diff --git a/.changeset/happy-tools-approve.md b/.changeset/happy-tools-approve.md
new file mode 100644
index 000000000000..5937ae9d7107
--- /dev/null
+++ b/.changeset/happy-tools-approve.md
@@ -0,0 +1,14 @@
+---
+"wrangler": minor
+---
+
+feat: allow preserving file names when defining rules for non-js modules
+
+The developer is now able to specify the `preserve_file_names property in wrangler.toml
+which specifies whether Wrangler will preserve the file names additional modules that are
+added to the deployment bundle of a Worker.
+
+If not set to true, files will be named using the pattern ${fileHash}-${basename}.
+For example, `34de60b44167af5c5a709e62a4e20c4f18c9e3b6-favicon.ico`.
+
+Resolves [#4741](https://github.com/cloudflare/workers-sdk/issues/4741)
diff --git a/packages/wrangler/src/__tests__/deploy.test.ts b/packages/wrangler/src/__tests__/deploy.test.ts
index ea8a61bd4630..dc5843ef112b 100644
--- a/packages/wrangler/src/__tests__/deploy.test.ts
+++ b/packages/wrangler/src/__tests__/deploy.test.ts
@@ -7418,6 +7418,69 @@ addEventListener('fetch', event => {});`
 		`);
 		});
 
+		it("should be able to preserve file names when defining rules for uploading non-js modules (sw)", async () => {
+			writeWranglerToml({
+				rules: [{ type: "Text", globs: ["**/*.file"], fallthrough: true }],
+				preserve_file_names: true,
+			});
+			fs.writeFileSync("./index.js", `import TEXT from './text.file';`);
+			fs.writeFileSync("./text.file", "SOME TEXT CONTENT");
+			mockSubDomainRequest();
+			mockUploadWorkerRequest({
+				expectedType: "sw",
+				expectedBindings: [
+					{
+						name: "__text_file",
+						part: "__text_file",
+						type: "text_blob",
+					},
+				],
+				expectedModules: {
+					__text_file: "SOME TEXT CONTENT",
+				},
+			});
+			await runWrangler("deploy index.js");
+			expect(std.out).toMatchInlineSnapshot(`
+			"Total Upload: xx KiB / gzip: xx KiB
+			Uploaded test-name (TIMINGS)
+			Published test-name (TIMINGS)
+			  https://test-name.test-sub-domain.workers.dev
+			Current Deployment ID: Galaxy-Class"
+		`);
+			expect(std.err).toMatchInlineSnapshot(`""`);
+			expect(std.warn).toMatchInlineSnapshot(`""`);
+		});
+
+		it("should be able to preserve file names when defining rules for uploading non-js modules (esm)", async () => {
+			writeWranglerToml({
+				rules: [{ type: "Text", globs: ["**/*.file"], fallthrough: true }],
+				preserve_file_names: true,
+			});
+			fs.writeFileSync(
+				"./index.js",
+				`import TEXT from './text.file'; export default {};`
+			);
+			fs.writeFileSync("./text.file", "SOME TEXT CONTENT");
+			mockSubDomainRequest();
+			mockUploadWorkerRequest({
+				expectedType: "esm",
+				expectedBindings: [],
+				expectedModules: {
+					"./text.file": "SOME TEXT CONTENT",
+				},
+			});
+			await runWrangler("deploy index.js");
+			expect(std.out).toMatchInlineSnapshot(`
+			"Total Upload: xx KiB / gzip: xx KiB
+			Uploaded test-name (TIMINGS)
+			Published test-name (TIMINGS)
+			  https://test-name.test-sub-domain.workers.dev
+			Current Deployment ID: Galaxy-Class"
+		`);
+			expect(std.err).toMatchInlineSnapshot(`""`);
+			expect(std.warn).toMatchInlineSnapshot(`""`);
+		});
+
 		describe("inject process.env.NODE_ENV", () => {
 			let actualProcessEnvNodeEnv: string | undefined;
 			beforeEach(() => {
diff --git a/packages/wrangler/src/config/environment.ts b/packages/wrangler/src/config/environment.ts
index b7057b43cdc5..613277e19a98 100644
--- a/packages/wrangler/src/config/environment.ts
+++ b/packages/wrangler/src/config/environment.ts
@@ -93,6 +93,14 @@ interface EnvironmentInheritable {
 	 */
 	find_additional_modules: boolean | undefined;
 
+	/**
+	 * Determines whether Wrangler will preserve bundled file names.
+	 * Defaults to false.
+	 * If left unset, files will be named using the pattern ${fileHash}-${basename},
+	 * for example, `34de60b44167af5c5a709e62a4e20c4f18c9e3b6-favicon.ico`.
+	 */
+	preserve_file_names: boolean | undefined;
+
 	/**
 	 * The directory in which module rules should be evaluated when including additional files into a worker deployment.
 	 * This defaults to the directory containing the `main` entry point of the worker if not specified.
diff --git a/packages/wrangler/src/config/validation.ts b/packages/wrangler/src/config/validation.ts
index 4ef791f213ec..570d61096612 100644
--- a/packages/wrangler/src/config/validation.ts
+++ b/packages/wrangler/src/config/validation.ts
@@ -1154,6 +1154,14 @@ function normalizeAndValidateEnvironment(
 			isBoolean,
 			undefined
 		),
+		preserve_file_names: inheritable(
+			diagnostics,
+			topLevelEnv,
+			rawEnv,
+			"preserve_file_names",
+			isBoolean,
+			undefined
+		),
 		base_dir: normalizeAndValidateBaseDirField(
 			configPath,
 			inheritable(
diff --git a/packages/wrangler/src/deploy/deploy.ts b/packages/wrangler/src/deploy/deploy.ts
index c853a7f4d03d..012adaa595ea 100644
--- a/packages/wrangler/src/deploy/deploy.ts
+++ b/packages/wrangler/src/deploy/deploy.ts
@@ -481,6 +481,7 @@ See https://developers.cloudflare.com/workers/platform/compatibility-dates for m
 			// `findAdditionalModules` always defaults to `false`
 			findAdditionalModules: config.find_additional_modules ?? false,
 			rules: props.rules,
+			preserveFileNames: config.preserve_file_names ?? false,
 		});
 
 		const { modules, dependencies, resolvedEntryPointPath, bundleType } =
diff --git a/packages/wrangler/src/deployment-bundle/module-collection.ts b/packages/wrangler/src/deployment-bundle/module-collection.ts
index 97218dee50d2..2f9ba47ce5c6 100644
--- a/packages/wrangler/src/deployment-bundle/module-collection.ts
+++ b/packages/wrangler/src/deployment-bundle/module-collection.ts
@@ -223,7 +223,9 @@ export function createModuleCollector(props: {
 								.createHash("sha1")
 								.update(fileContent)
 								.digest("hex");
-							const fileName = `./${fileHash}-${path.basename(args.path)}`;
+							const fileName = props.preserveFileNames
+								? args.path
+								: `./${fileHash}-${path.basename(args.path)}`;
 
 							const { rule } =
 								rulesMatchers.find(({ regex }) => regex.test(fileName)) || {};
@@ -338,7 +340,7 @@ export function createModuleCollector(props: {
 									.update(fileContent)
 									.digest("hex");
 								const fileName = props.preserveFileNames
-									? filePath
+									? args.path
 									: `./${fileHash}-${path.basename(args.path)}`;
 
 								// add the module to the array