diff --git a/client/components/LinkPreview.vue b/client/components/LinkPreview.vue
index 9a124ab8..89072e08 100644
--- a/client/components/LinkPreview.vue
+++ b/client/components/LinkPreview.vue
@@ -8,7 +8,11 @@
 	>
 		<div
 			ref="content"
-			:class="['toggle-content', 'toggle-type-' + link.type, {opened: isContentShown}]"
+			:class="[
+				'toggle-content',
+				'toggle-type-' + link.type,
+				{opened: isContentShown, 'with-filename': link.filename},
+			]"
 		>
 			<template v-if="link.type === 'link'">
 				<a
@@ -64,13 +68,20 @@
 			<template v-else-if="link.type === 'image'">
 				<a
 					:href="link.link"
-					class="toggle-thumbnail"
+					:title="link.filename"
+					:class="['toggle-thumbnail', {'wide-view': useWideImageView}]"
 					target="_blank"
 					rel="noopener"
 					@click="onThumbnailClick"
 				>
+					<div v-if="link.filename" class="image-filename">
+						<span class="inner-image-filename">
+							{{ link.filename }}
+						</span>
+					</div>
 					<img
 						v-show="link.sourceLoaded"
+						ref="image"
 						:src="link.thumb"
 						decoding="async"
 						alt=""
@@ -79,6 +90,7 @@
 				</a>
 			</template>
 			<template v-else-if="link.type === 'video'">
+				<span v-if="link.filename" class="video-filename">{{ link.filename }}</span>
 				<video
 					v-show="link.sourceLoaded"
 					preload="metadata"
@@ -89,14 +101,28 @@
 				</video>
 			</template>
 			<template v-else-if="link.type === 'audio'">
-				<audio
-					v-show="link.sourceLoaded"
-					controls
-					preload="metadata"
-					@canplay="onPreviewReady"
-				>
-					<source :src="link.media" :type="link.mediaType" />
-				</audio>
+				<div>
+					<a
+						v-if="link.filename"
+						:href="link.link"
+						:title="link.filename"
+						target="_blank"
+						rel="noopener"
+						class="audio-filename"
+					>
+						<span class="inner-audio-filename">
+							{{ link.filename }}
+						</span>
+					</a>
+					<audio
+						v-show="link.sourceLoaded"
+						controls
+						preload="metadata"
+						@canplay="onPreviewReady"
+					>
+						<source :src="link.media" :type="link.mediaType" />
+					</audio>
+				</div>
 			</template>
 			<template v-else-if="link.type === 'error'">
 				<em v-if="link.error === 'image-too-big'">
@@ -167,7 +193,9 @@ export default defineComponent({
 
 		const showMoreButton = ref(false);
 		const isContentShown = ref(false);
+		const useWideImageView = ref(false);
 		const imageViewer = inject(imageViewerKey);
+		const image = ref(null);
 
 		onBeforeRouteUpdate((to, from, next) => {
 			// cancel the navigation if the user is trying to close the image viewer
@@ -217,6 +245,20 @@ export default defineComponent({
 			}
 		};
 
+		const updateWideImageViewDecision = () => {
+			if (window.innerWidth < 480) {
+				// Mobile
+				useWideImageView.value =
+					(image.value && image.value.naturalWidth / image.value.naturalHeight <= 1.34) ||
+					false; // aspect ratio around 4:3 and slimmer
+			} else {
+				// Desktop
+				useWideImageView.value =
+					(image.value && image.value.naturalWidth / image.value.naturalHeight <= 1.6) ||
+					false; // aspect ratio 16:10 and slimmer
+			}
+		};
+
 		const onPreviewUpdate = () => {
 			// Don't display previews while they are loading on the server
 			if (props.link.type === "loading") {
@@ -233,6 +275,8 @@ export default defineComponent({
 				handleResize();
 				props.keepScrollPosition();
 			}
+
+			updateWideImageViewDecision();
 		};
 
 		const onThumbnailError = () => {
@@ -321,8 +365,11 @@ export default defineComponent({
 			onPreviewUpdate,
 			showMoreButton,
 			isContentShown,
+			useWideImageView,
+			image,
 			content,
 			container,
+			updateWideImageViewDecision,
 		};
 	},
 });
diff --git a/client/css/style.css b/client/css/style.css
index 0285ef5a..a0cc98be 100644
--- a/client/css/style.css
+++ b/client/css/style.css
@@ -1624,6 +1624,24 @@ textarea.input {
 	white-space: normal;
 }
 
+#chat .toggle-content .wide-view {
+	display: flex;
+	flex-direction: row;
+}
+
+#chat .toggle-content .wide-view .image-filename {
+	order: 2;
+}
+
+#chat .toggle-content .wide-view .image-filename span {
+	width: auto;
+	max-width: 500px;
+}
+
+#chat .toggle-content .wide-view img {
+	order: 1;
+}
+
 /* This applies to images of preview-type-image and thumbnails of preview-type-link */
 #chat .toggle-content img {
 	max-width: 100%;
@@ -1718,8 +1736,50 @@ textarea.input {
 	max-width: 100%;
 }
 
+#chat .toggle-type-image > a {
+	position: relative;
+	font-weight: 700;
+	color: inherit;
+}
+
+#chat .toggle-type-image.with-filename .image-filename {
+	padding: 8px 10px 10px;
+	display: flex;
+}
+
+#chat .toggle-type-image .inner-image-filename,
+#chat .toggle-type-audio .inner-audio-filename {
+	width: 0;
+	flex-grow: 1;
+}
+
+#chat .toggle-content.toggle-type-audio.with-filename {
+	padding: 8px 10px 10px;
+}
+
+#chat .toggle-content.toggle-type-audio .audio-filename {
+	font-weight: 700;
+	padding-bottom: 10px;
+	color: inherit;
+	display: flex;
+}
+
+#chat .toggle-type-audio .head {
+	padding-bottom: 10px;
+}
+
 #chat .toggle-type-video {
 	max-width: 640px;
+	position: relative;
+}
+
+#chat .toggle-type-video .video-filename {
+	position: absolute;
+	top: 0;
+	width: 100%;
+	padding: 1em;
+	background: linear-gradient(black, transparent);
+	color: white;
 }
 
 #chat video {
diff --git a/server/plugins/irc-events/link.ts b/server/plugins/irc-events/link.ts
index 63a86dc0..a6277025 100644
--- a/server/plugins/irc-events/link.ts
+++ b/server/plugins/irc-events/link.ts
@@ -10,11 +10,14 @@ import storage from "../storage";
 import Client from "../../client";
 import Chan from "../../models/chan";
 import Msg from "../../models/msg";
+import contentDisposition from "content-disposition";
+import path from "path";
 
 type FetchRequest = {
 	data: Buffer;
 	type: string;
 	size: number;
+	filename: string | null;
 };
 const currentFetchPromises = new Map<string, Promise<FetchRequest>>();
 const imageTypeRegex = /^image\/.+/;
@@ -30,6 +33,7 @@ export type LinkPreview = {
 	shown?: boolean | null;
 	error?: string;
 	message?: string;
+	filename: string | null;
 
 	media?: string;
 	mediaType?: string;
@@ -68,6 +72,7 @@ export default function (client: Client, chan: Chan, msg: Msg, cleanText: string
 			size: -1,
 			link: link.link, // Send original matched link to the client
 			shown: null,
+			filename: null,
 		};
 
 		cleanLinks.push(preview);
@@ -243,6 +248,7 @@ function parse(msg: Msg, chan: Chan, preview: LinkPreview, res: FetchRequest, cl
 	let promise: Promise<FetchRequest | null> | null = null;
 
 	preview.size = res.size;
+	preview.filename = res.filename;
 
 	switch (res.type) {
 		case "text/html":
@@ -431,6 +437,7 @@ function fetch(uri: string, headers: Record<string, string>) {
 		let contentLength = 0;
 		let contentType: string | undefined;
 		let limit = Config.values.prefetchMaxImageSize * 1024;
+		let filename: string | null = null;
 
 		try {
 			const gotStream = got.stream(uri, {
@@ -445,6 +452,17 @@ function fetch(uri: string, headers: Record<string, string>) {
 					contentLength = parseInt(res.headers["content-length"], 10) || 0;
 					contentType = res.headers["content-type"];
 
+					filename =
+						"content-disposition" in res.headers
+							? contentDisposition?.parse(res.headers["content-disposition"])
+									.parameters.filename || null
+							: null;
+
+					if (filename === null) {
+						const basename = decodeURI(path.basename(new URL(uri).pathname));
+						filename = basename.indexOf(".") > 0 ? basename : null;
+					}
+
 					if (contentType && imageTypeRegex.test(contentType)) {
 						// response is an image
 						// if Content-Length header reports a size exceeding the prefetch limit, abort fetch
@@ -488,7 +506,7 @@ function fetch(uri: string, headers: Record<string, string>) {
 						type = contentType.split(/ *; */).shift() || "";
 					}
 
-					resolve({data: buffer, type, size});
+					resolve({data: buffer, type, size, filename});
 				});
 		} catch (e: any) {
 			return reject(e);
diff --git a/server/plugins/uploader.ts b/server/plugins/uploader.ts
index 0a5e53a8..04fe659c 100644
--- a/server/plugins/uploader.ts
+++ b/server/plugins/uploader.ts
@@ -20,6 +20,7 @@ const inlineContentDispositionTypes = {
 	"audio/mpeg": "audio.mp3",
 	"audio/ogg": "audio.ogg",
 	"audio/vnd.wave": "audio.wav",
+	"audio/flac": "audio.flac",
 	"audio/x-flac": "audio.flac",
 	"audio/x-m4a": "audio.m4a",
 	"image/bmp": "image.bmp",
@@ -124,6 +125,12 @@ class Uploader {
 			detectedMimeType = "video/mp4";
 		}
 
+		if (detectedMimeType === "audio/x-flac") {
+			// Send a more common mime type for wave audio files
+			// so that browsers can play them correctly
+			detectedMimeType = "audio/flac";
+		}
+
 		res.setHeader("Content-Disposition", disposition);
 		res.setHeader("Cache-Control", "max-age=86400");
 		res.contentType(detectedMimeType);
diff --git a/test/plugins/link.ts b/test/plugins/link.ts
index 26f6070d..1b15cb7a 100644
--- a/test/plugins/link.ts
+++ b/test/plugins/link.ts
@@ -56,6 +56,7 @@ Vivamus bibendum vulputate tincidunt. Sed vitae ligula felis.`;
 		expect(message.previews).to.deep.equal([
 			{
 				body: "",
+				filename: null,
 				head: "",
 				link: url,
 				thumb: "",
@@ -93,6 +94,7 @@ Vivamus bibendum vulputate tincidunt. Sed vitae ligula felis.`;
 		expect(message.previews).to.deep.equal([
 			{
 				body: "",
+				filename: null,
 				head: "",
 				link: url,
 				thumb: "",
@@ -425,6 +427,7 @@ Vivamus bibendum vulputate tincidunt. Sed vitae ligula felis.`;
 		expect(message.previews).to.eql([
 			{
 				body: "",
+				filename: null,
 				head: "",
 				link: url_one,
 				thumb: "",
@@ -434,6 +437,7 @@ Vivamus bibendum vulputate tincidunt. Sed vitae ligula felis.`;
 			},
 			{
 				body: "",
+				filename: null,
 				head: "",
 				link: url_two,
 				thumb: "",
@@ -608,6 +612,7 @@ Vivamus bibendum vulputate tincidunt. Sed vitae ligula felis.`;
 		expect(message.previews).to.deep.equal([
 			{
 				type: "loading",
+				filename: null,
 				head: "",
 				body: "",
 				thumb: "",