Merge pull request #85 from abhinavxd/fix/email-channel-to-bcc-cc

Fix and Improve Email Recipients Handling in Conversations
2026-09-23 19:06:35 +00:00 · 2025-05-15 11:08:55 +05:30
parent 88e07c324d 6c9eca3d81
commit f657a873bc
21 changed files with 590 additions and 236 deletions
@@ -11,6 +11,7 @@ import (
 	"github.com/abhinavxd/libredesk/internal/automation/models"
 	cmodels "github.com/abhinavxd/libredesk/internal/conversation/models"
 	"github.com/abhinavxd/libredesk/internal/envelope"
+	"github.com/abhinavxd/libredesk/internal/stringutil"
 	umodels "github.com/abhinavxd/libredesk/internal/user/models"
 	"github.com/valyala/fasthttp"
 	"github.com/volatiletech/null/v9"
@@ -640,24 +641,29 @@ func handleCreateConversation(r *fastglue.Request) error {
 		firstName       = strings.TrimSpace(string(r.RequestCtx.PostArgs().Peek("first_name")))
 		lastName        = strings.TrimSpace(string(r.RequestCtx.PostArgs().Peek("last_name")))
 		subject         = strings.TrimSpace(string(r.RequestCtx.PostArgs().Peek("subject")))
-		content         = string(r.RequestCtx.PostArgs().Peek("content"))
+		content         = strings.TrimSpace(string(r.RequestCtx.PostArgs().Peek("content")))
+		to              = []string{email}
 	)
+
 	// Validate required fields
 	if inboxID <= 0 {
 		return r.SendErrorEnvelope(fasthttp.StatusBadRequest, app.i18n.Ts("globals.messages.fieldRequired", "name", "`inbox_id`"), nil, envelope.InputError)
 	}
-	if strings.TrimSpace(subject) == "" {
+	if subject == "" {
 		return r.SendErrorEnvelope(fasthttp.StatusBadRequest, app.i18n.Ts("globals.messages.fieldRequired", "name", "`subject`"), nil, envelope.InputError)
 	}
-	if strings.TrimSpace(content) == "" {
+	if content == "" {
 		return r.SendErrorEnvelope(fasthttp.StatusBadRequest, app.i18n.Ts("globals.messages.fieldRequired", "name", "`content`"), nil, envelope.InputError)
 	}
-	if strings.TrimSpace(email) == "" {
+	if email == "" {
 		return r.SendErrorEnvelope(fasthttp.StatusBadRequest, app.i18n.Ts("globals.messages.fieldRequired", "name", "`contact_email`"), nil, envelope.InputError)
 	}
 	if firstName == "" {
 		return r.SendErrorEnvelope(fasthttp.StatusBadRequest, app.i18n.Ts("globals.messages.fieldRequired", "name", "`first_name`"), nil, envelope.InputError)
 	}
+	if !stringutil.ValidEmail(email) {
+		return r.SendErrorEnvelope(fasthttp.StatusBadRequest, app.i18n.Ts("globals.messages.invalid", "name", "`contact_email`"), nil, envelope.InputError)
+	}

 	user, err := app.user.GetAgent(auser.ID, "")
 	if err != nil {
@@ -690,8 +696,8 @@ func handleCreateConversation(r *fastglue.Request) error {
 		contact.ID,
 		contact.ContactChannelID,
 		inboxID,
-		"", /** last_message **/
-		time.Now(),
+		"",         /** last_message **/
+		time.Now(), /** last_message_at **/
 		subject,
 		true, /** append reference number to subject **/
 	)
@@ -701,8 +707,8 @@ func handleCreateConversation(r *fastglue.Request) error {
 	}

 	// Send reply to the created conversation.
-	if err := app.conversation.SendReply(nil /**media**/, inboxID, auser.ID, conversationUUID, content, nil /**cc**/, nil /**bcc**/, map[string]any{} /**meta**/); err != nil {
-		// Delete the conversation if sending the reply fails.
+	if err := app.conversation.SendReply(nil /**media**/, inboxID, auser.ID /**sender_id**/, conversationUUID, content, to, nil /**cc**/, nil /**bcc**/, map[string]any{} /**meta**/); err != nil {
+		// Delete the conversation if reply fails.
 		if err := app.conversation.DeleteConversation(conversationUUID); err != nil {
 			app.lo.Error("error deleting conversation", "error", err)
 		}
@@ -15,6 +15,7 @@ type messageReq struct {
 	Attachments []int    `json:"attachments"`
 	Message     string   `json:"message"`
 	Private     bool     `json:"private"`
+	To          []string `json:"to"`
 	CC          []string `json:"cc"`
 	BCC         []string `json:"bcc"`
 }
@@ -140,7 +141,7 @@ func handleSendMessage(r *fastglue.Request) error {
 		return sendErrorEnvelope(r, err)
 	}

-	// Check permission
+	// Check access to conversation.
 	conv, err := enforceConversationAccess(app, cuuid, user)
 	if err != nil {
 		return sendErrorEnvelope(r, err)
@@ -151,6 +152,7 @@ func handleSendMessage(r *fastglue.Request) error {
 		return r.SendErrorEnvelope(fasthttp.StatusInternalServerError, app.i18n.Ts("globals.messages.errorParsing", "name", "{globals.terms.request}"), nil, envelope.InputError)
 	}

+	// Prepare attachments.
 	for _, id := range req.Attachments {
 		m, err := app.media.Get(id, "")
 		if err != nil {
@@ -165,7 +167,7 @@ func handleSendMessage(r *fastglue.Request) error {
 			return sendErrorEnvelope(r, err)
 		}
 	} else {
-		if err := app.conversation.SendReply(media, conv.InboxID, user.ID, cuuid, req.Message, req.CC, req.BCC, map[string]any{} /**meta**/); err != nil {
+		if err := app.conversation.SendReply(media, conv.InboxID, user.ID, cuuid, req.Message, req.To, req.CC, req.BCC, map[string]any{} /**meta**/); err != nil {
 			return sendErrorEnvelope(r, err)
 		}
 		// Evaluate automation rules.
@@ -183,15 +183,7 @@
 }

 .message-bubble {
-  @apply flex
-  flex-col
-  px-4
-  pt-2
-  pb-3
-  min-w-[30%] max-w-[70%]
-  border
-  overflow-x-auto
-  rounded-xl;
+  @apply flex flex-col px-4 pt-2 pb-3 w-fit min-w-[30%] max-w-full border overflow-x-auto rounded-xl;
  box-shadow: 0 1px 2px rgba(0, 0, 0, 0.05);
  table {
    width: 100% !important;
@@ -97,6 +97,18 @@
      </FormItem>
    </FormField>

+    <!-- Max Message Retries Field -->
+    <FormField v-slot="{ componentField }" name="max_msg_retries">
+      <FormItem>
+        <FormLabel>{{ $t('admin.inbox.maxRetries') }}</FormLabel>
+        <FormControl>
+          <Input type="number" placeholder="3" v-bind="componentField" />
+        </FormControl>
+        <FormMessage />
+        <FormDescription> {{ $t('admin.inbox.maxRetries.description') }} </FormDescription>
+      </FormItem>
+    </FormField>
+
    <!-- Authentication Protocol Field -->
    <FormField v-slot="{ componentField }" name="auth_protocol">
      <FormItem>
@@ -136,18 +148,6 @@
      </FormItem>
    </FormField>

-    <!-- Max Message Retries Field -->
-    <FormField v-slot="{ componentField }" name="max_msg_retries">
-      <FormItem>
-        <FormLabel>{{ $t('admin.inbox.maxRetries') }}</FormLabel>
-        <FormControl>
-          <Input type="number" placeholder="3" v-bind="componentField" />
-        </FormControl>
-        <FormMessage />
-        <FormDescription> {{ $t('admin.inbox.maxRetries.description') }} </FormDescription>
-      </FormItem>
-    </FormField>
-
    <!-- HELO Hostname Field -->
    <FormField v-slot="{ componentField }" name="hello_hostname">
      <FormItem>
@@ -53,30 +53,20 @@
          :isSending="isSending"
          :uploadingFiles="uploadingFiles"
          :clearEditorContent="clearEditorContent"
-          :htmlContent="htmlContent"
-          :textContent="textContent"
-          :selectedText="selectedText"
-          :isBold="isBold"
-          :isItalic="isItalic"
-          :cursorPosition="cursorPosition"
          :contentToSet="contentToSet"
-          :cc="cc"
-          :bcc="bcc"
-          :emailErrors="emailErrors"
-          :messageType="messageType"
-          :showBcc="showBcc"
-          @update:htmlContent="htmlContent = $event"
-          @update:textContent="textContent = $event"
-          @update:selectedText="selectedText = $event"
-          @update:isBold="isBold = $event"
-          @update:isItalic="isItalic = $event"
-          @update:cursorPosition="cursorPosition = $event"
-          @toggleFullscreen="isEditorFullscreen = false"
-          @update:messageType="messageType = $event"
-          @update:cc="cc = $event"
-          @update:bcc="bcc = $event"
-          @update:showBcc="showBcc = $event"
-          @updateEmailErrors="emailErrors = $event"
+          v-model:htmlContent="htmlContent"
+          v-model:textContent="textContent"
+          v-model:selectedText="selectedText"
+          v-model:isBold="isBold"
+          v-model:isItalic="isItalic"
+          v-model:cursorPosition="cursorPosition"
+          v-model:to="to"
+          v-model:cc="cc"
+          v-model:bcc="bcc"
+          v-model:emailErrors="emailErrors"
+          v-model:messageType="messageType"
+          v-model:showBcc="showBcc"
+          @toggleFullscreen="isEditorFullscreen = true"
          @send="processSend"
          @fileUpload="handleFileUpload"
          @inlineImageUpload="handleInlineImageUpload"
@@ -99,30 +89,20 @@
        :isSending="isSending"
        :uploadingFiles="uploadingFiles"
        :clearEditorContent="clearEditorContent"
-        :htmlContent="htmlContent"
-        :textContent="textContent"
-        :selectedText="selectedText"
-        :isBold="isBold"
-        :isItalic="isItalic"
-        :cursorPosition="cursorPosition"
        :contentToSet="contentToSet"
-        :cc="cc"
-        :bcc="bcc"
-        :emailErrors="emailErrors"
-        :messageType="messageType"
-        :showBcc="showBcc"
-        @update:htmlContent="htmlContent = $event"
-        @update:textContent="textContent = $event"
-        @update:selectedText="selectedText = $event"
-        @update:isBold="isBold = $event"
-        @update:isItalic="isItalic = $event"
-        @update:cursorPosition="cursorPosition = $event"
+        v-model:htmlContent="htmlContent"
+        v-model:textContent="textContent"
+        v-model:selectedText="selectedText"
+        v-model:isBold="isBold"
+        v-model:isItalic="isItalic"
+        v-model:cursorPosition="cursorPosition"
+        v-model:to="to"
+        v-model:cc="cc"
+        v-model:bcc="bcc"
+        v-model:emailErrors="emailErrors"
+        v-model:messageType="messageType"
+        v-model:showBcc="showBcc"
        @toggleFullscreen="isEditorFullscreen = true"
-        @update:messageType="messageType = $event"
-        @update:cc="cc = $event"
-        @update:bcc="bcc = $event"
-        @update:showBcc="showBcc = $event"
-        @updateEmailErrors="emailErrors = $event"
        @send="processSend"
        @fileUpload="handleFileUpload"
        @inlineImageUpload="handleInlineImageUpload"
@@ -183,6 +163,7 @@ const clearEditorContent = ref(false)
 const isEditorFullscreen = ref(false)
 const isSending = ref(false)
 const messageType = ref('reply')
+const to = ref('')
 const cc = ref('')
 const bcc = ref('')
 const showBcc = ref(false)
@@ -353,6 +334,7 @@ const processSend = async () => {
        .map((img) => img.getAttribute('title'))
        .filter(Boolean)

+      // TODO: Inline images are not supported yet, this is some old boilerplate code.
      conversationStore.conversation.mediaFiles = conversationStore.conversation.mediaFiles.filter(
        (file) =>
          // Keep if:
@@ -375,12 +357,18 @@ const processSend = async () => {
              .split(',')
              .map((email) => email.trim())
              .filter((email) => email)
+          : [],
+        to: to.value
+          ? to.value
+              .split(',')
+              .map((email) => email.trim())
+              .filter((email) => email)
          : []
      })
    }

    // Apply macro actions if any.
-    // For macros errors just show toast and clear the editor, as most likely it's the permission error.
+    // For macro errors just show toast and clear the editor.
    if (conversationStore.conversation?.macro?.actions?.length > 0) {
      try {
        await api.applyMacro(
@@ -390,7 +378,6 @@ const processSend = async () => {
        )
      } catch (error) {
        emitter.emit(EMITTER_EVENTS.SHOW_TOAST, {
-          title: 'Error',
          variant: 'destructive',
          description: handleHTTPError(error).message
        })
@@ -453,7 +440,7 @@ watch(
  { deep: true }
 )

-// Initialize cc and bcc from conversation store
+// Initialize to, cc, and bcc fields with the current conversation's values.
 watch(
  () => conversationStore.currentCC,
  (newVal) => {
@@ -462,6 +449,14 @@ watch(
  { deep: true, immediate: true }
 )

+watch(
+  () => conversationStore.currentTo,
+  (newVal) => {
+    to.value = newVal?.join(', ') || ''
+  },
+  { immediate: true }
+)
+
 watch(
  () => conversationStore.currentBCC,
  (newVal) => {
@@ -37,11 +37,21 @@
      </span>
    </div>

-    <!-- CC and BCC fields -->
+    <!-- To, CC, and BCC fields -->
    <div
      :class="['space-y-3', isFullscreen ? 'p-4 border-b border-border' : 'mb-4']"
      v-if="messageType === 'reply'"
    >
+      <div class="flex items-center space-x-2">
+        <label class="w-12 text-sm font-medium text-muted-foreground">To:</label>
+        <Input
+          type="text"
+          :placeholder="t('replyBox.emailAddresess')"
+          v-model="to"
+          class="flex-grow px-3 py-2 text-sm border rounded-md focus:ring-2 focus:ring-ring"
+          @blur="validateEmails('to')"
+        />
+      </div>
      <div class="flex items-center space-x-2">
        <label class="w-12 text-sm font-medium text-muted-foreground">CC:</label>
        <Input
@@ -71,7 +81,7 @@
      </div>
    </div>

-    <!-- CC and BCC field validation errors -->
+    <!-- email errors -->
    <div
      v-if="emailErrors.length > 0"
      class="mb-4 px-2 py-1 bg-destructive/10 border border-destructive text-destructive rounded"
@@ -148,9 +158,11 @@ import AttachmentsPreview from '@/features/conversation/message/attachment/Attac
 import MacroActionsPreview from '@/features/conversation/MacroActionsPreview.vue'
 import ReplyBoxMenuBar from '@/features/conversation/ReplyBoxMenuBar.vue'
 import { useI18n } from 'vue-i18n'
+import { validateEmail } from '@/utils/strings'

 // Define models for two-way binding
 const messageType = defineModel('messageType', { default: 'reply' })
+const to = defineModel('to', { default: '' })
 const cc = defineModel('cc', { default: '' })
 const bcc = defineModel('bcc', { default: '' })
 const showBcc = defineModel('showBcc', { default: false })
@@ -243,28 +255,27 @@ const enableSend = computed(() => {
 })

 /**
- * Validate email addresses in the CC and BCC fields
- * @param {string} field - 'cc' or 'bcc'
+ * Validate email addresses in the To, CC, and BCC fields
+ * @param {string} field - 'to', 'cc', or 'bcc'
 */
 const validateEmails = (field) => {
-  const emails = field === 'cc' ? cc.value : bcc.value
+  const emails = field === 'to' ? to.value : field === 'cc' ? cc.value : bcc.value
  const emailList = emails
    .split(',')
    .map((e) => e.trim())
    .filter((e) => e !== '')
-  const emailRegex = /^[^\s@]+@[^\s@]+\.[^\s@]+$/
-  const invalidEmails = emailList.filter((email) => !emailRegex.test(email))

-  // Remove any existing errors for this field
-  emailErrors.value = emailErrors.value.filter(
-    (error) => !error.startsWith(`${t('replyBox.invalidEmailsIn')} ${field.toUpperCase()}`)
-  )
+  const invalidEmails = emailList.filter((email) => !validateEmail(email))
+
+  // Clear existing errors
+  emailErrors.value = []

  // Add new error if there are invalid emails
  if (invalidEmails.length > 0) {
-    emailErrors.value.push(
-      `${t('replyBox.invalidEmailsIn')} ${field.toUpperCase()}: ${invalidEmails.join(', ')}`
-    )
+    emailErrors.value = [
+      ...emailErrors.value,
+      `${t('replyBox.invalidEmailsIn')} '${field}': ${invalidEmails.join(', ')}`
+    ]
  }
 }

@@ -272,6 +283,7 @@ const validateEmails = (field) => {
 * Send the reply or private note
 */
 const handleSend = async () => {
+  validateEmails('to')
  validateEmails('cc')
  validateEmails('bcc')
  if (emailErrors.value.length > 0) {
@@ -9,38 +9,46 @@

    <!-- Message Bubble -->
    <div class="flex flex-row gap-2 justify-end">
-      <div
-        class="flex flex-col message-bubble justify-end items-end relative rounded-lg p-3 max-w-[80%]"
-        :class="{
-          '!bg-[#FEF1E1]': message.private,
-          'bg-white border border-border': !message.private,
-          'opacity-50 animate-pulse': message.status === 'pending',
-          'bg-red-50 border-red-200': message.status === 'failed'
-        }"
-      >
-        <!-- Message Content -->
+      <!-- Bubble Wrapper with max 80% width -->
+      <div class="w-4/5 flex justify-end">
        <div
-          v-dompurify-html="messageContent"
-          class="whitespace-pre-wrap break-words overflow-wrap-anywhere native-html" 
-          :class="{ 'mb-3': message.attachments.length > 0 }"
-        />
+          class="flex flex-col justify-end message-bubble relative"
+          :class="{
+            '!bg-[#FEF1E1]': message.private,
+            'bg-white border border-border': !message.private,
+            'opacity-50 animate-pulse': message.status === 'pending',
+            'bg-red-50 border-red-200': message.status === 'failed'
+          }"
+        >
+          <!-- Message Envelope -->
+          <MessageEnvelope :message="message" v-if="showEnvelope" />

-        <!-- Attachments -->
-        <MessageAttachmentPreview :attachments="nonInlineAttachments" />
+          <hr class="mb-2" v-if="showEnvelope" />

-        <!-- Spinner for Pending Messages -->
-        <Spinner v-if="message.status === 'pending'" size="w-4 h-4" />
-
-        <!-- Icons -->
-        <div class="flex items-center space-x-2 mt-2">
-          <Lock :size="10" v-if="isPrivateMessage" class="text-muted-foreground" />
-          <Check :size="14" v-if="showCheckCheck" class="text-green-500" />
-          <RotateCcw
-            size="10"
-            @click="retryMessage(message)"
-            class="cursor-pointer text-muted-foreground hover:text-foreground transition-colors duration-200"
-            v-if="showRetry"
+          <!-- Message -->
+          <div
+            v-dompurify-html="messageContent"
+            class="whitespace-pre-wrap break-words overflow-wrap-anywhere native-html"
+            :class="{ 'mb-3': message.attachments.length > 0 }"
          />
+
+          <!-- Attachments -->
+          <MessageAttachmentPreview :attachments="nonInlineAttachments" />
+
+          <!-- Spinner for Pending Messages -->
+          <Spinner v-if="message.status === 'pending'" size="w-4 h-4" />
+
+          <!-- Icons -->
+          <div class="flex items-center space-x-2 mt-2 self-end">
+            <Lock :size="10" v-if="isPrivateMessage" class="text-muted-foreground" />
+            <Check :size="14" v-if="showCheckCheck" class="text-green-500" />
+            <RotateCcw
+              size="10"
+              @click="retryMessage(message)"
+              class="cursor-pointer text-muted-foreground hover:text-foreground transition-colors duration-200"
+              v-if="showRetry"
+            />
+          </div>
        </div>
      </div>

@@ -53,7 +61,7 @@
      </Avatar>
    </div>

-    <!-- Timestamp -->
+    <!-- Timestamp tooltip -->
    <div class="pr-[47px]">
      <Tooltip>
        <TooltipTrigger>
@@ -79,6 +87,7 @@ import { Tooltip, TooltipContent, TooltipTrigger } from '@/components/ui/tooltip
 import { Spinner } from '@/components/ui/spinner'
 import { Avatar, AvatarFallback, AvatarImage } from '@/components/ui/avatar'
 import MessageAttachmentPreview from '@/features/conversation/message/attachment/MessageAttachmentPreview.vue'
+import MessageEnvelope from './MessageEnvelope.vue'
 import api from '@/api'

 const props = defineProps({
@@ -128,6 +137,16 @@ const avatarFallback = computed(() => {
 const retryMessage = (msg) => {
  api.retryMessage(convStore.current.uuid, msg.uuid)
 }
+
+const showEnvelope = computed(() => {
+  return (
+    props.message.meta?.from?.length ||
+    props.message.meta?.to?.length ||
+    props.message.meta?.cc?.length ||
+    props.message.meta?.bcc?.length ||
+    props.message.meta?.subject
+  )
+})
 </script>

 <style scoped>
@@ -8,7 +8,7 @@
    </div>

    <!-- Message Bubble -->
-    <div class="flex flex-row gap-2">
+    <div class="flex flex-row gap-2 w-full">
      <!-- Avatar -->
      <Avatar class="cursor-pointer w-8 h-8">
        <AvatarImage :src="getAvatar" />
@@ -18,32 +18,40 @@
      </Avatar>

      <!-- Message Content -->
-      <div
-        class="flex flex-col justify-end message-bubble bg-white border border-border rounded-lg p-3 max-w-[80%]"
-        :class="{
-          'show-quoted-text': showQuotedText,
-          'hide-quoted-text': !showQuotedText
-        }"
-      >
-        <!-- Message Text -->
-        <Letter
-          :html="sanitizedMessageContent"
-          :allowedSchemas="['cid', 'https', 'http', 'mailto']"
-          class="mb-1 native-html"
-          :class="{ 'mb-3': message.attachments.length > 0 }"
-        />
-
-        <!-- Quoted Text Toggle -->
+      <div class="w-4/5">
        <div
-          v-if="hasQuotedContent"
-          @click="toggleQuote"
-          class="text-xs cursor-pointer text-muted-foreground px-2 py-1 w-max hover:bg-muted hover:text-primary rounded-md transition-all"
+          class="flex flex-col justify-end message-bubble"
+          :class="{
+            'show-quoted-text': showQuotedText,
+            'hide-quoted-text': !showQuotedText
+          }"
        >
-          {{ showQuotedText ? t('conversation.hideQuotedText') : t('conversation.showQuotedText') }}
-        </div>
+          <MessageEnvelope :message="message" v-if="showEnvelope" />

-        <!-- Attachments -->
-        <MessageAttachmentPreview :attachments="nonInlineAttachments" />
+          <hr class="mb-2" v-if="showEnvelope" />
+
+          <!-- Message Text -->
+          <Letter
+            :html="sanitizedMessageContent"
+            :allowedSchemas="['cid', 'https', 'http', 'mailto']"
+            class="mb-1 native-html"
+            :class="{ 'mb-3': message.attachments.length > 0 }"
+          />
+
+          <!-- Quoted Text Toggle -->
+          <div
+            v-if="hasQuotedContent"
+            @click="toggleQuote"
+            class="text-xs cursor-pointer text-muted-foreground px-2 py-1 w-max hover:bg-muted hover:text-primary rounded-md transition-all"
+          >
+            {{
+              showQuotedText ? t('conversation.hideQuotedText') : t('conversation.showQuotedText')
+            }}
+          </div>
+
+          <!-- Attachments -->
+          <MessageAttachmentPreview :attachments="nonInlineAttachments" />
+        </div>
      </div>
    </div>

@@ -75,6 +83,7 @@ import { Letter } from 'vue-letter'
 import { useAppSettingsStore } from '@/stores/appSettings'
 import { useI18n } from 'vue-i18n'
 import MessageAttachmentPreview from '@/features/conversation/message/attachment/MessageAttachmentPreview.vue'
+import MessageEnvelope from './MessageEnvelope.vue'

 const props = defineProps({
  message: Object
@@ -123,4 +132,14 @@ const avatarFallback = computed(() => {
  const contact = convStore.current?.contact || {}
  return (contact.first_name || '').toUpperCase().substring(0, 2)
 })
+
+const showEnvelope = computed(() => {
+  return (
+    props.message.meta?.from?.length ||
+    props.message.meta?.to?.length ||
+    props.message.meta?.cc?.length ||
+    props.message.meta?.bcc?.length ||
+    props.message.meta?.subject
+  )
+})
 </script>
@@ -0,0 +1,28 @@
+<template>
+  <div class="mb-1 space-y-0.5 text-xs text-muted-foreground">
+    <p v-if="message.meta.from?.length">
+      <span class="font-medium text-foreground">From:</span> {{ message.meta.from.join(', ') }}
+    </p>
+    <p v-if="message.meta.to?.length">
+      <span class="font-medium text-foreground">To:</span> {{ message.meta.to.join(', ') }}
+    </p>
+    <p v-if="message.meta.cc?.length">
+      <span class="font-medium text-foreground">CC:</span> {{ message.meta.cc.join(', ') }}
+    </p>
+    <p v-if="message.meta.bcc?.length">
+      <span class="font-medium text-foreground">BCC:</span> {{ message.meta.bcc.join(', ') }}
+    </p>
+    <p v-if="message.meta.subject">
+      <span class="font-medium text-foreground">Subject:</span> {{ message.meta.subject }}
+    </p>
+  </div>
+</template>
+
+<script setup>
+defineProps({
+  message: {
+    type: Object,
+    required: true
+  }
+})
+</script>
@@ -1,10 +1,14 @@
 <template>
  <div class="space-y-4">
-    <div class="flex flex-col">
+    <!-- Hide subject for email channel as each message shows the envelope -->
+    <div
+      class="flex flex-col"
+      v-if="conversation.subject && conversation.inbox_channel !== 'email'"
+    >
      <p class="font-medium">{{ $t('form.field.subject') }}</p>
      <Skeleton v-if="conversationStore.conversation.loading" class="w-32 h-4" />
      <p v-else>
-        {{ conversation.subject || '-' }}
+        {{ conversation.subject }}
      </p>
    </div>

@@ -180,7 +180,6 @@ const getValidationSchema = (attribute) => {
      // If regex is provided and valid, add it to the schema validation along with the hint
      if (attribute.regex) {
        try {
-          console.log('Creating regex:', attribute.regex)
          const regex = new RegExp(attribute.regex)
          schema = schema.regex(regex, {
            message: attribute.regex_hint
@@ -1,7 +1,8 @@
 import { defineStore } from 'pinia'
-import { computed, reactive, ref, nextTick } from 'vue'
+import { computed, reactive, ref, nextTick, watchEffect } from 'vue'
 import { CONVERSATION_LIST_TYPE, CONVERSATION_DEFAULT_STATUSES } from '@/constants/conversation'
 import { handleHTTPError } from '@/utils/http'
+import { computeRecipientsFromMessage } from '@/utils/email-recipients'
 import { useEmitter } from '@/composables/useEmitter'
 import { EMITTER_EVENTS } from '@/constants/emitterEvents'
 import MessageCache from '@/utils/conversation-message-cache'
@@ -12,6 +13,9 @@ export const useConversationStore = defineStore('conversation', () => {
  const MESSAGE_LIST_PAGE_SIZE = 30
  const priorities = ref([])
  const statuses = ref([])
+  const currentTo = ref([])
+  const currentBCC = ref([])
+  const currentCC = ref([])

  // Options for select fields
  const priorityOptions = computed(() => {
@@ -105,6 +109,8 @@ export const useConversationStore = defineStore('conversation', () => {
    data: new MessageCache(),
    loading: false,
    page: 1,
+    // To trigger reactivity on the messages cache, simpler than making MessageCache reactive.
+    version: 0,
  })

  let seenConversationUUIDs = new Map()
@@ -113,6 +119,8 @@ export const useConversationStore = defineStore('conversation', () => {
  }, 120000)
  const emitter = useEmitter()

+  const incrementMessageVersion = () => setTimeout(() => messages.version++, 0)
+
  function clearListReRenderInterval () {
    clearInterval(reRenderInterval)
  }
@@ -245,12 +253,29 @@ export const useConversationStore = defineStore('conversation', () => {
    return Object.keys(conversation.data || {}).length > 0
  })

-  const currentBCC = computed(() => {
-    return conversation.data?.bcc || []
-  })
+  // Watch for changes in the conversation and messages and update the to, cc, and bcc
+  watchEffect(async () => {
+    const _ = messages.version // eslint-disable-line no-unused-vars
+    const conv = conversation.data
+    const msgData = messages.data
+    const inboxEmail = conv?.inbox_mail
+    if (!conv || !msgData || !inboxEmail) return

-  const currentCC = computed(() => {
-    return conversation.data?.cc || []
+    const latestMessage = msgData.getLatestMessage(conv.uuid, ['incoming', 'outgoing'], true)
+    if (!latestMessage) return
+
+    if (!["received", "sent"].includes(latestMessage.status)) {
+      return
+    }
+
+    const { to, cc, bcc } = computeRecipientsFromMessage(
+      latestMessage,
+      conv.contact?.email || '',
+      inboxEmail
+    )
+    currentTo.value = to
+    currentCC.value = cc
+    currentBCC.value = bcc
  })

  async function fetchParticipants (uuid) {
@@ -288,7 +313,7 @@ export const useConversationStore = defineStore('conversation', () => {
  }

  /**
-   * Fetches messages for a conversation if not already cached.
+   * Fetches messages for a conversation if not already present in the cache.
   * 
   * @param {string} uuid
   * @returns 
@@ -312,6 +337,7 @@ export const useConversationStore = defineStore('conversation', () => {
      markConversationAsRead(uuid)
      // Cache messages
      messages.data.addMessages(uuid, newMessages, result.page, result.total_pages)
+      incrementMessageVersion()
    } catch (error) {
      emitter.emit(EMITTER_EVENTS.SHOW_TOAST, {
        title: 'Error',
@@ -328,7 +354,7 @@ export const useConversationStore = defineStore('conversation', () => {
  }

  /**
-   * Fetches a single message from the server and adds it to the cache.
+   * Fetches a single message from the server and adds it to the message cache.
   * 
   * @param {string} conversationUUID
   * @param {string} messageUUID
@@ -341,6 +367,7 @@ export const useConversationStore = defineStore('conversation', () => {
        const newMsg = response.data.data
        // Add message to cache.
        messages.data.addMessage(conversationUUID, newMsg)
+        incrementMessageVersion()
        return newMsg
      }
    } catch (error) {
@@ -606,6 +633,7 @@ export const useConversationStore = defineStore('conversation', () => {
    const exists = messages.data.hasMessage(message.conversation_uuid, message.uuid)
    if (exists) {
      messages.data.updateMessageField(message.conversation_uuid, message.uuid, message.prop, message.value)
+      incrementMessageVersion()
    }
  }

@@ -647,6 +675,7 @@ export const useConversationStore = defineStore('conversation', () => {
    hasConversationOpen,
    current,
    currentContactName,
+    currentTo,
    currentBCC,
    currentCC,
    clearListReRenderInterval,
@@ -1,7 +1,7 @@
 export default class MessageCache {
    /**
-     * Cache for conversation messages with LRU eviction
-     * @param {number} maxConvs - Max conversations to store
+     * Cache for conversation messages with eviction of old conversations
+     * @param {number} maxConvs - Max conversations to store before eviction
     */
    constructor(maxConvs = 100) {
        this.cache = new Map()
@@ -69,6 +69,34 @@ export default class MessageCache {
            .sort((a, b) => new Date(a.created_at) - new Date(b.created_at))
    }

+    /**
+     * Returns latest message for a conversation
+     * @param {string} convId - Conversation ID
+     * @param {string[]} type - Array of message types to filter - outgoing, incoming, etc.
+     * @param {boolean} excludePrivate - Exclude private messages
+     * 
+     * @returns {object} - Latest message object or null if not found
+     */
+    getLatestMessage (convId, type = [], excludePrivate = false) {
+        const conv = this.cache.get(convId)
+        if (!conv) return null
+
+        // Get all messages from all pages
+        let allMessages = Array.from(conv.pages.values()).flat()
+
+        // Apply filters
+        if (type.length > 0) {
+            allMessages = allMessages.filter(msg => type.includes(msg.type))
+        }
+        if (excludePrivate) {
+            allMessages = allMessages.filter(msg => !msg.private)
+        }
+
+        // Sort messages by created_at in descending order (newest first)
+        allMessages.sort((a, b) => new Date(b.created_at) - new Date(a.created_at))
+
+        return allMessages.length ? allMessages[0] : null
+    }
    /**
     * Updates message fields by applying update object
     */
@@ -0,0 +1,46 @@
+export function computeRecipientsFromMessage (message, contactEmail, inboxEmail) {
+    const meta = message?.meta || {}
+    const isIncoming = message.type === 'incoming'
+
+    // Build TO field
+    const toList = isIncoming
+        ? meta.from && meta.from.length
+            ? meta.from
+            : contactEmail
+                ? [contactEmail]
+                : []
+        : meta.to && meta.to.length
+            ? meta.to
+            : contactEmail
+                ? [contactEmail]
+                : []
+
+    // Build CC field
+    let ccList = meta.cc || []
+
+    if (isIncoming) {
+        // Include original 'to' recipients in CC to preserve full thread context (e.g. other participants)
+        if (Array.isArray(meta.to))
+            ccList = ccList.concat(meta.to)
+
+        // If someone else replies (not the original contact), re-add original contact to CC to keep them in the loop.
+        if (
+            contactEmail &&
+            !toList.includes(contactEmail) &&
+            !ccList.includes(contactEmail)
+        ) {
+            ccList.push(contactEmail)
+        }
+    }
+
+    // Dedup + remove inbox email
+    const clean = list =>
+        Array.from(new Set(list.filter(email => email && email !== inboxEmail)))
+
+    return {
+        to: clean(toList),
+        cc: clean(ccList),
+        // BCC stays empty user is supposed to add it manually.
+        bcc: [],
+    }
+}
@@ -28,6 +28,7 @@ import (
 	mmodels "github.com/abhinavxd/libredesk/internal/media/models"
 	notifier "github.com/abhinavxd/libredesk/internal/notification"
 	slaModels "github.com/abhinavxd/libredesk/internal/sla/models"
+	"github.com/abhinavxd/libredesk/internal/stringutil"
 	tmodels "github.com/abhinavxd/libredesk/internal/team/models"
 	"github.com/abhinavxd/libredesk/internal/template"
 	umodels "github.com/abhinavxd/libredesk/internal/user/models"
@@ -41,11 +42,11 @@ import (

 var (
 	//go:embed queries.sql
-	efs                                  embed.FS
-	errConversationNotFound              = errors.New("conversation not found")
-	conversationsAllowedFields = []string{"status_id", "priority_id", "assigned_team_id", "assigned_user_id", "inbox_id", "last_message_at", "created_at", "waiting_since", "next_sla_deadline_at", "priority_id"}
-	conversationStatusAllowedFields     = []string{"id", "name"}
-	csatReplyMessage                     = "Please rate your experience with us: <a href=\"%s\">Rate now</a>"
+	efs                             embed.FS
+	errConversationNotFound         = errors.New("conversation not found")
+	conversationsAllowedFields      = []string{"status_id", "priority_id", "assigned_team_id", "assigned_user_id", "inbox_id", "last_message_at", "created_at", "waiting_since", "next_sla_deadline_at", "priority_id"}
+	conversationStatusAllowedFields = []string{"id", "name"}
+	csatReplyMessage                = "Please rate your experience with us: <a href=\"%s\">Rate now</a>"
 )

 const (
@@ -184,7 +185,6 @@ func New(

 type queries struct {
 	// Conversation queries.
-	GetToAddress                       *sqlx.Stmt `query:"get-to-address"`
 	GetConversationUUID                *sqlx.Stmt `query:"get-conversation-uuid"`
 	GetConversation                    *sqlx.Stmt `query:"get-conversation"`
 	GetConversationsCreatedAfter       *sqlx.Stmt `query:"get-conversations-created-after"`
@@ -213,6 +213,7 @@ type queries struct {
 	UnsnoozeAll                        *sqlx.Stmt `query:"unsnooze-all"`
 	DeleteConversation                 *sqlx.Stmt `query:"delete-conversation"`
 	RemoveConversationAssignee         *sqlx.Stmt `query:"remove-conversation-assignee"`
+	GetLatestMessage                   *sqlx.Stmt `query:"get-latest-message"`

 	// Dashboard queries.
 	GetDashboardCharts string `query:"get-dashboard-charts"`
@@ -254,6 +255,14 @@ func (c *Manager) GetConversation(id int, uuid string) (models.Conversation, err
 		c.lo.Error("error fetching conversation", "error", err)
 		return conversation, envelope.NewError(envelope.GeneralError, c.i18n.Ts("globals.messages.errorFetching", "name", "{globals.terms.conversation}"), nil)
 	}
+
+	// Strip name and extract plain email from "Name <email>"
+	var err error
+	conversation.InboxMail, err = stringutil.ExtractEmail(conversation.InboxMail)
+	if err != nil {
+		c.lo.Error("error extracting email from inbox mail", "inbox_mail", conversation.InboxMail, "error", err)
+	}
+
 	return conversation, nil
 }

@@ -738,16 +747,6 @@ func (c *Manager) SetConversationTags(uuid string, action string, tagNames []str
 	return nil
 }

-// GetToAddress retrieves the recipient addresses for a conversation and channel.
-func (m *Manager) GetToAddress(conversationID int) ([]string, error) {
-	var addr []string
-	if err := m.q.GetToAddress.Select(&addr, conversationID); err != nil {
-		m.lo.Error("error fetching `to` address for message", "error", err, "conversation_id", conversationID)
-		return addr, err
-	}
-	return addr, nil
-}
-
 // GetMessageSourceIDs retrieves source IDs for messages in a conversation in descending order.
 // So the oldest message will be the last in the list.
 func (m *Manager) GetMessageSourceIDs(conversationID, limit int) ([]string, error) {
@@ -872,23 +871,53 @@ func (m *Manager) ApplyAction(action amodels.RuleAction, conv models.Conversatio

 	switch action.Type {
 	case amodels.ActionAssignTeam:
-		teamID, _ := strconv.Atoi(action.Value[0])
+		teamID, err := strconv.Atoi(action.Value[0])
+		if err != nil {
+			return fmt.Errorf("invalid team ID %q: %w", action.Value[0], err)
+		}
 		return m.UpdateConversationTeamAssignee(conv.UUID, teamID, user)
 	case amodels.ActionAssignUser:
-		agentID, _ := strconv.Atoi(action.Value[0])
+		agentID, err := strconv.Atoi(action.Value[0])
+		if err != nil {
+			return fmt.Errorf("invalid agent ID %q: %w", action.Value[0], err)
+		}
 		return m.UpdateConversationUserAssignee(conv.UUID, agentID, user)
 	case amodels.ActionSetPriority:
-		priorityID, _ := strconv.Atoi(action.Value[0])
+		priorityID, err := strconv.Atoi(action.Value[0])
+		if err != nil {
+			return fmt.Errorf("invalid priority ID %q: %w", action.Value[0], err)
+		}
 		return m.UpdateConversationPriority(conv.UUID, priorityID, "", user)
 	case amodels.ActionSetStatus:
-		statusID, _ := strconv.Atoi(action.Value[0])
+		statusID, err := strconv.Atoi(action.Value[0])
+		if err != nil {
+			return fmt.Errorf("invalid status ID %q: %w", action.Value[0], err)
+		}
 		return m.UpdateConversationStatus(conv.UUID, statusID, "", "", user)
 	case amodels.ActionSendPrivateNote:
 		return m.SendPrivateNote([]mmodels.Media{}, user.ID, conv.UUID, action.Value[0])
 	case amodels.ActionReply:
-		return m.SendReply([]mmodels.Media{}, conv.InboxID, user.ID, conv.UUID, action.Value[0], nil, nil, nil)
+		// Make recipient list.
+		to, cc, bcc, err := m.makeRecipients(conv.ID, conv.Contact.Email.String, conv.InboxMail)
+		if err != nil {
+			return fmt.Errorf("making recipients for reply action: %w", err)
+		}
+		return m.SendReply(
+			[]mmodels.Media{},
+			conv.InboxID,
+			user.ID,
+			conv.UUID,
+			action.Value[0],
+			to,
+			cc,
+			bcc,
+			map[string]any{}, /**meta**/
+		)
 	case amodels.ActionSetSLA:
-		slaID, _ := strconv.Atoi(action.Value[0])
+		slaID, err := strconv.Atoi(action.Value[0])
+		if err != nil {
+			return fmt.Errorf("invalid SLA ID %q: %w", action.Value[0], err)
+		}
 		return m.ApplySLA(conv, slaID, user)
 	case amodels.ActionAddTags, amodels.ActionSetTags, amodels.ActionRemoveTags:
 		return m.SetConversationTags(conv.UUID, action.Type, action.Value, user)
@@ -924,7 +953,14 @@ func (m *Manager) SendCSATReply(actorUserID int, conversation models.Conversatio
 	meta := map[string]interface{}{
 		"is_csat": true,
 	}
-	return m.SendReply([]mmodels.Media{}, conversation.InboxID, actorUserID, conversation.UUID, message, nil, nil, meta)
+
+	// Make recipient list.
+	to, cc, bcc, err := m.makeRecipients(conversation.ID, conversation.Contact.Email.String, conversation.InboxMail)
+	if err != nil {
+		return fmt.Errorf("making recipients for CSAT reply: %w", err)
+	}
+
+	return m.SendReply(nil /**media**/, conversation.InboxID, actorUserID, conversation.UUID, message, to, cc, bcc, meta)
 }

 // DeleteConversation deletes a conversation.
@@ -142,7 +142,7 @@ func (m *Manager) sendOutgoingMessage(message models.Message) {
 		return
 	}

-	// Render content  template
+	// Render content in template
 	if err := m.RenderContentInTemplate(inbox.Channel(), &message); err != nil {
 		handleError(err, "error rendering content in template")
 		return
@@ -154,12 +154,8 @@ func (m *Manager) sendOutgoingMessage(message models.Message) {
 		return
 	}

-	// Set from and to addresses
+	// Set from address of the inbox
 	message.From = inbox.FromAddress()
-	message.To, err = m.GetToAddress(message.ConversationID)
-	if handleError(err, "error fetching `to` address") {
-		return
-	}

 	// Set "In-Reply-To" and "References" headers, logging any errors but continuing to send the message.
 	// Include only the last 20 messages as references to avoid exceeding header size limits.
@@ -318,16 +314,24 @@ func (m *Manager) SendPrivateNote(media []mmodels.Media, senderID int, conversat
 }

 // SendReply inserts a reply message in a conversation.
-func (m *Manager) SendReply(media []mmodels.Media, inboxID, senderID int, conversationUUID, content string, cc, bcc []string, meta map[string]interface{}) error {
-	// Save cc and bcc as JSON in meta.
+func (m *Manager) SendReply(media []mmodels.Media, inboxID, senderID int, conversationUUID, content string, to, cc, bcc []string, meta map[string]interface{}) error {
+	// Save to, cc and bcc in meta.
+	to = stringutil.RemoveEmpty(to)
 	cc = stringutil.RemoveEmpty(cc)
 	bcc = stringutil.RemoveEmpty(bcc)
+
+	if len(to) == 0 {
+		return envelope.NewError(envelope.GeneralError, m.i18n.Ts("globals.messages.empty", "name", "`to`"), nil)
+	}
+	meta["to"] = to
+
 	if len(cc) > 0 {
 		meta["cc"] = cc
 	}
 	if len(bcc) > 0 {
 		meta["bcc"] = bcc
 	}
+
 	metaJSON, err := json.Marshal(meta)
 	if err != nil {
 		return envelope.NewError(envelope.GeneralError, m.i18n.Ts("globals.messages.errorMarshalling", "name", "{globals.terms.meta}"), nil)
@@ -355,7 +359,7 @@ func (m *Manager) SendReply(media []mmodels.Media, inboxID, senderID int, conver
 		ContentType:      models.ContentTypeHTML,
 		Private:          false,
 		Media:            media,
-		Meta:             string(metaJSON),
+		Meta:             metaJSON,
 		SourceID:         null.StringFrom(sourceID),
 	}
 	return m.InsertMessage(&message)
@@ -368,9 +372,8 @@ func (m *Manager) InsertMessage(message *models.Message) error {
 		message.Status = models.MessageStatusSent
 	}

-	// Handle empty meta.
-	if message.Meta == "" || message.Meta == "null" {
-		message.Meta = "{}"
+	if len(message.Meta) == 0 || string(message.Meta) == "null" {
+		message.Meta = json.RawMessage(`{}`)
 	}

 	// Convert HTML content to text for search.
@@ -566,11 +569,10 @@ func (m *Manager) processIncomingMessage(in models.IncomingMessage) error {
 	systemUser, err := m.userStore.GetSystemUser()
 	if err != nil {
 		m.lo.Error("error fetching system user", "error", err)
-		return fmt.Errorf("error fetching system user for reopening conversation: %w", err)
-	}
-	if err := m.ReOpenConversation(in.Message.ConversationUUID, systemUser); err != nil {
-		m.lo.Error("error reopening conversation", "error", err)
-		return fmt.Errorf("error reopening conversation: %w", err)
+	} else {
+		if err := m.ReOpenConversation(in.Message.ConversationUUID, systemUser); err != nil {
+			m.lo.Error("error reopening conversation", "error", err)
+		}
 	}

 	// Trigger automations on incoming message event.
@@ -839,3 +841,16 @@ func (m *Manager) uploadThumbnailForMedia(media mmodels.Media, content []byte) e
 	}
 	return nil
 }
+
+// getLatestMessage returns the latest message in a conversation.
+func (m *Manager) getLatestMessage(conversationID int, typ []string, status []string, excludePrivate bool) (models.Message, error) {
+	var message models.Message
+	if err := m.q.GetLatestMessage.Get(&message, conversationID, pq.Array(typ), pq.Array(status), excludePrivate); err != nil {
+		if err == sql.ErrNoRows {
+			return message, sql.ErrNoRows
+		}
+		m.lo.Error("error fetching latest message from DB", "error", err)
+		return message, fmt.Errorf("fetching latest message: %w", err)
+	}
+	return message, nil
+}
@@ -74,6 +74,7 @@ type Conversation struct {
 	WaitingSince          null.Time       `db:"waiting_since" json:"waiting_since"`
 	Subject               null.String     `db:"subject" json:"subject"`
 	UnreadMessageCount    int             `db:"unread_message_count" json:"unread_message_count"`
+	InboxMail             string          `db:"inbox_mail" json:"inbox_mail"`
 	InboxName             string          `db:"inbox_name" json:"inbox_name"`
 	InboxChannel          string          `db:"inbox_channel" json:"inbox_channel"`
 	Tags                  null.JSON       `db:"tags" json:"tags"`
@@ -89,6 +90,7 @@ type Conversation struct {
 	FirstResponseDueAt    null.Time       `db:"first_response_deadline_at" json:"first_response_deadline_at"`
 	ResolutionDueAt       null.Time       `db:"resolution_deadline_at" json:"resolution_deadline_at"`
 	SLAStatus             null.String     `db:"sla_status" json:"sla_status"`
+	To                    json.RawMessage `db:"to" json:"to"`
 	BCC                   json.RawMessage `db:"bcc" json:"bcc"`
 	CC                    json.RawMessage `db:"cc" json:"cc"`
 	PreviousConversations []Conversation  `db:"-" json:"previous_conversations"`
@@ -131,19 +133,19 @@ type Message struct {
 	SenderID         int                    `db:"sender_id" json:"sender_id"`
 	SenderType       string                 `db:"sender_type" json:"sender_type"`
 	InboxID          int                    `db:"inbox_id" json:"-"`
-	Meta             string                 `db:"meta" json:"meta"`
+	Meta             json.RawMessage        `db:"meta" json:"meta"`
 	Attachments      attachment.Attachments `db:"attachments" json:"attachments"`
 	ConversationUUID string                 `db:"conversation_uuid" json:"-"`
 	From             string                 `db:"from"  json:"-"`
-	To               []string               `db:"from"  json:"-"`
-	AltContent       string                 `db:"alt_content" json:"-"`
 	Subject          string                 `db:"subject" json:"-"`
 	Channel          string                 `db:"channel" json:"-"`
+	To               pq.StringArray         `db:"to"  json:"-"`
 	CC               pq.StringArray         `db:"cc" json:"-"`
 	BCC              pq.StringArray         `db:"bcc" json:"-"`
 	References       []string               `json:"-"`
 	InReplyTo        string                 `json:"-"`
 	Headers          textproto.MIMEHeader   `json:"-"`
+	AltContent       string                 `db:"-" json:"-"`
 	Media            []mmodels.Media        `db:"-" json:"-"`
 	IsCSAT           bool                   `db:"-" json:"-"`
 	Total            int                    `db:"total" json:"-"`
@@ -82,21 +82,6 @@ SELECT
 WHERE 1=1 %s

 -- name: get-conversation
-WITH last_reply AS (
-   SELECT 
-       conversation_id,
-       meta->'cc' as cc,
-       meta->'bcc' as bcc
-   FROM conversation_messages 
-   WHERE private = false
-   AND type IN ('outgoing', 'incoming')
-   AND (
-       ($1 > 0 AND conversation_id = $1)
-       OR ($2 != '' AND conversation_id = (SELECT id FROM conversations WHERE uuid = $2::uuid))
-   )
-   ORDER BY created_at DESC 
-   LIMIT 1
-)
 SELECT
   c.id,
   c.created_at,
@@ -104,6 +89,8 @@ SELECT
   c.closed_at,
   c.resolved_at,
   c.inbox_id,
+   COALESCE(inb.from, '') as inbox_mail,
+   COALESCE(inb.channel::TEXT, '') as inbox_channel,
   c.status_id,
   c.priority_id,
   p.name as priority,
@@ -118,6 +105,7 @@ SELECT
   c.subject,
   c.contact_id,
   c.sla_policy_id,
+   c.meta,
   sla.name as sla_policy_name,
   c.last_message,
   c.custom_attributes,
@@ -138,18 +126,16 @@ SELECT
   ct.phone_number as "contact.phone_number",
   ct.phone_number_calling_code as "contact.phone_number_calling_code",
   ct.custom_attributes as "contact.custom_attributes",
-   COALESCE(lr.cc, '[]'::jsonb) as cc,
-   COALESCE(lr.bcc, '[]'::jsonb) as bcc,
   as_latest.first_response_deadline_at,
   as_latest.resolution_deadline_at,
   as_latest.status as sla_status
 FROM conversations c
 JOIN users ct ON c.contact_id = ct.id
+JOIN inboxes inb ON c.inbox_id = inb.id
 LEFT JOIN sla_policies sla ON c.sla_policy_id = sla.id
 LEFT JOIN teams at ON at.id = c.assigned_team_id
 LEFT JOIN conversation_statuses s ON c.status_id = s.id
 LEFT JOIN conversation_priorities p ON c.priority_id = p.id
-LEFT JOIN last_reply lr ON lr.conversation_id = c.id
 LEFT JOIN LATERAL (
    SELECT first_response_deadline_at, resolution_deadline_at, status
    FROM applied_slas 
@@ -375,12 +361,6 @@ FROM conversation_tags ct
 JOIN tags t ON ct.tag_id = t.id
 WHERE ct.conversation_id = (SELECT id FROM conversations WHERE uuid = $1);

-- name: get-to-address
-SELECT cc.identifier 
-FROM conversations c 
-INNER JOIN contact_channels cc ON cc.id = c.contact_channel_id 
-WHERE c.id = $1;
-
 -- name: get-conversation-uuid-from-message-uuid
 SELECT c.uuid AS conversation_uuid
 FROM conversation_messages m
@@ -424,6 +404,7 @@ SELECT
    m.source_id,
    ARRAY(SELECT jsonb_array_elements_text(m.meta->'cc')) AS cc,
    ARRAY(SELECT jsonb_array_elements_text(m.meta->'bcc')) AS bcc,
+    ARRAY(SELECT jsonb_array_elements_text(m.meta->'to')) AS to,
    c.inbox_id,
    c.uuid as conversation_uuid,
    c.subject
@@ -576,4 +557,24 @@ WHERE
  )

 -- name: delete-conversation
-DELETE FROM conversations WHERE uuid = $1;
+DELETE FROM conversations WHERE uuid = $1;
+
+-- name: get-latest-message
+SELECT
+    m.created_at,
+    m.updated_at,
+    m.status,
+    m.type, 
+    m.content,
+    m.uuid,
+    m.private,
+    m.sender_id,
+    m.sender_type,
+    m.meta
+FROM conversation_messages m
+WHERE m.conversation_id = $1
+AND m.type = ANY($2)
+AND m.status = ANY($3)
+AND m.private = NOT $4
+ORDER BY m.created_at DESC
+LIMIT 1;
@@ -0,0 +1,33 @@
+package conversation
+
+import (
+	"encoding/json"
+	"fmt"
+
+	"github.com/abhinavxd/libredesk/internal/conversation/models"
+	"github.com/abhinavxd/libredesk/internal/stringutil"
+)
+
+// makeRecipients computes the recipients for a given conversation ID using the last message in the conversation.
+func (m *Manager) makeRecipients(conversationID int, contactEmail, inboxEmail string) (to, cc, bcc []string, err error) {
+	lastMessage, err := m.getLatestMessage(conversationID, []string{models.MessageIncoming, models.MessageOutgoing}, []string{models.MessageStatusReceived, models.MessageStatusSent}, true)
+	if err != nil {
+		return nil, nil, nil, fmt.Errorf("fetching message for makeRecipients: %w", err)
+	}
+
+	var meta struct {
+		From []string `json:"from"`
+		To   []string `json:"to"`
+		CC   []string `json:"cc"`
+		BCC  []string `json:"bcc"`
+	}
+	if err = json.Unmarshal(lastMessage.Meta, &meta); err != nil {
+		return nil, nil, nil, err
+	}
+
+	isIncoming := lastMessage.Type == models.MessageIncoming
+	to, cc, bcc = stringutil.ComputeRecipients(
+		meta.From, meta.To, meta.CC, meta.BCC, contactEmail, inboxEmail, isIncoming,
+	)
+	return
+}
@@ -186,7 +186,7 @@ func (e *Email) processEnvelope(ctx context.Context, client *imapclient.Client,
 		e.lo.Warn("no sender received for email", "message_id", env.MessageID)
 		return nil
 	}
-	var fromAddr = env.From[0].Addr()
+	var fromAddress = env.From[0].Addr()

 	// Check if the message already exists in the database.
 	// If it does, ignore it.
@@ -200,14 +200,14 @@ func (e *Email) processEnvelope(ctx context.Context, client *imapclient.Client,
 	}

 	// Check if contact with this email is blocked / disabed, if so, ignore the message.
-	if contact, err := e.userStore.GetContact(0, fromAddr); err != nil {
+	if contact, err := e.userStore.GetContact(0, fromAddress); err != nil {
 		envErr, ok := err.(envelope.Error)
 		if !ok || envErr.ErrorType != envelope.NotFoundError {
-			e.lo.Error("error checking if user is blocked", "email", fromAddr, "error", err)
+			e.lo.Error("error checking if user is blocked", "email", fromAddress, "error", err)
 			return fmt.Errorf("checking if user is blocked: %w", err)
 		}
 	} else if !contact.Enabled {
-		e.lo.Debug("contact is blocked, ignoring message", "email", fromAddr)
+		e.lo.Debug("contact is blocked, ignoring message", "email", fromAddress)
 		return nil
 	}

@@ -220,20 +220,43 @@ func (e *Email) processEnvelope(ctx context.Context, client *imapclient.Client,
 		FirstName:       firstName,
 		LastName:        lastName,
 		SourceChannel:   null.NewString(e.Channel(), true),
-		SourceChannelID: null.NewString(fromAddr, true),
-		Email:           null.NewString(fromAddr, true),
+		SourceChannelID: null.NewString(fromAddress, true),
+		Email:           null.NewString(fromAddress, true),
 		Type:            umodels.UserTypeContact,
 	}

-	// Set CC addresses in meta.
+	// Set `to`, `cc`, and `bcc` addresses in meta.
 	var ccAddr = make([]string, 0, len(env.Cc))
+	var toAddr = make([]string, 0, len(env.To))
+	var bccAddr = make([]string, 0, len(env.Bcc))
+	var fromAddr = make([]string, 0, len(env.From))
 	for _, cc := range env.Cc {
 		if cc.Addr() != "" {
 			ccAddr = append(ccAddr, cc.Addr())
 		}
 	}
+	for _, to := range env.To {
+		if to.Addr() != "" {
+			toAddr = append(toAddr, to.Addr())
+		}
+	}
+	for _, bcc := range env.Bcc {
+		if bcc.Addr() != "" {
+			bccAddr = append(bccAddr, bcc.Addr())
+		}
+	}
+	for _, from := range env.From {
+		if from.Addr() != "" {
+			fromAddr = append(fromAddr, from.Addr())
+		}
+	}
+
 	meta, err := json.Marshal(map[string]interface{}{
-		"cc": ccAddr,
+		"from":    fromAddr,
+		"cc":      ccAddr,
+		"bcc":     bccAddr,
+		"to":      toAddr,
+		"subject": env.Subject,
 	})
 	if err != nil {
 		e.lo.Error("error marshalling meta", "error", err)
@@ -248,7 +271,7 @@ func (e *Email) processEnvelope(ctx context.Context, client *imapclient.Client,
 			Status:     models.MessageStatusReceived,
 			Subject:    env.Subject,
 			SourceID:   null.StringFrom(env.MessageID),
-			Meta:       string(meta),
+			Meta:       meta,
 		},
 		Contact: contact,
 		InboxID: inboxID,
@@ -9,6 +9,7 @@ import (
 	"net/url"
 	"path/filepath"
 	"regexp"
+	"slices"
 	"strings"
 	"time"

@@ -191,3 +192,67 @@ func ValidEmail(email string) bool {
 	}
 	return addr.Name == "" && addr.Address == email
 }
+
+// ExtractEmail extracts the email address from a string.
+func ExtractEmail(s string) (string, error) {
+	addr, err := mail.ParseAddress(s)
+	if err != nil {
+		return "", err
+	}
+	return addr.Address, nil
+}
+
+// DedupAndExcludeString returns a deduplicated []string excluding empty and a specific value.
+func DedupAndExcludeString(list []string, exclude string) []string {
+	seen := make(map[string]struct{}, len(list))
+	cleaned := make([]string, 0, len(list))
+	for _, s := range list {
+		if s == "" || s == exclude {
+			continue
+		}
+		if _, ok := seen[s]; !ok {
+			seen[s] = struct{}{}
+			cleaned = append(cleaned, s)
+		}
+	}
+	return cleaned
+}
+
+// ComputeRecipients computes new recipients using last message's recipients and direction.
+func ComputeRecipients(
+	from, to, cc, bcc []string,
+	contactEmail, inboxEmail string,
+	lastMessageIncoming bool,
+) (finalTo, finalCC, finalBCC []string) {
+	if lastMessageIncoming {
+		if len(from) > 0 {
+			finalTo = from
+		} else if contactEmail != "" {
+			finalTo = []string{contactEmail}
+		}
+	} else {
+		if len(to) > 0 {
+			finalTo = to
+		} else if contactEmail != "" {
+			finalTo = []string{contactEmail}
+		}
+	}
+
+	finalCC = append([]string{}, cc...)
+
+	if lastMessageIncoming {
+		if len(to) > 0 {
+			finalCC = append(finalCC, to...)
+		}
+		if contactEmail != "" && !slices.Contains(finalTo, contactEmail) && !slices.Contains(finalCC, contactEmail) {
+			finalCC = append(finalCC, contactEmail)
+		}
+	}
+
+	finalTo = DedupAndExcludeString(finalTo, inboxEmail)
+	finalCC = DedupAndExcludeString(finalCC, inboxEmail)
+	// BCC is one-time only, user is supposed to add it manually.
+	finalBCC = []string{}
+
+	return
+}