diff --git a/src/Chunk.ts b/src/Chunk.ts
index 6b27aa02389..fb4856ae7d5 100644
--- a/src/Chunk.ts
+++ b/src/Chunk.ts
@@ -1042,8 +1042,9 @@ export default class Chunk {
 				if (options.sourcemap) {
 					timeStart('sourcemap', 3);
 
-					let file = options.file ? options.sourcemapFile || options.file : this.id;
-					if (file) file = resolve(typeof process !== 'undefined' ? process.cwd() : '', file);
+					const file = options.file
+						? options.sourcemapFile || options.file
+						: resolve(options.dir, this.id);
 
 					if (
 						this.graph.hasLoaders ||
diff --git a/src/rollup/index.ts b/src/rollup/index.ts
index f14ddf73ca7..e38ee145cfc 100644
--- a/src/rollup/index.ts
+++ b/src/rollup/index.ts
@@ -1,5 +1,5 @@
 import { getTimings, initialiseTimers, timeEnd, timeStart } from '../utils/timers';
-import { basename } from '../utils/path';
+import { basename, resolve, dirname } from '../utils/path';
 import { writeFile } from '../utils/fs';
 import { mapSequence } from '../utils/promise';
 import error from '../utils/error';
@@ -153,6 +153,8 @@ export default function rollup(
 				function generate(rawOutputOptions: GenericConfigObject) {
 					const outputOptions = normalizeOutputOptions(inputOptions, rawOutputOptions);
 
+					outputOptions.dir = dirname(resolve(inputOptions.input));
+
 					if (outputOptions.entryNames || outputOptions.chunkNames)
 						error({
 							code: 'INVALID_OPTION',
@@ -169,6 +171,7 @@ export default function rollup(
 						.then(addons => {
 							chunk.generateInternalExports(outputOptions);
 							chunk.preRender(outputOptions);
+							chunk.id = basename(inputOptions.input);
 							return chunk.render(outputOptions, addons);
 						})
 						.then(rendered => {
@@ -312,6 +315,12 @@ export default function rollup(
 						});
 					}
 
+					if (outputOptions.sourcemapFile)
+						error({
+							code: 'INVALID_OPTION',
+							message: '"sourcemapFile" is only supported for single-file builds.'
+						});
+
 					timeStart('GENERATE', 1);
 
 					const generated: { [chunkName: string]: OutputChunk } = {};
diff --git a/test/misc/index.js b/test/misc/index.js
index d90370a04dc..a340ec60ac8 100644
--- a/test/misc/index.js
+++ b/test/misc/index.js
@@ -1,6 +1,9 @@
 const assert = require('assert');
+const path = require('path');
 const rollup = require('../../dist/rollup');
 const { executeBundle, loader } = require('../utils.js');
+const { SourceMapConsumer } = require( 'source-map' );
+const { getLocator } = require( 'locate-character' );
 
 describe('sanity checks', () => {
 	it('exists', () => {
@@ -158,6 +161,31 @@ describe('sanity checks', () => {
 	});
 });
 
+describe('in-memory sourcemaps', () => {
+	it( 'generates an in-memory sourcemap', async () => {
+		const bundle = await rollup.rollup({
+			input: 'main',
+			plugins: [loader({ main: `console.log( 42 );` })],
+		});
+
+		const generated = await bundle.generate({
+			format: 'cjs',
+			sourcemap: true,
+			sourcemapFile: path.resolve( 'bundle.js' )
+		});
+
+		const smc = new SourceMapConsumer( generated.map );
+		const locator = getLocator( generated.code, { offsetLine: 1 });
+
+		let generatedLoc = locator( '42' );
+		let loc = smc.originalPositionFor( generatedLoc ); // 42
+		assert.equal( loc.source, 'main' );
+		assert.equal( loc.line, 1 );
+		assert.equal( loc.column, 13 );
+	});
+
+});
+
 describe('deprecations', () => {
 	it('warns on options.entry, but handles', () => {
 		const warnings = [];