diff --git a/packages/wrangler/src/__tests__/get-entry.test.ts b/packages/wrangler/src/__tests__/get-entry.test.ts
new file mode 100644
index 000000000000..534cc74e2f83
--- /dev/null
+++ b/packages/wrangler/src/__tests__/get-entry.test.ts
@@ -0,0 +1,128 @@
+import { writeFile } from "fs/promises";
+import path from "path";
+import dedent from "ts-dedent";
+import { Config } from "../config";
+import { defaultWranglerConfig } from "../config/config";
+import { Entry, getEntry } from "../deployment-bundle/entry";
+import guessWorkerFormat from "../deployment-bundle/guess-worker-format";
+import { mockConsoleMethods } from "./helpers/mock-console";
+import { runInTempDir } from "./helpers/run-in-tmp";
+import { seed } from "./helpers/seed";
+
+function normalize(entry: Entry): Entry {
+	return JSON.parse(
+		JSON.stringify(entry).replaceAll(process.cwd(), "/tmp/dir")
+	);
+}
+describe("getEntry()", () => {
+	runInTempDir();
+	mockConsoleMethods();
+	it.each([
+		[
+			"--script index.ts",
+			{
+				"index.ts": dedent/* javascript */ `
+						export default {
+							fetch() {
+
+							}
+						}
+					`,
+			},
+			{ script: "index.ts" },
+			{},
+			{
+				directory: "/tmp/dir",
+				file: "/tmp/dir/index.ts",
+				moduleRoot: "/tmp/dir",
+			},
+		],
+		[
+			"--script src/index.ts",
+			{
+				"src/index.ts": dedent/* javascript */ `
+						export default {
+							fetch() {
+
+							}
+						}
+					`,
+			},
+			{ script: "src/index.ts" },
+			{},
+			{
+				directory: "/tmp/dir",
+				file: "/tmp/dir/src/index.ts",
+				moduleRoot: "/tmp/dir/src",
+			},
+		],
+		[
+			"main = index.ts",
+			{
+				"index.ts": dedent/* javascript */ `
+						export default {
+							fetch() {
+
+							}
+						}
+					`,
+			},
+			{},
+			{ main: "index.ts" },
+			{
+				directory: "/tmp/dir",
+				file: "/tmp/dir/index.ts",
+				moduleRoot: "/tmp/dir",
+			},
+		],
+		[
+			"main = src/index.ts",
+			{
+				"src/index.ts": dedent/* javascript */ `
+						export default {
+							fetch() {
+
+							}
+						}
+					`,
+			},
+			{},
+			{ main: "src/index.ts" },
+			{
+				directory: "/tmp/dir",
+				file: "/tmp/dir/src/index.ts",
+				moduleRoot: "/tmp/dir/src",
+			},
+		],
+		[
+			"main = src/index.ts w/ configPath",
+			{
+				"other-worker/src/index.ts": dedent/* javascript */ `
+						export default {
+							fetch() {
+
+							}
+						}
+					`,
+			},
+			{},
+			{
+				main: "src/index.ts",
+				configPath: "other-worker/wrangler.toml",
+			},
+			{
+				directory: "/tmp/dir/other-worker",
+				file: "/tmp/dir/other-worker/src/index.ts",
+				moduleRoot: "/tmp/dir/other-worker/src",
+			},
+		],
+	])("%s", async (_name, files, args, config, result) => {
+		await seed(files);
+		const entry = await getEntry(
+			args,
+			{ ...defaultWranglerConfig, ...config },
+			"deploy"
+		);
+		expect(normalize(entry)).toMatchObject(result);
+	});
+});
diff --git a/packages/wrangler/src/deployment-bundle/entry.ts b/packages/wrangler/src/deployment-bundle/entry.ts
index 1be44b13f210..4e5e40a711e9 100644
--- a/packages/wrangler/src/deployment-bundle/entry.ts
+++ b/packages/wrangler/src/deployment-bundle/entry.ts
@@ -53,7 +53,9 @@ export async function getEntry(
 	const directory = process.cwd();
 	const entryPoint = config.site?.["entry-point"];
 
-	let paths: { absolutePath: string; relativePath: string } | undefined;
+	let paths:
+		| { absolutePath: string; relativePath: string; directory?: string }
+		| undefined;
 
 	if (args.script) {
 		paths = resolveEntryWithScript(args.script);
@@ -81,9 +83,10 @@ export async function getEntry(
 	}
 	await runCustomBuild(paths.absolutePath, paths.relativePath, config.build);
 
+	const projectRoot = paths.directory ?? directory;
 	const { format, exports } = await guessWorkerFormat(
 		paths.absolutePath,
-		directory,
+		projectRoot,
 		args.format ?? config.build?.upload?.format,
 		config.tsconfig
 	);
@@ -117,7 +120,7 @@ export async function getEntry(
 
 	return {
 		file: paths.absolutePath,
-		directory,
+		directory: projectRoot,
 		format,
 		moduleRoot:
 			args.moduleRoot ?? config.base_dir ?? path.dirname(paths.absolutePath),
diff --git a/packages/wrangler/src/deployment-bundle/resolve-entry.ts b/packages/wrangler/src/deployment-bundle/resolve-entry.ts
index 5a9efb535194..3d13b7c76be8 100644
--- a/packages/wrangler/src/deployment-bundle/resolve-entry.ts
+++ b/packages/wrangler/src/deployment-bundle/resolve-entry.ts
@@ -16,11 +16,12 @@ export function resolveEntryWithMain(
 ): {
 	absolutePath: string;
 	relativePath: string;
+	directory: string;
 } {
 	const directory = path.resolve(path.dirname(configPath ?? "."));
 	const file = path.resolve(directory, main);
 	const relativePath = path.relative(directory, file) || ".";
-	return { absolutePath: file, relativePath };
+	return { absolutePath: file, relativePath, directory };
 }
 
 export function resolveEntryWithEntryPoint(
@@ -29,13 +30,14 @@ export function resolveEntryWithEntryPoint(
 ): {
 	absolutePath: string;
 	relativePath: string;
+	directory: string;
 } {
 	const directory = path.resolve(path.dirname(configPath ?? "."));
 	const file = path.extname(entryPoint)
 		? path.resolve(entryPoint)
 		: path.resolve(entryPoint, "index.js");
 	const relativePath = path.relative(directory, file) || ".";
-	return { absolutePath: file, relativePath };
+	return { absolutePath: file, relativePath, directory };
 }
 
 export function resolveEntryWithAssets(): {