diff --git a/.changeset/big-chefs-return.md b/.changeset/big-chefs-return.md
new file mode 100644
index 000000000..d7b2e0d30
--- /dev/null
+++ b/.changeset/big-chefs-return.md
@@ -0,0 +1,5 @@
+---
+'sv': patch
+---
+
+fix: insert the `tailwindcss` vite plugin at the start of the plugin array
diff --git a/packages/addons/tailwindcss/index.ts b/packages/addons/tailwindcss/index.ts
index 18fe640ba..f003ceb42 100644
--- a/packages/addons/tailwindcss/index.ts
+++ b/packages/addons/tailwindcss/index.ts
@@ -67,7 +67,7 @@ export default defineAddon({
 
 			const pluginsArray = object.property(param1, 'plugins', array.createEmpty());
 			const pluginFunctionCall = functions.call(vitePluginName, []);
-			array.push(pluginsArray, pluginFunctionCall);
+			array.unshift(pluginsArray, pluginFunctionCall);
 
 			return generateCode();
 		});
diff --git a/packages/core/tests/js/arrays/object-array/output.ts b/packages/core/tests/js/arrays/push-object-array/output.ts
similarity index 100%
rename from packages/core/tests/js/arrays/object-array/output.ts
rename to packages/core/tests/js/arrays/push-object-array/output.ts
diff --git a/packages/core/tests/js/arrays/object-array/run.ts b/packages/core/tests/js/arrays/push-object-array/run.ts
similarity index 100%
rename from packages/core/tests/js/arrays/object-array/run.ts
rename to packages/core/tests/js/arrays/push-object-array/run.ts
diff --git a/packages/core/tests/js/arrays/string-array/output.ts b/packages/core/tests/js/arrays/push-string-array/output.ts
similarity index 100%
rename from packages/core/tests/js/arrays/string-array/output.ts
rename to packages/core/tests/js/arrays/push-string-array/output.ts
diff --git a/packages/core/tests/js/arrays/string-array/run.ts b/packages/core/tests/js/arrays/push-string-array/run.ts
similarity index 100%
rename from packages/core/tests/js/arrays/string-array/run.ts
rename to packages/core/tests/js/arrays/push-string-array/run.ts
diff --git a/packages/core/tests/js/arrays/unshift-object-array/output.ts b/packages/core/tests/js/arrays/unshift-object-array/output.ts
new file mode 100644
index 000000000..53443163d
--- /dev/null
+++ b/packages/core/tests/js/arrays/unshift-object-array/output.ts
@@ -0,0 +1,8 @@
+const array = [
+	{
+		test2: 'string'
+	},
+	{
+		test: true
+	}
+];
diff --git a/packages/core/tests/js/arrays/unshift-object-array/run.ts b/packages/core/tests/js/arrays/unshift-object-array/run.ts
new file mode 100644
index 000000000..e38203768
--- /dev/null
+++ b/packages/core/tests/js/arrays/unshift-object-array/run.ts
@@ -0,0 +1,16 @@
+import { array, object, common, variables } from '@sveltejs/cli-core/js';
+import type { ScriptFileEditor } from '@sveltejs/cli-core';
+
+export function run({ ast }: ScriptFileEditor<any>): void {
+	const array1 = array.createEmpty();
+
+	const object1 = object.create({ test: common.expressionFromString('true') });
+	const object2 = object.create({ test2: common.createLiteral('string') });
+	array.unshift(array1, object1);
+	array.unshift(array1, object2);
+	array.unshift(array1, object2); // avoid duplication
+
+	// create declaration so that we serialize everything
+	const declaration = variables.declaration(ast, 'const', 'array', array1);
+	ast.body.push(declaration);
+}
diff --git a/packages/core/tests/js/arrays/unshift-string-array/output.ts b/packages/core/tests/js/arrays/unshift-string-array/output.ts
new file mode 100644
index 000000000..0244d4843
--- /dev/null
+++ b/packages/core/tests/js/arrays/unshift-string-array/output.ts
@@ -0,0 +1 @@
+const array = ['test2', 'test'];
diff --git a/packages/core/tests/js/arrays/unshift-string-array/run.ts b/packages/core/tests/js/arrays/unshift-string-array/run.ts
new file mode 100644
index 000000000..c8282f26f
--- /dev/null
+++ b/packages/core/tests/js/arrays/unshift-string-array/run.ts
@@ -0,0 +1,13 @@
+import { array, variables } from '@sveltejs/cli-core/js';
+import type { ScriptFileEditor } from '@sveltejs/cli-core';
+
+export function run({ ast }: ScriptFileEditor<any>): void {
+	const array1 = array.createEmpty();
+	array.unshift(array1, 'test');
+	array.unshift(array1, 'test2');
+	array.unshift(array1, 'test'); // make sure items are not duplicated
+
+	// create declaration so that we serialize everything
+	const declaration = variables.declaration(ast, 'const', 'array', array1);
+	ast.body.push(declaration);
+}
diff --git a/packages/core/tooling/js/array.ts b/packages/core/tooling/js/array.ts
index 7b43cd916..947c76f9a 100644
--- a/packages/core/tooling/js/array.ts
+++ b/packages/core/tooling/js/array.ts
@@ -13,30 +13,36 @@ export function push(
 	ast: AstTypes.ArrayExpression,
 	data: string | AstKinds.ExpressionKind | AstKinds.SpreadElementKind
 ): void {
-	if (typeof data === 'string') {
-		const existingLiterals = ast.elements.filter(
-			(x): x is AstTypes.StringLiteral => x?.type == 'StringLiteral'
-		);
-		let literal = existingLiterals.find((x) => x.value == data);
+	insertElement(ast, data, true);
+}
+export function unshift(
+	ast: AstTypes.ArrayExpression,
+	data: string | AstKinds.ExpressionKind | AstKinds.SpreadElementKind
+): void {
+	insertElement(ast, data, false);
+}
 
+function insertElement(
+	ast: AstTypes.ArrayExpression,
+	data: string | AstKinds.ExpressionKind | AstKinds.SpreadElementKind,
+	insertEnd: boolean
+): void {
+	if (typeof data === 'string') {
+		const existingLiterals = ast.elements.filter((x) => x?.type === 'StringLiteral');
+		let literal = existingLiterals.find((x) => x.value === data);
 		if (!literal) {
-			literal = {
-				type: 'StringLiteral',
-				value: data
-			};
-			ast.elements.push(literal);
+			literal = { type: 'StringLiteral', value: data };
+
+			if (insertEnd) ast.elements.push(literal);
+			else ast.elements.unshift(literal);
 		}
 	} else {
-		let anyNodeEquals = false;
 		const elements = ast.elements as AstTypes.ASTNode[];
-		for (const node of elements) {
-			if (areNodesEqual(data, node)) {
-				anyNodeEquals = true;
-			}
-		}
+		const anyNodeEquals = elements.some((node) => areNodesEqual(data, node));
 
 		if (!anyNodeEquals) {
-			ast.elements.push(data);
+			if (insertEnd) ast.elements.push(data);
+			else ast.elements.unshift(data);
 		}
 	}
 }