diff --git a/cypress/e2e/project/project-view-kanban.spec.ts b/cypress/e2e/project/project-view-kanban.spec.ts
index 719319373..2c74ba9a9 100644
--- a/cypress/e2e/project/project-view-kanban.spec.ts
+++ b/cypress/e2e/project/project-view-kanban.spec.ts
@@ -5,6 +5,19 @@ import {ProjectFactory} from '../../factories/project'
 import {TaskFactory} from '../../factories/task'
 import {prepareProjects} from './prepareProjects'
 
+function createSingleTaskInBucket(count = 1, attrs = {}) {
+	const projects = ProjectFactory.create(1)
+	const buckets = BucketFactory.create(2, {
+		project_id: projects[0].id,
+	})
+	const tasks = TaskFactory.create(count, {
+		project_id: projects[0].id,
+		bucket_id: buckets[0].id,
+		...attrs,
+	})
+	return tasks[0]
+}
+
 describe('Project View Kanban', () => {
 	createFakeUserAndLogin()
 	prepareProjects()
@@ -207,15 +220,7 @@ describe('Project View Kanban', () => {
 	})
 	
 	it('Should remove a task from the board when deleting it', () => {
-		const projects = ProjectFactory.create(1)
-		const buckets = BucketFactory.create(2, {
-			project_id: projects[0].id,
-		})
-		const tasks = TaskFactory.create(5, {
-			project_id: 1,
-			bucket_id: buckets[0].id,
-		})
-		const task = tasks[0]
+		const task = createSingleTaskInBucket(5)
 		cy.visit('/projects/1/kanban')
 
 		cy.get('.kanban .bucket .tasks .task')
@@ -238,4 +243,43 @@ describe('Project View Kanban', () => {
 		cy.get('.kanban .bucket .tasks')
 			.should('not.contain', task.title)
 	})
+
+	it('Should show a task description icon if the task has a description', () => {
+		cy.intercept(Cypress.env('API_URL') + '/projects/1/buckets**').as('loadTasks')
+		const task = createSingleTaskInBucket(1, {
+			description: 'Lorem Ipsum',
+		})
+
+		cy.visit(`/projects/${task.project_id}/kanban`)
+		cy.wait('@loadTasks')
+
+		cy.get('.bucket .tasks .task .footer .icon svg')
+			.should('exist')
+	})
+
+	it('Should not show a task description icon if the task has an empty description', () => {
+		cy.intercept(Cypress.env('API_URL') + '/projects/1/buckets**').as('loadTasks')
+		const task = createSingleTaskInBucket(1, {
+			description: '',
+		})
+
+		cy.visit(`/projects/${task.project_id}/kanban`)
+		cy.wait('@loadTasks')
+
+		cy.get('.bucket .tasks .task .footer .icon svg')
+			.should('not.exist')
+	})
+
+	it('Should not show a task description icon if the task has a description containing only an empty p tag', () => {
+		cy.intercept(Cypress.env('API_URL') + '/projects/1/buckets**').as('loadTasks')
+		const task = createSingleTaskInBucket(1, {
+			description: '<p></p>',
+		})
+
+		cy.visit(`/projects/${task.project_id}/kanban`)
+		cy.wait('@loadTasks')
+
+		cy.get('.bucket .tasks .task .footer .icon svg')
+			.should('not.exist')
+	})
 })
\ No newline at end of file
diff --git a/cypress/e2e/task/task.spec.ts b/cypress/e2e/task/task.spec.ts
index c2019f08b..57cc87d7b 100644
--- a/cypress/e2e/task/task.spec.ts
+++ b/cypress/e2e/task/task.spec.ts
@@ -36,7 +36,7 @@ function uploadAttachmentAndVerify(taskId: number) {
 	cy.get('.task-view .action-buttons .button')
 		.contains('Add Attachments')
 		.click()
-	cy.get('input[type=file]', {timeout: 1000})
+	cy.get('input[type=file]#files', {timeout: 1000})
 		.selectFile('cypress/fixtures/image.jpg', {force: true}) // The input is not visible, but on purpose
 	cy.wait('@uploadAttachment')
 
@@ -112,10 +112,50 @@ describe('Task', () => {
 			.should('contain', 'Favorites')
 	})
 
+	it('Should show a task description icon if the task has a description', () => {
+		cy.intercept(Cypress.env('API_URL') + '/projects/1/tasks**').as('loadTasks')
+		TaskFactory.create(1, {
+			description: 'Lorem Ipsum',
+		})
+
+		cy.visit('/projects/1/list')
+		cy.wait('@loadTasks')
+
+		cy.get('.tasks .task .project-task-icon')
+			.should('exist')
+	})
+
+	it('Should not show a task description icon if the task has an empty description', () => {
+		cy.intercept(Cypress.env('API_URL') + '/projects/1/tasks**').as('loadTasks')
+		TaskFactory.create(1, {
+			description: '',
+		})
+
+		cy.visit('/projects/1/list')
+		cy.wait('@loadTasks')
+
+		cy.get('.tasks .task .project-task-icon')
+			.should('not.exist')
+	})
+
+	it('Should not show a task description icon if the task has a description containing only an empty p tag', () => {
+		cy.intercept(Cypress.env('API_URL') + '/projects/1/tasks**').as('loadTasks')
+		TaskFactory.create(1, {
+			description: '<p></p>',
+		})
+
+		cy.visit('/projects/1/list')
+		cy.wait('@loadTasks')
+
+		cy.get('.tasks .task .project-task-icon')
+			.should('not.exist')
+	})
+
 	describe('Task Detail View', () => {
 		beforeEach(() => {
 			TaskCommentFactory.truncate()
 			LabelTaskFactory.truncate()
+			TaskAttachmentFactory.truncate()
 		})
 
 		it('Shows all task details', () => {
@@ -213,6 +253,45 @@ describe('Task', () => {
 				.should('exist')
 		})
 
+		it('Shows an empty editor when the description of a task is empty', () => {
+			const tasks = TaskFactory.create(1, {
+				id: 1,
+				description: '',
+			})
+			cy.visit(`/tasks/${tasks[0].id}`)
+
+			cy.get('.task-view .details.content.description .tiptap.ProseMirror p')
+				.should('have.attr', 'data-placeholder')
+			cy.get('.task-view .details.content.description .tiptap button.done-edit')
+				.should('not.exist')
+		})
+
+		it('Shows a preview editor when the description of a task is not empty', () => {
+			const tasks = TaskFactory.create(1, {
+				id: 1,
+				description: 'Lorem Ipsum dolor sit amet',
+			})
+			cy.visit(`/tasks/${tasks[0].id}`)
+
+			cy.get('.task-view .details.content.description .tiptap.ProseMirror p')
+				.should('not.have.attr', 'data-placeholder')
+			cy.get('.task-view .details.content.description .tiptap button.done-edit')
+				.should('exist')
+		})
+
+		it('Shows a preview editor when the description of a task contains html', () => {
+			const tasks = TaskFactory.create(1, {
+				id: 1,
+				description: '<p>Lorem Ipsum dolor sit amet</p>',
+			})
+			cy.visit(`/tasks/${tasks[0].id}`)
+
+			cy.get('.task-view .details.content.description .tiptap.ProseMirror p')
+				.should('not.have.attr', 'data-placeholder')
+			cy.get('.task-view .details.content.description .tiptap button.done-edit')
+				.should('exist')
+		})
+
 		it('Can add a new comment', () => {
 			const tasks = TaskFactory.create(1, {
 				id: 1,
@@ -692,7 +771,7 @@ describe('Task', () => {
 				.should('exist')
 		})
 
-		it('Can check items off a checklist', () => {
+		it.only('Can check items off a checklist', () => {
 			const tasks = TaskFactory.create(1, {
 				id: 1,
 				description: `
@@ -761,7 +840,7 @@ describe('Task', () => {
 				.should('exist')
 		})
 
-		it.only('Should render an image from attachment', async () => {
+		it('Should render an image from attachment', async () => {
 
 			TaskAttachmentFactory.truncate()
 
diff --git a/src/components/input/editor/TipTap.vue b/src/components/input/editor/TipTap.vue
index 35021a398..7a967d1f7 100644
--- a/src/components/input/editor/TipTap.vue
+++ b/src/components/input/editor/TipTap.vue
@@ -118,7 +118,6 @@
 
 <script setup lang="ts">
 import {computed, nextTick, onBeforeUnmount, onMounted, ref, watch} from 'vue'
-import {refDebounced} from '@vueuse/core'
 
 import EditorToolbar from './EditorToolbar.vue'
 
@@ -173,6 +172,7 @@ import {Placeholder} from '@tiptap/extension-placeholder'
 import {eventToHotkeyString} from '@github/hotkey'
 import {mergeAttributes} from '@tiptap/core'
 import {createRandomID} from '@/helpers/randomId'
+import {isEditorContentEmpty} from '@/helpers/editorContentEmpty'
 
 const tiptapInstanceRef = ref<HTMLInputElement | null>(null)
 
@@ -200,7 +200,9 @@ const CustomTableCell = TableCell.extend({
 })
 
 type CacheKey = `${ITask['id']}-${IAttachment['id']}`
-const loadedAttachments = ref<{ [key: CacheKey]: string }>({})
+const loadedAttachments = ref<{
+	[key: CacheKey]: string
+}>({})
 
 const CustomImage = Image.extend({
 	addAttributes() {
@@ -272,7 +274,6 @@ const {
 	showSave = false,
 	placeholder = '',
 	editShortcut = '',
-	initialMode = 'edit',
 } = defineProps<{
 	modelValue: string,
 	uploadCallback?: UploadCallback,
@@ -281,13 +282,11 @@ const {
 	showSave?: boolean,
 	placeholder?: string,
 	editShortcut?: string,
-	initialMode?: Mode,
 }>()
 
 const emit = defineEmits(['update:modelValue', 'save'])
 
-const inputHTML = ref('')
-const internalMode = ref<Mode>(initialMode)
+const internalMode = ref<Mode>('edit')
 const isEditing = computed(() => internalMode.value === 'edit' && isEditEnabled)
 
 const editor = useEditor({
@@ -359,14 +358,28 @@ const editor = useEditor({
 		TaskItem.configure({
 			nested: true,
 			onReadOnlyChecked: (node: Node, checked: boolean): boolean => {
-				if (isEditEnabled) {
-					node.attrs.checked = checked
-					inputHTML.value = editor.value?.getHTML()
-					bubbleSave()
-					return true
+				if (!isEditEnabled) {
+					return false
 				}
 
-				return false
+				// The following is a workaround for this bug:
+				// https://github.com/ueberdosis/tiptap/issues/4521
+				// https://github.com/ueberdosis/tiptap/issues/3676
+
+				editor.value!.state.doc.descendants((subnode, pos) => {
+					if (node.eq(subnode)) {
+						const {tr} = editor.value!.state
+						tr.setNodeMarkup(pos, undefined, {
+							...node.attrs,
+							checked,
+						})
+						editor.value!.view.dispatch(tr)
+						bubbleSave()
+					}
+				})
+
+
+				return true
 			},
 		}),
 
@@ -376,52 +389,55 @@ const editor = useEditor({
 		BubbleMenu,
 	],
 	onUpdate: () => {
-		inputHTML.value = editor.value!.getHTML()
+		bubbleNow()
 	},
 })
 
-watch(
-	() => modelValue,
-	value => {
-		inputHTML.value = value
-
-		if (!editor?.value) return
-
-		if (editor.value.getHTML() === value) {
-			return
-		}
-
-		editor.value.commands.setContent(value, false)
-	},
-)
-
-const debouncedInputHTML = refDebounced(inputHTML, 1000)
-watch(debouncedInputHTML, () => bubbleNow())
-
-function bubbleNow() {
-	emit('update:modelValue', inputHTML.value)
-}
-
-function bubbleSave() {
-	bubbleNow()
-	emit('save', inputHTML.value)
-	if (isEditing.value) {
-		internalMode.value = 'preview'
-	}
-}
-
-function setEdit() {
-	internalMode.value = 'edit'
-	editor.value?.commands.focus()
-}
-
 watch(
 	() => isEditing.value,
 	() => {
 		editor.value?.setEditable(isEditing.value)
 	},
+	{immediate: true},
 )
 
+watch(
+	() => modelValue,
+	value => {
+		if (!editor?.value) return
+
+		if (editor.value.getHTML() === value) {
+			return
+		}
+
+		setModeAndValue(value)
+	},
+	{immediate: true},
+)
+
+function bubbleNow() {
+	if (editor.value?.getHTML() === modelValue) {
+		return
+	}
+
+	emit('update:modelValue', editor.value?.getHTML())
+}
+
+function bubbleSave() {
+	bubbleNow()
+	emit('save', editor.value?.getHTML())
+	if (isEditing.value) {
+		internalMode.value = 'preview'
+	}
+}
+
+function setEdit(focus: boolean = true) {
+	internalMode.value = 'edit'
+	if (focus) {
+		editor.value?.commands.focus()
+	}
+}
+
 onBeforeUnmount(() => editor.value?.destroy())
 
 const uploadInputRef = ref<HTMLInputElement | null>(null)
@@ -491,15 +507,17 @@ function setLink() {
 		.run()
 }
 
-onMounted(() => {
-	internalMode.value = initialMode
-	nextTick(() => {
-		const input = tiptapInstanceRef.value?.querySelectorAll('.tiptap__editor')[0]?.children[0]
-		input?.addEventListener('paste', handleImagePaste)
-	})
+onMounted(async () => {
 	if (editShortcut !== '') {
 		document.addEventListener('keydown', setFocusToEditor)
 	}
+
+	await nextTick()
+
+	const input = tiptapInstanceRef.value?.querySelectorAll('.tiptap__editor')[0]?.children[0]
+	input?.addEventListener('paste', handleImagePaste)
+
+	setModeAndValue(modelValue)
 })
 
 onBeforeUnmount(() => {
@@ -512,6 +530,11 @@ onBeforeUnmount(() => {
 	}
 })
 
+function setModeAndValue(value: string) {
+	internalMode.value = isEditorContentEmpty(value) ? 'edit' : 'preview'
+	editor.value?.commands.setContent(value, false)
+}
+
 function handleImagePaste(event) {
 	if (event?.clipboardData?.items?.length === 0) {
 		return
@@ -521,7 +544,6 @@ function handleImagePaste(event) {
 
 	const image = event.clipboardData.items[0]
 	if (image.kind === 'file' && image.type.startsWith('image/')) {
-		console.log('img', image.getAsFile())
 		uploadAndInsertFiles([image.getAsFile()])
 	}
 }
@@ -538,7 +560,7 @@ function setFocusToEditor(event) {
 	}
 	event.preventDefault()
 
-	if (initialMode === 'preview' && isEditEnabled && !isEditing.value) {
+	if (!isEditing.value && isEditEnabled) {
 		internalMode.value = 'edit'
 	}
 
diff --git a/src/components/tasks/partials/description.vue b/src/components/tasks/partials/description.vue
index 8e2186a77..9484f909a 100644
--- a/src/components/tasks/partials/description.vue
+++ b/src/components/tasks/partials/description.vue
@@ -26,7 +26,6 @@
 			v-model="description"
 			@update:model-value="saveWithDelay"
 			@save="save"
-			:initial-mode="isEditorContentEmpty(description) ? 'edit' : 'preview'"
 		/>
 	</div>
 </template>
@@ -39,7 +38,6 @@ import Editor from '@/components/input/AsyncEditor'
 
 import type {ITask} from '@/modelTypes/ITask'
 import {useTaskStore} from '@/stores/tasks'
-import {isEditorContentEmpty} from '@/helpers/editorContentEmpty'
 
 type AttachmentUploadFunction = (file: File, onSuccess: (attachmentUrl: string) => void) => Promise<string>
 
diff --git a/src/components/tasks/partials/kanban-card.vue b/src/components/tasks/partials/kanban-card.vue
index 4e34bdff3..9621c6ab4 100644
--- a/src/components/tasks/partials/kanban-card.vue
+++ b/src/components/tasks/partials/kanban-card.vue
@@ -60,7 +60,7 @@
 				<span class="icon" v-if="task.attachments.length > 0">
 					<icon icon="paperclip"/>	
 				</span>
-				<span v-if="task.description" class="icon">
+				<span v-if="!isEditorContentEmpty(task.description)" class="icon">
 					<icon icon="align-left"/>
 				</span>
 				<span class="icon" v-if="task.repeatAfter.amount > 0">
@@ -91,6 +91,7 @@ import {useTaskStore} from '@/stores/tasks'
 import AssigneeList from '@/components/tasks/partials/assigneeList.vue'
 import {useAuthStore} from '@/stores/auth'
 import {playPopSound} from '@/helpers/playPop'
+import {isEditorContentEmpty} from '@/helpers/editorContentEmpty'
 
 const router = useRouter()
 
diff --git a/src/components/tasks/partials/singleTaskInProject.vue b/src/components/tasks/partials/singleTaskInProject.vue
index f229b8810..c39a4330f 100644
--- a/src/components/tasks/partials/singleTaskInProject.vue
+++ b/src/components/tasks/partials/singleTaskInProject.vue
@@ -93,7 +93,7 @@
 				<span class="project-task-icon" v-if="task.attachments.length > 0">
 					<icon icon="paperclip"/>
 				</span>
-				<span class="project-task-icon" v-if="task.description">
+				<span class="project-task-icon" v-if="!isEditorContentEmpty(task.description)">
 					<icon icon="align-left"/>
 				</span>
 				<span class="project-task-icon" v-if="task.repeatAfter.amount > 0">
@@ -184,6 +184,7 @@ import AssigneeList from '@/components/tasks/partials/assigneeList.vue'
 import {useIntervalFn} from '@vueuse/core'
 import {playPopSound} from '@/helpers/playPop'
 import {useAuthStore} from '@/stores/auth'
+import {isEditorContentEmpty} from '@/helpers/editorContentEmpty'
 
 const {
 	theTask,
diff --git a/src/views/tasks/TaskDetailView.vue b/src/views/tasks/TaskDetailView.vue
index 71577580d..1e6b0d2e5 100644
--- a/src/views/tasks/TaskDetailView.vue
+++ b/src/views/tasks/TaskDetailView.vue
@@ -6,7 +6,8 @@
 			'is-modal': isModal,
 		}"
 	>
-		<div class="task-view">
+		<!-- Removing everything until the task is loaded to prevent empty initialization of other components -->
+		<div class="task-view" v-if="visible">
 			<Heading
 				:task="task"
 				@update:task="Object.assign(task, $event)"
@@ -605,7 +606,8 @@ watch(
 		}
 
 		try {
-			Object.assign(task.value, await taskService.get({id}))
+			const loaded = await taskService.get({id})
+			Object.assign(task.value, loaded)
 			attachmentStore.set(task.value.attachments)
 			taskColor.value = task.value.hexColor
 			setActiveFields()