diff --git a/apps/svelte.dev/src/routes/(authed)/playground/[id]/+page.svelte b/apps/svelte.dev/src/routes/(authed)/playground/[id]/+page.svelte
index 7976235f1b..00579ed7a0 100644
--- a/apps/svelte.dev/src/routes/(authed)/playground/[id]/+page.svelte
+++ b/apps/svelte.dev/src/routes/(authed)/playground/[id]/+page.svelte
@@ -72,7 +72,8 @@
 		if (!hash && !saved) {
 			repl?.set({
 				// TODO make this munging unnecessary (using JSON instead of structuredClone for better browser compat)
-				files: JSON.parse(JSON.stringify(data.gist.components)).map(munge)
+				files: JSON.parse(JSON.stringify(data.gist.components)).map(munge),
+				tailwind: false // TODO
 			});
 
 			modified = false;
@@ -92,7 +93,7 @@
 				name = recovered.name;
 			}
 
-			repl.set({ files });
+			repl.set({ files, tailwind: recovered.tailwind ?? false });
 		} catch {
 			alert(`Couldn't load the code from the URL. Make sure you copied the link correctly.`);
 		}
@@ -155,7 +156,8 @@
 	async function update_hash() {
 		// Only change hash when necessary to avoid polluting everyone's browser history
 		if (modified) {
-			const json = JSON.stringify({ name, files: repl.toJSON().files });
+			const { files, tailwind } = repl.toJSON();
+			const json = JSON.stringify({ name, files, tailwind });
 			await set_hash(json);
 		}
 	}
@@ -210,7 +212,8 @@
 		if (modified) {
 			// we can't save to the hash because it's an async operation, so we use
 			// a short-lived sessionStorage value instead
-			const json = JSON.stringify({ name, files: repl.toJSON().files });
+			const { files, tailwind } = repl.toJSON();
+			const json = JSON.stringify({ name, files, tailwind });
 			sessionStorage.setItem(STORAGE_KEY, json);
 		}
 	}}
diff --git a/apps/svelte.dev/src/routes/(authed)/playground/[id]/embed/+page.svelte b/apps/svelte.dev/src/routes/(authed)/playground/[id]/embed/+page.svelte
index 6db54545e2..ab843d9ad3 100644
--- a/apps/svelte.dev/src/routes/(authed)/playground/[id]/embed/+page.svelte
+++ b/apps/svelte.dev/src/routes/(authed)/playground/[id]/embed/+page.svelte
@@ -45,7 +45,8 @@
 
 		if (!hash) {
 			repl?.set({
-				files: data.gist.components.map(munge)
+				files: data.gist.components.map(munge),
+				tailwind: false // TODO
 			});
 
 			return;
@@ -53,7 +54,7 @@
 
 		try {
 			const recovered = JSON.parse(await decode_and_decompress_text(hash));
-			repl.set({ files: recovered.files });
+			repl.set({ files: recovered.files, tailwind: recovered.tailwind ?? false });
 		} catch {
 			alert(`Couldn't load the code from the URL. Make sure you copied the link correctly.`);
 		}
diff --git a/packages/editor/src/lib/Workspace.svelte.ts b/packages/editor/src/lib/Workspace.svelte.ts
index e8ec12d208..a4ec178e02 100644
--- a/packages/editor/src/lib/Workspace.svelte.ts
+++ b/packages/editor/src/lib/Workspace.svelte.ts
@@ -393,12 +393,14 @@ export class Workspace {
 		this.#onreset?.(this.#files);
 	}
 
-	reset(new_files: Item[], selected?: string) {
+	reset(new_files: Item[], options: { tailwind: boolean }, selected?: string) {
 		this.states.clear();
 		this.set(new_files, selected);
 
 		this.mark_saved();
 
+		this.#tailwind = options.tailwind;
+
 		this.#onreset(new_files);
 		this.#reset_diagnostics();
 	}
@@ -471,7 +473,7 @@ export class Workspace {
 
 	set tailwind(value) {
 		this.#tailwind = value;
-		this.#onreset(this.#files);
+		this.#onupdate(this.#current);
 	}
 
 	get vim() {
diff --git a/packages/repl/src/lib/Repl.svelte b/packages/repl/src/lib/Repl.svelte
index 0e023d797b..85bd3f520b 100644
--- a/packages/repl/src/lib/Repl.svelte
+++ b/packages/repl/src/lib/Repl.svelte
@@ -67,13 +67,14 @@
 	export function toJSON() {
 		return {
 			imports: $bundle?.imports ?? [],
-			files: workspace.files
+			files: workspace.files,
+			tailwind: workspace.tailwind
 		};
 	}
 
 	// TODO get rid
-	export async function set(data: { files: File[]; css?: string }) {
-		workspace.reset(data.files, 'App.svelte');
+	export async function set(data: { files: File[]; tailwind?: boolean }) {
+		workspace.reset(data.files, { tailwind: data.tailwind ?? false }, 'App.svelte');
 	}
 
 	// TODO get rid