@@ -0,0 +1,5 @@
+---
+"webpack": patch
+---
+
+Match `urlHints` rules written with `and`, `or` and `not` conditions.
@@ -5,7 +5,6 @@
 "use strict";
 
 const { RawSource } = require("webpack-sources");
-const ModuleFilenameHelpers = require("../devtool/ModuleFilenameHelpers");
 const isDependencyKind = require("../graph/isDependencyKind");
 const {
 	ASSET_URL_TYPE,
@@ -54,12 +53,13 @@ const parseResourceHintOptions = require("./parseResourceHintOptions");
  * @import {
  * 	ResourceHintsInitial as ResourceHintsConfig,
  * 	ResourceHintsOptions,
+ * 	RuleSetCondition,
+ * 	RuleSetLogicalConditions,
  * 	UrlHintRule
  * } from "../../declarations/WebpackOptions"
  */
 /** @import { HtmlResourceHint } from "../dependencies/html/HtmlEntryDependency" */
 /** @import { ResourceHintOptions } from "./parseResourceHintOptions" */
-/** @import { MatchObject } from "../devtool/ModuleFilenameHelpers" */
 
 /**
  * @typedef {object} ResolvedResourceHints
@@ -198,6 +198,38 @@ function* iterateHintedUrlAssets(compilation, chunks) {
 	}
 }
 
+/** @type {WeakMap<UrlHintRule, (request: string) => boolean>} */
+const urlHintMatchers = new WeakMap();
+
+/**
+ * A rule's `test`, `include` and `exclude` as one predicate, read as `module.rules`
+ * reads a condition, so `and`/`or`/`not`/`glob` work too. Compiled once per rule.
+ * @param {UrlHintRule} rule rule setting at least one of the three
+ * @returns {(request: string) => boolean} whether the rule applies to a request
+ */
+const getUrlHintMatcher = (rule) => {
+	let matcher = urlHintMatchers.get(rule);
+	if (matcher === undefined) {
+		/** @type {RuleSetCondition[]} */
+		const all = [];
+		if (rule.test !== undefined) all.push(rule.test);
+		if (rule.include !== undefined) all.push(rule.include);
+		/** @type {RuleSetLogicalConditions} */
+		const condition = {};
+		if (all.length > 0) condition.and = all;
+		if (rule.exclude !== undefined) condition.not = rule.exclude;
+
+		const RuleSetCompiler = require("../rules/RuleSetCompiler");
+
+		matcher = new RuleSetCompiler([]).compileCondition(
+			"urlHints",
+			condition
+		).fn;
+		urlHintMatchers.set(rule, matcher);
+	}
+	return matcher;
+};
+
 /**
  * Merge the matching `UrlHintRule`s for a request. Rules match by
  * `test`/`include`/`exclude` (omit all three → matches everything); later
@@ -216,14 +248,7 @@ const matchUrlHints = (rules, request) => {
 			(rule.test !== undefined ||
 				rule.include !== undefined ||
 				rule.exclude !== undefined) &&
-			!ModuleFilenameHelpers.matchObject(
-				/** @type {MatchObject} */ ({
-					test: rule.test,
-					include: rule.include,
-					exclude: rule.exclude
-				}),
-				request
-			)
+			!getUrlHintMatcher(rule)(request)
 		) {
 			continue;
 		}
 
@@ -0,0 +1,19 @@
+"use strict";
+
+const a = new URL("./a.png", import.meta.url);
+const b = new URL("./b.png", import.meta.url);
+const font = new URL("./font.woff2", import.meta.url);
+
+const findLink = (name) =>
+	document.head._children.find(
+		(el) => el._type === "link" && el.href.endsWith(`/${name}`)
+	);
+
+it("should match urlHints rules written as logical conditions", () => {
+	expect(a.href).toContain("a.png");
+	expect(b.href).toContain("b.png");
+	expect(font.href).toContain("font.woff2");
+	expect(findLink("a.png").rel).toBe("preload");
+	expect(findLink("b.png").rel).toBe("prefetch");
+	expect(findLink("font.woff2").rel).toBe("prefetch");
+});
@@ -0,0 +1,25 @@
+"use strict";
+
+/** @type {import("../../../../").Configuration} */
+module.exports = {
+	mode: "development",
+	target: "web",
+	output: {
+		assetModuleFilename: "[name][ext]",
+		publicPath: "https://example.com/public/",
+		resourceHints: {
+			urlHints: [
+				{
+					test: { and: [/\.png$/, { not: /b\.png$/ }] },
+					preload: true,
+					as: "image"
+				},
+				{ test: [{ not: /\.png$/ }], prefetch: true },
+				{ include: { or: [/b\.png$/] }, prefetch: true }
+			]
+		}
+	},
+	module: {
+		rules: [{ test: /\.(png|woff2)$/, type: "asset/resource" }]
+	}
+};
-Original file line number
+Diff line change
@@ @@ -0,0 +1,5 @@ @@
 +---
 +"webpack": patch
 +---
++
 +Match `urlHints` rules written with `and`, `or` and `not` conditions.