From a81ba43733a890e2c07ffd4f1ddd013451fb4177 Mon Sep 17 00:00:00 2001
From: Antoine Nguyen <tonio@ngyn.org>
Date: Mon, 2 Feb 2026 10:51:41 +0100
Subject: [PATCH] Continuation of email scheduling feature

---
 docker-compose.yml                            |   1 +
 frontend/src/api/webmail.js                   |   9 +
 .../components/webmail/ComposeEmailForm.vue   |  66 +++++-
 .../components/webmail/EmailAddressList.vue   |  25 +++
 frontend/src/components/webmail/EmailList.vue | 205 +++++++++++++++---
 .../webmail/EmailSchedulingForm.vue           | 118 ++++++++++
 .../src/components/webmail/MailboxList.vue    |   1 +
 frontend/src/plugins/rules.js                 |   8 +
 frontend/src/views/webmail/EmailView.vue      | 135 ++++++------
 .../commands/templates/cron_config.py.tpl     |   2 +
 modoboa/lib/sysutils.py                       |   2 +-
 modoboa/webmail/app_settings.py               |  37 ++++
 modoboa/webmail/constants.py                  |  22 +-
 modoboa/webmail/jobs.py                       |  26 +++
 modoboa/webmail/lib/__init__.py               |   3 +-
 modoboa/webmail/lib/imapemail.py              |  19 +-
 modoboa/webmail/lib/imapheader.py             |  38 ++--
 modoboa/webmail/lib/imaputils.py              |  34 ++-
 modoboa/webmail/lib/sendmail.py               | 197 ++++++++---------
 modoboa/webmail/lib/utils.py                  | 109 ++++++++++
 modoboa/webmail/migrations/0001_initial.py    | 102 +++++++++
 modoboa/webmail/migrations/__init__.py        |   0
 modoboa/webmail/models.py                     |  96 ++++++++
 modoboa/webmail/serializers.py                |  88 +++++++-
 modoboa/webmail/urls.py                       |   5 +
 modoboa/webmail/viewsets.py                   |  47 +++-
 test_project/test_project/cron_config.py      |   3 +
 27 files changed, 1149 insertions(+), 249 deletions(-)
 create mode 100644 frontend/src/components/webmail/EmailAddressList.vue
 create mode 100644 frontend/src/components/webmail/EmailSchedulingForm.vue
 create mode 100644 modoboa/webmail/jobs.py
 create mode 100644 modoboa/webmail/migrations/0001_initial.py
 create mode 100644 modoboa/webmail/migrations/__init__.py
 create mode 100644 modoboa/webmail/models.py

diff --git a/docker-compose.yml b/docker-compose.yml
index 4b07aa5bb..721a41ebe 100644
--- a/docker-compose.yml
+++ b/docker-compose.yml
@@ -41,6 +41,7 @@ services:
       sh -c "cd test_project; python3 manage.py rqworker dkim modoboa dovecot"
     volumes:
       - .:/code
+      - ./docker/radicale_config:/etc/radicale
 
   rq-scheduler:
     build:
diff --git a/frontend/src/api/webmail.js b/frontend/src/api/webmail.js
index 6ee58d7e7..8f1191fa4 100644
--- a/frontend/src/api/webmail.js
+++ b/frontend/src/api/webmail.js
@@ -128,4 +128,13 @@ export default {
       `/webmail/compose-sessions/${sessionUid}/attachments/${name}/`
     )
   },
+  getScheduledMessage(messageId) {
+    return repository.get(`/webmail/scheduled-messages/${messageId}/`)
+  },
+  updateScheduledMessage(messageId, data) {
+    return repository.patch(`/webmail/scheduled-messages/${messageId}/`, data)
+  },
+  deleteScheduledMessage(messageId) {
+    return repository.delete(`/webmail/scheduled-messages/${messageId}/`)
+  },
 }
diff --git a/frontend/src/components/webmail/ComposeEmailForm.vue b/frontend/src/components/webmail/ComposeEmailForm.vue
index efbab82b5..55a57d156 100644
--- a/frontend/src/components/webmail/ComposeEmailForm.vue
+++ b/frontend/src/components/webmail/ComposeEmailForm.vue
@@ -10,16 +10,29 @@
           variant="flat"
           @click="close"
         />
-        <v-btn
-          class="ml-2"
-          color="primary"
-          variant="tonal"
-          prepend-icon="mdi-send"
-          :loading="working"
-          :text="$gettext('Send')"
-          @click="submit"
-        >
-        </v-btn>
+        <v-btn-group color="primary" rounded="lg" density="compact" divided>
+          <v-btn
+            class="ml-2"
+            prepend-icon="mdi-send"
+            :loading="working"
+            :text="$gettext('Send')"
+            @click="submit"
+          >
+          </v-btn>
+          <v-btn size="small" icon>
+            <v-icon icon="mdi-chevron-down" />
+            <v-menu activator="parent">
+              <v-list>
+                <v-list-item
+                  prepend-icon="mdi-send-clock-outline"
+                  :title="$gettext('Schedule sending')"
+                  @click="openSchedulingForm"
+                />
+              </v-list>
+            </v-menu>
+          </v-btn>
+        </v-btn-group>
+
         <v-btn
           class="ml-2"
           variant="tonal"
@@ -167,6 +180,12 @@
         @close="closeAttachmentDialog"
       />
     </v-dialog>
+    <v-dialog v-model="showSchedulingForm" max-width="800">
+      <EmailSchedulingForm
+        @schedule="scheduleAndSubmit"
+        @close="closeSchedulingForm"
+      />
+    </v-dialog>
   </div>
 </template>
 
@@ -178,6 +197,7 @@ import { useAuthStore, useBusStore } from '@/stores'
 import debounce from 'debounce'
 import AttachmentsDialog from '@/components/webmail/AttachmentsDialog'
 import BodyEditor from '@/components/webmail/BodyEditor'
+import EmailSchedulingForm from '@/components/webmail/EmailSchedulingForm'
 import rules from '@/plugins/rules'
 import api from '@/api/webmail'
 import contactsApi from '@/api/contacts'
@@ -209,6 +229,7 @@ const formRef = ref()
 const showAttachmentsDialog = ref(false)
 const showCcField = ref(false)
 const showBccField = ref(false)
+const showSchedulingForm = ref(false)
 const working = ref(false)
 
 const close = () => {
@@ -275,7 +296,10 @@ const submit = async () => {
   try {
     await api.sendEmailFromComposeSession(route.query.uid, body)
     router.push({ name: 'MailboxView' })
-    displayNotification({ msg: $gettext('Email sent') })
+    const msg = body.scheduled_datetime
+      ? $gettext('Email scheduled')
+      : $gettext('Email seng')
+    displayNotification({ msg })
   } catch (error) {
     console.log(error)
   } finally {
@@ -283,6 +307,11 @@ const submit = async () => {
   }
 }
 
+const scheduleAndSubmit = async (datetime) => {
+  form.value.scheduled_datetime = datetime
+  await submit()
+}
+
 const openAttachmentsDialog = () => {
   showAttachmentsDialog.value = true
 }
@@ -316,6 +345,21 @@ const initialize = (body) => {
   editorMode.value = body.editor_format
 }
 
+const openSchedulingForm = () => {
+  if (!form.value.to?.length) {
+    displayNotification({
+      msg: $gettext('You must provide one recipient at least'),
+      type: 'info',
+    })
+    return
+  }
+  showSchedulingForm.value = true
+}
+
+const closeSchedulingForm = () => {
+  showSchedulingForm.value = false
+}
+
 watch(
   () => props.originalEmail,
   () => {
diff --git a/frontend/src/components/webmail/EmailAddressList.vue b/frontend/src/components/webmail/EmailAddressList.vue
new file mode 100644
index 000000000..f9506e78b
--- /dev/null
+++ b/frontend/src/components/webmail/EmailAddressList.vue
@@ -0,0 +1,25 @@
+<template>
+  <template v-for="(address, index) in addressesSample" :key="address">
+    <span v-if="address.name" :title="address.address">{{ address.name }}</span>
+    <span v-else>{{ address.address }}</span>
+    <span v-if="index < addressesSample.length - 1">, </span>
+    <span v-else-if="addressesSample.length < props.addresses.length"
+      >, ...</span
+    >
+  </template>
+</template>
+
+<script setup>
+import { computed } from 'vue'
+
+const props = defineProps({
+  addresses: {
+    type: Array,
+    default: null,
+  },
+})
+
+const addressesSample = computed(() =>
+  props.addresses.length > 2 ? props.addresses.slice(0, 2) : props.addresses
+)
+</script>
diff --git a/frontend/src/components/webmail/EmailList.vue b/frontend/src/components/webmail/EmailList.vue
index 4c7f2d8e3..e27a1ba39 100644
--- a/frontend/src/components/webmail/EmailList.vue
+++ b/frontend/src/components/webmail/EmailList.vue
@@ -24,6 +24,7 @@
         @keyup.enter="submitSearch"
       ></v-text-field>
       <v-btn
+        v-if="!inScheduledView"
         class="ml-2"
         color="error"
         variant="tonal"
@@ -33,28 +34,30 @@
         @click="deleteSelection"
       >
       </v-btn>
-      <v-btn
-        v-if="$route.params.mailbox !== 'Junk'"
-        class="ml-2"
-        color="warning"
-        variant="tonal"
-        icon="mdi-fire"
-        size="small"
-        :loading="working"
-        @click="markSelectionAsJunk"
-      >
-      </v-btn>
-      <v-btn
-        v-else
-        class="ml-2"
-        color="success"
-        variant="tonal"
-        icon="mdi-thumb-up"
-        size="small"
-        :loading="working"
-        @click="markSelectionAsNotJunk"
-      >
-      </v-btn>
+      <template v-if="!inScheduledView">
+        <v-btn
+          v-if="$route.params.mailbox !== 'Junk'"
+          class="ml-2"
+          color="warning"
+          variant="tonal"
+          icon="mdi-fire"
+          size="small"
+          :loading="working"
+          @click="markSelectionAsJunk"
+        >
+        </v-btn>
+        <v-btn
+          v-else
+          class="ml-2"
+          color="success"
+          variant="tonal"
+          icon="mdi-thumb-up"
+          size="small"
+          :loading="working"
+          @click="markSelectionAsNotJunk"
+        >
+        </v-btn>
+      </template>
       <v-btn class="ml-2" variant="tonal" icon size="small">
         <v-icon icon="mdi-cog" />
         <v-menu activator="parent">
@@ -80,7 +83,7 @@
               @click="() => flagSelection('unflagged')"
             />
             <v-list-item
-              v-if="$route.params.mailbox !== 'Trash'"
+              v-if="$route.query.mailbox === 'Trash'"
               :title="$gettext('Empty mailbox')"
               prepend-icon="mdi-trash-can"
               @click="emptyMailbox"
@@ -113,7 +116,23 @@
   </v-card>
   <v-skeleton-loader v-if="loading" type="card@2"></v-skeleton-loader>
   <template v-else>
-    <div class="emails position-absolute top-0 bottom-0 w-100 overflow-y-auto">
+    <v-alert
+      v-if="inScheduledView"
+      type="info"
+      variant="tonal"
+      density="compact"
+      class="mx-1"
+    >
+      {{
+        $gettext(
+          'Scheduled messages will be sent at the specified date and time. (visible on the right)'
+        )
+      }}
+    </v-alert>
+    <div
+      class="emails position-absolute bottom-0 w-100 overflow-y-auto"
+      :class="{ 'top-0': !inScheduledView, 'scheduling-top': inScheduledView }"
+    >
       <template v-if="emails.results?.length">
         <v-card
           v-for="email in emails.results"
@@ -138,20 +157,38 @@
               variant="flat"
               @click="toggleFollowState(email)"
             />
+            <v-menu v-if="inScheduledView" location="bottom">
+              <template #activator="{ props }">
+                <v-btn
+                  icon="mdi-dots-vertical"
+                  v-bind="props"
+                  size="small"
+                  variant="text"
+                >
+                </v-btn>
+              </template>
+              <MenuItems :items="getScheduledMessageActions()" :obj="email" />
+            </v-menu>
+
             <div class="ml-4 clickable" @click="openEmail(email.imapid)">
               <div>{{ email.subject }}</div>
               <div class="mt-1 text-grey">
-                <span
-                  v-if="email.from_address.name"
-                  :title="email.from_address.address"
-                  >{{ email.from_address.name }}</span
-                >
-                <span v-else>{{ email.from_address.address }}</span>
+                <EmailAddressList :addresses="getEmailAddresses(email)" />
               </div>
             </div>
             <v-spacer />
             <div class="text-right">
-              <div>{{ email.date }}</div>
+              <div v-if="!isScheduledDateOver(email)">
+                {{ getEmailDate(email) }}
+              </div>
+              <div
+                v-else
+                class="text-error font-weight-bold"
+                style="cursor: pointer"
+                @click="displaySchedulingError(email)"
+              >
+                {{ getEmailDate(email) }}
+              </div>
               <div class="mt-1">
                 <v-icon v-if="email.answered" icon="mdi-reply-outline" />
                 <v-icon v-if="email.forwarded" icon="mdi-share-outline" />
@@ -170,6 +207,28 @@
         variant="tonal"
       />
     </div>
+    <v-dialog v-model="showSchedulingForm" max-width="800">
+      <EmailSchedulingForm
+        :initial-date="selectedScheduledEmail.scheduled_datetime_raw"
+        @schedule="updateScheduledEmail"
+        @close="closeSchedulingForm"
+      />
+    </v-dialog>
+    <v-dialog v-model="showSchedulingError" max-width="400">
+      <v-card
+        max-width="400"
+        :text="schedulingError"
+        :title="$gettext('Sending failure')"
+      >
+        <template #:actions>
+          <v-btn
+            class="ms-auto"
+            :text="$gettext('Close')"
+            @click="showSchedulingError = false"
+          ></v-btn>
+        </template>
+      </v-card>
+    </v-dialog>
   </template>
 </template>
 
@@ -178,6 +237,10 @@ import { computed, onMounted, onUnmounted, ref, watch } from 'vue'
 import { useRouter, useRoute } from 'vue-router'
 import { useGettext } from 'vue3-gettext'
 import { useBusStore, useWebmailStore } from '@/stores'
+import { DateTime } from 'luxon'
+import EmailAddressList from './EmailAddressList.vue'
+import EmailSchedulingForm from './EmailSchedulingForm.vue'
+import MenuItems from '@/components/tools/MenuItems.vue'
 import api from '@/api/webmail'
 
 const props = defineProps({
@@ -193,11 +256,15 @@ const webmailStore = useWebmailStore()
 const router = useRouter()
 const route = useRoute()
 
+const selectedScheduledEmail = ref(null)
 const loading = ref(false)
 const emails = ref({})
 const page = ref(1)
+const schedulingError = ref('')
 const search = ref('')
 const selectAll = ref(false)
+const showSchedulingError = ref(false)
+const showSchedulingForm = ref(false)
 const working = ref(false)
 
 let intervalId = null
@@ -206,6 +273,79 @@ const currentMailbox = computed(() => {
   return route.query.mailbox || 'INBOX'
 })
 
+const inScheduledView = computed(() => props.mailbox === 'Scheduled')
+
+const getScheduledMessageActions = () => {
+  return [
+    {
+      label: $gettext('Reschedule'),
+      icon: 'mdi-send-clock-outline',
+      onClick: reScheduleMessage,
+    },
+    {
+      label: $gettext('Delete'),
+      icon: 'mdi-delete-outline',
+      onClick: deleteScheduledMessage,
+      color: 'red',
+    },
+  ]
+}
+
+const getEmailAddresses = (email) => {
+  if (inScheduledView.value) {
+    return email.recipients
+  }
+  return [email.from_address]
+}
+
+const getEmailDate = (email) => {
+  if (inScheduledView.value) {
+    return email.scheduled_datetime
+  }
+  return email.date
+}
+
+const isScheduledDateOver = (email) => {
+  if (!inScheduledView.value || !email.scheduled_datetime_raw) return false
+  const date = DateTime.fromISO(email.scheduled_datetime_raw)
+  return date < DateTime.now()
+}
+
+const reScheduleMessage = (email) => {
+  selectedScheduledEmail.value = email
+  showSchedulingForm.value = true
+}
+
+const updateScheduledEmail = async (datetime) => {
+  const data = {
+    scheduled_datetime: datetime,
+  }
+  await api.updateScheduledMessage(
+    selectedScheduledEmail.value.scheduled_id,
+    data
+  )
+  fetchEmails()
+  displayNotification({ msg: $gettext('Scheduling updated') })
+}
+
+const closeSchedulingForm = () => {
+  showSchedulingForm.value = false
+}
+
+const deleteScheduledMessage = async (email) => {
+  await api.deleteScheduledMessage(email.scheduled_id)
+  fetchEmails()
+  displayNotification({
+    msg: $gettext('Scheduled canceled and message move to trash folder'),
+  })
+}
+
+const displaySchedulingError = async (email) => {
+  const resp = await api.getScheduledMessage(email.scheduled_id)
+  schedulingError.value = resp.data.error
+  showSchedulingError.value = true
+}
+
 const openEmail = (emailid) => {
   router.push({
     name: 'EmailView',
@@ -380,4 +520,7 @@ watch(page, () => {
 .clickable {
   cursor: pointer;
 }
+.scheduling-top {
+  top: 45px;
+}
 </style>
diff --git a/frontend/src/components/webmail/EmailSchedulingForm.vue b/frontend/src/components/webmail/EmailSchedulingForm.vue
new file mode 100644
index 000000000..68b06da00
--- /dev/null
+++ b/frontend/src/components/webmail/EmailSchedulingForm.vue
@@ -0,0 +1,118 @@
+<template>
+  <v-card :title="$gettext('Schedule your sending')">
+    <v-card-text>
+      <v-form ref="formRef">
+        <div class="d-flex">
+          <v-date-picker
+            v-model="date"
+            class="w-50"
+            :allowed-dates="allowedDates"
+            :rules="[rules.required]"
+          />
+          <div
+            class="w-33 pt-2 text-uppercase text-overline font-weight-regular"
+          >
+            <label>{{ $gettext('Select time') }}</label>
+            <v-text-field
+              v-model="time"
+              variant="outlined"
+              class="mt-6"
+              :rules="[rules.required, rules.time]"
+            />
+          </div>
+        </div>
+      </v-form>
+    </v-card-text>
+    <v-card-actions>
+      <v-spacer />
+      <v-btn :text="$gettext('Close')" :loading="loading" @click="close" />
+      <v-btn
+        :text="$gettext('Schedule')"
+        color="primary"
+        :loading="loading"
+        @click="submit"
+      />
+    </v-card-actions>
+  </v-card>
+</template>
+
+<script setup>
+import { ref, watch } from 'vue'
+import { DateTime } from 'luxon'
+import { useGettext } from 'vue3-gettext'
+import { useBusStore } from '@/stores'
+import rules from '@/plugins/rules.js'
+
+const props = defineProps({
+  initialDate: {
+    type: String,
+    default: null,
+  },
+})
+const emit = defineEmits(['close', 'schedule'])
+
+const { $gettext } = useGettext()
+const { displayNotification } = useBusStore()
+
+const close = () => {
+  emit('close')
+}
+
+const allowedDates = (value) => {
+  const now = new Date()
+  return value > now
+}
+
+const validateDatetime = (value) => {
+  const now = new Date()
+  const msg = $gettext('Provided time must be one minute from now at least')
+  if (value <= now) {
+    displayNotification({ msg, type: 'error' })
+    return false
+  }
+  const delta = value - now
+  if (delta / 1000 < 60) {
+    displayNotification({ msg, type: 'error' })
+    return false
+  }
+  return true
+}
+
+const date = ref('')
+const formRef = ref()
+const loading = ref(false)
+const time = ref('')
+
+const now = DateTime.now()
+date.value = now.toJSDate()
+time.value = now.toFormat('HH:mm')
+
+const submit = async () => {
+  const { valid } = await formRef.value.validate()
+  if (!valid) {
+    return
+  }
+  const datetime = date.value
+  const parts = time.value.split(':')
+  datetime.setHours(parseInt(parts[0]), parseInt(parts[1]))
+  if (!validateDatetime(datetime)) {
+    return
+  }
+  loading.value = true
+  emit('schedule', datetime.toISOString())
+  emit('close')
+  loading.value = false
+}
+
+watch(
+  () => props.initialDate,
+  (value) => {
+    if (value) {
+      const initialDate = DateTime.fromISO(value)
+      date.value = initialDate.toJSDate()
+      time.value = initialDate.toFormat('HH:mm')
+    }
+  },
+  { immediate: true }
+)
+</script>
diff --git a/frontend/src/components/webmail/MailboxList.vue b/frontend/src/components/webmail/MailboxList.vue
index 6fb7d58f1..bdc9a60a5 100644
--- a/frontend/src/components/webmail/MailboxList.vue
+++ b/frontend/src/components/webmail/MailboxList.vue
@@ -106,6 +106,7 @@ const iconByMailboxType = {
   draft: 'mdi-file',
   junk: 'mdi-fire',
   sent: 'mdi-email-fast-outline',
+  scheduled: 'mdi-send-clock-outline',
   trash: 'mdi-trash-can-outline',
   normal: 'mdi-folder-outline',
 }
diff --git a/frontend/src/plugins/rules.js b/frontend/src/plugins/rules.js
index b8231f5ee..c1bf084a7 100644
--- a/frontend/src/plugins/rules.js
+++ b/frontend/src/plugins/rules.js
@@ -22,6 +22,13 @@ function samePassword(value, confirmation) {
   return value === confirmation
 }
 
+function validateTime(value) {
+  if (!/^([01]\d|2[0-3]):?([0-5]\d)$/.test(value)) {
+    return $gettext('Not a valid time')
+  }
+  return true
+}
+
 export default {
   required: (value) =>
     (value !== '' &&
@@ -43,4 +50,5 @@ export default {
     samePassword(value, confirmation) || $gettext('Passwords mismatch'),
   portNumber: (value) =>
     (value > 0 && value < 65536) || $gettext('Invalid port number'),
+  time: (value) => validateTime(value),
 }
diff --git a/frontend/src/views/webmail/EmailView.vue b/frontend/src/views/webmail/EmailView.vue
index 9261b70c3..4646ff3f2 100644
--- a/frontend/src/views/webmail/EmailView.vue
+++ b/frontend/src/views/webmail/EmailView.vue
@@ -3,63 +3,57 @@
     <v-toolbar color="white">
       <v-btn icon="mdi-arrow-left" size="small" variant="flat" @click="close" />
 
-      <v-btn
-        color="primary"
-        variant="tonal"
-        prepend-icon="mdi-reply"
-        @click="() => replyToEmail()"
-      >
-        {{ $gettext('Reply') }}
-        <template #append>
-          <v-btn size="x-small" variant="plain">
-            <v-icon icon="mdi-chevron-down" />
-            <v-menu activator="parent">
-              <v-list>
-                <v-list-item
-                  :title="$gettext('Reply all')"
-                  @click="() => replyToEmail(true)"
-                />
-                <v-list-item
-                  :title="$gettext('Forward')"
-                  @click="forwardEmail"
-                />
-              </v-list>
-            </v-menu>
-          </v-btn>
-        </template>
-      </v-btn>
-      <v-btn
-        class="ml-2"
-        color="error"
-        variant="tonal"
-        icon="mdi-trash-can"
-        size="small"
-        :loading="working"
-        @click="deleteEmail"
-      >
-      </v-btn>
-      <v-btn
-        v-if="route.params.mailbox !== 'Junk'"
-        class="ml-2"
-        color="warning"
-        variant="tonal"
-        icon="mdi-fire"
-        size="small"
-        :loading="working"
-        @click="markEmailAsJunk"
-      >
-      </v-btn>
-      <v-btn
-        v-else
-        class="ml-2"
-        color="success"
-        variant="tonal"
-        icon="mdi-thumb-up"
-        size="small"
-        :loading="working"
-        @click="markEmailAsNotJunk"
-      >
-      </v-btn>
+      <v-btn-group color="primary" rounded="lg" density="compact" divided>
+        <v-btn prepend-icon="mdi-reply" @click="() => replyToEmail()">
+          {{ $gettext('Reply') }}
+        </v-btn>
+        <v-btn size="small" icon>
+          <v-icon icon="mdi-chevron-down" />
+          <v-menu activator="parent">
+            <v-list>
+              <v-list-item
+                :title="$gettext('Reply all')"
+                @click="() => replyToEmail(true)"
+              />
+              <v-list-item :title="$gettext('Forward')" @click="forwardEmail" />
+            </v-list>
+          </v-menu>
+        </v-btn>
+      </v-btn-group>
+      <template v-if="$route.query.mailbox !== 'Scheduled'">
+        <v-btn
+          class="ml-2"
+          color="error"
+          variant="tonal"
+          icon="mdi-trash-can"
+          size="small"
+          :loading="working"
+          @click="deleteEmail"
+        >
+        </v-btn>
+        <v-btn
+          v-if="route.params.mailbox !== 'Junk'"
+          class="ml-2"
+          color="warning"
+          variant="tonal"
+          icon="mdi-fire"
+          size="small"
+          :loading="working"
+          @click="markEmailAsJunk"
+        >
+        </v-btn>
+        <v-btn
+          v-else
+          class="ml-2"
+          color="success"
+          variant="tonal"
+          icon="mdi-thumb-up"
+          size="small"
+          :loading="working"
+          @click="markEmailAsNotJunk"
+        >
+        </v-btn>
+      </template>
       <v-btn class="ml-2" variant="tonal" icon size="small">
         <v-icon icon="mdi-cog" />
         <v-menu activator="parent">
@@ -140,6 +134,17 @@
         </template>
       </div>
     </div>
+    <v-alert
+      v-if="email?.scheduled_datetime"
+      ref="schedulingInfo"
+      type="info"
+      variant="tonal"
+      density="compact"
+      class="mx-1"
+    >
+      {{ $gettext('Message scheduled at:') }}
+      {{ $date(email.scheduled_datetime) }}
+    </v-alert>
     <iframe class="email-frame" />
   </div>
   <v-dialog v-model="showEmailSource" max-width="1200">
@@ -176,6 +181,7 @@ const email = ref(null)
 const emailSource = ref(null)
 const headers = ref(null)
 const loaded = ref(false)
+const schedulingInfo = ref()
 const showEmailSource = ref(false)
 const working = ref(false)
 
@@ -201,7 +207,12 @@ const close = () => {
 
 const resizeEmailIframe = () => {
   const iframe = document.querySelector('iframe')
-  const rect = headers.value.getBoundingClientRect()
+  let rect
+  if (schedulingInfo.value) {
+    rect = schedulingInfo.value.$el.getBoundingClientRect()
+  } else {
+    rect = headers.value.getBoundingClientRect()
+  }
   iframe.style.top = `${rect.bottom}px`
   iframe.style.width = `${rect.width - 24}px`
   iframe.style.height = `${window.innerHeight - rect.bottom - 32}px`
@@ -221,9 +232,11 @@ const fetchMailContent = () => {
         const iframe = document.createElement('iframe')
         iframe.classList.add('email-frame')
         document.querySelector('iframe').replaceWith(iframe)
-        const iframeDoc = iframe.contentDocument
-        iframeDoc.write(email.value.body)
-        iframeDoc.close()
+        if (email.value.body) {
+          const iframeDoc = iframe.contentDocument
+          iframeDoc.write(email.value.body)
+          iframeDoc.close()
+        }
         loaded.value = true
         nextTick(resizeEmailIframe)
       })
diff --git a/modoboa/core/commands/templates/cron_config.py.tpl b/modoboa/core/commands/templates/cron_config.py.tpl
index 1354230d2..a1af5ab83 100644
--- a/modoboa/core/commands/templates/cron_config.py.tpl
+++ b/modoboa/core/commands/templates/cron_config.py.tpl
@@ -25,6 +25,8 @@ register(maillog_jobs.update_statistics, queue_name="modoboa", cron="0 * * * *")
 
 register(calendars_jobs.generate_rights, queue_name="privileged", cron="*/2 * * * *")
 
+register(webmail_jobs.send_scheduled_messages, queue_name="modoboa", cron="* * * * *")
+
 if "modoboa.amavis" in settings.MODOBOA_APPS:
     register(amavis_jobs.qcleanup, queue_name="modoboa", cron="0 0 * * *")
     register(amavis_jobs.amnotify, queue_name="modoboa", cron="0 12 * * *")
diff --git a/modoboa/lib/sysutils.py b/modoboa/lib/sysutils.py
index f97c0a0f8..281d00efa 100644
--- a/modoboa/lib/sysutils.py
+++ b/modoboa/lib/sysutils.py
@@ -43,7 +43,7 @@ def exec_cmd(cmd, sudo_user=None, pinput=None, capture_output=True, **kwargs):
     return process.returncode, output
 
 
-def doveadm_cmd(params, pinput=None, capture_output=True, **kwargs):
+def doveadm_cmd(params: str, pinput=None, capture_output=True, **kwargs):
     """Execute doveadm command.
 
     Run doveadm command using the current user. Set :keyword:`sudo_user` if
diff --git a/modoboa/webmail/app_settings.py b/modoboa/webmail/app_settings.py
index d9d59ccda..f1dca550d 100644
--- a/modoboa/webmail/app_settings.py
+++ b/modoboa/webmail/app_settings.py
@@ -107,6 +107,43 @@ GLOBAL_PARAMETERS_STRUCT = collections.OrderedDict(
                 ),
             },
         ),
+        (
+            "scheduling",
+            {
+                "label": gettext_lazy("Scheduling settings"),
+                "params": collections.OrderedDict(
+                    [
+                        (
+                            "scheduling_smtp_server",
+                            {
+                                "label": gettext_lazy("Server address"),
+                                "help_text": gettext_lazy(
+                                    "Address of your SMTP server"
+                                ),
+                            },
+                        ),
+                        (
+                            "scheduling_smtp_secured_mode",
+                            {
+                                "label": gettext_lazy("Secured connection mode"),
+                                "help_text": gettext_lazy(
+                                    "Use a secured connection to access SMTP server"
+                                ),
+                            },
+                        ),
+                        (
+                            "scheduling_smtp_port",
+                            {
+                                "label": gettext_lazy("Server port"),
+                                "help_text": gettext_lazy(
+                                    "Listening port of your SMTP server"
+                                ),
+                            },
+                        ),
+                    ]
+                ),
+            },
+        ),
     ]
 )
 
diff --git a/modoboa/webmail/constants.py b/modoboa/webmail/constants.py
index 31e5ffbf2..41e7459e1 100644
--- a/modoboa/webmail/constants.py
+++ b/modoboa/webmail/constants.py
@@ -5,7 +5,27 @@ from enum import Enum
 from django.utils.translation import gettext_lazy as _
 
 
-MAILBOX_TYPES = ["inbox", "draft", "sent", "junk", "trash", "normal"]
+MAILBOX_TYPES = ["inbox", "draft", "sent", "scheduled", "junk", "trash", "normal"]
+
+MAILBOX_NAME_SCHEDULED = "Scheduled"
+
+CUSTOM_HEADER_SCHEDULED_ID = "X-Scheduled-ID"
+CUSTOM_HEADER_SCHEDULED_DATETIME = "X-Scheduled-Datetime"
+
+
+class SchedulingState(Enum):
+    SCHEDULED = "scheduled"
+    SENDING = "sending"
+    SEND_ERROR = "send_error"
+    MOVE_ERROR = "move_error"
+
+
+EMAIL_SCHEDULING_STATES = (
+    (SchedulingState.SCHEDULED, "scheduled"),
+    (SchedulingState.SENDING, "sending"),
+    (SchedulingState.SEND_ERROR, "send_error"),
+    (SchedulingState.MOVE_ERROR, "move_error"),
+)
 
 
 class SmtpConnectionMode(Enum):
diff --git a/modoboa/webmail/jobs.py b/modoboa/webmail/jobs.py
new file mode 100644
index 000000000..0d6147d89
--- /dev/null
+++ b/modoboa/webmail/jobs.py
@@ -0,0 +1,26 @@
+"""Async (RQ) jobs definition."""
+
+from django.utils import timezone
+
+import django_rq
+
+from modoboa.webmail import constants, models
+from modoboa.webmail.lib import sendmail
+
+
+def send_scheduled_message(message_id: int):
+    message = models.ScheduledMessage.objects.get(id=message_id)
+    if sendmail.send_scheduled_message(message):
+        message.delete()
+
+
+def send_scheduled_messages():
+    messages = models.ScheduledMessage.objects.filter(
+        scheduled_datetime__lte=timezone.now(),
+        status=constants.SchedulingState.SCHEDULED,
+    )
+    queue = django_rq.get_queue("modoboa")
+    for message in messages:
+        message.state = constants.SchedulingState.SENDING
+        message.save()
+        queue.enqueue(send_scheduled_message, message_id=message.id)
diff --git a/modoboa/webmail/lib/__init__.py b/modoboa/webmail/lib/__init__.py
index c7d945c9e..2d78a671d 100644
--- a/modoboa/webmail/lib/__init__.py
+++ b/modoboa/webmail/lib/__init__.py
@@ -7,7 +7,7 @@ from .imapemail import ImapEmail, ReplyModifier, ForwardModifier
 from .imaputils import BodyStructure, IMAPconnector, get_imapconnector, separate_mailbox
 from .signature import EmailSignature
 from .utils import decode_payload
-from .sendmail import send_mail
+from .sendmail import send_mail, schedule_email
 
 
 __all__ = [
@@ -23,5 +23,6 @@ __all__ = [
     "get_imapconnector",
     "save_attachment",
     "send_mail",
+    "schedule_email",
     "separate_mailbox",
 ]
diff --git a/modoboa/webmail/lib/imapemail.py b/modoboa/webmail/lib/imapemail.py
index 04af9817a..72a029c98 100644
--- a/modoboa/webmail/lib/imapemail.py
+++ b/modoboa/webmail/lib/imapemail.py
@@ -18,6 +18,7 @@ from django.utils.translation import gettext as _
 from modoboa.contacts import models as contacts_models
 from modoboa.lib import u2u_decode
 from modoboa.lib.email_utils import Email
+from modoboa.webmail import constants
 
 from . import imapheader
 from .attachments import get_storage_path
@@ -51,13 +52,17 @@ class ImapEmail(Email):
 
     def fetch_headers(self, raw_addresses: bool = False) -> None:
         """Fetch message headers from server."""
+        requested_headers = self.headernames
+        if self.mbox == constants.MAILBOX_NAME_SCHEDULED:
+            requested_headers += [(constants.CUSTOM_HEADER_SCHEDULED_DATETIME, True)]
+        header_names = [header[0].upper() for header in requested_headers]
         msg = self.imapc.fetchmail(
-            self.mbox, self.mailid, readonly=False, what=" ".join(self.headers_as_list)
+            self.mbox, self.mailid, readonly=False, what=" ".join(header_names)
         )
-        headers = msg[f"BODY[HEADER.FIELDS ({self.headers_as_text})]"]
+        headers = msg[f"BODY[HEADER.FIELDS ({' '.join(header_names)})]"]
         self.fetch_body_structure(msg)
         msg = email.message_from_string(headers)
-        for hdr in self.headernames:
+        for hdr in requested_headers:
             label = hdr[0]
             hdrvalue = self.get_header(msg, label, raw=raw_addresses)
             if not hdrvalue:
@@ -110,14 +115,6 @@ class ImapEmail(Email):
             self.dformat if self.dformat in self.bs.contents else fallback_fmt
         )
 
-    @property
-    def headers_as_list(self):
-        return [hdr[0].upper() for hdr in self.headernames]
-
-    @property
-    def headers_as_text(self):
-        return " ".join(self.headers_as_list)
-
     @property
     def subject(self):
         """Just a shortcut to return a subject in any case."""
diff --git a/modoboa/webmail/lib/imapheader.py b/modoboa/webmail/lib/imapheader.py
index 987981d4b..81d648968 100644
--- a/modoboa/webmail/lib/imapheader.py
+++ b/modoboa/webmail/lib/imapheader.py
@@ -27,19 +27,19 @@ __all__ = [
 # according to https://en.wikipedia.org/wiki/Date_format_by_country
 # and https://en.wikipedia.org/wiki/Date_and_time_representation_by_country
 DATETIME_FORMATS = {
-    "cs": {"SHORT": "l, H:i", "LONG": "d. N Y H:i"},
-    "de": {"SHORT": "l, H:i", "LONG": "d. N Y H:i"},
-    "en": {"SHORT": "l, P", "LONG": "N j, Y P"},
-    "es": {"SHORT": "l, H:i", "LONG": "d. N Y H:i"},
-    "fr": {"SHORT": "l, H:i", "LONG": "d. N Y H:i"},
-    "it": {"SHORT": "l, H:i", "LONG": "d. N Y H:i"},
-    "ja_JP": {"SHORT": "l, P", "LONG": "N j, Y P"},
-    "nl": {"SHORT": "l, H:i", "LONG": "d. N Y H:i"},
-    "pl_PL": {"SHORT": "l, H:i", "LONG": "d. N Y H:i"},
-    "pt_PT": {"SHORT": "l, H:i", "LONG": "d. N Y H:i"},
-    "pt_BR": {"SHORT": "l, H:i", "LONG": "d. N Y H:i"},
-    "ru": {"SHORT": "l, H:i", "LONG": "d. N Y H:i"},
-    "sv": {"SHORT": "l, H:i", "LONG": "d. N Y H:i"},
+    "cs": {"SHORT": "l, H:i", "LONG": "d. N Y H:i", "TIME": "H:i"},
+    "de": {"SHORT": "l, H:i", "LONG": "d. N Y H:i", "TIME": "H:i"},
+    "en": {"SHORT": "l, P", "LONG": "N j, Y P", "TIME": "H:i"},
+    "es": {"SHORT": "l, H:i", "LONG": "d. N Y H:i", "TIME": "H:i"},
+    "fr": {"SHORT": "l, H:i", "LONG": "d. N Y H:i", "TIME": "H:i"},
+    "it": {"SHORT": "l, H:i", "LONG": "d. N Y H:i", "TIME": "H:i"},
+    "ja_JP": {"SHORT": "l, P", "LONG": "N j, Y P", "TIME": "H:i"},
+    "nl": {"SHORT": "l, H:i", "LONG": "d. N Y H:i", "TIME": "H:i"},
+    "pl_PL": {"SHORT": "l, H:i", "LONG": "d. N Y H:i", "TIME": "H:i"},
+    "pt_PT": {"SHORT": "l, H:i", "LONG": "d. N Y H:i", "TIME": "H:i"},
+    "pt_BR": {"SHORT": "l, H:i", "LONG": "d. N Y H:i", "TIME": "H:i"},
+    "ru": {"SHORT": "l, H:i", "LONG": "d. N Y H:i", "TIME": "H:i"},
+    "sv": {"SHORT": "l, H:i", "LONG": "d. N Y H:i", "TIME": "H:i"},
 }
 
 
@@ -123,6 +123,18 @@ def parse_date(value, **kwargs):
     )
 
 
+def parse_scheduled_datetime(value: str, **kwargs) -> str:
+    result = datetime.datetime.fromisoformat(value)
+    current_language = get_request().user.language
+    if timezone.now().date().day != result.date().day:
+        fmt = "LONG"
+    else:
+        fmt = "TIME"
+    return date_format(
+        result, DATETIME_FORMATS.get(current_language, DATETIME_FORMATS.get("en"))[fmt]
+    )
+
+
 def parse_message_id(value, **kwargs):
     """Parse a Message-ID: header."""
     return value.strip("\n")
diff --git a/modoboa/webmail/lib/imaputils.py b/modoboa/webmail/lib/imaputils.py
index d8eff0014..6e6dfabff 100644
--- a/modoboa/webmail/lib/imaputils.py
+++ b/modoboa/webmail/lib/imaputils.py
@@ -13,6 +13,7 @@ from modoboa.lib import imap_utf7  # noqa
 from modoboa.lib import oauth2
 from modoboa.lib.exceptions import InternalError
 from modoboa.parameters import tools as param_tools
+from modoboa.webmail import constants
 
 from ..exceptions import ImapError, WebmailInternalError
 from .fetch_parser import FetchResponseParser
@@ -490,6 +491,11 @@ class IMAPconnector:
                     "type": "sent",
                     "label": _("Sent"),
                 },
+                {
+                    "name": constants.MAILBOX_NAME_SCHEDULED,
+                    "type": "scheduled",
+                    "label": _("Scheduled"),
+                },
                 {
                     "name": user.parameters.get_value("trash_folder"),
                     "type": "trash",
@@ -581,10 +587,30 @@ class IMAPconnector:
         self._cmd("COPY", msgset, self._encode_mbox_name(newmailbox))
         self._cmd("STORE", msgset, "+FLAGS", r"(\Deleted \Seen)")
 
-    def push_mail(self, mbox: str, msg):
+    def push_mail(self, mbox: str, msg) -> int:
+        """
+        Append a new message to a mailbox.
+
+        Return the UID of the created message.
+        """
         now = imaplib.Time2Internaldate(time.time())
         msg = bytes(msg)
-        return self.m.append(self._encode_mbox_name(mbox), r"(\Seen)", now, msg)
+        typ, data = self.m.append(self._encode_mbox_name(mbox), r"(\Seen)", now, msg)
+        response = data[0].decode()
+        m = re.match(r"\[APPENDUID \d+ (\d+)\].+", response)
+        if m:
+            return int(m.group(1))
+        raise WebmailInternalError("Failed to retrieve message UID")
+
+    def delete_mail(self, mbox: str, uid: int) -> None:
+        """
+        Delete given message (set \Deleted flag) and expunge mailbox.
+
+        Do not use directly.
+        """
+        self.select_mailbox(mbox, False)
+        self._cmd("STORE", f"{uid}".encode(), "+FLAGS", r"(\Deleted)")
+        self._cmd("EXPUNGE")
 
     def empty(self, mbox: str):
         self.select_mailbox(mbox, False)
@@ -610,7 +636,7 @@ class IMAPconnector:
             name = f"{parent}{self.hdelimiter}{name}"
         typ, data = self.m.create(self._encode_mbox_name(name))
         if typ == "NO":
-            raise WebmailInternalError(data[0])
+            raise WebmailInternalError(str(data[0]))
         return True
 
     def rename_folder(self, oldname: str, newname: str) -> bool:
@@ -699,6 +725,8 @@ class IMAPconnector:
             submessages = [start]
             mrange = str(start)
         headers = "DATE FROM TO CC SUBJECT"
+        if mbox == constants.MAILBOX_NAME_SCHEDULED:
+            headers += " X-SCHEDULED-ID X-SCHEDULED-DATETIME"
         query = (
             f"(FLAGS BODYSTRUCTURE RFC822.SIZE BODY.PEEK[HEADER.FIELDS ({headers})])"
         )
diff --git a/modoboa/webmail/lib/sendmail.py b/modoboa/webmail/lib/sendmail.py
index e80995d22..d2178a703 100644
--- a/modoboa/webmail/lib/sendmail.py
+++ b/modoboa/webmail/lib/sendmail.py
@@ -1,116 +1,26 @@
-from email.header import Header
-from email.mime.image import MIMEImage
-from importlib.metadata import version
-import os
-
 import smtplib
-from urllib.parse import unquote, urlparse
-
-import lxml
 
 from django.conf import settings
 from django.core import mail
-from django.core.mail import EmailMessage, EmailMultiAlternatives
 
-from modoboa.core import models as core_models
 from modoboa.parameters import tools as param_tools
-from modoboa.webmail.lib.attachments import create_mail_attachment
-from modoboa.webmail.lib.utils import html2plaintext
+from modoboa.webmail import constants, models
+from modoboa.webmail.exceptions import WebmailInternalError
+from modoboa.webmail.lib.utils import create_message
 
 from . import get_imapconnector
 
 
-def make_body_images_inline(body: str) -> tuple[str, list]:
-    """Look for images inside the body and make them inline.
-
-    Before sending a message in HTML format, it is necessary to find
-    all img tags contained in the body in order to rewrite them. For
-    example, icons provided by CKeditor are stored on the server
-    filesystem and not accessible from the outside. We must embark
-    them as parts of the MIME message if we want recipients to
-    display them correctly.
-
-    :param body: the HTML body to parse
-    """
-    html = lxml.html.fromstring(body)
-    parts = []
-    for tag in html.iter("img"):
-        src = tag.get("src")
-        if src is None:
-            continue
-        o = urlparse(src)
-        path = unquote(os.path.join(settings.BASE_DIR, o.path[1:]))
-        if not os.path.exists(path):
-            continue
-        fname = os.path.basename(path)
-        cid = f"{os.path.splitext(fname)[0]}@modoboa"
-        tag.set("src", f"cid:{cid}")
-        with open(path, "rb") as fp:
-            part = MIMEImage(fp.read())
-        part["Content-ID"] = f"<{cid}>"
-        part.replace_header("Content-Type", f'{part["Content-Type"]}; name="{fname}"')
-        part["Content-Disposition"] = "inline"
-        parts.append(part)
-    return lxml.html.tostring(html, encoding="unicode"), parts
-
-
-def html_msg(attributes: dict) -> EmailMultiAlternatives:
-    """Create a multipart message.
-
-    We attach two alternatives:
-    * text/html
-    * text/plain
-    """
-    body = attributes.get("body")
-    if body:
-        tbody = html2plaintext(body)
-        body, images = make_body_images_inline(body)
-    else:
-        tbody = ""
-        images = []
-    msg = EmailMultiAlternatives()
-    msg.body = tbody
-    msg.attach_alternative(body, "text/html")
-    for img in images:
-        msg.attach(img)
-    return msg
-
-
-def plain_msg(attributes: dict) -> EmailMessage:
-    """Create a simple text message."""
-    msg = EmailMessage()
-    msg.body = attributes.get("body", "")
-    return msg
-
-
-def format_sender_address(user: core_models.User, address: str) -> str:
-    """Format address before message is sent."""
-    if user.first_name != "" or user.last_name != "":
-        return f'"{Header(user.fullname, "utf8")}" <{address}>'
-    return address
-
-
-def create_message(user: core_models.User, attributes: dict, attachments: list):
-    headers = {"User-Agent": "Modoboa {}".format(version("modoboa"))}
-    origmsgid = attributes.get("in_reply_to")
-    if origmsgid:
-        headers.update({"References": origmsgid, "In-Reply-To": origmsgid})
-    mode = user.parameters.get_value("editor")
-    sender = format_sender_address(user, attributes["sender"])
-    if mode == "html":
-        msg = html_msg(attributes)
-    else:
-        msg = plain_msg(attributes)
-    msg.from_email = sender
-    msg.to = attributes["to"]
-    msg.headers = headers
-    for hdr in ["subject", "cc", "bcc"]:
-        if hdr in attributes:
-            setattr(msg, hdr, attributes[hdr])
-
-    for attachment in attachments:
-        msg.attach(create_mail_attachment(attachment))
-    return msg
+def create_message_from_scheduled_message(sched_msg: models.ScheduledMessage):
+    attachments = [attachment.to_dict() for attachment in sched_msg.attachments.all()]
+    result = create_message(sched_msg.account, sched_msg.to_dict(), attachments)
+    result.extra_headers.update(
+        {
+            constants.CUSTOM_HEADER_SCHEDULED_ID: sched_msg.id,
+            constants.CUSTOM_HEADER_SCHEDULED_DATETIME: sched_msg.scheduled_datetime.isoformat(),
+        }
+    )
+    return result
 
 
 def send_mail(request, attributes: dict, attachments: list) -> tuple[bool, str | None]:
@@ -161,3 +71,84 @@ def send_mail(request, attributes: dict, attachments: list) -> tuple[bool, str |
     with get_imapconnector(request) as imapc:
         imapc.push_mail(sentfolder, msg.message())
     return True, None
+
+
+def schedule_email(
+    request, attributes: dict, attachments: list
+) -> models.ScheduledMessage:
+    """Schedule a new email sending."""
+    message = models.ScheduledMessage(
+        account=request.user,
+        sender=attributes["sender"],
+        scheduled_datetime=attributes["scheduled_datetime"],
+        to=",".join(attributes["to"]),
+        subject=attributes.get("subject", ""),
+        body=attributes.get("body", ""),
+        in_reply_to=attributes.get("in_reply_to", ""),
+    )
+    for attr in ["cc", "bcc"]:
+        if attr in attributes:
+            setattr(message, attr, ",".join(attributes[attr]))
+    message.save()
+
+    # Save a copy of this message into an IMAP mailbox
+    msg = create_message_from_scheduled_message(message)
+    with get_imapconnector(request) as imapc:
+        try:
+            imapc.create_folder(constants.MAILBOX_NAME_SCHEDULED)
+        except WebmailInternalError:
+            pass
+        # TODO: deal with UID Validity
+        message.imap_uid = imapc.push_mail(
+            constants.MAILBOX_NAME_SCHEDULED, msg.message()
+        )
+        message.save()
+
+    for attachment in attachments:
+        mattachment = models.MessageAttachment(
+            message=message,
+        )
+        if "content-type" in attachment:
+            mattachment.content_type = attachment["content-type"]
+        elif "Content-Type" in attachment:
+            mattachment.content_type = attachment["Content-Type"]
+        else:
+            continue
+        mattachment.file.name = attachment["tmpname"]
+        if "fname" in attachment:
+            mattachment.filename = attachment["fname"]
+        mattachment.save()
+
+    return message
+
+
+def send_scheduled_message(sched_msg: models.ScheduledMessage) -> bool:
+    """Send a scheduled message using configured SMTP server."""
+    msg = create_message_from_scheduled_message(sched_msg)
+    conf = dict(param_tools.get_global_parameters("webmail"))
+    options = {
+        "host": conf["scheduling_smtp_server"],
+        "port": conf["scheduling_smtp_port"],
+    }
+    if conf["scheduling_smtp_secured_mode"] == "ssl":
+        options.update({"use_ssl": True})
+    elif conf["scheduling_smtp_secured_mode"] == "starttls":
+        options.update({"use_tls": True})
+
+    try:
+        with mail.get_connection(**options) as connection:
+            msg.connection = connection
+            msg.send()
+    except (smtplib.SMTPResponseException, smtplib.SMTPRecipientsRefused) as inst:
+        if isinstance(inst, smtplib.SMTPRecipientsRefused):
+            error = ", ".join(
+                [f"{rcpt}: {error}" for rcpt, error in inst.recipients.items()]
+            )
+        else:
+            error = str(inst.smtp_error)
+        sched_msg.status = constants.SchedulingState.SEND_ERROR
+        sched_msg.error = error
+        sched_msg.save()
+        return False
+
+    return sched_msg.delete_imap_copy()
diff --git a/modoboa/webmail/lib/utils.py b/modoboa/webmail/lib/utils.py
index c81aaed47..861a698ef 100644
--- a/modoboa/webmail/lib/utils.py
+++ b/modoboa/webmail/lib/utils.py
@@ -1,7 +1,19 @@
 """Misc. utilities."""
 
+from email.header import Header
+from email.mime.image import MIMEImage
+from importlib.metadata import version
+import os
+from urllib.parse import unquote, urlparse
+
 import lxml
 
+from django.conf import settings
+from django.core.mail import EmailMessage, EmailMultiAlternatives
+
+from modoboa.core import models as core_models
+from modoboa.webmail.lib.attachments import create_mail_attachment
+
 
 def html2plaintext(content: str) -> str:
     """HTML to plain text translation.
@@ -43,3 +55,100 @@ def decode_payload(encoding, payload):
 
         return quopri.decodestring(payload)
     return payload
+
+
+def make_body_images_inline(body: str) -> tuple[str, list]:
+    """Look for images inside the body and make them inline.
+
+    Before sending a message in HTML format, it is necessary to find
+    all img tags contained in the body in order to rewrite them. For
+    example, icons provided by CKeditor are stored on the server
+    filesystem and not accessible from the outside. We must embark
+    them as parts of the MIME message if we want recipients to
+    display them correctly.
+
+    :param body: the HTML body to parse
+    """
+    html = lxml.html.fromstring(body)
+    parts = []
+    for tag in html.iter("img"):
+        src = tag.get("src")
+        if src is None:
+            continue
+        o = urlparse(src)
+        path = unquote(os.path.join(settings.BASE_DIR, o.path[1:]))
+        if not os.path.exists(path):
+            continue
+        fname = os.path.basename(path)
+        cid = f"{os.path.splitext(fname)[0]}@modoboa"
+        tag.set("src", f"cid:{cid}")
+        with open(path, "rb") as fp:
+            part = MIMEImage(fp.read())
+        part["Content-ID"] = f"<{cid}>"
+        part.replace_header("Content-Type", f'{part["Content-Type"]}; name="{fname}"')
+        part["Content-Disposition"] = "inline"
+        parts.append(part)
+    return lxml.html.tostring(html, encoding="unicode"), parts
+
+
+def html_msg(content: str) -> EmailMultiAlternatives:
+    """Create a multipart message.
+
+    We attach two alternatives:
+    * text/html
+    * text/plain
+    """
+    if content:
+        body = html2plaintext(content)
+        body, images = make_body_images_inline(body)
+    else:
+        body = ""
+        images = []
+    msg = EmailMultiAlternatives()
+    msg.body = body
+    msg.attach_alternative(body, "text/html")
+    for img in images:
+        msg.attach(img)
+    return msg
+
+
+def plain_msg(content: str) -> EmailMessage:
+    """Create a simple text message."""
+    msg = EmailMessage()
+    msg.body = content
+    return msg
+
+
+def format_sender_address(user: core_models.User, address: str) -> str:
+    """Format address before message is sent."""
+    if user.first_name != "" or user.last_name != "":
+        return f'"{Header(user.fullname, "utf8")}" <{address}>'
+    return address
+
+
+def create_message(
+    user: core_models.User, attributes: dict, attachments: list
+) -> EmailMessage:
+    """Create an EmailMessage instance ready to be sent."""
+    extra_headers = {"User-Agent": "Modoboa {}".format(version("modoboa"))}
+    headers = {}
+    origmsgid = attributes.get("in_reply_to")
+    if origmsgid:
+        headers.update({"References": origmsgid, "In-Reply-To": origmsgid})
+    mode = user.parameters.get_value("editor")
+    sender = format_sender_address(user, attributes["sender"])
+    if mode == "html":
+        msg = html_msg(attributes.get("body", ""))
+    else:
+        msg = plain_msg(attributes.get("body", ""))
+    msg.from_email = sender
+    msg.to = attributes["to"]
+    msg.headers = headers
+    msg.extra_headers = extra_headers
+    for hdr in ["subject", "cc", "bcc"]:
+        if hdr in attributes:
+            setattr(msg, hdr, attributes[hdr])
+
+    for attachment in attachments:
+        msg.attach(create_mail_attachment(attachment))
+    return msg
diff --git a/modoboa/webmail/migrations/0001_initial.py b/modoboa/webmail/migrations/0001_initial.py
new file mode 100644
index 000000000..a3638b259
--- /dev/null
+++ b/modoboa/webmail/migrations/0001_initial.py
@@ -0,0 +1,102 @@
+# Generated by Django 5.2.10 on 2026-01-31 10:44
+
+import django.db.models.deletion
+import modoboa.webmail.constants
+from django.conf import settings
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+
+    initial = True
+
+    dependencies = [
+        migrations.swappable_dependency(settings.AUTH_USER_MODEL),
+    ]
+
+    operations = [
+        migrations.CreateModel(
+            name="ScheduledMessage",
+            fields=[
+                (
+                    "id",
+                    models.AutoField(
+                        auto_created=True,
+                        primary_key=True,
+                        serialize=False,
+                        verbose_name="ID",
+                    ),
+                ),
+                ("sender", models.CharField(max_length=255)),
+                ("subject", models.CharField(max_length=255)),
+                ("body", models.TextField()),
+                ("to", models.TextField()),
+                ("cc", models.TextField(blank=True, null=True)),
+                ("bcc", models.TextField(blank=True, null=True)),
+                (
+                    "in_reply_to",
+                    models.CharField(blank=True, max_length=200, null=True),
+                ),
+                ("scheduled_datetime", models.DateTimeField()),
+                ("imap_uid", models.IntegerField(blank=True, null=True)),
+                (
+                    "status",
+                    models.CharField(
+                        choices=[
+                            (
+                                modoboa.webmail.constants.SchedulingState["SCHEDULED"],
+                                "scheduled",
+                            ),
+                            (
+                                modoboa.webmail.constants.SchedulingState["SENDING"],
+                                "sending",
+                            ),
+                            (
+                                modoboa.webmail.constants.SchedulingState["SEND_ERROR"],
+                                "send_error",
+                            ),
+                            (
+                                modoboa.webmail.constants.SchedulingState["MOVE_ERROR"],
+                                "move_error",
+                            ),
+                        ],
+                        default=modoboa.webmail.constants.SchedulingState["SCHEDULED"],
+                        max_length=15,
+                    ),
+                ),
+                ("error", models.CharField(blank=True, max_length=255, null=True)),
+                (
+                    "account",
+                    models.ForeignKey(
+                        on_delete=django.db.models.deletion.CASCADE,
+                        to=settings.AUTH_USER_MODEL,
+                    ),
+                ),
+            ],
+        ),
+        migrations.CreateModel(
+            name="MessageAttachment",
+            fields=[
+                (
+                    "id",
+                    models.AutoField(
+                        auto_created=True,
+                        primary_key=True,
+                        serialize=False,
+                        verbose_name="ID",
+                    ),
+                ),
+                ("file", models.FileField(upload_to="")),
+                ("content_type", models.CharField(max_length=150)),
+                ("filename", models.CharField(max_length=255)),
+                (
+                    "message",
+                    models.ForeignKey(
+                        on_delete=django.db.models.deletion.CASCADE,
+                        related_name="attachments",
+                        to="webmail.scheduledmessage",
+                    ),
+                ),
+            ],
+        ),
+    ]
diff --git a/modoboa/webmail/migrations/__init__.py b/modoboa/webmail/migrations/__init__.py
new file mode 100644
index 000000000..e69de29bb
diff --git a/modoboa/webmail/models.py b/modoboa/webmail/models.py
new file mode 100644
index 000000000..df4fb8f81
--- /dev/null
+++ b/modoboa/webmail/models.py
@@ -0,0 +1,96 @@
+"""
+Webmail related models.
+"""
+
+from django.core.mail import EmailMessage
+from django.db import models
+
+from modoboa.lib.sysutils import doveadm_cmd
+from modoboa.webmail import constants
+from modoboa.webmail.lib.utils import create_message
+
+
+class ScheduledMessage(models.Model):
+    account = models.ForeignKey("core.User", on_delete=models.CASCADE)
+    sender = models.CharField(max_length=255)
+    subject = models.CharField(max_length=255)
+    body = models.TextField()
+    to = models.TextField()
+    cc = models.TextField(blank=True, null=True)
+    bcc = models.TextField(blank=True, null=True)
+    in_reply_to = models.CharField(max_length=200, blank=True, null=True)
+    scheduled_datetime = models.DateTimeField()
+    imap_uid = models.IntegerField(blank=True, null=True)
+    status = models.CharField(
+        choices=constants.EMAIL_SCHEDULING_STATES,
+        default=constants.SchedulingState.SCHEDULED,
+        max_length=15,
+        db_index=True,
+    )
+    error = models.CharField(max_length=255, null=True, blank=True)
+
+    def __str__(self):
+        return f"{self.subject} - {self.sender.username} - {self.scheduled_datetime}"
+
+    def to_dict(self) -> dict:
+        result = {
+            "in_reply_to": self.in_reply_to,
+            "sender": self.sender,
+            "to": self.to.split(","),
+        }
+        if self.subject:
+            result["subject"] = self.subject
+        if self.body:
+            result["body"] = self.body
+        for hdr in ["cc", "bcc"]:
+            if getattr(self, hdr):
+                result[hdr] = getattr(self, hdr).split(",")
+        return result
+
+    def delete_imap_copy(self) -> bool:
+        """Move IMAP message to Sent folder using doveadm."""
+        # TODO: use doveadm HTTP API when dovecot is not local
+        sent_folder = self.account.parameters.get_value("sent_folder")
+        code, output = doveadm_cmd(
+            f"move -u {self.account.email} {sent_folder} "
+            f"mailbox {constants.MAILBOX_NAME_SCHEDULED} "
+            f"header {constants.CUSTOM_HEADER_SCHEDULED_ID} {self.id}"
+        )
+        if code:
+            self.status = constants.SchedulingState.MOVE_ERROR
+            self.error = output
+            self.save()
+            return False
+
+        return True
+
+    def to_email_message(self) -> EmailMessage:
+        """Convert this scheduled message to an EmailMessage instance."""
+        attachments = [attachment.to_dict() for attachment in self.attachments.all()]
+        result = create_message(self.account, self.to_dict(), attachments)
+        result.extra_headers.update(
+            {
+                constants.CUSTOM_HEADER_SCHEDULED_ID: self.id,
+                constants.CUSTOM_HEADER_SCHEDULED_DATETIME: self.scheduled_datetime.isoformat(),
+            }
+        )
+        return result
+
+
+class MessageAttachment(models.Model):
+    message = models.ForeignKey(
+        ScheduledMessage, on_delete=models.CASCADE, related_name="attachments"
+    )
+    file = models.FileField()
+    content_type = models.CharField(max_length=150)
+    filename = models.CharField(max_length=255)
+
+    def __str__(self):
+        return f"Attachment for {self.message.subject}"
+
+    def to_dict(self) -> dict:
+        return {
+            "content-type": self.content_type,
+            "tmpname": self.file.name,
+            "fname": self.filename,
+        }
diff --git a/modoboa/webmail/serializers.py b/modoboa/webmail/serializers.py
index 0eb51e49d..d8ee5049d 100644
--- a/modoboa/webmail/serializers.py
+++ b/modoboa/webmail/serializers.py
@@ -1,10 +1,14 @@
 """Webmail serializers."""
 
+from django.utils.translation import gettext as _
+from django.utils import timezone
+
 from rest_framework import serializers
 
 from modoboa.lib import email_utils
-from modoboa.webmail import constants
+from modoboa.webmail import constants, models
 from modoboa.webmail.lib import imapheader, signature
+from modoboa.webmail.lib.imaputils import get_imapconnector
 
 
 class GlobalParametersSerializer(serializers.Serializer):
@@ -22,6 +26,13 @@ class GlobalParametersSerializer(serializers.Serializer):
     smtp_port = serializers.IntegerField(default=25)
     smtp_authentication = serializers.BooleanField(default=False)
 
+    scheduling_smtp_server = serializers.CharField(default="127.0.0.1")
+    scheduling_smtp_secured_mode = serializers.ChoiceField(
+        default=constants.SmtpConnectionMode.NONE.value,
+        choices=constants.SMTP_CONNECTION_MODES,
+    )
+    scheduling_smtp_port = serializers.IntegerField(default=25)
+
 
 class UserPreferencesSerializer(serializers.Serializer):
     displaymode = serializers.ChoiceField(
@@ -116,6 +127,7 @@ class EmailHeadersSerializer(serializers.Serializer):
     imapid = serializers.CharField()
     subject = serializers.SerializerMethodField()
     from_address = serializers.SerializerMethodField()
+    recipients = serializers.SerializerMethodField()
     date = serializers.SerializerMethodField()
     size = serializers.IntegerField()
     answered = serializers.BooleanField(default=False)
@@ -124,6 +136,14 @@ class EmailHeadersSerializer(serializers.Serializer):
     flagged = serializers.BooleanField(default=False)
     style = serializers.CharField(required=False)
 
+    scheduled_id = serializers.IntegerField(
+        source=constants.CUSTOM_HEADER_SCHEDULED_ID, required=False
+    )
+    scheduled_datetime = serializers.SerializerMethodField(required=False)
+    scheduled_datetime_raw = serializers.CharField(
+        source=constants.CUSTOM_HEADER_SCHEDULED_DATETIME, required=False
+    )
+
     def get_subject(self, obj) -> str:
         if "Subject" in obj:
             return imapheader.parse_subject(obj["Subject"])
@@ -134,11 +154,23 @@ class EmailHeadersSerializer(serializers.Serializer):
             return imapheader.parse_address(obj["From"])
         return ""
 
+    def get_recipients(self, obj):
+        if "To" in obj:
+            return imapheader.parse_address_list(obj["To"])
+        return ""
+
     def get_date(self, obj) -> str:
         if "Date" in obj:
             return imapheader.parse_date(obj["Date"])
         return ""
 
+    def get_scheduled_datetime(self, obj) -> str:
+        if constants.CUSTOM_HEADER_SCHEDULED_DATETIME in obj:
+            return imapheader.parse_scheduled_datetime(
+                obj[constants.CUSTOM_HEADER_SCHEDULED_DATETIME]
+            )
+        return ""
+
 
 class PaginatedEmailListSerializer(serializers.Serializer):
 
@@ -162,6 +194,11 @@ class EmailSerializer(serializers.Serializer):
     reply_to = serializers.EmailField(source="Reply_To", required=False)
     attachments = serializers.SerializerMethodField()
 
+    scheduled_datetime = serializers.DateTimeField(
+        source=constants.CUSTOM_HEADER_SCHEDULED_DATETIME.replace("-", "_"),
+        required=False,
+    )
+
     def get_attachments(self, email):
         result = []
         if email.attachments:
@@ -177,6 +214,13 @@ class MoveSelectionSerializer(serializers.Serializer):
     destination = serializers.CharField(required=False)
     selection = serializers.ListField(child=serializers.CharField())
 
+    def validate_source(self, value):
+        if value == constants.MAILBOX_NAME_SCHEDULED:
+            raise serializers.ValidationError(
+                _("Moving scheduled messages is forbidden")
+            )
+        return value
+
     def validate_selection(self, value):
         return [item for item in value if item.isdigit()]
 
@@ -198,7 +242,25 @@ class FlagSelectionSerializer(serializers.Serializer):
         return [item for item in value if item.isdigit()]
 
 
-class SendEmailSerializer(serializers.Serializer):
+class ScheduledDatetimeMixin:
+    """Mixin to inject scheduled_datetime logic into a serializer."""
+
+    scheduled_datetime = serializers.DateTimeField(required=False)
+
+    def validate_scheduled_datetime(self, value):
+        if value <= timezone.now():
+            raise serializers.ValidationError(
+                _("Only datetime in the future is allowed")
+            )
+        delta = value - timezone.now()
+        if delta.total_seconds() < 60:
+            raise serializers.ValidationError(
+                _("Provived datetime must be one minute in the future at least")
+            )
+        return value
+
+
+class SendEmailSerializer(ScheduledDatetimeMixin, serializers.Serializer):
 
     sender = serializers.EmailField()
     to = serializers.ListField(child=serializers.EmailField())
@@ -209,8 +271,7 @@ class SendEmailSerializer(serializers.Serializer):
 
     in_reply_to = serializers.CharField(required=False)
 
-    def validate_sender(self, value):
-        return value
+    scheduled_datetime = serializers.DateTimeField(required=False)
 
     def validate_to(self, value):
         return email_utils.prepare_addresses(value, "envelope")
@@ -239,3 +300,22 @@ class ComposeSessionSerializer(serializers.Serializer):
 class AllowedSenderSerializer(serializers.Serializer):
 
     address = serializers.EmailField()
+
+
+class ScheduledMessageSerializer(ScheduledDatetimeMixin, serializers.ModelSerializer):
+
+    class Meta:
+        model = models.ScheduledMessage
+        fields = ["error", "scheduled_datetime"]
+        read_only_fields = ["error"]
+
+    def update(self, instance, validated_data):
+        instance = super().update(instance, validated_data)
+        message = instance.to_email_message()
+        with get_imapconnector(self.context["request"]) as imapc:
+            imapc.delete_mail(constants.MAILBOX_NAME_SCHEDULED, instance.imap_uid)
+            instance.imap_uid = imapc.push_mail(
+                constants.MAILBOX_NAME_SCHEDULED, message.message()
+            )
+            instance.save()
+        return instance
diff --git a/modoboa/webmail/urls.py b/modoboa/webmail/urls.py
index 8688a9bbe..694166303 100644
--- a/modoboa/webmail/urls.py
+++ b/modoboa/webmail/urls.py
@@ -13,5 +13,10 @@ router.register(
     viewsets.ComposeSessionViewSet,
     basename="webmail-compose-session",
 )
+router.register(
+    "scheduled-messages",
+    viewsets.ScheduledMessageViewSet,
+    basename="webmail-scheduled-message",
+)
 
 urlpatterns = router.urls
diff --git a/modoboa/webmail/viewsets.py b/modoboa/webmail/viewsets.py
index 36db0a687..2dc5063db 100644
--- a/modoboa/webmail/viewsets.py
+++ b/modoboa/webmail/viewsets.py
@@ -5,14 +5,14 @@ from django.core.validators import validate_email
 from django.http import Http404, HttpResponse
 from django.utils.translation import gettext as _
 
-from rest_framework import parsers, response, viewsets
+from rest_framework import mixins, parsers, response, viewsets
 from rest_framework.decorators import action
 from rest_framework.permissions import IsAuthenticated
 
 from modoboa.lib import exceptions
 from modoboa.lib.paginator import Paginator
 from modoboa.lib.viewsets import HasMailbox
-from modoboa.webmail import lib, serializers
+from modoboa.webmail import lib, models, serializers
 from modoboa.webmail.lib import attachments
 
 
@@ -156,11 +156,12 @@ class UserEmailViewSet(viewsets.GenericViewSet):
 
             content = imapc.fetch(page.id_start, page.id_stop, mbox=mailbox)
         content = [dict(msg) for msg in content]
+        first_index = (page_num - 1) * messages_per_page + 1
         serializer = self.get_serializer(
             {
                 "count": total,
-                "first_index": page_num * messages_per_page,
-                "last_index": (page_num * messages_per_page) + len(content),
+                "first_index": first_index,
+                "last_index": first_index + len(content) - 1,
                 "prev_page": page.previous_page_number if page.has_previous else None,
                 "next_page": page.next_page_number if page.has_next else None,
                 "results": content,
@@ -376,10 +377,38 @@ class ComposeSessionViewSet(viewsets.GenericViewSet):
         serializer = self.get_serializer(data=request.data)
         serializer.is_valid(raise_exception=True)
         manager = attachments.ComposeSessionManager(request.user.username)
-        status, error = lib.send_mail(
-            request, serializer.validated_data, manager.get_content(pk)["attachments"]
-        )
-        if status:
-            attachments.remove_attachments_and_session(manager, pk)
+        if serializer.validated_data["scheduled_datetime"]:
+            lib.schedule_email(
+                request,
+                serializer.validated_data,
+                manager.get_content(pk)["attachments"],
+            )
             return response.Response(status=204)
+        else:
+            status, error = lib.send_mail(
+                request,
+                serializer.validated_data,
+                manager.get_content(pk)["attachments"],
+            )
+            if status:
+                attachments.remove_attachments_and_session(manager, pk)
+                return response.Response(status=204)
         return response.Response({"error": error}, status=400)
+
+
+class ScheduledMessageViewSet(
+    mixins.RetrieveModelMixin,
+    mixins.UpdateModelMixin,
+    mixins.DestroyModelMixin,
+    viewsets.GenericViewSet,
+):
+
+    permission_classes = (IsAuthenticated, HasMailbox)
+    serializer_class = serializers.ScheduledMessageSerializer
+
+    def get_queryset(self):
+        return models.ScheduledMessage.objects.filter(account=self.request.user)
+
+    def perform_destroy(self, instance):
+        if instance.delete_imap_copy():
+            instance.delete()
diff --git a/test_project/test_project/cron_config.py b/test_project/test_project/cron_config.py
index 787ee8199..e150d25d8 100644
--- a/test_project/test_project/cron_config.py
+++ b/test_project/test_project/cron_config.py
@@ -7,6 +7,7 @@ from modoboa.calendars import jobs as calendars_jobs
 from modoboa.core import jobs as core_jobs
 from modoboa.admin import jobs as admin_jobs
 from modoboa.maillog import jobs as maillog_jobs
+from modoboa.webmail import jobs as webmail_jobs
 
 
 register(core_jobs.clean_logs, queue_name="modoboa", cron="0 0 * * *")
@@ -26,6 +27,8 @@ register(maillog_jobs.update_statistics, queue_name="modoboa", cron="0 * * * *")
 
 register(calendars_jobs.generate_rights, queue_name="modoboa", cron="*/2 * * * *")
 
+register(webmail_jobs.send_scheduled_messages, queue_name="modoboa", cron="* * * * *")
+
 if "modoboa.amavis" in settings.MODOBOA_APPS:
     register(amavis_jobs.qcleanup, queue_name="modoboa", cron="0 0 * * *")
     register(amavis_jobs.amnotify, queue_name="modoboa", cron="0 12 * * *")