diff --git a/frontend/src/components/misc/Icon.ts b/frontend/src/components/misc/Icon.ts
index db333c0dd..8a5cab738 100644
--- a/frontend/src/components/misc/Icon.ts
+++ b/frontend/src/components/misc/Icon.ts
@@ -5,8 +5,10 @@ import {
 	faAnglesUp,
 	faArchive,
 	faArrowLeft,
+	faArrowDownShortWide,
 	faArrowUpFromBracket,
 	faArrowUpRightFromSquare,
+	faArrowUpShortWide,
 	faBold,
 	faItalic,
 	faStrikethrough,
@@ -183,7 +185,9 @@ library.add(faTimesCircle)
 library.add(faTrashAlt)
 library.add(faUser)
 library.add(faUsers)
+library.add(faArrowDownShortWide)
 library.add(faArrowUpFromBracket)
+library.add(faArrowUpShortWide)
 library.add(faX)
 library.add(faAnglesUp)
 library.add(faBolt)
diff --git a/frontend/src/components/tasks/partials/Comments.vue b/frontend/src/components/tasks/partials/Comments.vue
index 2d25e0df4..336092f34 100644
--- a/frontend/src/components/tasks/partials/Comments.vue
+++ b/frontend/src/components/tasks/partials/Comments.vue
@@ -6,12 +6,23 @@
 	>
 		<h3
 			v-if="canWrite || comments.length > 0"
+			class="comments-heading"
 			:class="{'d-print-none': comments.length === 0}"
 		>
-			<span class="icon is-grey">
-				<Icon :icon="['far', 'comments']" />
+			<span>
+				<span class="icon is-grey">
+					<Icon :icon="['far', 'comments']" />
+				</span>
+				{{ $t('task.comment.title') }}
 			</span>
-			{{ $t('task.comment.title') }}
+			<BaseButton
+				v-if="comments.length > 0"
+				class="comment-sort-button"
+				@click="toggleSortOrder"
+			>
+				<Icon :icon="commentSortOrder === 'asc' ? 'arrow-down-short-wide' : 'arrow-up-short-wide'" />
+				{{ commentSortOrder === 'asc' ? $t('task.comment.sortOldestFirst') : $t('task.comment.sortNewestFirst') }}
+			</BaseButton>
 		</h3>
 		<div class="comments">
 			<span
@@ -214,6 +225,7 @@
 import {ref, reactive, computed, shallowReactive, watch} from 'vue'
 import {useI18n} from 'vue-i18n'
 
+import BaseButton from '@/components/base/BaseButton.vue'
 import CustomTransition from '@/components/misc/CustomTransition.vue'
 import Editor from '@/components/input/AsyncEditor'
 import PaginationEmit from '@/components/misc/PaginationEmit.vue'
@@ -250,6 +262,9 @@ const {t} = useI18n({useScope: 'global'})
 const configStore = useConfigStore()
 const authStore = useAuthStore()
 
+const localSortOrder = ref<'asc' | 'desc' | null>(null)
+const commentSortOrder = computed(() => localSortOrder.value ?? authStore.settings.frontendSettings.commentSortOrder ?? 'asc')
+
 const comments = ref<ITaskComment[]>([])
 
 const showDeleteModal = ref(false)
@@ -338,14 +353,14 @@ async function loadComments(taskId: ITask['id']) {
 	commentEdit.taskId = taskId
 	commentToDelete.taskId = taskId
 
-	if (typeof props.initialComments !== 'undefined' && currentPage.value === 1) {
+	if (commentSortOrder.value === 'asc' && typeof props.initialComments !== 'undefined' && currentPage.value === 1) {
 		if (props.initialComments.length < configStore.maxItemsPerPage) {
 			comments.value = props.initialComments
 			return
 		}
 	}
 
-	comments.value = await taskCommentService.getAll({taskId}, {}, currentPage.value)
+	comments.value = await taskCommentService.getAll({taskId}, {order_by: commentSortOrder.value}, currentPage.value)
 }
 
 async function changePage(page: number) {
@@ -354,6 +369,30 @@ async function changePage(page: number) {
 	await loadComments(props.taskId)
 }
 
+async function toggleSortOrder() {
+	const newOrder = commentSortOrder.value === 'asc' ? 'desc' : 'asc'
+	if (!authStore.isLinkShareAuth) {
+		await authStore.saveUserSettings({
+			settings: {
+				...authStore.settings,
+				frontendSettings: {
+					...authStore.settings.frontendSettings,
+					commentSortOrder: newOrder,
+				},
+			},
+			showMessage: false,
+		})
+	} else {
+		localSortOrder.value = newOrder
+	}
+	if (taskCommentService.totalPages > 1) {
+		currentPage.value = 1
+		await loadComments(props.taskId)
+	} else {
+		comments.value.reverse()
+	}
+}
+
 watch(
 	() => [props.taskId, props.initialComments],
 	() => {
@@ -378,12 +417,24 @@ async function addComment() {
 		newComment.taskId = props.taskId
 		newComment.comment = newCommentText.value
 		const comment = await taskCommentService.create(newComment)
-		comments.value.push(comment)
+
+		if (commentSortOrder.value === 'desc' && currentPage.value > 1) {
+			currentPage.value = 1
+			await loadComments(props.taskId)
+		} else if (commentSortOrder.value === 'desc') {
+			comments.value.unshift(comment)
+		} else {
+			comments.value.push(comment)
+		}
 		newCommentText.value = ''
 
 		// Ensure draft is cleared from localStorage
 		clearEditorDraft(commentStorageKey.value)
 
+		if (commentSortOrder.value === 'desc') {
+			commentsRef.value?.scrollIntoView({behavior: 'smooth', block: 'start', inline: 'nearest'})
+		}
+
 		success({message: t('task.comment.addedSuccess')})
 	} finally {
 		creating.value = false
@@ -510,6 +561,25 @@ function getCommentUrl(commentId: string) {
 	inline-size: calc(100% - 48px - 2rem);
 }
 
+.comments-heading {
+	display: flex;
+	align-items: center;
+	justify-content: space-between;
+}
+
+.comment-sort-button {
+	font-size: .75rem;
+	font-weight: normal;
+	color: var(--grey-500);
+	display: inline-flex;
+	align-items: center;
+	gap: .25rem;
+
+	&:hover {
+		color: var(--grey-700);
+	}
+}
+
 .comments-container {
 	scroll-margin-block-start: 4rem;
 }
diff --git a/frontend/src/i18n/lang/en.json b/frontend/src/i18n/lang/en.json
index b8390c31f..93d63561c 100644
--- a/frontend/src/i18n/lang/en.json
+++ b/frontend/src/i18n/lang/en.json
@@ -928,7 +928,9 @@
       "deleteText1": "Are you sure you want to delete this comment?",
       "deleteSuccess": "The comment was deleted successfully.",
       "addedSuccess": "The comment was added successfully.",
-      "permalink": "Copy permalink to this comment"
+      "permalink": "Copy permalink to this comment",
+      "sortNewestFirst": "Newest first",
+      "sortOldestFirst": "Oldest first"
     },
     "mention": {
       "noUsersFound": "No users found"
diff --git a/frontend/src/modelTypes/IUserSettings.ts b/frontend/src/modelTypes/IUserSettings.ts
index d66412a57..8edbd438f 100644
--- a/frontend/src/modelTypes/IUserSettings.ts
+++ b/frontend/src/modelTypes/IUserSettings.ts
@@ -24,6 +24,7 @@ export interface IFrontendSettings {
 	backgroundBrightness: number | null
 	alwaysShowBucketTaskCount: boolean
 	sidebarWidth: number | null
+	commentSortOrder: 'asc' | 'desc'
 }
 
 export interface IExtraSettingsLink {
diff --git a/frontend/src/models/userSettings.ts b/frontend/src/models/userSettings.ts
index d79d0b852..7b61a50ed 100644
--- a/frontend/src/models/userSettings.ts
+++ b/frontend/src/models/userSettings.ts
@@ -32,6 +32,7 @@ export default class UserSettingsModel extends AbstractModel<IUserSettings> impl
 		defaultTaskRelationType: RELATION_KIND.RELATED,
 		alwaysShowBucketTaskCount: false,
 		sidebarWidth: null,
+		commentSortOrder: 'asc',
 	}
 	extraSettingsLinks = {}
 
diff --git a/frontend/src/stores/auth.ts b/frontend/src/stores/auth.ts
index 21c3b9f63..a947b2ab1 100644
--- a/frontend/src/stores/auth.ts
+++ b/frontend/src/stores/auth.ts
@@ -139,6 +139,7 @@ export const useAuthStore = defineStore('auth', () => {
 				defaultTaskRelationType: RELATION_KIND.RELATED,
 				backgroundBrightness: 100,
 				sidebarWidth: null,
+				commentSortOrder: 'asc',
 				...newSettings.frontendSettings,
 			},
 		})