diff --git a/src/components/base/EditorToolbar.vue b/src/components/base/EditorToolbar.vue
index 94de3d2fa..5b9436c87 100644
--- a/src/components/base/EditorToolbar.vue
+++ b/src/components/base/EditorToolbar.vue
@@ -151,7 +151,7 @@
 		</div>
 
 		<div class="editor-toolbar__segment">
-			<BaseButton class="editor-toolbar__button" @click="addImage" title="Add image from URL">
+			<BaseButton class="editor-toolbar__button" @click="uploadInputRef?.click()" title="Add image">
 				<span class="icon">
 					<icon icon="fa-image" />
 				</span>
@@ -369,38 +369,64 @@
 				</BaseButton>
 			</div>
 		</div>
+		<input type="file" ref="uploadInputRef" class="is-hidden" @change="addImage"/>
 	</div>
 </template>
 
 <script setup lang="ts">
-import {ref, type PropType} from 'vue'
+import {ref} from 'vue'
 import {Editor} from '@tiptap/vue-3'
 
 import BaseButton from '@/components/base/BaseButton.vue'
 
-const props = defineProps({
-	editor: {
-		default: null,
-		type: Editor as PropType<Editor>,
-	},
-})
+export type UploadCallback = (files: File[] | FileList) => Promise<string[]>
+
+const {
+	editor = null,
+	uploadCallback,
+} = defineProps<{
+	editor: Editor,
+	uploadCallback?: UploadCallback,
+}>()
+
+const emit = defineEmits(['imageAdded'])
 
 const tableMode = ref(false)
+const uploadInputRef = ref<HTMLInputElement | null>(null)
 
 function toggleTableMode() {
 	tableMode.value = !tableMode.value
 }
 
 function addImage() {
+	
+	if (typeof uploadCallback !== 'undefined') {
+		const files = uploadInputRef.value?.files
+
+		if (!files || files.length === 0) {
+			return
+		}
+		
+		uploadCallback(files).then(urls => {
+			urls.forEach(url => {
+				editor?.chain().focus().setImage({ src: url }).run()
+			})
+			emit('imageAdded')
+		})
+
+		return
+	}
+	
 	const url = window.prompt('URL')
 
 	if (url) {
-		props.editor?.chain().focus().setImage({ src: url }).run()
+		editor?.chain().focus().setImage({ src: url }).run()
+		emit('imageAdded')
 	}
 }
 
 function setLink() {
-	const previousUrl = props.editor.getAttributes('link').href
+	const previousUrl = editor.getAttributes('link').href
 	const url = window.prompt('URL', previousUrl)
 
 	// cancelled
@@ -410,13 +436,13 @@ function setLink() {
 
 	// empty
 	if (url === '') {
-		props.editor.chain().focus().extendMarkRange('link').unsetLink().run()
+		editor.chain().focus().extendMarkRange('link').unsetLink().run()
 
 		return
 	}
 
 	// update link
-	props.editor
+	editor
 		.chain()
 		.focus()
 		.extendMarkRange('link')
diff --git a/src/components/base/TipTap.vue b/src/components/base/TipTap.vue
index d93f2dcac..bf7fd79a9 100644
--- a/src/components/base/TipTap.vue
+++ b/src/components/base/TipTap.vue
@@ -1,6 +1,11 @@
 <template>
 	<div class="tiptap">
-		<EditorToolbar v-if="editor" :editor="editor" />
+		<EditorToolbar 
+			v-if="editor"
+			:editor="editor"
+			:upload-callback="uploadCallback"
+			@image-added="bubbleChanges"
+		/>
 		<editor-content class="tiptap__editor" :editor="editor" />
 	</div>
 </template>
@@ -42,6 +47,7 @@ import {EditorContent, useEditor, VueNodeViewRenderer} from '@tiptap/vue-3'
 import {lowlight} from 'lowlight'
 
 import CodeBlock from './CodeBlock.vue'
+import type {UploadCallback} from '@/components/base/EditorToolbar.vue'
 
 // const CustomDocument = Document.extend({
 // 	content: 'taskList',
@@ -72,34 +78,38 @@ const CustomTableCell = TableCell.extend({
 	},
 })
 
-const props = withDefaults(defineProps<{
+const {
+	modelValue = '',
+	uploadCallback,
+} = defineProps<{
 	modelValue?: string,
-}>(), {
-	modelValue: '',
-})
+	uploadCallback?: UploadCallback,
+}>()
 
 const emit = defineEmits(['update:modelValue', 'change'])
 
 const inputHTML = ref('')
 watch(
-	() => props.modelValue,
+	() => modelValue,
 	() => {
-		if (!props.modelValue.startsWith(TIPTAP_TEXT_VALUE_PREFIX)) {
+		if (!modelValue.startsWith(TIPTAP_TEXT_VALUE_PREFIX)) {
 			// convert Markdown to HTML
-			return TIPTAP_TEXT_VALUE_PREFIX + marked.parse(props.modelValue)
+			return TIPTAP_TEXT_VALUE_PREFIX + marked.parse(modelValue)
 		}
 
-		return props.modelValue.replace(tiptapRegex, '')
+		return modelValue.replace(tiptapRegex, '')
 	},
 	{ immediate: true },
 )
 
 const debouncedInputHTML = refDebounced(inputHTML, 1000)
 
-watch(debouncedInputHTML, (value) => {
-	emit('update:modelValue', TIPTAP_TEXT_VALUE_PREFIX + value)
-	emit('change', TIPTAP_TEXT_VALUE_PREFIX + value) // FIXME: remove this
-})
+watch(debouncedInputHTML, () => bubbleChanges())
+
+function bubbleChanges() {
+	emit('update:modelValue', TIPTAP_TEXT_VALUE_PREFIX + inputHTML.value)
+	emit('change', TIPTAP_TEXT_VALUE_PREFIX + inputHTML.value) // FIXME: remove this
+}
 
 const editor = useEditor({
 	content: inputHTML.value,
@@ -122,7 +132,7 @@ const editor = useEditor({
 		// // start
 		// Document,
 		// // Text,
-		// Image,
+		Image,
 
 		// // Tasks
 		// CustomDocument,
diff --git a/src/components/tasks/partials/description.vue b/src/components/tasks/partials/description.vue
index c1ceedcba..fdc974324 100644
--- a/src/components/tasks/partials/description.vue
+++ b/src/components/tasks/partials/description.vue
@@ -18,8 +18,7 @@
 		</h3>
 		<editor
 			:is-edit-enabled="canWrite"
-			:upload-callback="attachmentUpload"
-			:upload-enabled="true"
+			:upload-callback="uploadCallback"
 			:placeholder="$t('task.description.placeholder')"
 			:empty-text="$t('task.description.empty')"
 			:show-save="true"
@@ -41,19 +40,17 @@ import type {ITask} from '@/modelTypes/ITask'
 import {useTaskStore} from '@/stores/tasks'
 import TaskModel from '@/models/task'
 
-const props = defineProps({
-	modelValue: {
-		type: Object as PropType<ITask>,
-		required: true,
-	},
-	attachmentUpload: {
-		required: true,
-	},
-	canWrite: {
-		type: Boolean,
-		required: true,
-	},
-})
+type AttachmentUploadFunction = (file: File, onSuccess: (attachmentUrl: string) => void) => Promise<string>
+
+const {
+	modelValue,
+	attachmentUpload,
+	canWrite,
+} = defineProps<{
+	modelValue: ITask,
+	attachmentUpload: AttachmentUploadFunction,
+	canWrite: boolean,
+}>()
 
 const emit = defineEmits(['update:modelValue'])
 
@@ -67,7 +64,7 @@ const taskStore = useTaskStore()
 const loading = computed(() => taskStore.isLoading)
 
 watch(
-	props.modelValue,
+	() => modelValue,
 	(value) => {
 		task.value = value
 	},
@@ -106,5 +103,20 @@ async function save() {
 		saving.value = false
 	}
 }
+
+async function uploadCallback(files: File[] | FileList): (Promise<string[]>) {
+
+	const uploadPromises: Promise<string>[] = []
+
+	files.forEach((file: File) => {
+		const promise = new Promise<string>((resolve) => {
+			attachmentUpload(file, (uploadedFileUrl: string) => resolve(uploadedFileUrl))
+		})
+
+		uploadPromises.push(promise)
+	})
+
+	return await Promise.all(uploadPromises)
+}
 </script>