diff --git a/website/client/src/components/tasks/modal-controls/selectMulti.vue b/website/client/src/components/tasks/modal-controls/selectMulti.vue
index 5c993196f2..f8781a8d73 100644
--- a/website/client/src/components/tasks/modal-controls/selectMulti.vue
+++ b/website/client/src/components/tasks/modal-controls/selectMulti.vue
@@ -1,4 +1,4 @@
-multi<template>
+<template>
   <div>
     <b-dropdown
       ref="dropdown"
diff --git a/website/client/src/components/tasks/modal-controls/selectSingle.vue b/website/client/src/components/tasks/modal-controls/selectSingle.vue
new file mode 100644
index 0000000000..11e881910f
--- /dev/null
+++ b/website/client/src/components/tasks/modal-controls/selectSingle.vue
@@ -0,0 +1,291 @@
+<template>
+  <div>
+    <b-dropdown
+      ref="dropdown"
+      class="inline-dropdown select-multi"
+      :toggle-class="isOpened ? 'active' : null"
+      @show="wasOpened()"
+      @hide="hideCallback($event)"
+      @toggle="openOrClose($event)"
+    >
+      <b-dropdown-header>
+        <div class="mb-2">
+          <b-form-input
+            v-model="search"
+            type="text"
+            :placeholder="searchPlaceholder"
+            @keyup.enter="handleSubmit"
+          />
+        </div>
+      </b-dropdown-header>
+      <template v-slot:button-content>
+        <div
+          v-if="selectedItem !== null"
+          v-markdown="allItemsMap[selectedItem].name"
+          class="label"
+        ></div>
+      </template>
+      <div
+        v-if="addNew || availableToSelect.length > 0"
+        :class="{
+          'item-group': true,
+          'add-new': availableToSelect.length === 0 && search !== '',
+          'scroll': availableToSelect.length > 5
+        }"
+      >
+        <b-dropdown-item-button
+          v-for="item in availableToSelect"
+          :key="item.id"
+          class="ignore-hide multi-item"
+          :class="{ 'none': item.id === 'none', selectListItem: true }"
+          @click.prevent.stop="selectItem(item)"
+        >
+          <div
+            v-markdown="item.name"
+            class="label"
+          ></div>
+          <div
+            v-if="item.challenge"
+            class="addl-text"
+          >
+            {{ $t('challenge') }}
+          </div>
+          <div
+            v-else-if="item.addlText"
+            class="addl-text"
+          >
+            {{ item.addlText }}
+          </div>
+        </b-dropdown-item-button>
+
+        <div
+          v-if="addNew"
+          class="hint"
+        >
+          {{ $t('pressEnterToAddTag', { tagName: search }) }}
+        </div>
+      </div>
+    </b-dropdown>
+  </div>
+</template>
+
+<style lang="scss">
+  @import '~@/assets/scss/colors.scss';
+
+  $itemHeight: 2rem;
+
+  .select-multi {
+    .dropdown-toggle {
+      padding-left: 0.75rem;
+    }
+
+    .dropdown-header {
+      background-color: $gray-700;
+      padding-bottom: 0;
+      min-height: 3rem;
+    }
+
+    .dropdown-item, .dropdown-header {
+      padding-left: 0.75rem;
+      padding-right: 0.75rem;
+    }
+
+    .none {
+      cursor: default;
+      pointer-events: none;
+    }
+
+    .multi-item button {
+      height: $itemHeight;
+      display: flex;
+
+      .label {
+        height: 1.5rem;
+        font-size: 14px;
+        line-height: 1.71;
+        flex: 1;
+      }
+
+      .addl-text {
+        height: 1rem;
+        font-size: 12px;
+        font-weight: normal;
+        font-stretch: normal;
+        font-style: normal;
+        line-height: 1.33;
+        letter-spacing: normal;
+        text-align: right;
+        color: $gray-100;
+        align-self: center;
+        margin-top: 0.5rem;
+        margin-bottom: 0.5rem;
+        margin-right: 0.25rem;
+      }
+
+      &:hover {
+        .addl-text {
+          color: $purple-300;
+        }
+      }
+    }
+
+    .item-group {
+      max-height: #{5*$itemHeight};
+
+      &.add-new {
+        height: 30px;
+
+        .hint {
+          display: block;
+        }
+      }
+      &.scroll {
+        overflow-y: scroll;
+      }
+    }
+
+    .hint {
+      display: none;
+      height: 2rem;
+      font-size: 12px;
+      font-weight: normal;
+      font-stretch: normal;
+      font-style: normal;
+      line-height: 1.33;
+      letter-spacing: normal;
+      color: $gray-100;
+
+      margin-left: 0.75rem;
+      margin-top: 0.5rem;
+    }
+  }
+
+</style>
+
+<script>
+import Vue from 'vue';
+import markdownDirective from '@/directives/markdown';
+
+export default {
+  directives: {
+    markdown: markdownDirective,
+  },
+  components: {
+  },
+  props: {
+    addNew: {
+      type: Boolean,
+      default: false,
+    },
+    allItems: {
+      type: Array,
+    },
+    emptyMessage: {
+      type: String,
+    },
+    pillInvert: {
+      type: Boolean,
+      default: false,
+    },
+    searchPlaceholder: {
+      type: String,
+    },
+    selectedItem: {
+      type: String,
+    },
+  },
+  data () {
+    return {
+      preventHide: true,
+      isOpened: false,
+      selected: this.selectedItem,
+      search: '',
+    };
+  },
+  computed: {
+    allItemsMap () {
+      const obj = {};
+      this.allItems.forEach(t => {
+        obj[t.id] = t;
+      });
+      return obj;
+    },
+    selectedItemAsObject () {
+      return this.selected ? this.allItemsMap[this.selected] : null;
+    },
+    availableToSelect () {
+      const availableItems = this.allItems.filter(t => t.id !== this.selected);
+
+      const searchString = this.search.toLowerCase();
+
+      const filteredItems = availableItems.filter(i => i.name.toLowerCase().includes(searchString));
+
+      return filteredItems;
+    },
+  },
+  watch: {
+    selected () {
+      this.$emit('changed', this.selected);
+    },
+  },
+  created () {
+    document.addEventListener('keyup', this.handleEsc);
+  },
+  beforeDestroy () {
+    document.removeEventListener('keyup', this.handleEsc);
+  },
+  mounted () {
+    this.$refs.dropdown.clickOutHandler = () => {
+      this.closeSelectPopup();
+    };
+  },
+  methods: {
+    closeSelectPopup () {
+      this.preventHide = false;
+      this.isOpened = false;
+      Vue.nextTick(() => {
+        this.$refs.dropdown.hide();
+      });
+    },
+    openOrClose ($event) {
+      if (this.isOpened) {
+        this.closeSelectPopup();
+        $event.preventDefault();
+      }
+    },
+    closeIfOpen () {
+      this.closeSelectPopup();
+    },
+    selectItem (item) {
+      this.$emit('toggle', item.id);
+    },
+    removeItem () {
+      this.$emit('toggle', null);
+    },
+    hideCallback ($event) {
+      if (this.preventHide) {
+        $event.preventDefault();
+        return;
+      }
+
+      this.isOpened = false;
+    },
+    wasOpened () {
+      this.isOpened = true;
+      this.preventHide = true;
+    },
+    handleEsc (e) {
+      if (e.keyCode === 27) {
+        this.closeSelectPopup();
+      }
+    },
+    handleSubmit () {
+      if (!this.addNew) return;
+      const { search } = this;
+      this.$emit('addNew', search);
+
+      this.search = '';
+    },
+  },
+};
+</script>
diff --git a/website/client/src/components/tasks/taskModal.vue b/website/client/src/components/tasks/taskModal.vue
index b85e48bc43..7fe26c9561 100644
--- a/website/client/src/components/tasks/taskModal.vue
+++ b/website/client/src/components/tasks/taskModal.vue
@@ -454,13 +454,11 @@
               class="col-12 mb-1"
             >{{ $t('assignedTo') }}</label>
             <div class="col-12">
-              <select-multi
-                ref="assignMembers"
+              <select-single
                 :all-items="membersNameAndId"
                 :empty-message="$t('unassigned')"
-                :pill-invert="true"
                 :search-placeholder="$t('chooseTeamMember')"
-                :selected-items="assignedMembers"
+                :selected-item="assignedMember"
                 @toggle="toggleAssignment($event)"
               />
             </div>
@@ -1044,9 +1042,11 @@ import goldIcon from '@/assets/svg/gold.svg';
 import chevronIcon from '@/assets/svg/chevron.svg';
 import calendarIcon from '@/assets/svg/calendar.svg';
 import gripIcon from '@/assets/svg/grip.svg';
+import SelectSingle from './modal-controls/selectSingle';
 
 export default {
   components: {
+    SelectSingle,
     SelectMulti,
     Datepicker,
     checklist,
@@ -1079,7 +1079,7 @@ export default {
       members: [],
       membersNameAndId: [],
       memberNamesById: {},
-      assignedMembers: [],
+      assignedMember: null,
       managers: [],
       showAdvancedOptions: false,
       attributesStrings: {
@@ -1270,9 +1270,10 @@ export default {
           });
           this.memberNamesById[member._id] = member.profile.name;
         });
-        this.assignedMembers = [];
-        if (this.task.group && this.task.group.assignedUsers) {
-          this.assignedMembers = this.task.group.assignedUsers;
+        this.assignedMember = null;
+        if (this.task.group?.assignedUsers?.length > 0) {
+          // eslint-disable-next-line prefer-destructuring
+          this.assignedMember = this.task.group.assignedUsers[0];
         }
       }
 
@@ -1457,12 +1458,11 @@ export default {
             tasks: [this.task],
           });
           Object.assign(this.task, response);
-          const promises = this.assignedMembers.map(memberId => this.$store.dispatch('tasks:assignTask', {
+          await this.$store.dispatch('tasks:assignTask', {
             taskId: this.task._id,
-            userId: memberId,
-          }));
-          Promise.all(promises);
-          this.task.group.assignedUsers = this.assignedMembers;
+            userId: this.assignedMember,
+          });
+          this.task.group.assignedUsers = [this.assignedMember];
           this.$emit('taskCreated', this.task);
         } else {
           this.createTask(this.task);
@@ -1493,9 +1493,7 @@ export default {
         return;
       }
 
-      const assignedIndex = this.assignedMembers.indexOf(memberId);
-
-      if (assignedIndex === -1) {
+      if (this.assignedMember === null) {
         await this.$store.dispatch('tasks:unassignTask', {
           taskId: this.task._id,
           userId: memberId,
@@ -1506,6 +1504,8 @@ export default {
           userId: memberId,
         });
       }
+
+      this.assignedMember = memberId;
     },
     focusInput () {
       this.$refs.inputToFocus.focus();