diff --git a/app/src/components/v-upload/v-upload.vue b/app/src/components/v-upload/v-upload.vue
index 0b0d3b69e8..0fad1a6123 100644
--- a/app/src/components/v-upload/v-upload.vue
+++ b/app/src/components/v-upload/v-upload.vue
@@ -88,6 +88,7 @@
 <script lang="ts">
 import { defineComponent, ref, computed, watch } from '@vue/composition-api';
 import uploadFiles from '@/utils/upload-files';
+import uploadFile from '@/utils/upload-file';
 import DrawerCollection from '@/views/private/components/drawer-collection';
 import api from '@/api';
 import useItem from '@/composables/use-item';
@@ -103,6 +104,10 @@ export default defineComponent({
 			type: Object,
 			default: () => ({}),
 		},
+		fileId: {
+			type: String,
+			default: null,
+		},
 		fromUrl: {
 			type: Boolean,
 			default: false,
@@ -155,16 +160,29 @@ export default defineComponent({
 				try {
 					numberOfFiles.value = files.length;
 
-					const uploadedFiles = await uploadFiles(Array.from(files), {
-						onProgressChange: (percentage) => {
-							progress.value = Math.round(percentage.reduce((acc, cur) => (acc += cur)) / files.length);
-							done.value = percentage.filter((p) => p === 100).length;
-						},
-						preset: props.preset,
-					});
+					if (props.multiple === true) {
+						const uploadedFiles = await uploadFiles(Array.from(files), {
+							onProgressChange: (percentage) => {
+								progress.value = Math.round(
+									percentage.reduce((acc, cur) => (acc += cur)) / files.length
+								);
+								done.value = percentage.filter((p) => p === 100).length;
+							},
+							preset: props.preset,
+						});
 
-					if (uploadedFiles) {
-						emit('input', props.multiple ? uploadedFiles : uploadedFiles[0]);
+						uploadedFiles && emit('input', uploadedFiles);
+					} else {
+						const uploadedFile = await uploadFile(Array.from(files)[0], {
+							onProgressChange: (percentage) => {
+								progress.value = percentage;
+								done.value = percentage === 100 ? 1 : 0;
+							},
+							fileId: props.fileId,
+							preset: props.preset,
+						});
+
+						uploadedFile && emit('input', uploadedFile);
 					}
 				} catch (err) {
 					console.error(err);
diff --git a/app/src/composables/use-item/use-item.ts b/app/src/composables/use-item/use-item.ts
index ebe5e61b61..a1f0466456 100644
--- a/app/src/composables/use-item/use-item.ts
+++ b/app/src/composables/use-item/use-item.ts
@@ -9,7 +9,7 @@ import { APIError } from '@/types';
 export function useItem(collection: Ref<string>, primaryKey: Ref<string | number | null>) {
 	const { info: collectionInfo, primaryKeyField } = useCollection(collection);
 
-	const item = ref<any>(null);
+	const item = ref<Record<string, any> | null>(null);
 	const error = ref(null);
 	const validationErrors = ref([]);
 	const loading = ref(false);
@@ -203,7 +203,7 @@ export function useItem(collection: Ref<string>, primaryKey: Ref<string | number
 		if (unarchiveValue === 'false') unarchiveValue = false;
 
 		try {
-			let value: any = item.value[field] === archiveValue ? unarchiveValue : archiveValue;
+			let value: any = item.value && item.value[field] === archiveValue ? unarchiveValue : archiveValue;
 
 			if (value === 'true') value = true;
 			if (value === 'false') value = false;
diff --git a/app/src/lang/en-US/index.json b/app/src/lang/en-US/index.json
index 702486b578..182be512bf 100644
--- a/app/src/lang/en-US/index.json
+++ b/app/src/lang/en-US/index.json
@@ -792,6 +792,7 @@
 	"create_folder": "Create Folder",
 	"folder_name": "Folder Name...",
 	"add_file": "Add File",
+	"replace_file": "Replace File",
 
 	"no_results": "No Results",
 	"no_results_copy": "Adjust or clear search filters to see results.",
diff --git a/app/src/layouts/cards/cards.vue b/app/src/layouts/cards/cards.vue
index 6075f8b781..a48a747020 100644
--- a/app/src/layouts/cards/cards.vue
+++ b/app/src/layouts/cards/cards.vue
@@ -337,6 +337,7 @@ export default defineComponent({
 				const fields = [primaryKeyField.value.field];
 
 				if (imageSource.value) {
+					fields.push(`${imageSource.value}.modified_on`);
 					fields.push(`${imageSource.value}.type`);
 					fields.push(`${imageSource.value}.filename_disk`);
 					fields.push(`${imageSource.value}.storage`);
@@ -344,6 +345,7 @@ export default defineComponent({
 				}
 
 				if (props.collection === 'directus_files' && imageSource.value === '$file') {
+					fields.push('modified_on');
 					fields.push('type');
 				}
 
diff --git a/app/src/layouts/cards/components/card.vue b/app/src/layouts/cards/components/card.vue
index 507dea8a80..4cabb180bd 100644
--- a/app/src/layouts/cards/components/card.vue
+++ b/app/src/layouts/cards/components/card.vue
@@ -38,6 +38,7 @@ type File = {
 	[key: string]: any;
 	id: string;
 	type: string;
+	modified_on: Date;
 };
 
 export default defineComponent({
@@ -101,7 +102,7 @@ export default defineComponent({
 				key = 'system-medium-contain';
 			}
 
-			return getRootPath() + `assets/${props.file.id}?key=${key}`;
+			return getRootPath() + `assets/${props.file.id}?key=${key}&modified=${props.file.modified_on}`;
 		});
 
 		const svgSource = computed(() => {
@@ -109,7 +110,7 @@ export default defineComponent({
 			if (props.file.type.startsWith('image') === false) return null;
 			if (props.file.type.includes('svg') === false) return null;
 
-			return getRootPath() + `assets/${props.file.id}`;
+			return getRootPath() + `assets/${props.file.id}&modified=${props.file.modified_on}`;
 		});
 
 		const selectionIcon = computed(() => {
diff --git a/app/src/modules/files/components/file-info-sidebar-detail.vue b/app/src/modules/files/components/file-info-sidebar-detail.vue
index 31e9d24930..b1cc415469 100644
--- a/app/src/modules/files/components/file-info-sidebar-detail.vue
+++ b/app/src/modules/files/components/file-info-sidebar-detail.vue
@@ -64,10 +64,17 @@
 				</dd>
 			</div>
 
+			<div>
+				<dt>{{ $t('file') }}</dt>
+				<dd>
+					<a :href="`${getRootPath()}assets/${file.id}`" target="_blank">{{ $t('open') }}</a>
+				</dd>
+			</div>
+
 			<div>
 				<dt>{{ $t('folder') }}</dt>
 				<dd>
-					<button @click="$emit('move-folder')">{{ folder ? folder.name : $t('file_library') }}</button>
+					<router-link :to="folderLink">{{ folder ? folder.name : $t('file_library') }}</router-link>
 				</dd>
 			</div>
 
@@ -115,6 +122,7 @@ import i18n from '@/lang';
 import marked from 'marked';
 import localizedFormat from '@/utils/localized-format';
 import api from '@/api';
+import getRootPath from '@/utils/get-root-path';
 import { userName } from '@/utils/user-name';
 
 export default defineComponent({
@@ -140,9 +148,20 @@ export default defineComponent({
 
 		const { creationDate, modificationDate } = useDates();
 		const { userCreated, userModified } = useUser();
-		const { folder } = useFolder();
+		const { folder, folderLink } = useFolder();
 
-		return { readableMimeType, size, creationDate, modificationDate, userCreated, userModified, folder, marked };
+		return {
+			readableMimeType,
+			size,
+			creationDate,
+			modificationDate,
+			userCreated,
+			userModified,
+			folder,
+			marked,
+			folderLink,
+			getRootPath,
+		};
 
 		function useDates() {
 			const creationDate = ref<string | null>(null);
@@ -230,16 +249,23 @@ export default defineComponent({
 
 		function useFolder() {
 			type Folder = {
-				id: number;
+				id: string;
 				name: string;
 			};
 
 			const loading = ref(false);
 			const folder = ref<Folder | null>(null);
 
+			const folderLink = computed(() => {
+				if (folder.value === null) {
+					return `/files`;
+				}
+				return `/files/?folder=${folder.value.id}`;
+			});
+
 			watch(() => props.file, fetchFolder, { immediate: true });
 
-			return { folder };
+			return { folder, folderLink };
 
 			async function fetchFolder() {
 				if (!props.file) return null;
diff --git a/app/src/modules/files/components/replace-file.vue b/app/src/modules/files/components/replace-file.vue
new file mode 100644
index 0000000000..ff9ed0713b
--- /dev/null
+++ b/app/src/modules/files/components/replace-file.vue
@@ -0,0 +1,57 @@
+<template>
+	<v-dialog :active="active" @toggle="$emit('toggle', false)" @esc="$emit('toggle', false)">
+		<v-card v-if="file">
+			<v-card-title>{{ $t('replace_file') }}</v-card-title>
+			<v-card-text>
+				<v-upload :preset="preset" :file-id="file.id" @input="uploaded" from-url />
+			</v-card-text>
+			<v-card-actions>
+				<v-button secondary @click="$emit('toggle', false)">{{ $t('done') }}</v-button>
+			</v-card-actions>
+		</v-card>
+	</v-dialog>
+</template>
+
+<script lang="ts">
+import { defineComponent, ref } from '@vue/composition-api';
+import api from '@/api';
+import router from '@/router';
+import { PropType } from 'vue';
+
+export default defineComponent({
+	model: {
+		prop: 'active',
+		event: 'toggle',
+	},
+	props: {
+		active: {
+			type: Boolean,
+			default: false,
+		},
+		file: {
+			type: Object,
+			default: () => ({}),
+		},
+		preset: {
+			type: Object,
+			default: () => ({}),
+		},
+	},
+	setup(props, { emit }) {
+		return { uploaded };
+		function uploaded() {
+			emit('toggle', false);
+			emit('replaced');
+		}
+	},
+});
+</script>
+
+<style lang="scss" scoped>
+.add-new {
+	--v-button-background-color: var(--primary-25);
+	--v-button-color: var(--primary);
+	--v-button-background-color-hover: var(--primary-50);
+	--v-button-color-hover: var(--primary);
+}
+</style>
diff --git a/app/src/modules/files/routes/item.vue b/app/src/modules/files/routes/item.vue
index 35a624ae57..67fb6bd885 100644
--- a/app/src/modules/files/routes/item.vue
+++ b/app/src/modules/files/routes/item.vue
@@ -119,15 +119,13 @@
 				:width="item.width"
 				:height="item.height"
 				:title="item.title"
-				@click="previewActive = true"
+				@click="replaceFileDialogActive = true"
 			/>
 
-			<file-lightbox v-if="item" :id="item.id" v-model="previewActive" />
-
 			<image-editor
 				v-if="item && item.type.startsWith('image')"
 				:id="item.id"
-				@refresh="changeCacheBuster"
+				@refresh="refresh"
 				v-model="editActive"
 			/>
 
@@ -156,7 +154,7 @@
 		</v-dialog>
 
 		<template #sidebar>
-			<file-info-sidebar-detail :file="item" @move-folder="moveToDialogActive = true" />
+			<file-info-sidebar-detail :file="item" />
 			<revisions-drawer-detail
 				v-if="isBatch === false && isNew === false"
 				collection="directus_files"
@@ -169,6 +167,8 @@
 				:primary-key="primaryKey"
 			/>
 		</template>
+
+		<replace-file v-model="replaceFileDialogActive" @replaced="refresh" :file="item" />
 	</private-view>
 </template>
 
@@ -184,7 +184,6 @@ import SaveOptions from '@/views/private/components/save-options';
 import FilePreview from '@/views/private/components/file-preview';
 import ImageEditor from '@/views/private/components/image-editor';
 import { nanoid } from 'nanoid';
-import FileLightbox from '@/views/private/components/file-lightbox';
 import { useFieldsStore } from '@/stores/';
 import { Field } from '@/types';
 import FileInfoSidebarDetail from '../components/file-info-sidebar-detail.vue';
@@ -194,6 +193,7 @@ import api from '@/api';
 import getRootPath from '@/utils/get-root-path';
 import FilesNotFound from './not-found.vue';
 import useShortcut from '@/composables/use-shortcut';
+import ReplaceFile from '../components/replace-file.vue';
 
 type Values = {
 	[field: string]: any;
@@ -220,10 +220,10 @@ export default defineComponent({
 		SaveOptions,
 		FilePreview,
 		ImageEditor,
-		FileLightbox,
 		FileInfoSidebarDetail,
 		FolderPicker,
 		FilesNotFound,
+		ReplaceFile,
 	},
 	props: {
 		primaryKey: {
@@ -236,6 +236,7 @@ export default defineComponent({
 		const { primaryKey } = toRefs(props);
 		const { breadcrumb } = useBreadcrumb();
 		const fieldsStore = useFieldsStore();
+		const replaceFileDialogActive = ref(false);
 
 		const revisionsDrawerDetail = ref<Vue | null>(null);
 
@@ -256,13 +257,15 @@ export default defineComponent({
 
 		const hasEdits = computed<boolean>(() => Object.keys(edits.value).length > 0);
 		const confirmDelete = ref(false);
-		const cacheBuster = ref(nanoid());
 		const editActive = ref(false);
-		const previewActive = ref(false);
 		const fileSrc = computed(() => {
-			return (
-				getRootPath() + `assets/${props.primaryKey}?cache-buster=${cacheBuster.value}&key=system-large-contain`
-			);
+			if (item.value && item.value.modified_on) {
+				return (
+					getRootPath() +
+					`assets/${props.primaryKey}?cache-buster=${item.value.modified_on}&key=system-large-contain`
+				);
+			}
+			return getRootPath() + `assets/${props.primaryKey}?key=system-large-contain`;
 		});
 
 		// These are the fields that will be prevented from showing up in the form because they'll be shown in the sidebar
@@ -318,10 +321,7 @@ export default defineComponent({
 			saveAndStay,
 			saveAsCopyAndNavigate,
 			isBatch,
-			changeCacheBuster,
-			cacheBuster,
 			editActive,
-			previewActive,
 			revisionsDrawerDetail,
 			formFields,
 			confirmLeave,
@@ -335,12 +335,10 @@ export default defineComponent({
 			fileSrc,
 			form,
 			to,
+			replaceFileDialogActive,
+			refresh,
 		};
 
-		function changeCacheBuster() {
-			cacheBuster.value = nanoid();
-		}
-
 		function useBreadcrumb() {
 			const breadcrumb = computed(() => {
 				if (!item?.value?.folder) {
@@ -405,7 +403,7 @@ export default defineComponent({
 			const selectedFolder = ref<number | null>();
 
 			watch(item, () => {
-				selectedFolder.value = item.value.folder;
+				selectedFolder.value = item.value?.folder || null;
 			});
 
 			return { moveToDialogActive, moving, moveToFolder, selectedFolder };
diff --git a/app/src/modules/settings/routes/roles/item/item.vue b/app/src/modules/settings/routes/roles/item/item.vue
index fd7161f136..3cbacd5f55 100644
--- a/app/src/modules/settings/routes/roles/item/item.vue
+++ b/app/src/modules/settings/routes/roles/item/item.vue
@@ -133,7 +133,7 @@ export default defineComponent({
 			const values = {
 				...item.value,
 				...edits.value,
-			};
+			} as Record<string, any>;
 
 			return !!values.admin_access;
 		});
diff --git a/app/src/modules/settings/routes/webhooks/item.vue b/app/src/modules/settings/routes/webhooks/item.vue
index bbcb6bd156..5744bb66c0 100644
--- a/app/src/modules/settings/routes/webhooks/item.vue
+++ b/app/src/modules/settings/routes/webhooks/item.vue
@@ -115,7 +115,7 @@ export default defineComponent({
 		const title = computed(() => {
 			if (loading.value) return i18n.t('loading');
 			if (isNew.value) return i18n.t('creating_webhook');
-			return item.value.name;
+			return item.value?.name;
 		});
 
 		return {
diff --git a/app/src/modules/users/routes/item.vue b/app/src/modules/users/routes/item.vue
index 9c44f53655..24c42cd262 100644
--- a/app/src/modules/users/routes/item.vue
+++ b/app/src/modules/users/routes/item.vue
@@ -384,7 +384,7 @@ export default defineComponent({
 		}
 
 		async function refreshCurrentUser() {
-			if (userStore.state.currentUser!.id === item.value.id) {
+			if (userStore.state.currentUser!.id === item.value?.id) {
 				await userStore.hydrate();
 			}
 		}
diff --git a/app/src/utils/is-allowed.ts b/app/src/utils/is-allowed.ts
index 904b10c379..6555154264 100644
--- a/app/src/utils/is-allowed.ts
+++ b/app/src/utils/is-allowed.ts
@@ -2,7 +2,7 @@ import { usePermissionsStore, useUserStore } from '@/stores';
 import { Permission } from '@/types';
 import generateJoi from '@/utils/generate-joi';
 
-export function isAllowed(collection: string, action: Permission['action'], value: Record<string, any>) {
+export function isAllowed(collection: string, action: Permission['action'], value: Record<string, any> | null) {
 	const permissionsStore = usePermissionsStore();
 	const userStore = useUserStore();
 
diff --git a/app/src/utils/upload-file/upload-file.ts b/app/src/utils/upload-file/upload-file.ts
index 138b4e8e3b..9043ad7808 100644
--- a/app/src/utils/upload-file/upload-file.ts
+++ b/app/src/utils/upload-file/upload-file.ts
@@ -11,6 +11,7 @@ export default async function uploadFile(
 		onProgressChange?: (percentage: number) => void;
 		notifications?: boolean;
 		preset?: Record<string, any>;
+		fileId?: string;
 	}
 ) {
 	const progressHandler = options?.onProgressChange || (() => undefined);
@@ -25,9 +26,17 @@ export default async function uploadFile(
 	formData.append('file', file);
 
 	try {
-		const response = await api.post(`/files`, formData, {
-			onUploadProgress,
-		});
+		let response = null;
+
+		if (options?.fileId !== undefined) {
+			response = await api.patch(`/files/${options.fileId}`, formData, {
+				onUploadProgress,
+			});
+		} else {
+			response = await api.post(`/files`, formData, {
+				onUploadProgress,
+			});
+		}
 
 		if (options?.notifications) {
 			notify({
diff --git a/app/src/views/private/components/file-preview/file-preview.vue b/app/src/views/private/components/file-preview/file-preview.vue
index 4ccc07b16d..e6c3b9cd23 100644
--- a/app/src/views/private/components/file-preview/file-preview.vue
+++ b/app/src/views/private/components/file-preview/file-preview.vue
@@ -1,16 +1,21 @@
 <template>
 	<div class="file-preview" v-if="type">
-		<div v-if="type === 'image'" class="image" :class="{ svg: isSVG, 'max-size': inModal === false }" @click="$emit('click')">
+		<div
+			v-if="type === 'image'"
+			class="image"
+			:class="{ svg: isSVG, 'max-size': inModal === false }"
+			@click="$emit('click')"
+		>
 			<img
 				:src="src"
 				:width="width"
 				:height="height"
 				:style="{
-					'maxWidth': width ? width + 'px' : '100%'
+					maxWidth: width ? width + 'px' : '100%',
 				}"
 				:alt="title"
 			/>
-			<v-icon v-if="inModal === false" name="fullscreen" />
+			<v-icon v-if="inModal === false" name="upload" />
 		</div>
 
 		<video v-else-if="type === 'video'" controls :src="src" />
@@ -106,9 +111,9 @@ audio {
 	}
 
 	img {
-		max-height: inherit;
 		z-index: 1;
 		display: block;
+		max-height: inherit;
 		margin: 0 auto;
 	}