diff --git a/src/components/MessagesList/MessagesGroup/Message/MessageButtonsBar/MessageButtonsBar.vue b/src/components/MessagesList/MessagesGroup/Message/MessageButtonsBar/MessageButtonsBar.vue
index 1fab21db53f..a995174c635 100644
--- a/src/components/MessagesList/MessagesGroup/Message/MessageButtonsBar/MessageButtonsBar.vue
+++ b/src/components/MessagesList/MessagesGroup/Message/MessageButtonsBar/MessageButtonsBar.vue
@@ -172,26 +172,6 @@
 						</template>
 						{{ t('spreed', 'Mark as unread') }}
 					</NcActionButton>
-					<template v-if="isFileShare">
-						<NcActionSeparator />
-						<NcActionLink :href="messageFile.link">
-							<template #icon>
-								<IconFileOutline :size="20" />
-							</template>
-							{{ isSharedFolder ? t('spreed', 'Go to folder') : t('spreed', 'Go to file') }}
-						</NcActionLink>
-						<NcActionLink
-							v-if="!hideDownloadOption"
-							:href="linkToFileDownload"
-							:download="downloadFileName"
-							closeAfterClick>
-							<template #icon>
-								<NcIconSvgWrapper :svg="IconFileDownload" :size="20" />
-							</template>
-							<!-- TRANSLATORS: to download a folder/file -->
-							{{ isSharedFolder ? t('spreed', 'Download folder') : t('spreed', 'Download file') }}
-						</NcActionLink>
-					</template>
 					<template v-if="isThreadStarterMessage">
 						<NcActionSeparator />
 						<NcActionButton
@@ -415,7 +395,6 @@
 </template>
 
 <script>
-import { getCurrentUser } from '@nextcloud/auth'
 import { showError, showSuccess } from '@nextcloud/dialogs'
 import { t } from '@nextcloud/l10n'
 import { spawnDialog } from '@nextcloud/vue/functions/dialog'
@@ -425,13 +404,11 @@ import { toRefs } from 'vue'
 import NcActionButton from '@nextcloud/vue/components/NcActionButton'
 import NcActionCaption from '@nextcloud/vue/components/NcActionCaption'
 import NcActionInput from '@nextcloud/vue/components/NcActionInput'
-import NcActionLink from '@nextcloud/vue/components/NcActionLink'
 import NcActions from '@nextcloud/vue/components/NcActions'
 import NcActionSeparator from '@nextcloud/vue/components/NcActionSeparator'
 import NcActionText from '@nextcloud/vue/components/NcActionText'
 import NcButton from '@nextcloud/vue/components/NcButton'
 import NcEmojiPicker from '@nextcloud/vue/components/NcEmojiPicker'
-import NcIconSvgWrapper from '@nextcloud/vue/components/NcIconSvgWrapper'
 import IconAccountOutline from 'vue-material-design-icons/AccountOutline.vue'
 import IconAlarm from 'vue-material-design-icons/Alarm.vue'
 import IconArrowLeft from 'vue-material-design-icons/ArrowLeft.vue'
@@ -447,7 +424,6 @@ import IconCloseCircleOutline from 'vue-material-design-icons/CloseCircleOutline
 import IconContentCopy from 'vue-material-design-icons/ContentCopy.vue'
 import IconDotsHorizontal from 'vue-material-design-icons/DotsHorizontal.vue'
 import IconEmoticonOutline from 'vue-material-design-icons/EmoticonOutline.vue'
-import IconFileOutline from 'vue-material-design-icons/FileOutline.vue'
 import IconForumOutline from 'vue-material-design-icons/ForumOutline.vue'
 import IconMessageBadgeOutline from 'vue-material-design-icons/MessageBadgeOutline.vue'
 import IconNoteEditOutline from 'vue-material-design-icons/NoteEditOutline.vue'
@@ -459,7 +435,6 @@ import IconPlus from 'vue-material-design-icons/Plus.vue'
 import IconTranslate from 'vue-material-design-icons/Translate.vue'
 import IconTrashCanOutline from 'vue-material-design-icons/TrashCanOutline.vue'
 import MessageTranslateDialog from './MessageTranslateDialog.vue'
-import IconFileDownload from '../../../../../../img/material-icons/file-download.svg?raw'
 import { useGetThreadId } from '../../../../../composables/useGetThreadId.ts'
 import { useMessageInfo } from '../../../../../composables/useMessageInfo.ts'
 import { ATTENDEE, CONVERSATION, MESSAGE, PARTICIPANT, SHARED_ITEM } from '../../../../../constants.ts'
@@ -471,11 +446,9 @@ import { useIntegrationsStore } from '../../../../../stores/integrations.js'
 import { useReactionsStore } from '../../../../../stores/reactions.js'
 import { useSharedItemsStore } from '../../../../../stores/sharedItems.ts'
 import { isClassifiedConversation } from '../../../../../utils/conversation.ts'
-import { generatePublicShareDownloadUrl, generateUserFileUrl, generateUserFolderUrl } from '../../../../../utils/davUtils.ts'
 import { convertToUnix, formatDateTime, ONE_DAY_IN_MS } from '../../../../../utils/formattedTime.ts'
 import { getCustomDateOptions } from '../../../../../utils/getCustomDateOptions.ts'
 import { copyConversationLinkToClipboard } from '../../../../../utils/handleUrl.ts'
-import { getFileKeys } from '../../../../../utils/message.ts'
 import { parseMentions } from '../../../../../utils/textParse.ts'
 
 const PIN_DURATION_OPTIONS = [
@@ -492,13 +465,11 @@ export default {
 		NcActionButton,
 		NcActionCaption,
 		NcActionInput,
-		NcActionLink,
 		NcActionSeparator,
 		NcActionText,
 		NcActions,
 		NcButton,
 		NcEmojiPicker,
-		NcIconSvgWrapper,
 		// Icons
 		IconAccountOutline,
 		IconAlarm,
@@ -515,7 +486,6 @@ export default {
 		IconTrashCanOutline,
 		IconEmoticonOutline,
 		IconMessageBadgeOutline,
-		IconFileOutline,
 		IconForumOutline,
 		IconNoteEditOutline,
 		IconOpenInNew,
@@ -603,7 +573,6 @@ export default {
 			isCurrentUserOwnMessage,
 			isFileShare,
 			isFileShareWithoutCaption,
-			hideDownloadOption,
 			isConversationReadOnly,
 			isConversationModifiable,
 		} = useMessageInfo(message)
@@ -615,7 +584,6 @@ export default {
 			?? getTalkConfig(message.value.token, 'chat', 'translations')?.length > 0
 
 		return {
-			IconFileDownload,
 			messageActions,
 			supportReminders,
 			reactionsStore,
@@ -623,7 +591,6 @@ export default {
 			isCurrentUserOwnMessage,
 			isFileShare,
 			isFileShareWithoutCaption,
-			hideDownloadOption,
 			isDeleteable,
 			isConversationReadOnly,
 			isConversationModifiable,
@@ -671,27 +638,6 @@ export default {
 				&& !this.isClassified
 		},
 
-		messageFile() {
-			const firstFileKey = getFileKeys(this.message).at(0)
-			return this.message.messageParameters[firstFileKey]
-		},
-
-		isSharedFolder() {
-			return this.messageFile?.mimetype === 'httpd/unix-directory'
-		},
-
-		downloadFileName() {
-			return this.messageFile.name + (this.isSharedFolder ? '.zip' : '')
-		},
-
-		linkToFileDownload() {
-			return getCurrentUser()
-				? (this.isSharedFolder
-						? generateUserFolderUrl(this.messageFile.path)
-						: generateUserFileUrl(this.messageFile.path))
-				: generatePublicShareDownloadUrl(this.messageFile.link)
-		},
-
 		isCurrentGuest() {
 			return this.actorStore.isActorGuest
 		},
diff --git a/src/components/MessagesList/MessagesGroup/Message/MessageItem.vue b/src/components/MessagesList/MessagesGroup/Message/MessageItem.vue
index a0e7e904c07..9af87edeacd 100644
--- a/src/components/MessagesList/MessagesGroup/Message/MessageItem.vue
+++ b/src/components/MessagesList/MessagesGroup/Message/MessageItem.vue
@@ -113,7 +113,7 @@ import { hasTalkFeature } from '../../../../services/CapabilitiesManager.ts'
 import { EventBus } from '../../../../services/EventBus.ts'
 import { useActorStore } from '../../../../stores/actor.ts'
 import { useChatExtrasStore } from '../../../../stores/chatExtras.ts'
-import { isFilePreviewParameter, isTemporaryId } from '../../../../utils/message.ts'
+import { isFilePreviewParameter, isTemporaryId, isTemporaryMessage } from '../../../../utils/message.ts'
 
 const LocationCard = defineAsyncComponent(() => import('./MessagePart/LocationCard.vue'))
 
@@ -187,7 +187,7 @@ export default {
 		},
 
 		isTemporary() {
-			return !this.isScheduledMessage && isTemporaryId(this.message.id)
+			return !this.isScheduledMessage && isTemporaryMessage(this.message)
 		},
 
 		isDeletedMessage() {
@@ -490,10 +490,6 @@ export default {
 				background-color: var(--color-primary-element-light-hover);
 				border: 1px solid var(--color-border-dark);
 			}
-
-			:deep(.file-preview__progress) {
-				inset-inline-start: calc((var(--progress-bar-height) + var(--default-grid-baseline) * 3) * -1)
-			}
 		}
 
 		&.incoming {
diff --git a/src/components/MessagesList/MessagesGroup/Message/MessagePart/FilePreview.vue b/src/components/MessagesList/MessagesGroup/Message/MessagePart/FilePreview.vue
index 99d702cd4c3..17c6e8b4fe8 100644
--- a/src/components/MessagesList/MessagesGroup/Message/MessagePart/FilePreview.vue
+++ b/src/components/MessagesList/MessagesGroup/Message/MessagePart/FilePreview.vue
@@ -52,6 +52,7 @@
 					@load="onLoad"
 					@error="onError">
 				<template v-if="!isLoading || fallbackLocalUrl">
+					<span v-if="moreCount > 0" class="more-overlay">+{{ moreCount }}</span>
 					<span v-if="isPlayable && !smallPreview" class="play-video-button">
 						<IconPlayCircleOutline
 							:size="48"
@@ -60,8 +61,9 @@
 					<NcProgressBar
 						v-if="showUploadProgress"
 						class="file-preview__progress"
+						:class="{ 'file-preview__progress--pending': !uploadProgress }"
 						type="circular"
-						:value="uploadProgress" />
+						:value="uploadProgress || 30" />
 					<span
 						v-if="fileSizeLabel"
 						class="file-preview__size"
@@ -94,7 +96,13 @@
 			</template>
 		</NcButton>
 		<div v-if="shouldShowFileDetail" class="name-container">
-			{{ fileDetail }}
+			<template v-if="rowLayout">
+				<span class="name-container__name">{{ fileDetail }}</span>
+				<span v-if="fileMetaLabel" class="name-container__meta">{{ fileMetaLabel }}</span>
+			</template>
+			<template v-else>
+				{{ fileDetail }}
+			</template>
 		</div>
 	</component>
 </template>
@@ -203,6 +211,24 @@ export default {
 			type: String,
 			default: '',
 		},
+
+		/**
+		 * Sibling image files from the same upload group (message), in upload order.
+		 * Used to scope the Viewer's swipeable list to this group instead of all conversation media.
+		 */
+		mediaGroup: {
+			type: Array,
+			default: undefined,
+		},
+
+		/**
+		 * When set, this tile shows a "+N" overlay instead of its own preview,
+		 * for the collapsed tail of an image row.
+		 */
+		moreCount: {
+			type: Number,
+			default: 0,
+		},
 	},
 
 	emits: ['removeFile'],
@@ -250,6 +276,22 @@ export default {
 			return this.file.name
 		},
 
+		// Extension shown on the second, muted line of the row layout ('PDF', 'DOCX', …)
+		fileExtension() {
+			const dotIndex = this.file.name.lastIndexOf('.')
+			return dotIndex > 0 ? this.file.name.slice(dotIndex + 1).toUpperCase() : ''
+		},
+
+		// File size shown on the second, muted line of the row layout
+		fileRowSize() {
+			const size = parseInt(this.file.size, 10)
+			return size ? formatFileSize(size, true) : ''
+		},
+
+		fileMetaLabel() {
+			return [this.fileExtension, this.fileRowSize].filter(Boolean).join(' · ')
+		},
+
 		fileSizeLabel() {
 			if (!this.isUploadEditor || !this.uploadFile) {
 				return ''
@@ -305,7 +347,7 @@ export default {
 
 		previewImageClass() {
 			let classes = ''
-			if (this.smallPreview) {
+			if (this.smallPreview || this.rowLayout) {
 				classes += 'preview-small '
 			} else if (this.mediumPreview) {
 				classes += 'preview-medium '
@@ -334,6 +376,11 @@ export default {
 				return {}
 			}
 
+			// Row layout always shows a small fixed-size icon, never a medium/full preview
+			if (this.rowLayout) {
+				return { width: '24px', height: '24px' }
+			}
+
 			// Fallback for loading mimeicons (preview for audio files is not provided)
 			if (this.file['preview-available'] !== 'yes' || this.file.mimetype.startsWith('audio/') || this.failed) {
 				return {
@@ -596,7 +643,7 @@ export default {
 			event.stopPropagation()
 			event.preventDefault()
 
-			if (this.itemType === SHARED_ITEM.TYPES.MEDIA) {
+			if (this.itemType === SHARED_ITEM.TYPES.MEDIA && this.isSharedItems) {
 				const getRevertedList = (items) => Object.values(items).reverse()
 					.map((item) => item.messageParameters.file)
 
@@ -609,6 +656,9 @@ export default {
 				}
 
 				this.openViewer(this.internalAbsolutePath, list, this.file, loadMore)
+			} else if (this.itemType === SHARED_ITEM.TYPES.MEDIA && this.mediaGroup?.length) {
+				// Message context: only swipe through images from the same upload group (this message)
+				this.openViewer(this.internalAbsolutePath, this.mediaGroup, this.file)
 			} else {
 				this.openViewer(this.internalAbsolutePath, [this.file], this.file)
 			}
@@ -649,9 +699,21 @@ export default {
 
 	&__progress {
 		position: absolute;
-		top: 50%;
-		inset-inline-end: calc(var(--progress-bar-height) * -1);
-		transform: translateY(-50%);
+		inset-block-end: var(--default-grid-baseline);
+		inset-inline-end: var(--default-grid-baseline);
+		border-radius: 50%;
+		z-index: 1;
+
+		// Override NcProgressBar styles to fake indeterminate state and mimic NcLoadingIcon
+		:deep(circle:first-of-type) {
+			stroke: var(--color-loading-dark);
+		}
+		:deep(circle:last-of-type) {
+			stroke: var(--color-loading-light);
+		}
+		&--pending {
+			animation: rotate var(--animation-duration, 0.8s) linear infinite;
+		}
 	}
 
 	&__size {
@@ -711,6 +773,21 @@ export default {
 		max-height: 100%;
 		border-radius: var(--border-radius);
 
+		// "+X more" overlay for the collapsed tail of an image row (see FilePreviewsWrapper)
+		.more-overlay {
+			position: absolute;
+			inset: 0;
+			display: flex;
+			align-items: center;
+			justify-content: center;
+			border-radius: var(--border-radius);
+			background-color: rgba(0, 0, 0, 0.5);
+			color: #ffffff;
+			font-size: var(--font-size-large);
+			font-weight: bold;
+			z-index: 1;
+		}
+
 		// Classified: signal that the hidden preview is clickable (not failed)
 		.classified-preview-button {
 			position: absolute;
@@ -829,6 +906,9 @@ export default {
 		align-items: center;
 		border-radius: var(--border-radius);
 		padding: 2px 4px;
+		// Reserve space for the hover actions button (see FilePreviewActions), so it never
+		// overlaps the file name and the row doesn't shift width on hover.
+		padding-inline-end: var(--default-clickable-area);
 
 		.image-container {
 			flex-shrink: 0;
@@ -836,8 +916,21 @@ export default {
 		}
 
 		.name-container {
+			display: flex;
+			flex-direction: column;
 			padding: 0 4px;
 			font-weight: normal;
+			font-size: var(--font-size-small);
+
+			&__name {
+				overflow: hidden;
+				white-space: nowrap;
+				text-overflow: ellipsis;
+			}
+
+			&__meta {
+				color: var(--color-text-maxcontrast);
+			}
 		}
 	}
 
diff --git a/src/components/MessagesList/MessagesGroup/Message/MessagePart/FilePreviewActions.vue b/src/components/MessagesList/MessagesGroup/Message/MessagePart/FilePreviewActions.vue
new file mode 100644
index 00000000000..d28d295f33c
--- /dev/null
+++ b/src/components/MessagesList/MessagesGroup/Message/MessagePart/FilePreviewActions.vue
@@ -0,0 +1,108 @@
+<!--
+  - SPDX-FileCopyrightText: 2026 Nextcloud GmbH and Nextcloud contributors
+  - SPDX-License-Identifier: AGPL-3.0-or-later
+-->
+
+<!--
+  Hover actions for a single file inside a FilePreviewsWrapper ('Go to file', 'Download file').
+  FilePreviewsWrapper renders a single instance of this component, repositioned over whichever
+  file tile is currently hovered, instead of one action menu per tile.
+-->
+<script setup lang="ts">
+import { getCurrentUser } from '@nextcloud/auth'
+import { t } from '@nextcloud/l10n'
+import { computed } from 'vue'
+import NcActionLink from '@nextcloud/vue/components/NcActionLink'
+import NcActions from '@nextcloud/vue/components/NcActions'
+import NcIconSvgWrapper from '@nextcloud/vue/components/NcIconSvgWrapper'
+import IconFileOutline from 'vue-material-design-icons/FileOutline.vue'
+import IconFileDownload from '../../../../../../img/material-icons/file-download.svg?raw'
+import { generatePublicShareDownloadUrl, generateUserFileUrl, generateUserFolderUrl } from '../../../../../utils/davUtils.ts'
+
+// Loosely typed on purpose: a RichObjectParameter file entry from a message, not every field is
+// guaranteed present in the schema, but 'Go to file'/'Download file' only need these.
+const props = defineProps<{
+	file: {
+		name: string
+		mimetype?: string
+		path?: string
+		link?: string
+		'hide-download'?: string
+	}
+	/**
+	 * Row-layout tiles anchor the button vertically centered at the row's end (next to the
+	 * name), instead of the image tiles' default bottom-right corner.
+	 */
+	alignCenter?: boolean
+}>()
+
+const emit = defineEmits<{
+	/**
+	 * Fired whenever the actions popover opens or closes, so FilePreviewsWrapper can keep this
+	 * component mounted (and not clear the hover state) while the popover is open, even once
+	 * the pointer leaves the tile for the (teleported) popover content.
+	 */
+	'update:open': [value: boolean]
+}>()
+
+const isSharedFolder = computed(() => props.file.mimetype === 'httpd/unix-directory')
+
+const hideDownloadOption = computed(() => props.file['hide-download'] === 'yes')
+
+const downloadFileName = computed(() => props.file.name + (isSharedFolder.value ? '.zip' : ''))
+
+const linkToFileDownload = computed(() => {
+	return getCurrentUser()
+		? (isSharedFolder.value
+				? generateUserFolderUrl(props.file.path ?? '')
+				: generateUserFileUrl(props.file.path ?? ''))
+		: generatePublicShareDownloadUrl(props.file.link ?? '')
+})
+</script>
+
+<template>
+	<!-- NcActions doesn't reliably forward class/positioning to its own root element, so it's
+		 positioned via this plain wrapper instead. -->
+	<span
+		class="file-preview-actions"
+		:class="{ 'file-preview-actions--center': alignCenter }">
+		<NcActions
+			:aria-label="t('spreed', 'File actions')"
+			placement="bottom-end"
+			@update:open="emit('update:open', $event)">
+			<NcActionLink :href="file.link">
+				<template #icon>
+					<IconFileOutline :size="20" />
+				</template>
+				{{ isSharedFolder ? t('spreed', 'Go to folder') : t('spreed', 'Go to file') }}
+			</NcActionLink>
+			<NcActionLink
+				v-if="!hideDownloadOption"
+				:href="linkToFileDownload"
+				:download="downloadFileName"
+				closeAfterClick>
+				<template #icon>
+					<NcIconSvgWrapper :svg="IconFileDownload" :size="20" />
+				</template>
+				<!-- TRANSLATORS: to download a folder/file -->
+				{{ isSharedFolder ? t('spreed', 'Download folder') : t('spreed', 'Download file') }}
+			</NcActionLink>
+		</NcActions>
+	</span>
+</template>
+
+<style lang="scss" scoped>
+.file-preview-actions {
+	position: absolute;
+	inset-inline-end: 4px;
+	inset-block-end: 4px;
+	pointer-events: auto;
+
+	// Row layout: centered next to the name, matching the icon's own vertical centering
+	&--center {
+		inset-block-end: auto;
+		top: 50%;
+		transform: translateY(-50%);
+	}
+}
+</style>
diff --git a/src/components/MessagesList/MessagesGroup/Message/MessagePart/FilePreviewsWrapper.vue b/src/components/MessagesList/MessagesGroup/Message/MessagePart/FilePreviewsWrapper.vue
index 95e3ce07c4a..e00532815e6 100644
--- a/src/components/MessagesList/MessagesGroup/Message/MessagePart/FilePreviewsWrapper.vue
+++ b/src/components/MessagesList/MessagesGroup/Message/MessagePart/FilePreviewsWrapper.vue
@@ -6,8 +6,9 @@
 <script setup lang="ts">
 import type { ChatMessage } from '../../../../../types/index.ts'
 
-import { computed } from 'vue'
+import { computed, ref } from 'vue'
 import FilePreview from './FilePreview.vue'
+import FilePreviewActions from './FilePreviewActions.vue'
 import { getItemTypeFromMessage } from '../../../../../utils/getItemTypeFromMessage.ts'
 import { getFilePreviewKeys } from '../../../../../utils/message.ts'
 
@@ -15,8 +16,110 @@ const props = defineProps<{
 	message: ChatMessage
 }>()
 
+// Maximum number of image tiles shown in the row before collapsing the rest into a "+X more" tile.
+// When the count exceeds this, only MAX_VISIBLE_IMAGES - 1 thumbnails are shown, so the last slot
+// can hold the "+X more" overlay.
+const MAX_VISIBLE_IMAGES = 4
+
 const fileKeys = computed(() => getFilePreviewKeys(props.message))
 
+const isCombined = computed(() => fileKeys.value.length > 1)
+
+/**
+ * Whether a file parameter is an image with a server-side preview available.
+ * Such files are grouped into a single row of thumbnails, without a name shown.
+ *
+ * @param key key of the file parameter ('file', 'file-1', …)
+ */
+function isImageKey(key: string): boolean {
+	const file = props.message.messageParameters[key]
+	return (file.mimetype?.startsWith('image/') ?? false) && file['preview-available'] === 'yes'
+}
+
+const imageKeys = computed(() => fileKeys.value.filter(isImageKey))
+const otherKeys = computed(() => fileKeys.value.filter((key) => !isImageKey(key)))
+
+// Full list of image files in this message, in upload order. Passed to every image tile so the
+// Viewer can swipe through siblings from the same upload group only (not all conversation media).
+const mediaGroup = computed(() => imageKeys.value.map((key) => props.message.messageParameters[key]))
+
+const hiddenImageCount = computed(() => {
+	return imageKeys.value.length > MAX_VISIBLE_IMAGES
+		? imageKeys.value.length - (MAX_VISIBLE_IMAGES - 1)
+		: 0
+})
+
+const visibleImageKeys = computed(() => {
+	return hiddenImageCount.value > 0
+		? imageKeys.value.slice(0, MAX_VISIBLE_IMAGES - 1)
+		: imageKeys.value
+})
+
+// The first hidden image is rendered as the "+X more" tile, so opening it lands the Viewer on the
+// first image that was not directly visible.
+const moreTileKey = computed(() => {
+	return hiddenImageCount.value > 0 ? imageKeys.value[MAX_VISIBLE_IMAGES - 1] : undefined
+})
+
+// A single FilePreviewActions instance is shown per wrapper (not one per tile), repositioned
+// over whichever file is currently hovered.
+const hoveredKey = ref('')
+const hoverStyle = ref({})
+// While the actions popover is open, the pointer may leave the tile for the popover's
+// (teleported) content — don't tear the popover down on that mouseleave.
+const isActionsMenuOpen = ref(false)
+
+const hoveredFile = computed(() => {
+	return hoveredKey.value ? props.message.messageParameters[hoveredKey.value] : undefined
+})
+
+// Row-layout tiles anchor the actions button vertically centered at the row's end (next to the
+// name), instead of the image tiles' bottom-right corner.
+const hoveredIsRowLayout = computed(() => otherKeys.value.includes(hoveredKey.value))
+
+/**
+ * Track the hovered file and the CSS rect of its tile, so the single FilePreviewActions
+ * instance can be repositioned on top of it.
+ *
+ * @param key key of the hovered file parameter
+ * @param event the native mouseenter event
+ */
+function onTileMouseEnter(key: string, event: MouseEvent): void {
+	hoveredKey.value = key
+	const el = event.currentTarget as HTMLElement
+	hoverStyle.value = {
+		top: `${el.offsetTop}px`,
+		left: `${el.offsetLeft}px`,
+		width: `${el.offsetWidth}px`,
+		height: `${el.offsetHeight}px`,
+	}
+}
+
+/**
+ * Clear the hovered file: when the pointer leaves the whole wrapper, or when it enters the
+ * "+X more" tile, which does not get its own hover actions. Ignored while the actions popover
+ * is open, since leaving the tile for the popover itself must not close it.
+ */
+function clearHoveredFile(): void {
+	if (isActionsMenuOpen.value) {
+		return
+	}
+	hoveredKey.value = ''
+}
+
+/**
+ * Track the actions popover's open state, and clear the hovered file as soon as it closes
+ * (the pointer has likely already left the tile by then).
+ *
+ * @param open whether the popover is now open
+ */
+function onActionsMenuOpenChange(open: boolean): void {
+	isActionsMenuOpen.value = open
+	if (!open) {
+		hoveredKey.value = ''
+	}
+}
+
 /**
  * Get referenceId of a file parameter to look up a local preview (if available).
  * Client-only workaround for combined file messages
@@ -32,33 +135,92 @@ function getReferenceId(key: string): string {
 <template>
 	<div
 		class="file-previews-wrapper"
-		:class="{ 'file-previews-wrapper--combined': fileKeys.length > 1 }">
-		<FilePreview
-			v-for="key in fileKeys"
-			:key="key"
-			:token="message.token"
-			:messageId="message.id"
-			:itemType="getItemTypeFromMessage(message, key)"
-			:referenceId="getReferenceId(key)"
-			:file="message.messageParameters[key]" />
+		:class="{ 'file-previews-wrapper--combined': isCombined }"
+		@mouseleave="clearHoveredFile">
+		<div v-if="imageKeys.length" class="file-previews-wrapper__image-row">
+			<FilePreview
+				v-for="key in visibleImageKeys"
+				:key="key"
+				:token="message.token"
+				:messageId="message.id"
+				:itemType="getItemTypeFromMessage(message, key)"
+				:referenceId="getReferenceId(key)"
+				:mediaGroup="mediaGroup"
+				:file="message.messageParameters[key]"
+				@mouseenter="onTileMouseEnter(key, $event)" />
+			<FilePreview
+				v-if="moreTileKey"
+				:key="moreTileKey"
+				:token="message.token"
+				:messageId="message.id"
+				:itemType="getItemTypeFromMessage(message, moreTileKey)"
+				:referenceId="getReferenceId(moreTileKey)"
+				:mediaGroup="mediaGroup"
+				:moreCount="hiddenImageCount"
+				:file="message.messageParameters[moreTileKey]"
+				@mouseenter="clearHoveredFile" />
+		</div>
+		<div v-if="otherKeys.length" class="file-previews-wrapper__other-column">
+			<FilePreview
+				v-for="key in otherKeys"
+				:key="key"
+				rowLayout
+				:token="message.token"
+				:messageId="message.id"
+				:itemType="getItemTypeFromMessage(message, key)"
+				:referenceId="getReferenceId(key)"
+				:file="message.messageParameters[key]"
+				@mouseenter="onTileMouseEnter(key, $event)" />
+		</div>
+		<div
+			v-if="hoveredFile"
+			class="file-previews-wrapper__hover-overlay"
+			:style="hoverStyle">
+			<FilePreviewActions
+				:file="hoveredFile"
+				:alignCenter="hoveredIsRowLayout"
+				@update:open="onActionsMenuOpenChange" />
+		</div>
 	</div>
 </template>
 
 <style lang="scss" scoped>
 .file-previews-wrapper {
+	position: relative;
 	display: flex;
-	flex-wrap: wrap;
+	flex-direction: column;
 	align-items: flex-start;
 	gap: var(--default-grid-baseline);
+
+	&__image-row {
+		display: flex;
+		align-items: flex-start;
+		gap: var(--default-grid-baseline);
+	}
+
+	&__other-column {
+		display: flex;
+		flex-direction: column;
+		align-items: stretch;
+		gap: calc(var(--default-grid-baseline) / 2);
+	}
+
+	// Repositioned over whichever tile is hovered (see onTileMouseEnter); never itself
+	// intercepts clicks, only the actions button inside it does.
+	&__hover-overlay {
+		position: absolute;
+		pointer-events: none;
+	}
 }
 
 .file-previews-wrapper--combined {
-	:deep(.file-preview) {
+	// Image tiles never show a name (see isImageKey), so the tile is exactly the image's own
+	// size — this also keeps the hover-actions overlay rect matching the visible thumbnail.
+	:deep(.file-previews-wrapper__image-row .file-preview) {
 		--preview-size: 80px;
-		--preview-name-height: 24px;
 		flex-shrink: 0;
 		width: var(--preview-size);
-		height: calc(var(--preview-size) + var(--preview-name-height));
+		height: var(--preview-size);
 
 		.image-container {
 			width: var(--preview-size) !important;
@@ -76,12 +238,6 @@ function getReferenceId(key: string): string {
 				object-fit: contain;
 			}
 		}
-
-		.name-container {
-			height: var(--preview-name-height);
-			font-weight: normal;
-			font-size: var(--font-size-small);
-		}
 	}
 }
 </style>
diff --git a/src/components/MessagesList/MessagesGroup/Message/MessagePart/MessageBody.vue b/src/components/MessagesList/MessagesGroup/Message/MessagePart/MessageBody.vue
index 4a2a42d7bc8..229501be23e 100644
--- a/src/components/MessagesList/MessagesGroup/Message/MessagePart/MessageBody.vue
+++ b/src/components/MessagesList/MessagesGroup/Message/MessagePart/MessageBody.vue
@@ -226,7 +226,7 @@ import {
 	getFileKeys,
 	getFilePreviewKeys,
 	isFilePreviewParameter,
-	isTemporaryId,
+	isTemporaryMessage,
 } from '../../../../../utils/message.ts'
 import { parseMentions, parseSpecialSymbols } from '../../../../../utils/textParse.ts'
 
@@ -438,7 +438,7 @@ export default {
 		},
 
 		isTemporary() {
-			return !this.isScheduledMessage && isTemporaryId(this.message.id)
+			return !this.isScheduledMessage && isTemporaryMessage(this.message)
 		},
 
 		isScheduledSendingFailure() {
diff --git a/src/stores/upload.ts b/src/stores/upload.ts
index 55dcc1ed7c5..1f38ef57a25 100644
--- a/src/stores/upload.ts
+++ b/src/stores/upload.ts
@@ -492,14 +492,19 @@ export const useUploadStore = defineStore('upload', () => {
 
 		// Tag previously indexed files and add temporary messages to the MessagesList
 		// If caption is provided, attach to the last temporary message
-		const lastIndex = getInitialisedUploads(uploadId).at(-1)![0]
-		for (const [index, uploadedFile] of getInitialisedUploads(uploadId)) {
-			// Compress before building the temporary message, so that the caption,
-			// the parent and the final file parameters are applied in a single pass
-			// and the backend receives the final file names (e.g. .webp instead of .png)
-			const compressed = compressImages
-				? await compressUploadedImage(uploadId, index)
-				: null
+		const initialisedUploads = getInitialisedUploads(uploadId)
+		const lastIndex = initialisedUploads.at(-1)![0]
+
+		// Compress all images in parallel first, then build each temporary message in a
+		// single pass over the precompressed results, so that the caption, the parent and
+		// the final file parameters are applied consistently and the backend receives the
+		// final file names (e.g. .webp instead of .png).
+		const compressedFiles = compressImages
+			? await Promise.all(initialisedUploads.map(([index]) => compressUploadedImage(uploadId, index)))
+			: []
+
+		for (const [key, [index, uploadedFile]] of initialisedUploads.entries()) {
+			const compressed = compressedFiles[key] ?? null
 			dismissCompressImage(uploadedFile.temporaryMessage.referenceId)
 
 			// Store the previously created temporary message
@@ -525,9 +530,9 @@ export const useUploadStore = defineStore('upload', () => {
 			uploads[uploadId].files[index].temporaryMessage = message
 			// Add temporary messages (files) to the messages list
 			vuexStore.dispatch('addTemporaryMessage', { token, message })
-			// Scroll the message list
-			EventBus.emit('scroll-chat-to-bottom', { smooth: true, force: true })
 		}
+		// Scroll the message list
+		EventBus.emit('scroll-chat-to-bottom', { smooth: true, force: true })
 
 		// With the conversation-subfolders feature enabled,
 		// stage uploads inside the backend-provided Draft folder and
diff --git a/src/utils/combineFileMessages.ts b/src/utils/combineFileMessages.ts
index bbe2ed48c88..1d47331a42d 100644
--- a/src/utils/combineFileMessages.ts
+++ b/src/utils/combineFileMessages.ts
@@ -6,7 +6,7 @@
 import type { ChatMessage } from '../types/index.ts'
 
 import { MESSAGE } from '../constants.ts'
-import { getFileKeys, hasOnlyFilePlaceholders, isTemporaryId } from './message.ts'
+import { getFileKeys, hasOnlyFilePlaceholders } from './message.ts'
 
 export type CombinedFileMessage = ChatMessage & {
 	/** Ids of all messages combined into this one, in chronological order */
@@ -25,9 +25,9 @@ function isCombinableFileMessage(message: ChatMessage): boolean {
 	}
 
 	// TODO threads?
-	// TODO unified uploader?
-	// Temporary messages, which are not sent yet (or failed to be sent), are shown separately
-	if (isTemporaryId(message.id) || (message as ChatMessage & { sendingFailure?: string }).sendingFailure) {
+	// Messages that failed to send are shown separately, not combined into a group
+	// (sendingFailure is only ever set on temporary messages).
+	if ((message as ChatMessage & { sendingFailure?: string }).sendingFailure) {
 		return false
 	}
 
@@ -82,7 +82,10 @@ function canBeCombinedWith(message1: ChatMessage, message2: ChatMessage): boolea
  * Create a single message out of several file shares.
  * The combined message is based on the last message of the group, so that the timestamp,
  * the reading state, the reactions and the message actions refer to an existing message
- * (reactions of the other messages of the group are not shown)
+ * (reactions of the other messages of the group are not shown).
+ * If any of the combined ids is still temporary, the combined message is treated as
+ * temporary too (see isTemporaryMessage) and its actions stay disabled until every
+ * file in the group has been sent.
  *
  * @param messages array of grouped file share messages, in chronological order
  */
diff --git a/src/utils/message.ts b/src/utils/message.ts
index 9dff3db5915..664676bad07 100644
--- a/src/utils/message.ts
+++ b/src/utils/message.ts
@@ -245,6 +245,22 @@ export function isTemporaryId(id: ChatMessage['id'] | string): boolean {
 	return id.toString().startsWith('temp-')
 }
 
+/**
+ * Returns whether the given message is not sent yet. A combined file share's own id is
+ * taken from whichever message is currently last in the group, so it can already be a
+ * confirmed (non-temporary) id even while other files of the same group are still in
+ * flight. combinedMessageIds is checked instead, so any still-temporary file in the
+ * group is caught.
+ *
+ * @param message Chat message
+ */
+export function isTemporaryMessage(message: ChatMessage): boolean {
+	const combinedMessageIds = (message as ChatMessage & { combinedMessageIds?: ChatMessage['id'][] }).combinedMessageIds
+	return combinedMessageIds
+		? combinedMessageIds.some(isTemporaryId)
+		: isTemporaryId(message.id)
+}
+
 /**
  * Returns whether the given system message should be hidden in the UI
  *