diff --git a/messages/en.json b/messages/en.json
index de1c67d..92c73e9 100644
--- a/messages/en.json
+++ b/messages/en.json
@@ -44,7 +44,7 @@
 			"partial_support": "This format can only be converted as {direction}.",
 			"direction_input": "input (from)",
 			"direction_output": "output (to)",
-			"video_server_processing": "Video uploads to a server for processing by default, learn how to set it up locally here."
+			"video_server_processing": "When possible, VERT converts videos locally in your browser. Some conversions may require server-side processing, learn how to set it up locally here."
 		}
 	},
 	"convert": {
@@ -62,9 +62,10 @@
 		"large_file_warning": "Due to browser / device limitations, video to audio conversion is disabled for this file as it is larger than {limit}GB. We recommend using Firefox or Safari for files of this size since they have less limitations.",
 		"external_warning": {
 			"title": "External server warning",
-			"text": "If you choose to convert into a video format, those files will be uploaded to an external server to be converted. Do you want to continue?",
-			"yes": "Yes",
-			"no": "No"
+			"text": "Converting {filename} with its current settings is not supported locally and requires server-side processing. Do you want to continue?",
+			"yes": "Convert on server",
+			"no": "Cancel conversion",
+			"dont_show_again": "Don't show again"
 		},
 		"panel": {
 			"convert_all": "Convert all",
@@ -149,6 +150,7 @@
 		"errors": {
 			"cant_convert": "We can't convert this file.",
 			"converter_fallback": {
+				"title": "Change converter?",
 				"body": "Conversion failed for {filename}. Would you like to try the next compatible converter {converter}?",
 				"yes": "Next converter",
 				"no": "Cancel conversion",
diff --git a/src/lib/components/functional/popups/FallbackToast.svelte b/src/lib/components/functional/popups/FallbackToast.svelte
index 3f27151..a96afcc 100644
--- a/src/lib/components/functional/popups/FallbackToast.svelte
+++ b/src/lib/components/functional/popups/FallbackToast.svelte
@@ -2,7 +2,7 @@
 	import { m } from "$lib/paraglide/messages";
 
 	type Additional = {
-		fileName: string;
+		filename: string;
 		nextConverter: string;
 		onNext: () => void | Promise<void>;
 		onCancel: () => void;
@@ -10,13 +10,13 @@
 
 	let { additional }: { additional: Additional } = $props();
 
-	export const title = "An error occurred";
+	export const title = m["convert.errors.converter_fallback.title"]();
 </script>
 
 <div class="flex flex-col gap-4">
 	<p class="text-black">
 		{m["convert.errors.converter_fallback.body"]({
-			filename: additional.fileName,
+			filename: additional.filename,
 			converter: additional.nextConverter,
 		})}
 	</p>
diff --git a/src/lib/components/functional/popups/ServerUploadWarning.svelte b/src/lib/components/functional/popups/ServerUploadWarning.svelte
new file mode 100644
index 0000000..86957a4
--- /dev/null
+++ b/src/lib/components/functional/popups/ServerUploadWarning.svelte
@@ -0,0 +1,47 @@
+<script lang="ts" module>
+	export interface ServerUploadWarningProps {
+		filename: string;
+		onProceed: () => void;
+		onCancel: () => void;
+		onDontShowAgain: () => void;
+	}
+</script>
+
+<script lang="ts">
+	import { m } from "$lib/paraglide/messages";
+	import type { ToastProps } from "$lib/util/toast.svelte";
+
+	const toast: ToastProps<ServerUploadWarningProps> = $props();
+
+	export const title = m["convert.external_warning.title"]();
+</script>
+
+<div class="flex flex-col gap-4">
+	<p class="text-black">
+		{m["convert.external_warning.text"]({
+            filename: toast.additional.filename,
+        })}
+	</p>
+	<div class="flex flex-col gap-2">
+		<button
+			onclick={toast.additional.onDontShowAgain}
+			class="btn rounded-lg h-fit py-2 w-full bg-accent-blue text-black"
+		>
+			{m["convert.external_warning.dont_show_again"]()}
+		</button>
+		<div class="flex gap-4">
+			<button
+				onclick={toast.additional.onProceed}
+				class="btn rounded-lg h-fit py-2 w-full bg-accent-red-alt text-white"
+			>
+				{m["convert.external_warning.yes"]()}
+			</button>
+			<button
+				onclick={toast.additional.onCancel}
+				class="btn rounded-lg h-fit py-2 w-full"
+			>
+				{m["convert.external_warning.no"]()}
+			</button>
+		</div>
+	</div>
+</div>
diff --git a/src/lib/components/functional/popups/VertdError.svelte b/src/lib/components/functional/popups/VertdError.svelte
index 43733fe..f1e4003 100644
--- a/src/lib/components/functional/popups/VertdError.svelte
+++ b/src/lib/components/functional/popups/VertdError.svelte
@@ -5,7 +5,7 @@
 		from?: string;
 		to?: string;
 		errorMessage?: string;
-		fileName?: string;
+		filename?: string;
 	}
 </script>
 
@@ -21,7 +21,7 @@
 
 	let submitting = $state(false);
 
-	export const title = "An error occurred";
+	export const title = m["convert.errors.vertd_generic_title"]();
 
 	const remove = () => {
 		ToastManager.remove(toast.id);
diff --git a/src/lib/components/visual/Tooltip.svelte b/src/lib/components/visual/Tooltip.svelte
index 3ca218f..493569a 100644
--- a/src/lib/components/visual/Tooltip.svelte
+++ b/src/lib/components/visual/Tooltip.svelte
@@ -112,8 +112,8 @@
 <style lang="postcss">
 	.tooltip {
 		--border-size: 1px;
-		@apply fixed bg-panel-alt text-foreground border border-stone-400 dynadark:border-white drop-shadow-lg text-xs rounded-full pointer-events-none z-[999] max-w-xs break-words whitespace-normal;
-		@apply px-5 py-2.5;
+		@apply fixed bg-panel-alt text-foreground border border-stone-400 dynadark:border-white drop-shadow-lg text-xs pointer-events-none z-[999] max-w-[200px] break-words whitespace-normal;
+		@apply px-3.5 py-2 rounded-xl;
 	}
 
 	.tooltip-top {
diff --git a/src/lib/store/index.svelte.ts b/src/lib/store/index.svelte.ts
index b1aa096..b0b438e 100644
--- a/src/lib/store/index.svelte.ts
+++ b/src/lib/store/index.svelte.ts
@@ -4,7 +4,6 @@ import { error, log } from "$lib/util/logger";
 import { VertFile } from "$lib/types";
 import { parseBlob, selectCover } from "music-metadata";
 import { writable } from "svelte/store";
-import { addDialog } from "./DialogProvider";
 import PQueue from "p-queue";
 import { getLocale, setLocale } from "$lib/paraglide/runtime";
 import { m } from "$lib/paraglide/messages";
@@ -236,7 +235,6 @@ class Files {
 		}
 	}
 
-	private _warningShown = false;
 	private async _add(file: VertFile | File) {
 		if (file instanceof VertFile) {
 			this.files.push(file);
@@ -302,43 +300,6 @@ class Files {
 					},
 				});
 			}
-
-			// TODO: only show if vertd is needed/requested
-			const isServerVideo = convName === "vertd";
-			const acceptedExternalWarning =
-				localStorage.getItem("acceptedExternalWarning") === "true";
-			if (isServerVideo && !acceptedExternalWarning && !this._warningShown) {
-				this._warningShown = true;
-				const title = m["convert.external_warning.title"]();
-				const message = m["convert.external_warning.text"]();
-				const buttons = [
-					{
-						text: m["convert.external_warning.no"](),
-						action: () => {
-							this.files = [
-								...this.files.filter(
-									(f) =>
-										!f.converters
-											.map((c) => c.name)
-											.includes("vertd"),
-								),
-							];
-							this._warningShown = false;
-						},
-					},
-					{
-						text: m["convert.external_warning.yes"](),
-						action: () => {
-							localStorage.setItem(
-								"acceptedExternalWarning",
-								"true",
-							);
-							this._warningShown = false;
-						},
-					},
-				];
-				addDialog(title, message, buttons, "warning");
-			}
 		}
 	}
 
@@ -378,7 +339,7 @@ class Files {
 		if (this.files.length === 0) return;
 		// eslint-disable-next-line @typescript-eslint/no-explicit-any
 		const dlFiles: any[] = [];
-		const fileNames: string[] = [];
+		const filenames: string[] = [];
 
 		for (let i = 0; i < this.files.length; i++) {
 			const file = this.files[i];
@@ -392,7 +353,7 @@ class Files {
 			let to = result.to;
 			if (!to.startsWith(".")) to = `.${to}`;
 
-			fileNames.push(file.file.name.replace(/\.[^/.]+$/, "") + to);
+			filenames.push(file.file.name.replace(/\.[^/.]+$/, "") + to);
 		}
 
 		for (let i = 0; i < this.files.length; i++) {
@@ -401,19 +362,19 @@ class Files {
 
 			if (!result) continue;
 
-			let fileName = fileNames[i];
+			let filename = filenames[i];
 			
 			// check if this filename appears more than once
-			const isDuplicate = fileNames.filter((name) => name === fileName).length > 1;
+			const isDuplicate = filenames.filter((name) => name === filename).length > 1;
 			if (isDuplicate) {
-				const nameParts = fileName.lastIndexOf(".");
-				const nameWithoutExt = fileName.substring(0, nameParts);
-				const ext = fileName.substring(nameParts);
-				fileName = `${nameWithoutExt} (${i + 1})${ext}`;
+				const nameParts = filename.lastIndexOf(".");
+				const nameWithoutExt = filename.substring(0, nameParts);
+				const ext = filename.substring(nameParts);
+				filename = `${nameWithoutExt} (${i + 1})${ext}`;
 			}
 
 			dlFiles.push({
-				name: fileName,
+				name: filename,
 				lastModified: Date.now(),
 				input: await result.file.arrayBuffer(),
 			});
diff --git a/src/lib/types/file.svelte.ts b/src/lib/types/file.svelte.ts
index b767033..eccbf5e 100644
--- a/src/lib/types/file.svelte.ts
+++ b/src/lib/types/file.svelte.ts
@@ -5,6 +5,7 @@ import { ToastManager } from "$lib/util/toast.svelte";
 import type { Component } from "svelte";
 import { MAX_ARRAY_BUFFER_SIZE } from "$lib/store/index.svelte";
 import FallbackToast from "$lib/components/functional/popups/FallbackToast.svelte";
+import ServerUploadWarning from "$lib/components/functional/popups/ServerUploadWarning.svelte";
 import type {
 	ConversionSettings,
 	SettingDefinition,
@@ -41,6 +42,7 @@ export class VertFile {
 	private fallbackToastId: number | null = null;
 	private attemptedConverters = new Set<string>();
 	private retryingFallback = false;
+	private vertdWarningToastId: number | null = null;
 
 	public isZip = $state(() => this.from === ".zip");
 
@@ -168,6 +170,13 @@ export class VertFile {
 		}
 
 		if (!converter) throw new Error("No converter found");
+
+		const canProceed = await this.confirmServerWarning(converter);
+		if (!canProceed) {
+			this.cancelled = true;
+			return;
+		}
+
 		this.attemptedConverters.add(converter.name);
 		log(["file", "convert"], `using converter: ${converter.name}`);
 
@@ -215,7 +224,7 @@ export class VertFile {
 					disappearing: false,
 					message: FallbackToast,
 					additional: {
-						fileName: this.file.name,
+						filename: this.file.name,
 						nextConverter: nextConverter.name,
 						onNext: async () => {
 							if (this.fallbackToastId !== null)
@@ -262,6 +271,47 @@ export class VertFile {
 		return res;
 	}
 
+	private async confirmServerWarning(converter: Converter): Promise<boolean> {
+		if (converter.name !== "vertd") return true;
+		if (localStorage.getItem("acceptedExternalWarning") === "true")
+			return true;
+
+		return new Promise((resolve) => {
+			let resolved = false;
+
+			const finish = (shouldProceed: boolean) => {
+				if (resolved) return;
+				resolved = true;
+				if (this.vertdWarningToastId !== null)
+					ToastManager.remove(this.vertdWarningToastId);
+				this.vertdWarningToastId = null;
+				resolve(shouldProceed);
+			};
+
+			if (this.vertdWarningToastId !== null)
+				ToastManager.remove(this.vertdWarningToastId);
+
+			this.vertdWarningToastId = ToastManager.add({
+				type: "warning",
+				disappearing: false,
+				message: ServerUploadWarning,
+				additional: {
+					filename: this.file.name,
+					onProceed: () => {
+						finish(true);
+					},
+					onCancel: () => {
+						finish(false);
+					},
+					onDontShowAgain: () => {
+						localStorage.setItem("acceptedExternalWarning", "true");
+						finish(true);
+					},
+				},
+			});
+		});
+	}
+
 	private async convertZip(converter: Converter): Promise<VertFile> {
 		const { extractZip, createZip } = await import("$lib/util/zip");
 		const { default: PQueue } = await import("p-queue");