diff --git a/frontend/src/components/Calendar/Attendee.vue b/frontend/src/components/Calendar/Attendee.vue
index 57f62d6f..4b550f75 100644
--- a/frontend/src/components/Calendar/Attendee.vue
+++ b/frontend/src/components/Calendar/Attendee.vue
@@ -1,89 +1,82 @@
 <template>
   <div>
     <div
-      class="flex items-center justify-between px-4.5 py-[7px] text-ink-gray-7 [&>div]:w-full"
+      class="flex items-center justify-between text-ink-gray-7 [&>div]:w-full"
     >
-      <Combobox v-model="selectedValue" nullable class="w-full">
-        <Popover v-model:show="showOptions">
-          <template #target="{ togglePopover }">
-            <TextInput
-              ref="search"
-              type="text"
-              size="md"
-              class="w-full"
-              variant="outline"
-              v-model="query"
-              :debounce="300"
-              :placeholder="placeholder"
-              @click="togglePopover"
-              @keydown.delete.capture.stop="removeLastValue"
+      <Popover v-model:show="showOptions">
+        <template #target="{ togglePopover }">
+          <TextInput
+            ref="search"
+            type="text"
+            :size="size"
+            class="w-full"
+            variant="outline"
+            v-model="query"
+            :debounce="300"
+            :placeholder="placeholder"
+            @click="togglePopover"
+            @keydown="onKeydown"
+          >
+            <template #suffix>
+              <FeatherIcon
+                name="chevron-down"
+                class="h-4 text-ink-gray-5"
+                @click.stop="togglePopover()"
+              />
+            </template>
+          </TextInput>
+        </template>
+        <template #body="{ isOpen }">
+          <div v-show="isOpen">
+            <div
+              class="mt-1 rounded-lg bg-surface-modal shadow-2xl ring-1 ring-black ring-opacity-5 focus:outline-none"
             >
-              <template #suffix>
-                <FeatherIcon
-                  name="chevron-down"
-                  class="h-4 text-ink-gray-5"
-                  @click.stop="togglePopover()"
-                />
-              </template>
-            </TextInput>
-          </template>
-          <template #body="{ isOpen }">
-            <div v-show="isOpen">
-              <div
-                class="mt-1 rounded-lg bg-surface-modal shadow-2xl ring-1 ring-black ring-opacity-5 focus:outline-none"
+              <ul
+                v-if="options.length"
+                role="listbox"
+                class="p-1.5 max-h-[12rem] overflow-y-auto"
               >
-                <ComboboxOptions
-                  class="p-1.5 max-h-[12rem] overflow-y-auto"
-                  static
+                <li
+                  v-for="(option, idx) in options"
+                  :key="option.value"
+                  role="option"
+                  :aria-selected="idx === highlightIndex"
+                  @click="selectOption(option)"
+                  @mouseenter="highlightIndex = idx"
+                  class="flex cursor-pointer items-center rounded px-2 py-1 text-base"
+                  :class="{ 'bg-surface-gray-3': idx === highlightIndex }"
                 >
-                  <div
-                    v-if="!options.length"
-                    class="flex gap-2 rounded px-2 py-1 text-base text-ink-gray-5"
-                  >
-                    <FeatherIcon
-                      v-if="fetchContacts"
-                      name="search"
-                      class="h-4"
-                    />
-                    {{
-                      fetchContacts
-                        ? __('No results found')
-                        : __('Type an email address to add attendee')
-                    }}
+                  <UserAvatar class="mr-2" :user="option.value" size="lg" />
+                  <div class="flex flex-col gap-1 p-1 text-ink-gray-8">
+                    <div class="text-base font-medium">
+                      {{ option.label }}
+                    </div>
+                    <div class="text-sm text-ink-gray-5">
+                      {{ option.value }}
+                    </div>
                   </div>
-                  <ComboboxOption
-                    v-for="option in options"
-                    :key="option.value"
-                    :value="option"
-                    v-slot="{ active }"
-                  >
-                    <li
-                      :class="[
-                        'flex cursor-pointer items-center rounded px-2 py-1 text-base',
-                        { 'bg-surface-gray-3': active },
-                      ]"
-                    >
-                      <UserAvatar class="mr-2" :user="option.value" size="lg" />
-                      <div class="flex flex-col gap-1 p-1 text-ink-gray-8">
-                        <div class="text-base font-medium">
-                          {{ option.label }}
-                        </div>
-                        <div class="text-sm text-ink-gray-5">
-                          {{ option.value }}
-                        </div>
-                      </div>
-                    </li>
-                  </ComboboxOption>
-                </ComboboxOptions>
+                </li>
+              </ul>
+              <div
+                v-else
+                class="flex gap-2 rounded px-2 py-1 text-base text-ink-gray-5"
+              >
+                <FeatherIcon v-if="fetchContacts" name="search" class="h-4" />
+                {{
+                  fetchContacts
+                    ? __('No results found')
+                    : __('Type an email address to add attendee')
+                }}
               </div>
             </div>
-          </template>
-        </Popover>
-      </Combobox>
+          </div>
+        </template>
+      </Popover>
     </div>
     <div
       v-if="values.length"
-      class="flex flex-col gap-2 px-4.5 py-[7px] max-h-[165px] overflow-y-auto"
+      class="flex flex-col gap-2 mt-2 max-h-[165px] overflow-y-auto"
+      ref="optionsRef"
     >
       <Button
         ref="emails"
@@ -93,7 +86,6 @@
         theme="gray"
         class="rounded-full w-fit"
         :tooltip="getTooltip(att.email)"
-        @keydown.delete.capture.stop="removeLastValue"
       >
         <template #prefix>
           <UserAvatar :user="att.email" class="-ml-1 !size-5.5" />
@@ -112,13 +104,10 @@
 </template>
 
 <script setup>
-import { Combobox, ComboboxOptions, ComboboxOption } from '@headlessui/vue'
 import UserAvatar from '@/components/UserAvatar.vue'
-import Popover from '@/components/frappe-ui/Popover.vue'
-import { createResource, TextInput } from 'frappe-ui'
-import { ref, computed, nextTick } from 'vue'
+import { createResource, TextInput, Popover } from 'frappe-ui'
+import { ref, computed, nextTick, watch } from 'vue'
 import { watchDebounced } from '@vueuse/core'
-import FeatherIcon from 'frappe-ui/src/components/FeatherIcon.vue'
 
 const props = defineProps({
   validate: {
@@ -129,6 +118,10 @@ const props = defineProps({
     type: String,
     default: 'subtle',
   },
+  size: {
+    type: String,
+    default: 'sm',
+  },
   placeholder: {
     type: String,
     default: 'Add attendee',
@@ -160,6 +153,8 @@ const info = ref(null)
 const query = ref('')
 const text = ref('')
 const showOptions = ref(false)
+const optionsRef = ref(null)
+const highlightIndex = ref(-1)
 
 const metaByEmail = computed(() => {
   const out = {}
@@ -179,17 +174,6 @@ function getTooltip(email) {
   return parts.length ? parts.join(': ') : email
 }
 
-const selectedValue = computed({
-  get: () => query.value || '',
-  set: (val) => {
-    query.value = ''
-    if (val) {
-      showOptions.value = false
-    }
-    addValue(val)
-  },
-})
-
 watchDebounced(
   query,
   (val) => {
@@ -250,6 +234,34 @@ function reload(val) {
   filterOptions.reload()
 }
 
+watch(
+  () => options.value,
+  () => {
+    highlightIndex.value = options.value.length ? 0 : -1
+  },
+)
+
+function selectOption(option) {
+  if (!option) return
+  addValue(option)
+  !error.value && (query.value = '')
+  showOptions.value = false
+}
+
+function onKeydown(e) {
+  if (e.key === 'Enter') {
+    if (highlightIndex.value >= 0 && options.value[highlightIndex.value]) {
+      selectOption(options.value[highlightIndex.value])
+    } else if (query.value) {
+      // Add entered email directly
+      selectOption({ name: 'new', label: query.value, value: query.value })
+    }
+    e.preventDefault()
+  } else if (e.key === 'Escape') {
+    showOptions.value = false
+  }
+}
+
 const addValue = (option) => {
   // Safeguard for falsy option
   if (!option || !option.value) return
@@ -285,34 +297,23 @@ const addValue = (option) => {
     current.push(entry)
   }
 
-  if (!error.value) {
-    values.value = current
-  }
+  values.value = current
+  // Scroll to the bottom so the last added value is visible
+  nextTick(() => {
+    // use requestAnimationFrame to ensure DOM paint
+    requestAnimationFrame(() => {
+      const el = optionsRef.value
+      if (el) {
+        el.scrollTo({ top: el.scrollHeight, behavior: 'smooth' })
+      }
+    })
+  })
 }
 
 const removeValue = (email) => {
   values.value = (values.value || []).filter((a) => a.email !== email)
 }
 
-const removeLastValue = () => {
-  if (query.value) return
-
-  let emailRef = emails.value[emails.value.length - 1]?.$el
-  if (document.activeElement === emailRef) {
-    values.value.pop()
-    nextTick(() => {
-      if (values.value.length) {
-        emailRef = emails.value[emails.value.length - 1].$el
-        emailRef?.focus()
-      } else {
-        setFocus()
-      }
-    })
-  } else {
-    emailRef?.focus()
-  }
-}
-
 function setFocus() {
   search.value.$el.focus()
 }
diff --git a/frontend/src/components/Calendar/CalendarEventPanel.vue b/frontend/src/components/Calendar/CalendarEventPanel.vue
index fca827bc..4e93c695 100644
--- a/frontend/src/components/Calendar/CalendarEventPanel.vue
+++ b/frontend/src/components/Calendar/CalendarEventPanel.vue
@@ -294,6 +294,7 @@
       </div>
       <div class="mx-4.5 my-2.5 border-t border-outline-gray-1" />
       <Attendee
+        class="px-4.5 py-[7px]"
         v-model="peoples"
         :validate="validateEmail"
         :error-message="