrentMacroActions = () => {
+    const macro = conversationStore.getMacro(MACRO_CONTEXT.REPLY)
+    return macro ? macro.actions : []
   }
 
   /**
@@ -61,8 +111,12 @@ export function useDraftManager (key) {
     async (newKey, oldKey) => {
       // Save old draft first if content has changed.
       if (newKey != oldKey && isDirty.value && hasDraftContent()) {
-        draftStore.setDraft(oldKey, htmlContent.value, textContent.value)
-        isDirty.value = false
+        try {
+          await saveDraft(oldKey)
+          isDirty.value = false
+        } catch (error) {
+          // pass
+        }
       }
 
       // Load new draft.
@@ -70,35 +124,44 @@ export function useDraftManager (key) {
         await loadDraft(newKey)
       } else if (!newKey && oldKey) {
         // Clear state.
-        isLoadingDraft.value = true
-        htmlContent.value = ''
-        textContent.value = ''
-        isDirty.value = false
-        isLoadingDraft.value = false
+        isLoading.value = true
+        resetState()
+        isLoading.value = false
       }
     },
     { immediate: true }
   )
 
-  // Auto-save draft when content changes (debounced to avoid excessive writes)
+  // Auto-save draft when content, macro, or uploaded files change (debounced)
+  const watchSources = [
+    htmlContent,
+    textContent,
+    () => conversationStore.macros[MACRO_CONTEXT.REPLY]
+  ]
+  if (uploadedFiles) {
+    watchSources.push(uploadedFiles)
+  }
+
   watchDebounced(
-    [htmlContent, textContent],
+    watchSources,
     async () => {
-      if (!isLoadingDraft.value && key.value) {
+      if (!isLoading.value && key.value) {
         isDirty.value = true
         await saveDraft(key.value)
       }
     },
-    { debounce: 500 }
+    { debounce: 250, deep: true }
   )
 
   return {
+    meta,
     htmlContent,
     textContent,
-    isLoadingDraft,
+    isLoading,
     loadDraft,
     saveDraft,
     clearDraft,
-    hasDraftContent
+    hasDraftContent,
+    loadedAttachments
   }
 }
\ No newline at end of file
diff --git a/frontend/src/composables/useFileUpload.js b/frontend/src/composables/useFileUpload.js
index 5f43f3a4..2b58ffeb 100644
--- a/frontend/src/composables/useFileUpload.js
+++ b/frontend/src/composables/useFileUpload.js
@@ -127,6 +127,19 @@ export function useFileUpload (options = {}) {
         }
     }
 
+    /**
+     * Replace all media files with new files
+     * @param {Array} files - Array of file objects to set
+     */
+    const setMediaFiles = (files) => {
+        if (Array.isArray(mediaFiles.value)) {
+            mediaFiles.value = files
+        } else {
+            mediaFiles.length = 0
+            mediaFiles.push(...files)
+        }
+    }
+
     return {
         // State
         uploadingFiles: readonly(uploadingFiles),
@@ -137,6 +150,7 @@ export function useFileUpload (options = {}) {
         handleFileUpload,
         handleFileDelete,
         uploadFiles,
-        clearMediaFiles
+        clearMediaFiles,
+        setMediaFiles
     }
 }
\ No newline at end of file
diff --git a/frontend/src/constants/conversation.js b/frontend/src/constants/conversation.js
index 7f294cff..8b8f2840 100644
--- a/frontend/src/constants/conversation.js
+++ b/frontend/src/constants/conversation.js
@@ -13,4 +13,9 @@ export const CONVERSATION_DEFAULT_STATUSES = {
   CLOSED: 'Closed',
 }
 
-export const CONVERSATION_DEFAULT_STATUSES_LIST = Object.values(CONVERSATION_DEFAULT_STATUSES);
\ No newline at end of file
+export const CONVERSATION_DEFAULT_STATUSES_LIST = Object.values(CONVERSATION_DEFAULT_STATUSES);
+
+export const MACRO_CONTEXT = {
+  REPLY: 'reply',
+  NEW_CONVERSATION: 'new-conversation'
+}
\ No newline at end of file
diff --git a/frontend/src/features/command/CommandBox.vue b/frontend/src/features/command/CommandBox.vue
index fb5e0497..00f04cc5 100644
--- a/frontend/src/features/command/CommandBox.vue
+++ b/frontend/src/features/command/CommandBox.vue
@@ -211,7 +211,7 @@ import { useMagicKeys } from '@vueuse/core'
 import { CalendarIcon } from 'lucide-vue-next'
 import { useConversationStore } from '@/stores/conversation'
 import { useMacroStore } from '@/stores/macro'
-import { CONVERSATION_DEFAULT_STATUSES } from '@/constants/conversation'
+import { CONVERSATION_DEFAULT_STATUSES, MACRO_CONTEXT } from '@/constants/conversation'
 import { Users, User, Pin, Rocket, Tags, Zap } from 'lucide-vue-next'
 import {
   CommandDialog,
@@ -267,9 +267,9 @@ function handleApplyMacro(macro) {
   // Create a deep copy.
   const plainMacro = JSON.parse(JSON.stringify(macro))
   if (nestedCommand.value === 'apply-macro-to-new-conversation') {
-    conversationStore.setMacro(plainMacro, 'new-conversation')
+    conversationStore.setMacro(plainMacro, MACRO_CONTEXT.NEW_CONVERSATION)
   } else {
-    conversationStore.setMacro(plainMacro, 'reply')
+    conversationStore.setMacro(plainMacro, MACRO_CONTEXT.REPLY)
   }
   toggleOpen()
 }
diff --git a/frontend/src/features/conversation/CreateConversation.vue b/frontend/src/features/conversation/CreateConversation.vue
index 4ce2c66e..e7b6901d 100644
--- a/frontend/src/features/conversation/CreateConversation.vue
+++ b/frontend/src/features/conversation/CreateConversation.vue
@@ -185,10 +185,10 @@
 
                     <!-- Macro preview -->
                     <MacroActionsPreview
-                      v-if="conversationStore.getMacro('new-conversation').actions?.length > 0"
-                      :actions="conversationStore.getMacro('new-conversation')?.actions || []"
+                      v-if="conversationStore.getMacro(MACRO_CONTEXT.NEW_CONVERSATION).actions?.length > 0"
+                      :actions="conversationStore.getMacro(MACRO_CONTEXT.NEW_CONVERSATION)?.actions || []"
                       :onRemove="
-                        (action) => conversationStore.removeMacroAction(action, 'new-conversation')
+                        (action) => conversationStore.removeMacroAction(action, MACRO_CONTEXT.NEW_CONVERSATION)
                       "
                       class="mt-2 flex-shrink-0"
                     />
@@ -245,6 +245,7 @@ import { useConversationStore } from '@/stores/conversation'
 import MacroActionsPreview from '@/features/conversation/MacroActionsPreview.vue'
 import ReplyBoxMenuBar from '@/features/conversation/ReplyBoxMenuBar.vue'
 import { EMITTER_EVENTS } from '@/constants/emitterEvents.js'
+import { MACRO_CONTEXT } from '@/constants/conversation'
 import { useEmitter } from '@/composables/useEmitter'
 import { handleHTTPError } from '@/utils/http'
 import { useInboxStore } from '@/stores/inbox'
@@ -328,7 +329,7 @@ const formSchema = z.object({
 onUnmounted(() => {
   clearTimeout(timeoutId)
   clearMediaFiles()
-  conversationStore.resetMacro('new-conversation')
+  conversationStore.resetMacro(MACRO_CONTEXT.NEW_CONVERSATION)
   emitter.emit(EMITTER_EVENTS.SET_NESTED_COMMAND, {
     command: null,
     open: false
@@ -406,7 +407,7 @@ const createConversation = form.handleSubmit(async (values) => {
     const conversationUUID = conversation.data.data.uuid
 
     // Get macro from context, and set if any actions are available.
-    const macro = conversationStore.getMacro('new-conversation')
+    const macro = conversationStore.getMacro(MACRO_CONTEXT.NEW_CONVERSATION)
     if (conversationUUID !== '' && macro?.id && macro?.actions?.length > 0) {
       try {
         await api.applyMacro(conversationUUID, macro.id, macro.actions)
@@ -433,9 +434,9 @@ const createConversation = form.handleSubmit(async (values) => {
  * Watches for changes in the macro id and update message content.
  */
 watch(
-  () => conversationStore.getMacro('new-conversation').id,
+  () => conversationStore.getMacro(MACRO_CONTEXT.NEW_CONVERSATION).id,
   () => {
-    form.setFieldValue('content', conversationStore.getMacro('new-conversation').message_content)
+    form.setFieldValue('content', conversationStore.getMacro(MACRO_CONTEXT.NEW_CONVERSATION).message_content)
   },
   { deep: true }
 )
diff --git a/frontend/src/features/conversation/ReplyBox.vue b/frontend/src/features/conversation/ReplyBox.vue
index 783667b3..8cd8894f 100644
--- a/frontend/src/features/conversation/ReplyBox.vue
+++ b/frontend/src/features/conversation/ReplyBox.vue
@@ -51,6 +51,7 @@
           :isFullscreen="true"
           :aiPrompts="aiPrompts"
           :isSending="isSending"
+          :isDraftLoading="isDraftLoading"
           :uploadingFiles="uploadingFiles"
           :uploadedFiles="mediaFiles"
           v-model:htmlContent="htmlContent"
@@ -81,6 +82,7 @@
         :isFullscreen="false"
         :aiPrompts="aiPrompts"
         :isSending="isSending"
+        :isDraftLoading="isDraftLoading"
         :uploadingFiles="uploadingFiles"
         :uploadedFiles="mediaFiles"
         v-model:htmlContent="htmlContent"
@@ -102,9 +104,10 @@
 </template>
 
 <script setup>
-import { ref, watch, computed } from 'vue'
+import { ref, watch, computed, toRaw } from 'vue'
 import { handleHTTPError } from '@/utils/http'
 import { EMITTER_EVENTS } from '@/constants/emitterEvents.js'
+import { MACRO_CONTEXT } from '@/constants/conversation'
 import { useUserStore } from '@/stores/user'
 import { useDraftManager } from '@/composables/useDraftManager'
 import api from '@/api'
@@ -147,19 +150,27 @@ const emitter = useEmitter()
 const userStore = useUserStore()
 
 // Setup file upload composable
-const { uploadingFiles, handleFileUpload, handleFileDelete, mediaFiles, clearMediaFiles } =
-  useFileUpload({
-    linkedModel: 'messages'
-  })
+const {
+  uploadingFiles,
+  handleFileUpload,
+  handleFileDelete,
+  mediaFiles,
+  clearMediaFiles,
+  setMediaFiles
+} = useFileUpload({
+  linkedModel: 'messages'
+})
 
 // Setup draft management composable
 const currentDraftKey = computed(() => conversationStore.current?.uuid || null)
 const {
   htmlContent,
   textContent,
-  isLoadingDraft,
-  clearDraft
-} = useDraftManager(currentDraftKey)
+  isLoading: isDraftLoading,
+  meta: draftMeta,
+  clearDraft,
+  loadedAttachments
+} = useDraftManager(currentDraftKey, mediaFiles)
 
 // Rest of existing state
 const openAIKeyPrompt = ref(false)
@@ -285,8 +296,8 @@ const processSend = async () => {
     }
 
     // Apply macro actions if any, for macro errors just show toast and clear the editor.
-    const macroID = conversationStore.getMacro('reply')?.id
-    const macroActions = conversationStore.getMacro('reply')?.actions || []
+    const macroID = conversationStore.getMacro(MACRO_CONTEXT.REPLY)?.id
+    const macroActions = conversationStore.getMacro(MACRO_CONTEXT.REPLY)?.actions || []
     if (macroID > 0 && macroActions.length > 0) {
       try {
         await api.applyMacro(conversationStore.current.uuid, macroID, macroActions)
@@ -306,11 +317,11 @@ const processSend = async () => {
   } finally {
     // If API has NOT errored clear state.
     if (hasMessageSendingErrored === false) {
-      // Clear draft using composable
+      // Clear draft from backend.
       clearDraft(currentDraftKey.value)
-      
-      // Clear macro.
-      conversationStore.resetMacro('reply')
+
+      // Clear macro for this conversation reply.
+      conversationStore.resetMacro(MACRO_CONTEXT.REPLY)
 
       // Clear media files.
       clearMediaFiles()
@@ -321,20 +332,53 @@ const processSend = async () => {
     isSending.value = false
   }
 }
+
 /**
  * Watches for changes in the conversation's macro id and update message content.
  */
 watch(
   () => conversationStore.getMacro('reply').id,
   (newId, oldId) => {
-    // Only update if macro ID actually changed and is not undefined/0
-    if (newId && newId !== oldId && conversationStore.getMacro('reply').message_content) {
+    // No macro set.
+    if (!newId) return
+
+    // If macro ID has changed and there is message content, update editor content.
+    if (newId !== oldId && conversationStore.getMacro('reply').message_content) {
       htmlContent.value = conversationStore.getMacro('reply').message_content
     }
   },
   { deep: true }
 )
 
+/**
+ * Watch changes in draft meta which has macro actions and update conversation store.
+ */
+watch(
+  () => draftMeta,
+  (newMeta) => {
+    if (newMeta.value?.macro_actions) {
+      conversationStore.setMacroActions(
+        [...toRaw(newMeta.value.macro_actions)],
+        MACRO_CONTEXT.REPLY
+      )
+    }
+  },
+  { deep: true }
+)
+
+/**
+ * Watch for loaded attachments from draft and restore them to mediaFiles.
+ */
+watch(
+  loadedAttachments,
+  (newAttachments) => {
+    if (newAttachments && newAttachments.length > 0) {
+      setMediaFiles([...newAttachments])
+    }
+  },
+  { deep: true }
+)
+
 // Initialize to, cc, and bcc fields with the current conversation's values.
 watch(
   () => conversationStore.currentCC,
@@ -364,4 +408,13 @@ watch(
   },
   { deep: true, immediate: true }
 )
-</script>
\ No newline at end of file
+
+// Clear media files and reset macro when conversation changes.
+watch(
+  () => conversationStore.current?.uuid,
+  () => {
+    clearMediaFiles()
+    conversationStore.resetMacro(MACRO_CONTEXT.REPLY)
+  }
+)
+</script>
diff --git a/frontend/src/features/conversation/ReplyBoxContent.vue b/frontend/src/features/conversation/ReplyBoxContent.vue
index f475b6ad..d3b214b3 100644
--- a/frontend/src/features/conversation/ReplyBoxContent.vue
+++ b/frontend/src/features/conversation/ReplyBoxContent.vue
@@ -97,9 +97,9 @@
 
     <!-- Macro preview -->
     <MacroActionsPreview
-      v-if="conversationStore.getMacro('reply')?.actions?.length > 0"
-      :actions="conversationStore.getMacro('reply').actions"
-      :onRemove="(action) => conversationStore.removeMacroAction(action, 'reply')"
+      v-if="conversationStore.getMacro(MACRO_CONTEXT.REPLY)?.actions?.length > 0"
+      :actions="conversationStore.getMacro(MACRO_CONTEXT.REPLY).actions"
+      :onRemove="(action) => conversationStore.removeMacroAction(action, MACRO_CONTEXT.REPLY)"
       class="mt-2"
     />
 
@@ -128,6 +128,7 @@
 <script setup>
 import { ref, computed, nextTick, watch } from 'vue'
 import { EMITTER_EVENTS } from '@/constants/emitterEvents.js'
+import { MACRO_CONTEXT } from '@/constants/conversation'
 import { Maximize2, Minimize2 } from 'lucide-vue-next'
 import Editor from '@/components/editor/TextEditor.vue'
 import { useConversationStore } from '@/stores/conversation'
@@ -173,6 +174,11 @@ const props = defineProps({
     type: Array,
     required: false,
     default: () => []
+  },
+  isDraftLoading: {
+    type: Boolean,
+    required: false,
+    default: false
   }
 })
 
@@ -211,7 +217,7 @@ const enableSend = computed(() => {
       conversationStore.getMacro('reply')?.actions?.length > 0 ||
       props.uploadedFiles.length > 0) &&
     emailErrors.value.length === 0 &&
-    !props.uploadingFiles.length
+    !props.uploadingFiles.length && !props.isDraftLoading
   )
 })
 
diff --git a/frontend/src/stores/conversation.js b/frontend/src/stores/conversation.js
index 9d30b76c..4f84ae96 100644
--- a/frontend/src/stores/conversation.js
+++ b/frontend/src/stores/conversation.js
@@ -662,10 +662,17 @@ export const useConversationStore = defineStore('conversation', () => {
 
 
   /** Macros set for new conversation or an open conversation **/
-  async function setMacro (macro, context) {
+  function setMacro (macro, context) {
     macros.value[context] = macro
   }
 
+  function setMacroActions (actions, context) {
+    if (!macros.value[context]) {
+      macros.value[context] = {}
+    }
+    macros.value[context].actions = actions
+  }
+
   function getMacro (context) {
     return macros.value[context] || {}
   }
@@ -680,6 +687,7 @@ export const useConversationStore = defineStore('conversation', () => {
   }
 
   return {
+    macros,
     conversations,
     conversation,
     messages,
@@ -721,6 +729,7 @@ export const useConversationStore = defineStore('conversation', () => {
     getMacro,
     setMacro,
     resetMacro,
+    setMacroActions,
     removeAssignee,
     getListSortField,
     getListStatus,
diff --git a/frontend/src/stores/draftStore.js b/frontend/src/stores/draftStore.js
index d1f85bef..9a995962 100644
--- a/frontend/src/stores/draftStore.js
+++ b/frontend/src/stores/draftStore.js
@@ -14,7 +14,8 @@ export const useDraftStore = defineStore('drafts', () => {
       return {
         htmlContent: draft.content || '',
         // We only store HTML in backend.
-        textContent: ''
+        textContent: '',
+        meta: draft.meta || {}
       }
     } catch (error) {
       return { htmlContent: '', textContent: '' }
@@ -24,14 +25,11 @@ export const useDraftStore = defineStore('drafts', () => {
   /**
    * Save draft to backend 
    */
-  const setDraft = async (uuid, htmlContent, textContent) => {
+  const setDraft = async (uuid, htmlContent, textContent, meta = {}) => {
     if (!uuid) return
 
-    if (!textContent || textContent.trim() === '') return
-    if (!htmlContent || htmlContent.trim() === '') return
-
     try {
-      await api.saveDraft(uuid, { content: htmlContent })
+      await api.saveDraft(uuid, { content: htmlContent, meta })
     } catch (error) {
       // pass
     }
diff --git a/internal/conversation/drafts.go b/internal/conversation/drafts.go
index 81bab8ba..9521f281 100644
--- a/internal/conversation/drafts.go
+++ b/internal/conversation/drafts.go
@@ -3,6 +3,7 @@ package conversation
 import (
 	"context"
 	"database/sql"
+	"encoding/json"
 	"fmt"
 	"time"
 
@@ -11,10 +12,10 @@ import (
 )
 
 // UpsertConversationDraft saves or updates a draft for a conversation.
-func (m *Manager) UpsertConversationDraft(conversationID, userID int, content string) (models.ConversationDraft, error) {
+func (m *Manager) UpsertConversationDraft(conversationID, userID int, content string, meta json.RawMessage) (models.ConversationDraft, error) {
 	var draft models.ConversationDraft
 
-	if err := m.q.UpsertConversationDraft.Get(&draft, conversationID, userID, content); err != nil {
+	if err := m.q.UpsertConversationDraft.Get(&draft, conversationID, userID, content, meta); err != nil {
 		m.lo.Error("error upserting conversation draft", "conversation_id", conversationID, "user_id", userID, "error", err)
 		return draft, envelope.NewError(envelope.GeneralError, m.i18n.Ts("globals.messages.errorUpdating", "name", "draft"), nil)
 	}
diff --git a/internal/conversation/models/models.go b/internal/conversation/models/models.go
index 092a9b07..e48f75d6 100644
--- a/internal/conversation/models/models.go
+++ b/internal/conversation/models/models.go
@@ -272,10 +272,11 @@ type Priority struct {
 
 // ConversationDraft represents a draft reply for a conversation.
 type ConversationDraft struct {
-	ID             int64     `db:"id" json:"id"`
-	ConversationID int64     `db:"conversation_id" json:"conversation_id"`
-	UserID         int64     `db:"user_id" json:"user_id"`
-	Content        string    `db:"content" json:"content"`
-	CreatedAt      time.Time `db:"created_at" json:"created_at"`
-	UpdatedAt      time.Time `db:"updated_at" json:"updated_at"`
+	ID             int64           `db:"id" json:"id"`
+	ConversationID int64           `db:"conversation_id" json:"conversation_id"`
+	UserID         int64           `db:"user_id" json:"user_id"`
+	Content        string          `db:"content" json:"content"`
+	CreatedAt      time.Time       `db:"created_at" json:"created_at"`
+	UpdatedAt      time.Time       `db:"updated_at" json:"updated_at"`
+	Meta           json.RawMessage `db:"meta" json:"meta"`
 }
diff --git a/internal/conversation/queries.sql b/internal/conversation/queries.sql
index 9a75e098..5ec2ed85 100644
--- a/internal/conversation/queries.sql
+++ b/internal/conversation/queries.sql
@@ -559,10 +559,10 @@ ORDER BY m.created_at DESC
 LIMIT 1;
 
 -- name: upsert-conversation-draft
-INSERT INTO conversation_drafts (conversation_id, user_id, content, updated_at)
-VALUES ($1, $2, $3, NOW())
+INSERT INTO conversation_drafts (conversation_id, user_id, content, meta, updated_at)
+VALUES ($1, $2, $3, $4, NOW())
 ON CONFLICT (conversation_id, user_id)
-DO UPDATE SET content = EXCLUDED.content, updated_at = NOW()
+DO UPDATE SET content = EXCLUDED.content, meta = EXCLUDED.meta, updated_at = NOW()
 RETURNING *;
 
 -- name: get-conversation-draft
diff --git a/internal/migrations/v0.9.1.go b/internal/migrations/v0.9.1.go
index e5953bad..6d0121f0 100644
--- a/internal/migrations/v0.9.1.go
+++ b/internal/migrations/v0.9.1.go
@@ -17,7 +17,7 @@ func V0_9_1(db *sqlx.DB, fs stuffbin.FileSystem, ko *koanf.Koanf) error {
 			conversation_id BIGINT REFERENCES conversations(id) ON DELETE CASCADE ON UPDATE CASCADE NOT NULL,
 			user_id BIGINT REFERENCES users(id) ON DELETE CASCADE ON UPDATE CASCADE NOT NULL,
 			content TEXT NOT NULL,
-			CONSTRAINT constraint_conversation_drafts_on_content CHECK (length(content) <= 10000)
+			meta JSONB DEFAULT '{}'::jsonb NOT NULL
 		);
 	`)
 	if err != nil {
diff --git a/schema.sql b/schema.sql
index ae283ed5..017a2ed3 100644
--- a/schema.sql
+++ b/schema.sql
@@ -306,6 +306,7 @@ CREATE TABLE conversation_drafts (
     conversation_id BIGINT REFERENCES conversations(id) ON DELETE CASCADE ON UPDATE CASCADE NOT NULL,
     user_id BIGINT REFERENCES users(id) ON DELETE CASCADE ON UPDATE CASCADE NOT NULL,
     content TEXT NOT NULL,
+	meta JSONB DEFAULT '{}'::jsonb NOT NULL
 );
 CREATE UNIQUE INDEX index_uniq_conversation_drafts_on_conversation_id_and_user_id ON conversation_drafts (conversation_id, user_id);