diff --git a/.changeset/hot-places-ask.md b/.changeset/hot-places-ask.md
new file mode 100644
index 000000000000..9b1c28ef7d36
--- /dev/null
+++ b/.changeset/hot-places-ask.md
@@ -0,0 +1,5 @@
+---
+'@astrojs/cloudflare': patch
+---
+
+Fixes dev dependency scan failing when a frontmatter line starts with `import.meta` or `import(`
diff --git a/packages/integrations/cloudflare/src/rolldown-plugin-astro-frontmatter.ts b/packages/integrations/cloudflare/src/rolldown-plugin-astro-frontmatter.ts
index 38756e822694..9bb7d74577e4 100644
--- a/packages/integrations/cloudflare/src/rolldown-plugin-astro-frontmatter.ts
+++ b/packages/integrations/cloudflare/src/rolldown-plugin-astro-frontmatter.ts
@@ -7,6 +7,30 @@ const FRONTMATTER_RE = /^---\r?\n([\s\S]*?)\r?\n---/;
 // Used to hoist imports to module scope when wrapping frontmatter in a function.
 const IMPORT_STMT_RE = /^\s*import\b[\s\S]*?(?:from\s+['"][^'"]*['"]|['"][^'"]*['"]);?\s*$/gm;
 
+function isImportExpression(code: string): boolean {
+	let index = code.indexOf('import') + 'import'.length;
+	while (index < code.length) {
+		if (/\s/.test(code[index])) {
+			index++;
+			continue;
+		}
+		if (code.startsWith('/*', index)) {
+			const commentEnd = code.indexOf('*/', index + 2);
+			if (commentEnd === -1) return true;
+			index = commentEnd + 2;
+			continue;
+		}
+		if (code.startsWith('//', index)) {
+			const lineBreak = code.slice(index + 2).search(/[\r\n]/);
+			if (lineBreak === -1) return true;
+			index += lineBreak + 3;
+			continue;
+		}
+		return code[index] === '.' || code[index] === '(';
+	}
+	return true;
+}
+
 /**
  * Wraps frontmatter code in an async function so that top-level `return`
  * statements are valid syntax for the bundler's parser. Static import
@@ -16,6 +40,7 @@ const IMPORT_STMT_RE = /^\s*import\b[\s\S]*?(?:from\s+['"][^'"]*['"]|['"][^'"]*[
 export function wrapFrontmatter(code: string): string {
 	const imports: string[] = [];
 	const body = code.replace(IMPORT_STMT_RE, (match) => {
+		if (isImportExpression(match)) return match;
 		imports.push(match.trim());
 		return '';
 	});
diff --git a/packages/integrations/cloudflare/test/units/wrap-frontmatter.test.ts b/packages/integrations/cloudflare/test/units/wrap-frontmatter.test.ts
index cc31f4e77b18..3a02105e722b 100644
--- a/packages/integrations/cloudflare/test/units/wrap-frontmatter.test.ts
+++ b/packages/integrations/cloudflare/test/units/wrap-frontmatter.test.ts
@@ -88,4 +88,63 @@ describe('wrapFrontmatter', () => {
 		const result = wrapFrontmatter(input);
 		assert.ok(result.startsWith('import type { Foo } from "pkg";'));
 	});
+
+	it('does not hoist import.meta at start of line with string literals (#18144)', () => {
+		const input = [
+			'import { something } from "astro";',
+			'const assetBase =',
+			'  import.meta.env.BASE_URL.replace(/\\/$/, "") + "/assets/dir";',
+			'const label = "repro";',
+		].join('\n');
+		const result = wrapFrontmatter(input);
+		const funcStart = result.indexOf('async function __astro__()');
+		const metaPos = result.indexOf('import.meta.env');
+		assert.ok(metaPos > funcStart, 'import.meta.env should be inside the function body');
+		assert.ok(
+			result.includes('const assetBase =\n  import.meta.env'),
+			'assignment and import.meta expression should stay together',
+		);
+	});
+
+	it('does not hoist dynamic import() expressions (#18144)', () => {
+		const input = [
+			'import { something } from "astro";',
+			'const mod = await',
+			'  import("./dynamic-module");',
+			'const label = "repro";',
+		].join('\n');
+		const result = wrapFrontmatter(input);
+		const funcStart = result.indexOf('async function __astro__()');
+		const importCallPos = result.indexOf('import("./dynamic-module")');
+		assert.ok(importCallPos > funcStart, 'dynamic import() should be inside the function body');
+		assert.ok(result.includes('const label = "repro"'), 'subsequent code should not be swallowed');
+	});
+
+	it('does not hoist import.meta expressions separated by comments (#18144)', () => {
+		for (const expression of [
+			'import /* comment */.meta.url.replace("file:", "");',
+			'import // comment\n  .meta.url.replace("file:", "");',
+		]) {
+			const input = ['const url =', `  ${expression}`, 'const label = "repro";'].join('\n');
+			const result = wrapFrontmatter(input);
+			assert.ok(
+				result.includes(`const url =\n  ${expression}`),
+				'import.meta expression should stay with its assignment',
+			);
+		}
+	});
+
+	it('does not hoist dynamic import() expressions separated by comments (#18144)', () => {
+		for (const expression of [
+			'import /* comment */ ("./dynamic-module");',
+			'import // comment\n  ("./dynamic-module");',
+		]) {
+			const input = ['const mod = await', `  ${expression}`, 'const label = "repro";'].join('\n');
+			const result = wrapFrontmatter(input);
+			assert.ok(
+				result.includes(`const mod = await\n  ${expression}`),
+				'dynamic import() expression should stay with its assignment',
+			);
+		}
+	});
 });