diff --git a/.changeset/shaggy-peas-notice.md b/.changeset/shaggy-peas-notice.md
new file mode 100644
index 000000000000..9c847d9b830f
--- /dev/null
+++ b/.changeset/shaggy-peas-notice.md
@@ -0,0 +1,11 @@
+---
+"@cloudflare/workers-shared": patch
+"miniflare": patch
+"wrangler": patch
+---
+
+fix: remove filepath encoding on asset upload and handle sometimes-encoded characters
+
+Some characters like [ ] @ are encoded by encodeURIComponent() but are often requested at an unencoded URL path.
+This change will make assets with filenames with these characters accessible at both the encoded and unencoded paths,
+but to use the encoded path as the canonical one, and to redirect requests to the canonical path if necessary.
diff --git a/fixtures/asset-config/html-handling.test.ts b/fixtures/asset-config/html-handling.test.ts
index 274d69b0b574..e024bfd956cc 100644
--- a/fixtures/asset-config/html-handling.test.ts
+++ b/fixtures/asset-config/html-handling.test.ts
@@ -3,6 +3,8 @@ import { afterEach, beforeEach, describe, expect, it, vi } from "vitest";
 import { applyConfigurationDefaults } from "../../packages/workers-shared/asset-worker/src/configuration";
 import Worker from "../../packages/workers-shared/asset-worker/src/index";
 import { getAssetWithMetadataFromKV } from "../../packages/workers-shared/asset-worker/src/utils/kv";
+import { encodingTestCases } from "./test-cases/encoding-test-cases";
+import { htmlHandlingTestCases } from "./test-cases/html-handling-test-cases";
 import type { AssetMetadata } from "../../packages/workers-shared/asset-worker/src/utils/kv";
 
 const IncomingRequest = Request<unknown, IncomingRequestCfProperties>;
@@ -20,7 +22,7 @@ const existsMock = (fileList: Set<string>) => {
 };
 const BASE_URL = "http://example.com";
 
-type TestCase = {
+export type TestCase = {
 	title: string;
 	files: string[];
 	requestPath: string;
@@ -28,756 +30,18 @@ type TestCase = {
 	finalPath?: string;
 };
 
-const testCases: {
-	html_handling:
-		| "auto-trailing-slash"
-		| "drop-trailing-slash"
-		| "force-trailing-slash"
-		| "none";
-	cases: TestCase[];
-}[] = [
+const testSuites = [
 	{
-		html_handling: "auto-trailing-slash",
-		cases: [
-			{
-				title: "/ -> 200 (with /index.html)",
-				files: ["/index.html"],
-				requestPath: "/index.html",
-				matchedFile: "/index.html",
-				finalPath: "/",
-			},
-			{
-				title: "/index -> / 307 (with /index.html)",
-				files: ["/index.html"],
-				requestPath: "/index",
-				matchedFile: "/index.html",
-				finalPath: "/",
-			},
-			{
-				title: "/index.html -> / 307 (with /index.html)",
-				files: ["/index.html"],
-				requestPath: "/index.html",
-				matchedFile: "/index.html",
-				finalPath: "/",
-			},
-			{
-				title: "/both -> 200 (with /both.html)",
-				files: ["/both.html", "/both/index.html"],
-				requestPath: "/both",
-				matchedFile: "/both.html",
-				finalPath: "/both",
-			},
-			{
-				title: "/both.html -> /both 307 (with /both.html)",
-				files: ["/both.html", "/both/index.html"],
-				requestPath: "/both.html",
-				matchedFile: "/both.html",
-				finalPath: "/both",
-			},
-			{
-				title: "/both/ -> 200 (with /both/index.html)",
-				files: ["/both.html", "/both/index.html"],
-				requestPath: "/both/",
-				matchedFile: "/both/index.html",
-				finalPath: "/both/",
-			},
-			{
-				title: "/both/index.html -> /both/ 307 (with /both/index.html)",
-				files: ["/both.html", "/both/index.html"],
-				requestPath: "/both/index.html",
-				matchedFile: "/both/index.html",
-				finalPath: "/both/",
-			},
-			{
-				title: "/both/index -> /both/ 307 (with /both/index.html)",
-				files: ["/both.html", "/both/index.html"],
-				requestPath: "/both/index",
-				matchedFile: "/both/index.html",
-				finalPath: "/both/",
-			},
-			{
-				title: "/file -> 200 (with file.html)",
-				files: ["/file.html"],
-				requestPath: "/file",
-				matchedFile: "/file.html",
-				finalPath: "/file",
-			},
-			{
-				title: "/file.html -> /file 307 (with file.html)",
-				files: ["/file.html"],
-				requestPath: "/file.html",
-				matchedFile: "/file.html",
-				finalPath: "/file",
-			},
-			{
-				title: "/file/ -> /file 307 (with file.html)",
-				files: ["/file.html"],
-				requestPath: "/file/",
-				matchedFile: "/file.html",
-				finalPath: "/file",
-			},
-			{
-				title: "/file/index -> /file 307 (with file.html)",
-				files: ["/file.html"],
-				requestPath: "/file/index",
-				matchedFile: "/file.html",
-				finalPath: "/file",
-			},
-			{
-				title: "/file/index.html -> /file 307 (with file.html)",
-				files: ["/file.html"],
-				requestPath: "/file/index.html",
-				matchedFile: "/file.html",
-				finalPath: "/file",
-			},
-			{
-				title: "/folder -> /folder/ 307 (with /folder/index.html)",
-				files: ["/folder/index.html"],
-				requestPath: "/folder",
-				matchedFile: "/folder/index.html",
-				finalPath: "/folder/",
-			},
-			{
-				title: "/folder.html -> /folder/ 307 (with /folder/index.html)",
-				files: ["/folder/index.html"],
-				requestPath: "/folder.html",
-				matchedFile: "/folder/index.html",
-				finalPath: "/folder/",
-			},
-			{
-				title: "/folder/ -> 200 (with /folder/index.html)",
-				files: ["/folder/index.html"],
-				requestPath: "/folder/",
-				matchedFile: "/folder/index.html",
-				finalPath: "/folder/",
-			},
-			{
-				title: "/folder/index -> /folder/ 307 (with /folder/index.html)",
-				files: ["/folder/index.html"],
-				requestPath: "/folder/index",
-				matchedFile: "/folder/index.html",
-				finalPath: "/folder/",
-			},
-			{
-				title: "/folder/index.html -> /folder/ 307 (with /folder/index.html)",
-				files: ["/folder/index.html"],
-				requestPath: "/folder/index.html",
-				matchedFile: "/folder/index.html",
-				finalPath: "/folder/",
-			},
-			{
-				title: "/bin -> /bin/ 307 (with /bin/index.html)",
-				files: ["/bin%2F", "/bin/index.html"],
-				requestPath: "/bin",
-				matchedFile: "/bin/index.html",
-				finalPath: "/bin/",
-			},
-			{
-				title: "/bin.html -> /bin/ 307 (with /bin/index.html)",
-				files: ["/bin%2F", "/bin/index.html"],
-				requestPath: "/bin.html",
-				matchedFile: "/bin/index.html",
-				finalPath: "/bin/",
-			},
-			{
-				title: "/bin%2F -> 200 (with /bin%2F)",
-				files: ["/bin%2F", "/bin/index.html"],
-				requestPath: "/bin%2F",
-				matchedFile: "/bin%2F",
-				finalPath: "/bin%2F",
-			},
-			{
-				title: "/bin/ -> 200 (with /bin/index.html not /bin%2F",
-				files: ["/bin%2F", "/bin/index.html"],
-				requestPath: "/bin/",
-				matchedFile: "/bin/index.html",
-				finalPath: "/bin/",
-			},
-			{
-				title: "/bin/index -> 307 /bin/ (with /bin/index.html)",
-				files: ["/bin%2F", "/bin/index.html"],
-				requestPath: "/bin/index",
-				matchedFile: "/bin/index.html",
-				finalPath: "/bin/",
-			},
-			{
-				title: "/bin/index.html -> 307 /bin/ (with /bin/index.html)",
-				files: ["/bin%2F", "/bin/index.html"],
-				requestPath: "/bin/index.html",
-				matchedFile: "/bin/index.html",
-				finalPath: "/bin/",
-			},
-			// prefers exact match
-			{
-				title: "/file-bin -> 200 ",
-				files: ["/file-bin", "/file-bin.html"],
-				requestPath: "/file-bin",
-				matchedFile: "/file-bin",
-				finalPath: "/file-bin",
-			},
-			// (doesn't rewrite if resulting path would match another asset)
-			{
-				title: "/file-bin.html -> 200 ",
-				files: ["/file-bin", "/file-bin.html"],
-				requestPath: "/file-bin.html",
-				matchedFile: "/file-bin.html",
-				finalPath: "/file-bin.html",
-			},
-			// (finds file-bin.html --rewrite--> /file-bin, but /file-bin exists)
-			{
-				title: "/file-bin/ -> 404 ",
-				files: ["/file-bin", "/file-bin.html"],
-				requestPath: "/file-bin/",
-			},
-			{
-				title: "/file-bin/index -> 404 ",
-				files: ["/file-bin", "/file-bin.html"],
-				requestPath: "/file-bin/index",
-			},
-			{
-				title: "/file-bin/index.html -> 404 ",
-				files: ["/file-bin", "/file-bin.html"],
-				requestPath: "/file-bin/index.html",
-			},
-		],
+		title: "htmlHanding options",
+		suite: htmlHandlingTestCases,
 	},
 	{
-		html_handling: "drop-trailing-slash",
-		cases: [
-			// note that we don't drop the "/" if that is the only path component
-			{
-				title: "/ -> 200 (with /index.html)",
-				files: ["/index.html"],
-				requestPath: "/index.html",
-				matchedFile: "/index.html",
-				finalPath: "/",
-			},
-			{
-				title: "/index -> / 307 (with /index.html)",
-				files: ["/index.html"],
-				requestPath: "/index",
-				matchedFile: "/index.html",
-				finalPath: "/",
-			},
-			{
-				title: "/index.html -> / 307 (with /index.html)",
-				files: ["/index.html"],
-				requestPath: "/index.html",
-				matchedFile: "/index.html",
-				finalPath: "/",
-			},
-			{
-				title: "/both -> 200 (with /both.html)",
-				files: ["/both.html", "/both/index.html"],
-				requestPath: "/both",
-				matchedFile: "/both.html",
-				finalPath: "/both",
-			},
-			{
-				title: "/both.html -> /both 307 (with /both.html)",
-				files: ["/both.html", "/both/index.html"],
-				requestPath: "/both.html",
-				matchedFile: "/both.html",
-				finalPath: "/both",
-			},
-			// drops trailing slash and so it tries /both.html first
-			{
-				title: "/both/ -> /both 307 (with /both.html)",
-				files: ["/both.html", "/both/index.html"],
-				requestPath: "/both/",
-				matchedFile: "/both.html",
-				finalPath: "/both",
-			},
-			{
-				title: "/both/index -> 307 (with /both.html)",
-				files: ["/both.html", "/both/index.html"],
-				requestPath: "/both/index",
-				matchedFile: "/both.html",
-				finalPath: "/both",
-			},
-			// can't rewrite /both/index.html: would be /both/ -> /both -> /both.html
-			// ie can only access /both/index.html by exact match
-			{
-				title: "/both/index.html -> 200 (with /both/index.html)",
-				files: ["/both.html", "/both/index.html"],
-				requestPath: "/both/index.html",
-				matchedFile: "/both/index.html",
-				finalPath: "/both/index.html",
-			},
-			{
-				title: "/file -> 200 (with file.html)",
-				files: ["/file.html"],
-				requestPath: "/file",
-				matchedFile: "/file.html",
-				finalPath: "/file",
-			},
-			{
-				title: "/file.html -> /file 307 (with file.html)",
-				files: ["/file.html"],
-				requestPath: "/file.html",
-				matchedFile: "/file.html",
-				finalPath: "/file",
-			},
-			{
-				title: "/file/ -> /file 307 (with file.html)",
-				files: ["/file.html"],
-				requestPath: "/file/",
-				matchedFile: "/file.html",
-				finalPath: "/file",
-			},
-			{
-				title: "/file/index -> /file 307 (with file.html)",
-				files: ["/file.html"],
-				requestPath: "/file/index",
-				matchedFile: "/file.html",
-				finalPath: "/file",
-			},
-			{
-				title: "/file/index.html -> /file 307 (with file.html)",
-				files: ["/file.html"],
-				requestPath: "/file/index.html",
-				matchedFile: "/file.html",
-				finalPath: "/file",
-			},
-			{
-				title: "/folder -> 200 (with /folder/index.html)",
-				files: ["/folder/index.html"],
-				requestPath: "/folder",
-				matchedFile: "/folder/index.html",
-				finalPath: "/folder",
-			},
-			{
-				title: "/folder.html -> /folder 307 (with /folder/index.html)",
-				files: ["/folder/index.html"],
-				requestPath: "/folder.html",
-				matchedFile: "/folder/index.html",
-				finalPath: "/folder",
-			},
-			{
-				title: "/folder/ -> /folder 307 (with /folder/index.html)",
-				files: ["/folder/index.html"],
-				requestPath: "/folder/",
-				matchedFile: "/folder/index.html",
-				finalPath: "/folder",
-			},
-			{
-				title: "/folder/index -> /folder 307 (with /folder/index.html)",
-				files: ["/folder/index.html"],
-				requestPath: "/folder/index",
-				matchedFile: "/folder/index.html",
-				finalPath: "/folder",
-			},
-			{
-				title: "/folder/index.html -> /folder 307 (with /folder/index.html)",
-				files: ["/folder/index.html"],
-				requestPath: "/folder/index.html",
-				matchedFile: "/folder/index.html",
-				finalPath: "/folder",
-			},
-			{
-				title: "/bin -> 200 (with /bin/index.html)",
-				files: ["/bin%2F", "/bin/index.html"],
-				requestPath: "/bin",
-				matchedFile: "/bin/index.html",
-				finalPath: "/bin",
-			},
-			{
-				title: "/bin.html -> /bin 307 (with /bin/index.html)",
-				files: ["/bin%2F", "/bin/index.html"],
-				requestPath: "/bin.html",
-				matchedFile: "/bin/index.html",
-				finalPath: "/bin",
-			},
-			{
-				title: "/bin%2F -> 200 (with /bin%2F)",
-				files: ["/bin%2F", "/bin/index.html"],
-				requestPath: "/bin%2F",
-				matchedFile: "/bin%2F",
-				finalPath: "/bin%2F",
-			},
-			{
-				title: "/bin/ -> /bin 307 (with /bin/index.html not /bin%2F",
-				files: ["/bin%2F", "/bin/index.html"],
-				requestPath: "/bin/",
-				matchedFile: "/bin/index.html",
-				finalPath: "/bin",
-			},
-			{
-				title: "/bin/index -> /bin 307 (with /bin/index.html not /bin%2F",
-				files: ["/bin%2F", "/bin/index.html"],
-				requestPath: "/bin/index",
-				matchedFile: "/bin/index.html",
-				finalPath: "/bin",
-			},
-			{
-				title: "/bin/index.html -> /bin 307 (with /bin/index.html not /bin%2F",
-				files: ["/bin%2F", "/bin/index.html"],
-				requestPath: "/bin/index.html",
-				matchedFile: "/bin/index.html",
-				finalPath: "/bin",
-			},
-			{
-				title: "/file-bin -> 200",
-				files: ["/file-bin", "/file-bin.html"],
-				requestPath: "/file-bin",
-				matchedFile: "/file-bin",
-				finalPath: "/file-bin",
-			},
-			// doesn't redirect to /file-bin because that also exists
-			{
-				title: "/file-bin.html -> 200 (with /file-bin.html)",
-				files: ["/file-bin", "/file-bin.html"],
-				requestPath: "/file-bin.html",
-				matchedFile: "/file-bin.html",
-				finalPath: "/file-bin.html",
-			},
-			// 404s because ambiguity between /file-bin or /file-bin.html?
-			{
-				title: "/file-bin/ -> 404",
-				files: ["/file-bin", "/file-bin.html"],
-				requestPath: "/file-bin/",
-			},
-			{
-				title: "/file-bin/index -> 404",
-				files: ["/file-bin", "/file-bin.html"],
-				requestPath: "/file-bin/index",
-			},
-			{
-				title: "/file-bin/index.html -> 404",
-				files: ["/file-bin", "/file-bin.html"],
-				requestPath: "/file-bin/index.html",
-			},
-		],
-	},
-	{
-		html_handling: "force-trailing-slash",
-		cases: [
-			{
-				title: "/ -> 200 (with /index.html)",
-				files: ["/index.html"],
-				requestPath: "/index.html",
-				matchedFile: "/index.html",
-				finalPath: "/",
-			},
-			{
-				title: "/index -> / 307 (with /index.html)",
-				files: ["/index.html"],
-				requestPath: "/index",
-				matchedFile: "/index.html",
-				finalPath: "/",
-			},
-			{
-				title: "/index.html -> / 307 (with /index.html)",
-				files: ["/index.html"],
-				requestPath: "/index.html",
-				matchedFile: "/index.html",
-				finalPath: "/",
-			},
-			// ie tries /both/index.html first
-			{
-				title: "/both -> /both/ 307 (with /both/index.html)",
-				files: ["/both.html", "/both/index.html"],
-				requestPath: "/both",
-				matchedFile: "/both/index.html",
-				finalPath: "/both/",
-			},
-			// can't rewrite /both.html: would be /both -> /both/ -> /both/index.html
-			// ie can only access /both.html by exact match
-			{
-				title: "/both.html -> 200",
-				files: ["/both.html", "/both/index.html"],
-				requestPath: "/both.html",
-				matchedFile: "/both.html",
-				finalPath: "/both.html",
-			},
-			{
-				title: "/both/ -> 200 (with /both/index.html)",
-				files: ["/both.html", "/both/index.html"],
-				requestPath: "/both/",
-				matchedFile: "/both/index.html",
-				finalPath: "/both/",
-			},
-			{
-				title: "/both/index -> /both/ 307 (with /both/index.html)",
-				files: ["/both.html", "/both/index.html"],
-				requestPath: "/both/index",
-				matchedFile: "/both/index.html",
-				finalPath: "/both/",
-			},
-			{
-				title: "/both/index.html -> /both/ 307 (with /both/index.html)",
-				files: ["/both.html", "/both/index.html"],
-				requestPath: "/both/index.html",
-				matchedFile: "/both/index.html",
-				finalPath: "/both/",
-			},
-			// always ends in a trailing slash
-			{
-				title: "/file -> /file/ 307 (with file.html)",
-				files: ["/file.html"],
-				requestPath: "/file",
-				matchedFile: "/file.html",
-				finalPath: "/file/",
-			},
-			{
-				title: "/file.html -> /file/ 307 (with file.html)",
-				files: ["/file.html"],
-				requestPath: "/file.html",
-				matchedFile: "/file.html",
-				finalPath: "/file/",
-			},
-
-			{
-				title: "/file/ -> 200 (with file.html)",
-				files: ["/file.html"],
-				requestPath: "/file/",
-				matchedFile: "/file.html",
-				finalPath: "/file/",
-			},
-			{
-				title: "/file/index -> /file/ 307 (with file.html)",
-				files: ["/file.html"],
-				requestPath: "/file/index",
-				matchedFile: "/file.html",
-				finalPath: "/file/",
-			},
-			{
-				title: "/file/index.html -> /file/ 307 (with file.html)",
-				files: ["/file.html"],
-				requestPath: "/file/index.html",
-				matchedFile: "/file.html",
-				finalPath: "/file/",
-			},
-			{
-				title: "/folder -> /folder/ 307 (with /folder/index.html)",
-				files: ["/folder/index.html"],
-				requestPath: "/folder",
-				matchedFile: "/folder/index.html",
-				finalPath: "/folder/",
-			},
-			{
-				title: "/folder.html -> /folder/ 307 (with /folder/index.html)",
-				files: ["/folder/index.html"],
-				requestPath: "/folder.html",
-				matchedFile: "/folder/index.html",
-				finalPath: "/folder/",
-			},
-			{
-				title: "/folder/ -> 200 (with /folder/index.html)",
-				files: ["/folder/index.html"],
-				requestPath: "/folder/",
-				matchedFile: "/folder/index.html",
-				finalPath: "/folder/",
-			},
-			{
-				title: "/folder/index -> /folder/ 307 (with /folder/index.html)",
-				files: ["/folder/index.html"],
-				requestPath: "/folder/index",
-				matchedFile: "/folder/index.html",
-				finalPath: "/folder/",
-			},
-			{
-				title: "/folder/index.html -> /folder/ 307 (with /folder/index.html)",
-				files: ["/folder/index.html"],
-				requestPath: "/folder/index.html",
-				matchedFile: "/folder/index.html",
-				finalPath: "/folder/",
-			},
-			{
-				title: "/bin -> /bin/ 307 (with /bin/index.html)",
-				files: ["/bin%2F", "/bin/index.html"],
-				requestPath: "/bin",
-				matchedFile: "/bin/index.html",
-				finalPath: "/bin/",
-			},
-			{
-				title: "/bin.html -> /bin/ 307 (with /bin/index.html)",
-				files: ["/bin%2F", "/bin/index.html"],
-				requestPath: "/bin.html",
-				matchedFile: "/bin/index.html",
-				finalPath: "/bin/",
-			},
-			{
-				title: "/bin%2F -> 200 (with /bin%2F)",
-				files: ["/bin%2F", "/bin/index.html"],
-				requestPath: "/bin%2F",
-				matchedFile: "/bin%2F",
-				finalPath: "/bin%2F",
-			},
-			{
-				title: "/bin/ -> 200 (with /bin/index.html not /bin%2F",
-				files: ["/bin%2F", "/bin/index.html"],
-				requestPath: "/bin/",
-				matchedFile: "/bin/index.html",
-				finalPath: "/bin/",
-			},
-			{
-				title: "/bin/index -> /bin/ 307 (with /bin/index.html)",
-				files: ["/bin%2F", "/bin/index.html"],
-				requestPath: "/bin/index",
-				matchedFile: "/bin/index.html",
-				finalPath: "/bin/",
-			},
-			{
-				title: "/bin/index.html -> /bin/ 307 (with /bin/index.html)",
-				files: ["/bin%2F", "/bin/index.html"],
-				requestPath: "/bin/index.html",
-				matchedFile: "/bin/index.html",
-				finalPath: "/bin/",
-			},
-			// doesn't force a trailing slash here because it would redirect to /file-bin.html
-			{
-				title: "/file-bin -> 200",
-				files: ["/file-bin", "/file-bin.html"],
-				requestPath: "/file-bin",
-				matchedFile: "/file-bin",
-				finalPath: "/file-bin",
-			},
-			{
-				title: "/file-bin.html -> /file-bin/ 307 (with /file-bin.html)",
-				files: ["/file-bin", "/file-bin.html"],
-				requestPath: "/file-bin.html",
-				matchedFile: "/file-bin.html",
-				finalPath: "/file-bin/",
-			},
-			{
-				title: "/file-bin/ -> 200",
-				files: ["/file-bin", "/file-bin.html"],
-				requestPath: "/file-bin/",
-				matchedFile: "/file-bin.html",
-				finalPath: "/file-bin/",
-			},
-			{
-				title: "/file-bin/index -> /file-bin/ 307 (with /file-bin.html)",
-				files: ["/file-bin", "/file-bin.html"],
-				requestPath: "/file-bin/index",
-				matchedFile: "/file-bin.html",
-				finalPath: "/file-bin/",
-			},
-			{
-				title: "/file-bin/index.html -> /file-bin/ 307 (with /file-bin.html)",
-				files: ["/file-bin", "/file-bin.html"],
-				requestPath: "/file-bin/index.html",
-				matchedFile: "/file-bin.html",
-				finalPath: "/file-bin/",
-			},
-		],
-	},
-	{
-		html_handling: "none",
-		cases: [
-			{
-				title: "/ -> 404",
-				files: ["/index.html"],
-				requestPath: "/",
-			},
-			{
-				title: "/index -> 404",
-				files: ["/index.html"],
-				requestPath: "/index",
-			},
-			{
-				title: "/index.html -> 200",
-				files: ["/index.html"],
-				requestPath: "/index.html",
-				matchedFile: "/index.html",
-				finalPath: "/index.html",
-			},
-			{
-				title: "/both -> 404",
-				files: ["/both.html", "/both/index.html"],
-				requestPath: "/both",
-			},
-			{
-				title: "/both.html -> 200",
-				files: ["/both.html", "/both/index.html"],
-				requestPath: "/both.html",
-				matchedFile: "/both.html",
-				finalPath: "/both.html",
-			},
-			{
-				title: "/both/ -> 404",
-				files: ["/both.html", "/both/index.html"],
-				requestPath: "/both/",
-			},
-			{
-				title: "/both/index.html -> 200",
-				files: ["/both.html", "/both/index.html"],
-				requestPath: "/both/index.html",
-				matchedFile: "/both/index.html",
-				finalPath: "/both/index.html",
-			},
-			{
-				title: "/file/index.html -> 404",
-				files: ["/file.html"],
-				requestPath: "/file/index.html",
-			},
-			{
-				title: "/folder.html -> 404",
-				files: ["/folder/index.html"],
-				requestPath: "/folder.html",
-			},
-			{
-				title: "/bin -> 404",
-				files: ["/bin%2F", "/bin/index.html"],
-				requestPath: "/bin",
-			},
-			{
-				title: "/bin.html -> 404",
-				files: ["/bin%2F", "/bin/index.html"],
-				requestPath: "/bin.html",
-			},
-			{
-				title: "/bin%2F -> 200",
-				files: ["/bin%2F", "/bin/index.html"],
-				requestPath: "/bin%2F",
-				matchedFile: "/bin%2F",
-				finalPath: "/bin%2F",
-			},
-			{
-				title: "/bin/ -> 404",
-				files: ["/bin%2F", "/bin/index.html"],
-				requestPath: "/bin/",
-			},
-			{
-				title: "/bin/index -> 404",
-				files: ["/bin%2F", "/bin/index.html"],
-				requestPath: "/bin/index",
-			},
-			{
-				title: "/file-bin -> 200",
-				files: ["/file-bin", "/file-bin.html"],
-				requestPath: "/file-bin",
-				matchedFile: "/file-bin",
-				finalPath: "/file-bin",
-			},
-			{
-				title: "/file-bin.html -> 200",
-				files: ["/file-bin", "/file-bin.html"],
-				requestPath: "/file-bin.html",
-				matchedFile: "/file-bin.html",
-				finalPath: "/file-bin.html",
-			},
-			{
-				title: "/file-bin/ -> 404",
-				files: ["/file-bin", "/file-bin.html"],
-				requestPath: "/file-bin/",
-			},
-			{
-				title: "/file-bin/index -> 404",
-				files: ["/file-bin", "/file-bin.html"],
-				requestPath: "/file-bin/index",
-			},
-			{
-				title: "/file-bin/index.html -> 404",
-				files: ["/file-bin", "/file-bin.html"],
-				requestPath: "/file-bin/index.html",
-			},
-		],
+		title: "encoding options",
+		suite: encodingTestCases,
 	},
 ];
 
-describe("htmlHanding options", () => {
+describe.each(testSuites)("$title", ({ title, suite }) => {
 	beforeEach(() => {
 		vi.mocked(getAssetWithMetadataFromKV).mockImplementation(
 			() =>
@@ -794,7 +58,7 @@ describe("htmlHanding options", () => {
 	afterEach(() => {
 		vi.mocked(getAssetWithMetadataFromKV).mockRestore();
 	});
-	describe.each(testCases)(`$html_handling`, ({ html_handling, cases }) => {
+	describe.each(suite)(`$html_handling`, ({ html_handling, cases }) => {
 		beforeEach(() => {
 			vi.mocked(applyConfigurationDefaults).mockImplementation(() => {
 				return {
@@ -815,7 +79,6 @@ describe("htmlHanding options", () => {
 						undefined,
 						matchedFile
 					);
-					console.dir(response.status);
 					expect(response.status).toBe(200);
 					expect(response.url).toBe(BASE_URL + finalPath);
 					// can't check intermediate 307 directly:
diff --git a/fixtures/asset-config/test-cases/encoding-test-cases.ts b/fixtures/asset-config/test-cases/encoding-test-cases.ts
new file mode 100644
index 000000000000..0da5719f1947
--- /dev/null
+++ b/fixtures/asset-config/test-cases/encoding-test-cases.ts
@@ -0,0 +1,631 @@
+import { TestCase } from "../html-handling.test";
+
+export const encodingTestCases: {
+	html_handling:
+		| "auto-trailing-slash"
+		| "drop-trailing-slash"
+		| "force-trailing-slash"
+		| "none";
+	cases: TestCase[];
+}[] = [
+	{
+		html_handling: "auto-trailing-slash",
+		cases: [
+			{
+				title: "/[boop] -> /%5Bboop%5D 307 (with /[boop].html)",
+				files: ["/[boop].html"],
+				requestPath: "/[boop]",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/%5Bboop%5D -> 200 (with /[boop].html)",
+				files: ["/[boop].html"],
+				requestPath: "/%5Bboop%5D",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			// auto-trailing-slash html handling still works
+			{
+				title: "/%5Bboop%5D.html -> /%5Bboop%5D 307 (with /[boop].html)",
+				files: ["/[boop].html"],
+				requestPath: "/%5Bboop%5D.html",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/[boop].html -> /%5Bboop%5D 307 (with /[boop].html)",
+				files: ["/[boop].html"],
+				requestPath: "/[boop].html",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/%5Bboop%5D/ -> /%5Bboop%5D 307 (with /[boop].html)",
+				files: ["/[boop].html"],
+				requestPath: "/%5Bboop%5D/",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/[boop]/ -> /%5Bboop%5D 307 (with /[boop].html)",
+				files: ["/[boop].html"],
+				requestPath: "/[boop]/",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/[boop] -> /%5Bboop%5D 307 (with /[boop].html)",
+				files: ["/[boop].html", "/[boop]/index.html"],
+				requestPath: "/[boop]",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/%5Bboop%5D -> 200 (with /[boop].html)",
+				files: ["/[boop].html", "/[boop]/index.html"],
+				requestPath: "/%5Bboop%5D",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/[boop].html -> /%5Bboop%5D 307 (with /[boop].html)",
+				files: ["/[boop].html", "/[boop]/index.html"],
+				requestPath: "/[boop].html",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/%5Bboop%5D.html -> /%5Bboop%5D 307 (with /[boop].html)",
+				files: ["/[boop].html", "/[boop]/index.html"],
+				requestPath: "/%5Bboop%5D.html",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/[boop]/ -> /%5Bboop%5D/ 307 (with /[boop]/index.html)",
+				files: ["/[boop].html", "/[boop]/index.html"],
+				requestPath: "/[boop]/",
+				matchedFile: "/[boop]/index.html",
+				finalPath: "/%5Bboop%5D/",
+			},
+			{
+				title: "/%5Bboop%5D/ -> 200 (with /[boop]/index.html)",
+				files: ["/[boop].html", "/[boop]/index.html"],
+				requestPath: "/%5Bboop%5D/",
+				matchedFile: "/[boop]/index.html",
+				finalPath: "/%5Bboop%5D/",
+			},
+			{
+				title:
+					"/[boop]/index.html -> /%5Bboop%5D/ 307 (with /[boop]/index.html)",
+				files: ["/[boop].html", "/[boop]/index.html"],
+				requestPath: "/[boop]/index.html",
+				matchedFile: "/[boop]/index.html",
+				finalPath: "/%5Bboop%5D/",
+			},
+			{
+				title:
+					"/%5Bboop%5D/index.html -> /%5Bboop%5D/ 307 (with /[boop]/index.html)",
+				files: ["/[boop].html", "/[boop]/index.html"],
+				requestPath: "/%5Bboop%5D/index.html",
+				matchedFile: "/[boop]/index.html",
+				finalPath: "/%5Bboop%5D/",
+			},
+			// paths with a mix of encoded and unencoded characters
+			{
+				title:
+					"/beep/[b%C3%B2op] -> /beep/%5Bb%C3%B2op%5D 307 (with /beep/[bòop].html)",
+				files: ["/beep/[bòop].html"],
+				requestPath: "/beep/[b%C3%B2op]",
+				matchedFile: "/beep/[bòop].html",
+				finalPath: "/beep/%5Bb%C3%B2op%5D",
+			},
+			// user-encoded paths should only be accessible at the (double) encoded path
+			{
+				title: "/[boop] -> /%5Bboop%5D 307 (with /[boop].html)",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/[boop]",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/[boop].html -> /%5Bboop%5D 307 (with /[boop].html)",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/[boop].html",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/%5Bboop%5D -> 200 (with /[boop].html)",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/%5Bboop%5D",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/%5Bboop%5D.html -> /%5Bboop%5D 307 (with /[boop].html)",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/%5Bboop%5D.html",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/%5Bboop%5D -> 200 (with /[boop].html)",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/%5Bboop%5D",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/%255Bboop%255D -> 200 (with /%5Bboop%5D.html)",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/%255Bboop%255D",
+				matchedFile: "/%5Bboop%5D.html",
+				finalPath: "/%255Bboop%255D",
+			},
+			{
+				title:
+					"/%255Bboop%255D.html -> /%255Bboop%255D 307 (with /%5Bboop%5D.html)",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/%255Bboop%255D.html",
+				matchedFile: "/%5Bboop%5D.html",
+				finalPath: "/%255Bboop%255D",
+			},
+			{
+				title: "/beep?boop -> 404",
+				files: ["/beep?boop.html"],
+				requestPath: "/beep?boop",
+			},
+			{
+				title: "/beep%3Fboop -> 200 (with /beep?boop.html)",
+				files: ["/beep?boop.html"],
+				requestPath: "/beep%3Fboop",
+				matchedFile: "/beep?boop.html",
+				finalPath: "/beep%3Fboop",
+			},
+			{
+				title: "/beep%3Fboop/ -> /beep%3Fboop 307 (with /beep?boop.html)",
+				files: ["/beep?boop.html"],
+				requestPath: "/beep%3Fboop/",
+				matchedFile: "/beep?boop.html",
+				finalPath: "/beep%3Fboop",
+			},
+		],
+	},
+	{
+		html_handling: "drop-trailing-slash",
+		cases: [
+			{
+				title: "/[boop] -> /%5Bboop%5D 307 (with /[boop].html)",
+				files: ["/[boop].html"],
+				requestPath: "/[boop]",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/%5Bboop%5D -> 200 (with /[boop].html)",
+				files: ["/[boop].html"],
+				requestPath: "/%5Bboop%5D",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			// drop-trailing-slash html handling still works
+			{
+				title: "/%5Bboop%5D.html -> /%5Bboop%5D 307 (with /[boop].html)",
+				files: ["/[boop].html"],
+				requestPath: "/%5Bboop%5D.html",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/[boop].html -> /%5Bboop%5D 307 (with /[boop].html)",
+				files: ["/[boop].html"],
+				requestPath: "/[boop].html",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/%5Bboop%5D/ -> /%5Bboop%5D 307 (with /[boop].html)",
+				files: ["/[boop].html"],
+				requestPath: "/%5Bboop%5D/",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/[boop]/ -> /%5Bboop%5D 307 (with /[boop].html)",
+				files: ["/[boop].html"],
+				requestPath: "/[boop]/",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/[boop] -> /%5Bboop%5D 307 (with /[boop].html)",
+				files: ["/[boop].html", "/[boop]/index.html"],
+				requestPath: "/[boop]",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/%5Bboop%5D -> 200 (with /[boop].html)",
+				files: ["/[boop].html", "/[boop]/index.html"],
+				requestPath: "/%5Bboop%5D",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/[boop].html -> /%5Bboop%5D 307 (with /[boop].html)",
+				files: ["/[boop].html", "/[boop]/index.html"],
+				requestPath: "/[boop].html",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/%5Bboop%5D.html -> /%5Bboop%5D 307 (with /[boop].html)",
+				files: ["/[boop].html", "/[boop]/index.html"],
+				requestPath: "/%5Bboop%5D.html",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/[boop]/ -> /%5Bboop%5D 307 (with /[boop].html)",
+				files: ["/[boop].html", "/[boop]/index.html"],
+				requestPath: "/[boop]/",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/%5Bboop%5D/ -> /%5Bboop%5D 307 (with /[boop].html)",
+				files: ["/[boop].html", "/[boop]/index.html"],
+				requestPath: "/%5Bboop%5D/",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title:
+					"/[boop]/index.html -> /%5Bboop%5D/index.html 307 (with /[boop]/index.html)",
+				files: ["/[boop].html", "/[boop]/index.html"],
+				requestPath: "/[boop]/index.html",
+				matchedFile: "/[boop]/index.html",
+				finalPath: "/%5Bboop%5D/index.html",
+			},
+			{
+				title: "/%5Bboop%5D/index.html -> 200 (with /[boop]/index.html)",
+				files: ["/[boop].html", "/[boop]/index.html"],
+				requestPath: "/%5Bboop%5D/index.html",
+				matchedFile: "/[boop]/index.html",
+				finalPath: "/%5Bboop%5D/index.html",
+			},
+			// paths with a mix of encoded and unencoded characters
+			{
+				title:
+					"/beep/[b%C3%B2op] -> /beep/%5Bb%C3%B2op%5D 307 (with /beep/[bòop].html)",
+				files: ["/beep/[bòop].html"],
+				requestPath: "/beep/[b%C3%B2op]",
+				matchedFile: "/beep/[bòop].html",
+				finalPath: "/beep/%5Bb%C3%B2op%5D",
+			},
+			// user-encoded paths should only be accessible at the (double) encoded path
+			{
+				title: "/[boop] -> /%5Bboop%5D 307 (with /[boop].html)",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/[boop]",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/[boop].html -> /%5Bboop%5D 307 (with /[boop].html)",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/[boop].html",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/%5Bboop%5D -> 200 (with /[boop].html)",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/%5Bboop%5D",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/%5Bboop%5D.html -> /%5Bboop%5D 307 (with /[boop].html)",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/%5Bboop%5D.html",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/%5Bboop%5D -> 200 (with /[boop].html)",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/%5Bboop%5D",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/%255Bboop%255D -> 200 (with /%5Bboop%5D.html)",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/%255Bboop%255D",
+				matchedFile: "/%5Bboop%5D.html",
+				finalPath: "/%255Bboop%255D",
+			},
+			{
+				title:
+					"/%255Bboop%255D.html -> /%255Bboop%255D 307 (with /%5Bboop%5D.html)",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/%255Bboop%255D.html",
+				matchedFile: "/%5Bboop%5D.html",
+				finalPath: "/%255Bboop%255D",
+			},
+			{
+				title: "/beep?boop -> 404",
+				files: ["/beep?boop.html"],
+				requestPath: "/beep?boop",
+			},
+			{
+				title: "/beep%3Fboop -> 200 (with /beep?boop.html)",
+				files: ["/beep?boop.html"],
+				requestPath: "/beep%3Fboop",
+				matchedFile: "/beep?boop.html",
+				finalPath: "/beep%3Fboop",
+			},
+			{
+				title: "/beep%3Fboop/ -> /beep%3Fboop 307 (with /beep?boop.html)",
+				files: ["/beep?boop.html"],
+				requestPath: "/beep%3Fboop/",
+				matchedFile: "/beep?boop.html",
+				finalPath: "/beep%3Fboop",
+			},
+		],
+	},
+	{
+		html_handling: "force-trailing-slash",
+		cases: [
+			{
+				title: "/%5Bboop%5D/ -> 200 (with /[boop].html)",
+				files: ["/[boop].html"],
+				requestPath: "/%5Bboop%5D/",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D/",
+			},
+			{
+				title: "/[boop]/ -> /%5Bboop%5D/ 307 (with /[boop].html)",
+				files: ["/[boop].html"],
+				requestPath: "/[boop]/",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D/",
+			},
+			// force-trailing-slash html handling still works
+			{
+				title: "/[boop] -> /%5Bboop%5D/ 307 (with /[boop]/index.html)",
+				files: ["/[boop].html", "/[boop]/index.html"],
+				requestPath: "/[boop]",
+				matchedFile: "/[boop]/index.html",
+				finalPath: "/%5Bboop%5D/",
+			},
+			{
+				title: "/%5Bboop%5D -> /%5Bboop%5D/ 307 (with /[boop]/index.html)",
+				files: ["/[boop].html", "/[boop]/index.html"],
+				requestPath: "/%5Bboop%5D",
+				matchedFile: "/[boop]/index.html",
+				finalPath: "/%5Bboop%5D/",
+			},
+			{
+				title: "/[boop].html -> /%5Bboop%5D.html 307 (with /[boop].html)",
+				files: ["/[boop].html", "/[boop]/index.html"],
+				requestPath: "/[boop].html",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D.html",
+			},
+			{
+				title: "/%5Bboop%5D.html -> 200 (with /[boop].html)",
+				files: ["/[boop].html", "/[boop]/index.html"],
+				requestPath: "/%5Bboop%5D.html",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D.html",
+			},
+			{
+				title: "/[boop]/ -> /%5Bboop%5D/ 307 (with /[boop]/index.html)",
+				files: ["/[boop].html", "/[boop]/index.html"],
+				requestPath: "/[boop]/",
+				matchedFile: "/[boop]/index.html",
+				finalPath: "/%5Bboop%5D/",
+			},
+			{
+				title: "/%5Bboop%5D/ -> 200 (with /[boop]/index.html)",
+				files: ["/[boop].html", "/[boop]/index.html"],
+				requestPath: "/%5Bboop%5D/",
+				matchedFile: "/[boop]/index.html",
+				finalPath: "/%5Bboop%5D/",
+			},
+			{
+				title:
+					"/[boop]/index.html -> /%5Bboop%5D/ 307 (with /[boop]/index.html)",
+				files: ["/[boop].html", "/[boop]/index.html"],
+				requestPath: "/[boop]/index.html",
+				matchedFile: "/[boop]/index.html",
+				finalPath: "/%5Bboop%5D/",
+			},
+			{
+				title:
+					"/%5Bboop%5D/index.html -> /%5Bboop%5D/ 307 (with /[boop]/index.html)",
+				files: ["/[boop].html", "/[boop]/index.html"],
+				requestPath: "/%5Bboop%5D/index.html",
+				matchedFile: "/[boop]/index.html",
+				finalPath: "/%5Bboop%5D/",
+			},
+			// paths with a mix of encoded and unencoded characters
+			{
+				title:
+					"/beep/[b%C3%B2op]/ -> /beep/%5Bb%C3%B2op%5D/ 307 (with /beep/[bòop].html)",
+				files: ["/beep/[bòop].html"],
+				requestPath: "/beep/[b%C3%B2op]/",
+				matchedFile: "/beep/[bòop].html",
+				finalPath: "/beep/%5Bb%C3%B2op%5D/",
+			},
+			// user-encoded paths should only be accessible at the (double) encoded path
+			{
+				title: "/[boop] -> /%5Bboop%5D/ 307 (with /[boop].html)",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/[boop]",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D/",
+			},
+			{
+				title: "/[boop].html -> /%5Bboop%5D/ 307 (with /[boop].html)",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/[boop].html",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D/",
+			},
+			{
+				title: "/%5Bboop%5D -> /%5Bboop%5D/ 307 (with /[boop].html)",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/%5Bboop%5D",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D/",
+			},
+			{
+				title: "/%5Bboop%5D.html -> /%5Bboop%5D/ 307 (with /[boop].html)",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/%5Bboop%5D.html",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D/",
+			},
+			{
+				title: "/%5Bboop%5D -> /%5Bboop%5D/ 307 (with /[boop].html)",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/%5Bboop%5D",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D/",
+			},
+			{
+				title:
+					"/%255Bboop%255D -> /%255Bboop%255D/ 307 (with /%5Bboop%5D.html)",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/%255Bboop%255D",
+				matchedFile: "/%5Bboop%5D.html",
+				finalPath: "/%255Bboop%255D/",
+			},
+			{
+				title:
+					"/%255Bboop%255D.html -> /%255Bboop%255D/ 307 (with /%5Bboop%5D.html)",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/%255Bboop%255D.html",
+				matchedFile: "/%5Bboop%5D.html",
+				finalPath: "/%255Bboop%255D/",
+			},
+			{
+				title: "/beep?boop/ -> 404",
+				files: ["/beep?boop.html"],
+				requestPath: "/beep?boop/",
+			},
+			{
+				title: "/beep%3Fboop -> /beep%3Fboop/ 307 (with /beep?boop.html)",
+				files: ["/beep?boop.html"],
+				requestPath: "/beep%3Fboop",
+				matchedFile: "/beep?boop.html",
+				finalPath: "/beep%3Fboop/",
+			},
+			{
+				title: "/beep%3Fboop/ -> 200 (with /beep?boop.html)",
+				files: ["/beep?boop.html"],
+				requestPath: "/beep%3Fboop/",
+				matchedFile: "/beep?boop.html",
+				finalPath: "/beep%3Fboop/",
+			},
+		],
+	},
+	{
+		html_handling: "none",
+		cases: [
+			{
+				title: "/[boop] -> 404",
+				files: ["/[boop].html"],
+				requestPath: "/[boop]",
+			},
+			{
+				title: "/%5Bboop%5D -> 404",
+				files: ["/[boop].html"],
+				requestPath: "/%5Bboop%5D",
+			},
+			// encoding still operates when html_handling is set to 'none'
+			{
+				title: "/[boop].html -> /%5Bboop%5D.html 307 (with /[boop].html)",
+				files: ["/[boop].html"],
+				requestPath: "/[boop].html",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D.html",
+			},
+			{
+				title: "/%5Bboop%5D.html -> 200 (with /[boop].html)",
+				files: ["/[boop].html"],
+				requestPath: "/%5Bboop%5D.html",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D.html",
+			},
+			// mix of encoded and unencoded paths
+			{
+				title:
+					"/beep/[b%C3%B2op].html -> /beep/%5Bb%C3%B2op%5D.html 307 (with /beep/[bòop].html)",
+				files: ["/beep/[bòop].html"],
+				requestPath: "/beep/[b%C3%B2op].html",
+				matchedFile: "/beep/[bòop].html",
+				finalPath: "/beep/%5Bb%C3%B2op%5D.html",
+			},
+			// user-encoded paths should only be accessible at the (double) encoded path
+			{
+				title: "/[boop].html -> /%5Bboop%5D.html 307 (with /[boop].html)",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/[boop].html",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D.html",
+			},
+			{
+				title: "/%5Bboop%5D.html -> 200 (with /[boop].html)",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/%5Bboop%5D.html",
+				matchedFile: "/[boop].html",
+				finalPath: "/%5Bboop%5D.html",
+			},
+			{
+				title: "/[boop] -> 404",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/[boop]",
+			},
+			{
+				title: "/%5Bboop%5D -> 404",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/%5Bboop%5D",
+			},
+			{
+				title: "/%255Bboop%255D.html -> 200 (with /%5Bboop%5D.html)",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/%255Bboop%255D.html",
+				matchedFile: "/%5Bboop%5D.html",
+				finalPath: "/%255Bboop%255D.html",
+			},
+			{
+				title: "/%255Bboop%255D -> 404",
+				files: ["/%5Bboop%5D.html", "/[boop].html"],
+				requestPath: "/%255Bboop%255D",
+			},
+			{
+				title: "/beep?boop/ -> 404",
+				files: ["/beep?boop.html"],
+				requestPath: "/beep?boop/",
+			},
+			{
+				title: "/beep%3Fboop.html -> 200 (with /beep?boop.html)",
+				files: ["/beep?boop.html"],
+				requestPath: "/beep%3Fboop.html",
+				matchedFile: "/beep?boop.html",
+				finalPath: "/beep%3Fboop.html",
+			},
+			{
+				title: "/beep%3Fboop -> 404",
+				files: ["/beep?boop.html"],
+				requestPath: "/beep%3Fboop",
+			},
+		],
+	},
+];
diff --git a/fixtures/asset-config/test-cases/html-handling-test-cases.ts b/fixtures/asset-config/test-cases/html-handling-test-cases.ts
new file mode 100644
index 000000000000..8c65ebac26aa
--- /dev/null
+++ b/fixtures/asset-config/test-cases/html-handling-test-cases.ts
@@ -0,0 +1,788 @@
+import { TestCase } from "../html-handling.test";
+
+export const htmlHandlingTestCases: {
+	html_handling:
+		| "auto-trailing-slash"
+		| "drop-trailing-slash"
+		| "force-trailing-slash"
+		| "none";
+	cases: TestCase[];
+}[] = [
+	{
+		html_handling: "auto-trailing-slash",
+		cases: [
+			{
+				title: "/ -> 200 (with /index.html)",
+				files: ["/index.html"],
+				requestPath: "/index.html",
+				matchedFile: "/index.html",
+				finalPath: "/",
+			},
+			{
+				title: "/index -> / 307 (with /index.html)",
+				files: ["/index.html"],
+				requestPath: "/index",
+				matchedFile: "/index.html",
+				finalPath: "/",
+			},
+			{
+				title: "/index.html -> / 307 (with /index.html)",
+				files: ["/index.html"],
+				requestPath: "/index.html",
+				matchedFile: "/index.html",
+				finalPath: "/",
+			},
+			{
+				title: "/both -> 200 (with /both.html)",
+				files: ["/both.html", "/both/index.html"],
+				requestPath: "/both",
+				matchedFile: "/both.html",
+				finalPath: "/both",
+			},
+			{
+				title: "/both.html -> /both 307 (with /both.html)",
+				files: ["/both.html", "/both/index.html"],
+				requestPath: "/both.html",
+				matchedFile: "/both.html",
+				finalPath: "/both",
+			},
+			{
+				title: "/both/ -> 200 (with /both/index.html)",
+				files: ["/both.html", "/both/index.html"],
+				requestPath: "/both/",
+				matchedFile: "/both/index.html",
+				finalPath: "/both/",
+			},
+			{
+				title: "/both/index.html -> /both/ 307 (with /both/index.html)",
+				files: ["/both.html", "/both/index.html"],
+				requestPath: "/both/index.html",
+				matchedFile: "/both/index.html",
+				finalPath: "/both/",
+			},
+			{
+				title: "/both/index -> /both/ 307 (with /both/index.html)",
+				files: ["/both.html", "/both/index.html"],
+				requestPath: "/both/index",
+				matchedFile: "/both/index.html",
+				finalPath: "/both/",
+			},
+			{
+				title: "/file -> 200 (with file.html)",
+				files: ["/file.html"],
+				requestPath: "/file",
+				matchedFile: "/file.html",
+				finalPath: "/file",
+			},
+			{
+				title: "/file.html -> /file 307 (with file.html)",
+				files: ["/file.html"],
+				requestPath: "/file.html",
+				matchedFile: "/file.html",
+				finalPath: "/file",
+			},
+			{
+				title: "/file/ -> /file 307 (with file.html)",
+				files: ["/file.html"],
+				requestPath: "/file/",
+				matchedFile: "/file.html",
+				finalPath: "/file",
+			},
+			{
+				title: "/file/index -> /file 307 (with file.html)",
+				files: ["/file.html"],
+				requestPath: "/file/index",
+				matchedFile: "/file.html",
+				finalPath: "/file",
+			},
+			{
+				title: "/file/index.html -> /file 307 (with file.html)",
+				files: ["/file.html"],
+				requestPath: "/file/index.html",
+				matchedFile: "/file.html",
+				finalPath: "/file",
+			},
+			{
+				title: "/folder -> /folder/ 307 (with /folder/index.html)",
+				files: ["/folder/index.html"],
+				requestPath: "/folder",
+				matchedFile: "/folder/index.html",
+				finalPath: "/folder/",
+			},
+			{
+				title: "/folder.html -> /folder/ 307 (with /folder/index.html)",
+				files: ["/folder/index.html"],
+				requestPath: "/folder.html",
+				matchedFile: "/folder/index.html",
+				finalPath: "/folder/",
+			},
+			{
+				title: "/folder/ -> 200 (with /folder/index.html)",
+				files: ["/folder/index.html"],
+				requestPath: "/folder/",
+				matchedFile: "/folder/index.html",
+				finalPath: "/folder/",
+			},
+			{
+				title: "/folder/index -> /folder/ 307 (with /folder/index.html)",
+				files: ["/folder/index.html"],
+				requestPath: "/folder/index",
+				matchedFile: "/folder/index.html",
+				finalPath: "/folder/",
+			},
+			{
+				title: "/folder/index.html -> /folder/ 307 (with /folder/index.html)",
+				files: ["/folder/index.html"],
+				requestPath: "/folder/index.html",
+				matchedFile: "/folder/index.html",
+				finalPath: "/folder/",
+			},
+			// see encoding tests, but tldr only accessible at the (double) encoded path
+			{
+				title: "/bin -> /bin/ 307 (with /bin/index.html)",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin",
+				matchedFile: "/bin/index.html",
+				finalPath: "/bin/",
+			},
+			{
+				title: "/bin.html -> /bin/ 307 (with /bin/index.html)",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin.html",
+				matchedFile: "/bin/index.html",
+				finalPath: "/bin/",
+			},
+			// This is a bit rogue, but then so is the test case
+			{
+				title: "/bin%2F -> /bin 307 (with /bin/index.html)",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin%2F",
+				matchedFile: "/bin/index.html",
+				finalPath: "/bin/",
+			},
+			{
+				title: "/bin%252F -> 200 (with /bin%2F)",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin%252F",
+				matchedFile: "/bin%2F",
+				finalPath: "/bin%252F",
+			},
+			{
+				title: "/bin/ -> 200 (with /bin/index.html not /bin%2F",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin/",
+				matchedFile: "/bin/index.html",
+				finalPath: "/bin/",
+			},
+			{
+				title: "/bin/index -> 307 /bin/ (with /bin/index.html)",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin/index",
+				matchedFile: "/bin/index.html",
+				finalPath: "/bin/",
+			},
+			{
+				title: "/bin/index.html -> 307 /bin/ (with /bin/index.html)",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin/index.html",
+				matchedFile: "/bin/index.html",
+				finalPath: "/bin/",
+			},
+			// prefers exact match
+			{
+				title: "/file-bin -> 200 ",
+				files: ["/file-bin", "/file-bin.html"],
+				requestPath: "/file-bin",
+				matchedFile: "/file-bin",
+				finalPath: "/file-bin",
+			},
+			// (doesn't rewrite if resulting path would match another asset)
+			{
+				title: "/file-bin.html -> 200 ",
+				files: ["/file-bin", "/file-bin.html"],
+				requestPath: "/file-bin.html",
+				matchedFile: "/file-bin.html",
+				finalPath: "/file-bin.html",
+			},
+			// (finds file-bin.html --rewrite--> /file-bin, but /file-bin exists)
+			{
+				title: "/file-bin/ -> 404 ",
+				files: ["/file-bin", "/file-bin.html"],
+				requestPath: "/file-bin/",
+			},
+			{
+				title: "/file-bin/index -> 404 ",
+				files: ["/file-bin", "/file-bin.html"],
+				requestPath: "/file-bin/index",
+			},
+			{
+				title: "/file-bin/index.html -> 404 ",
+				files: ["/file-bin", "/file-bin.html"],
+				requestPath: "/file-bin/index.html",
+			},
+		],
+	},
+	{
+		html_handling: "drop-trailing-slash",
+		cases: [
+			// note that we don't drop the "/" if that is the only path component
+			{
+				title: "/ -> 200 (with /index.html)",
+				files: ["/index.html"],
+				requestPath: "/index.html",
+				matchedFile: "/index.html",
+				finalPath: "/",
+			},
+			{
+				title: "/index -> / 307 (with /index.html)",
+				files: ["/index.html"],
+				requestPath: "/index",
+				matchedFile: "/index.html",
+				finalPath: "/",
+			},
+			{
+				title: "/index.html -> / 307 (with /index.html)",
+				files: ["/index.html"],
+				requestPath: "/index.html",
+				matchedFile: "/index.html",
+				finalPath: "/",
+			},
+			{
+				title: "/both -> 200 (with /both.html)",
+				files: ["/both.html", "/both/index.html"],
+				requestPath: "/both",
+				matchedFile: "/both.html",
+				finalPath: "/both",
+			},
+			{
+				title: "/both.html -> /both 307 (with /both.html)",
+				files: ["/both.html", "/both/index.html"],
+				requestPath: "/both.html",
+				matchedFile: "/both.html",
+				finalPath: "/both",
+			},
+			// drops trailing slash and so it tries /both.html first
+			{
+				title: "/both/ -> /both 307 (with /both.html)",
+				files: ["/both.html", "/both/index.html"],
+				requestPath: "/both/",
+				matchedFile: "/both.html",
+				finalPath: "/both",
+			},
+			{
+				title: "/both/index -> 307 (with /both.html)",
+				files: ["/both.html", "/both/index.html"],
+				requestPath: "/both/index",
+				matchedFile: "/both.html",
+				finalPath: "/both",
+			},
+			// can't rewrite /both/index.html: would be /both/ -> /both -> /both.html
+			// ie can only access /both/index.html by exact match
+			{
+				title: "/both/index.html -> 200 (with /both/index.html)",
+				files: ["/both.html", "/both/index.html"],
+				requestPath: "/both/index.html",
+				matchedFile: "/both/index.html",
+				finalPath: "/both/index.html",
+			},
+			{
+				title: "/file -> 200 (with file.html)",
+				files: ["/file.html"],
+				requestPath: "/file",
+				matchedFile: "/file.html",
+				finalPath: "/file",
+			},
+			{
+				title: "/file.html -> /file 307 (with file.html)",
+				files: ["/file.html"],
+				requestPath: "/file.html",
+				matchedFile: "/file.html",
+				finalPath: "/file",
+			},
+			{
+				title: "/file/ -> /file 307 (with file.html)",
+				files: ["/file.html"],
+				requestPath: "/file/",
+				matchedFile: "/file.html",
+				finalPath: "/file",
+			},
+			{
+				title: "/file/index -> /file 307 (with file.html)",
+				files: ["/file.html"],
+				requestPath: "/file/index",
+				matchedFile: "/file.html",
+				finalPath: "/file",
+			},
+			{
+				title: "/file/index.html -> /file 307 (with file.html)",
+				files: ["/file.html"],
+				requestPath: "/file/index.html",
+				matchedFile: "/file.html",
+				finalPath: "/file",
+			},
+			{
+				title: "/folder -> 200 (with /folder/index.html)",
+				files: ["/folder/index.html"],
+				requestPath: "/folder",
+				matchedFile: "/folder/index.html",
+				finalPath: "/folder",
+			},
+			{
+				title: "/folder.html -> /folder 307 (with /folder/index.html)",
+				files: ["/folder/index.html"],
+				requestPath: "/folder.html",
+				matchedFile: "/folder/index.html",
+				finalPath: "/folder",
+			},
+			{
+				title: "/folder/ -> /folder 307 (with /folder/index.html)",
+				files: ["/folder/index.html"],
+				requestPath: "/folder/",
+				matchedFile: "/folder/index.html",
+				finalPath: "/folder",
+			},
+			{
+				title: "/folder/index -> /folder 307 (with /folder/index.html)",
+				files: ["/folder/index.html"],
+				requestPath: "/folder/index",
+				matchedFile: "/folder/index.html",
+				finalPath: "/folder",
+			},
+			{
+				title: "/folder/index.html -> /folder 307 (with /folder/index.html)",
+				files: ["/folder/index.html"],
+				requestPath: "/folder/index.html",
+				matchedFile: "/folder/index.html",
+				finalPath: "/folder",
+			},
+			{
+				title: "/bin -> 200 (with /bin/index.html)",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin",
+				matchedFile: "/bin/index.html",
+				finalPath: "/bin",
+			},
+			{
+				title: "/bin.html -> /bin 307 (with /bin/index.html)",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin.html",
+				matchedFile: "/bin/index.html",
+				finalPath: "/bin",
+			},
+			// This is a bit rogue, but then so is the test case
+			{
+				title: "/bin%2F -> /bin 307 (with /bin/index.html)",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin%2F",
+				matchedFile: "/bin/index.html",
+				finalPath: "/bin",
+			},
+			{
+				title: "/bin%252F -> 200 (with /bin%2F)",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin%252F",
+				matchedFile: "/bin%2F",
+				finalPath: "/bin%252F",
+			},
+			{
+				title: "/bin/ -> /bin 307 (with /bin/index.html not /bin%2F",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin/",
+				matchedFile: "/bin/index.html",
+				finalPath: "/bin",
+			},
+			{
+				title: "/bin/index -> /bin 307 (with /bin/index.html not /bin%2F",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin/index",
+				matchedFile: "/bin/index.html",
+				finalPath: "/bin",
+			},
+			{
+				title: "/bin/index.html -> /bin 307 (with /bin/index.html not /bin%2F",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin/index.html",
+				matchedFile: "/bin/index.html",
+				finalPath: "/bin",
+			},
+			{
+				title: "/file-bin -> 200",
+				files: ["/file-bin", "/file-bin.html"],
+				requestPath: "/file-bin",
+				matchedFile: "/file-bin",
+				finalPath: "/file-bin",
+			},
+			// doesn't redirect to /file-bin because that also exists
+			{
+				title: "/file-bin.html -> 200 (with /file-bin.html)",
+				files: ["/file-bin", "/file-bin.html"],
+				requestPath: "/file-bin.html",
+				matchedFile: "/file-bin.html",
+				finalPath: "/file-bin.html",
+			},
+			// 404s because ambiguity between /file-bin or /file-bin.html?
+			{
+				title: "/file-bin/ -> 404",
+				files: ["/file-bin", "/file-bin.html"],
+				requestPath: "/file-bin/",
+			},
+			{
+				title: "/file-bin/index -> 404",
+				files: ["/file-bin", "/file-bin.html"],
+				requestPath: "/file-bin/index",
+			},
+			{
+				title: "/file-bin/index.html -> 404",
+				files: ["/file-bin", "/file-bin.html"],
+				requestPath: "/file-bin/index.html",
+			},
+		],
+	},
+	{
+		html_handling: "force-trailing-slash",
+		cases: [
+			{
+				title: "/ -> 200 (with /index.html)",
+				files: ["/index.html"],
+				requestPath: "/index.html",
+				matchedFile: "/index.html",
+				finalPath: "/",
+			},
+			{
+				title: "/index -> / 307 (with /index.html)",
+				files: ["/index.html"],
+				requestPath: "/index",
+				matchedFile: "/index.html",
+				finalPath: "/",
+			},
+			{
+				title: "/index.html -> / 307 (with /index.html)",
+				files: ["/index.html"],
+				requestPath: "/index.html",
+				matchedFile: "/index.html",
+				finalPath: "/",
+			},
+			// ie tries /both/index.html first
+			{
+				title: "/both -> /both/ 307 (with /both/index.html)",
+				files: ["/both.html", "/both/index.html"],
+				requestPath: "/both",
+				matchedFile: "/both/index.html",
+				finalPath: "/both/",
+			},
+			// can't rewrite /both.html: would be /both -> /both/ -> /both/index.html
+			// ie can only access /both.html by exact match
+			{
+				title: "/both.html -> 200",
+				files: ["/both.html", "/both/index.html"],
+				requestPath: "/both.html",
+				matchedFile: "/both.html",
+				finalPath: "/both.html",
+			},
+			{
+				title: "/both/ -> 200 (with /both/index.html)",
+				files: ["/both.html", "/both/index.html"],
+				requestPath: "/both/",
+				matchedFile: "/both/index.html",
+				finalPath: "/both/",
+			},
+			{
+				title: "/both/index -> /both/ 307 (with /both/index.html)",
+				files: ["/both.html", "/both/index.html"],
+				requestPath: "/both/index",
+				matchedFile: "/both/index.html",
+				finalPath: "/both/",
+			},
+			{
+				title: "/both/index.html -> /both/ 307 (with /both/index.html)",
+				files: ["/both.html", "/both/index.html"],
+				requestPath: "/both/index.html",
+				matchedFile: "/both/index.html",
+				finalPath: "/both/",
+			},
+			// always ends in a trailing slash
+			{
+				title: "/file -> /file/ 307 (with file.html)",
+				files: ["/file.html"],
+				requestPath: "/file",
+				matchedFile: "/file.html",
+				finalPath: "/file/",
+			},
+			{
+				title: "/file.html -> /file/ 307 (with file.html)",
+				files: ["/file.html"],
+				requestPath: "/file.html",
+				matchedFile: "/file.html",
+				finalPath: "/file/",
+			},
+
+			{
+				title: "/file/ -> 200 (with file.html)",
+				files: ["/file.html"],
+				requestPath: "/file/",
+				matchedFile: "/file.html",
+				finalPath: "/file/",
+			},
+			{
+				title: "/file/index -> /file/ 307 (with file.html)",
+				files: ["/file.html"],
+				requestPath: "/file/index",
+				matchedFile: "/file.html",
+				finalPath: "/file/",
+			},
+			{
+				title: "/file/index.html -> /file/ 307 (with file.html)",
+				files: ["/file.html"],
+				requestPath: "/file/index.html",
+				matchedFile: "/file.html",
+				finalPath: "/file/",
+			},
+			{
+				title: "/folder -> /folder/ 307 (with /folder/index.html)",
+				files: ["/folder/index.html"],
+				requestPath: "/folder",
+				matchedFile: "/folder/index.html",
+				finalPath: "/folder/",
+			},
+			{
+				title: "/folder.html -> /folder/ 307 (with /folder/index.html)",
+				files: ["/folder/index.html"],
+				requestPath: "/folder.html",
+				matchedFile: "/folder/index.html",
+				finalPath: "/folder/",
+			},
+			{
+				title: "/folder/ -> 200 (with /folder/index.html)",
+				files: ["/folder/index.html"],
+				requestPath: "/folder/",
+				matchedFile: "/folder/index.html",
+				finalPath: "/folder/",
+			},
+			{
+				title: "/folder/index -> /folder/ 307 (with /folder/index.html)",
+				files: ["/folder/index.html"],
+				requestPath: "/folder/index",
+				matchedFile: "/folder/index.html",
+				finalPath: "/folder/",
+			},
+			{
+				title: "/folder/index.html -> /folder/ 307 (with /folder/index.html)",
+				files: ["/folder/index.html"],
+				requestPath: "/folder/index.html",
+				matchedFile: "/folder/index.html",
+				finalPath: "/folder/",
+			},
+			{
+				title: "/bin -> /bin/ 307 (with /bin/index.html)",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin",
+				matchedFile: "/bin/index.html",
+				finalPath: "/bin/",
+			},
+			{
+				title: "/bin.html -> /bin/ 307 (with /bin/index.html)",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin.html",
+				matchedFile: "/bin/index.html",
+				finalPath: "/bin/",
+			},
+			{
+				title: "/bin%2F -> /bin/ 307 (with /bin%2F)",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin%2F",
+				matchedFile: "/bin/index.html",
+				finalPath: "/bin/",
+			},
+			// This is a bit rogue, but then so is the test case
+			{
+				title: "/bin%2F -> /bin/ 307 (with /bin/index.html)",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin%2F",
+				matchedFile: "/bin/index.html",
+				finalPath: "/bin/",
+			},
+			{
+				title: "/bin%252F -> 200 (with /bin%2F)",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin%252F",
+				matchedFile: "/bin%2F",
+				finalPath: "/bin%252F",
+			},
+			{
+				title: "/bin/ -> 200 (with /bin/index.html not /bin%2F",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin/",
+				matchedFile: "/bin/index.html",
+				finalPath: "/bin/",
+			},
+			{
+				title: "/bin/index -> /bin/ 307 (with /bin/index.html)",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin/index",
+				matchedFile: "/bin/index.html",
+				finalPath: "/bin/",
+			},
+			{
+				title: "/bin/index.html -> /bin/ 307 (with /bin/index.html)",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin/index.html",
+				matchedFile: "/bin/index.html",
+				finalPath: "/bin/",
+			},
+			// doesn't force a trailing slash here because it would redirect to /file-bin.html
+			{
+				title: "/file-bin -> 200",
+				files: ["/file-bin", "/file-bin.html"],
+				requestPath: "/file-bin",
+				matchedFile: "/file-bin",
+				finalPath: "/file-bin",
+			},
+			{
+				title: "/file-bin.html -> /file-bin/ 307 (with /file-bin.html)",
+				files: ["/file-bin", "/file-bin.html"],
+				requestPath: "/file-bin.html",
+				matchedFile: "/file-bin.html",
+				finalPath: "/file-bin/",
+			},
+			{
+				title: "/file-bin/ -> 200",
+				files: ["/file-bin", "/file-bin.html"],
+				requestPath: "/file-bin/",
+				matchedFile: "/file-bin.html",
+				finalPath: "/file-bin/",
+			},
+			{
+				title: "/file-bin/index -> /file-bin/ 307 (with /file-bin.html)",
+				files: ["/file-bin", "/file-bin.html"],
+				requestPath: "/file-bin/index",
+				matchedFile: "/file-bin.html",
+				finalPath: "/file-bin/",
+			},
+			{
+				title: "/file-bin/index.html -> /file-bin/ 307 (with /file-bin.html)",
+				files: ["/file-bin", "/file-bin.html"],
+				requestPath: "/file-bin/index.html",
+				matchedFile: "/file-bin.html",
+				finalPath: "/file-bin/",
+			},
+		],
+	},
+	{
+		html_handling: "none",
+		cases: [
+			{
+				title: "/ -> 404",
+				files: ["/index.html"],
+				requestPath: "/",
+			},
+			{
+				title: "/index -> 404",
+				files: ["/index.html"],
+				requestPath: "/index",
+			},
+			{
+				title: "/index.html -> 200",
+				files: ["/index.html"],
+				requestPath: "/index.html",
+				matchedFile: "/index.html",
+				finalPath: "/index.html",
+			},
+			{
+				title: "/both -> 404",
+				files: ["/both.html", "/both/index.html"],
+				requestPath: "/both",
+			},
+			{
+				title: "/both.html -> 200",
+				files: ["/both.html", "/both/index.html"],
+				requestPath: "/both.html",
+				matchedFile: "/both.html",
+				finalPath: "/both.html",
+			},
+			{
+				title: "/both/ -> 404",
+				files: ["/both.html", "/both/index.html"],
+				requestPath: "/both/",
+			},
+			{
+				title: "/both/index.html -> 200",
+				files: ["/both.html", "/both/index.html"],
+				requestPath: "/both/index.html",
+				matchedFile: "/both/index.html",
+				finalPath: "/both/index.html",
+			},
+			{
+				title: "/file/index.html -> 404",
+				files: ["/file.html"],
+				requestPath: "/file/index.html",
+			},
+			{
+				title: "/folder.html -> 404",
+				files: ["/folder/index.html"],
+				requestPath: "/folder.html",
+			},
+			{
+				title: "/bin -> 404",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin",
+			},
+			{
+				title: "/bin.html -> 404",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin.html",
+			},
+			// encoding is independent of html handling
+			{
+				title: "/bin%2F -> 404",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin%2F", // -> /bin/ -> 404
+			},
+			{
+				title: "/bin%252F -> 200",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin%252F",
+				matchedFile: "/bin%2F",
+				finalPath: "/bin%252F",
+			},
+			{
+				title: "/bin/ -> 404",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin/",
+			},
+			{
+				title: "/bin/index -> 404",
+				files: ["/bin%2F", "/bin/index.html"],
+				requestPath: "/bin/index",
+			},
+			{
+				title: "/file-bin -> 200",
+				files: ["/file-bin", "/file-bin.html"],
+				requestPath: "/file-bin",
+				matchedFile: "/file-bin",
+				finalPath: "/file-bin",
+			},
+			{
+				title: "/file-bin.html -> 200",
+				files: ["/file-bin", "/file-bin.html"],
+				requestPath: "/file-bin.html",
+				matchedFile: "/file-bin.html",
+				finalPath: "/file-bin.html",
+			},
+			{
+				title: "/file-bin/ -> 404",
+				files: ["/file-bin", "/file-bin.html"],
+				requestPath: "/file-bin/",
+			},
+			{
+				title: "/file-bin/index -> 404",
+				files: ["/file-bin", "/file-bin.html"],
+				requestPath: "/file-bin/index",
+			},
+			{
+				title: "/file-bin/index.html -> 404",
+				files: ["/file-bin", "/file-bin.html"],
+				requestPath: "/file-bin/index.html",
+			},
+		],
+	},
+];
diff --git a/fixtures/workers-with-assets-only/public/about/%5Bboop%5D.html b/fixtures/workers-with-assets-only/public/about/%5Bboop%5D.html
new file mode 100644
index 000000000000..3d447362efc7
--- /dev/null
+++ b/fixtures/workers-with-assets-only/public/about/%5Bboop%5D.html
@@ -0,0 +1 @@
+<p>%255Bboop%255D.html</p>
diff --git a/fixtures/workers-with-assets-only/public/about/[boop].html b/fixtures/workers-with-assets-only/public/about/[boop].html
new file mode 100644
index 000000000000..37af005091b5
--- /dev/null
+++ b/fixtures/workers-with-assets-only/public/about/[boop].html
@@ -0,0 +1 @@
+<p>[boop].html</p>
diff --git "a/fixtures/workers-with-assets-only/public/about/[f\303\274nky].txt" "b/fixtures/workers-with-assets-only/public/about/[f\303\274nky].txt"
new file mode 100644
index 000000000000..dbb84844bd43
--- /dev/null
+++ "b/fixtures/workers-with-assets-only/public/about/[f\303\274nky].txt"
@@ -0,0 +1 @@
+This should work.
\ No newline at end of file
diff --git a/fixtures/workers-with-assets-only/tests/index.test.ts b/fixtures/workers-with-assets-only/tests/index.test.ts
index 9737d11b1dba..16a3b2803b8a 100644
--- a/fixtures/workers-with-assets-only/tests/index.test.ts
+++ b/fixtures/workers-with-assets-only/tests/index.test.ts
@@ -149,4 +149,30 @@ describe("[Workers + Assets] static-assets only site`", () => {
 		});
 		expect(response.status).toBe(404);
 	});
+
+	it("should work with encoded path names", async ({ expect }) => {
+		let response = await fetch(`http://${ip}:${port}/about/[fünky].txt`);
+		let text = await response.text();
+		expect(response.status).toBe(200);
+		expect(response.url).toBe(
+			`http://${ip}:${port}/about/%5Bf%C3%BCnky%5D.txt`
+		);
+		expect(text).toContain(`This should work.`);
+
+		response = await fetch(`http://${ip}:${port}/about/[boop]`);
+		text = await response.text();
+		expect(response.status).toBe(200);
+		expect(response.url).toBe(`http://${ip}:${port}/about/%5Bboop%5D`);
+		expect(text).toContain(`[boop].html`);
+
+		response = await fetch(`http://${ip}:${port}/about/%5Bboop%5D`);
+		text = await response.text();
+		expect(response.status).toBe(200);
+		expect(text).toContain(`[boop].html`);
+
+		response = await fetch(`http://${ip}:${port}/about/%255Bboop%255D`);
+		text = await response.text();
+		expect(response.status).toBe(200);
+		expect(text).toContain(`%255Bboop%255D.html`);
+	});
 });
diff --git a/fixtures/workers-with-assets/public/about/%5Bboop%5D.html b/fixtures/workers-with-assets/public/about/%5Bboop%5D.html
new file mode 100644
index 000000000000..7a0e3696b1dc
--- /dev/null
+++ b/fixtures/workers-with-assets/public/about/%5Bboop%5D.html
@@ -0,0 +1 @@
+<p>%5Bboop%5D.html</p>
diff --git a/fixtures/workers-with-assets/public/about/%5Bwomp%5D.html b/fixtures/workers-with-assets/public/about/%5Bwomp%5D.html
new file mode 100644
index 000000000000..de76167b2399
--- /dev/null
+++ b/fixtures/workers-with-assets/public/about/%5Bwomp%5D.html
@@ -0,0 +1 @@
+<p>womp</p>
diff --git a/fixtures/workers-with-assets/public/about/[boop].html b/fixtures/workers-with-assets/public/about/[boop].html
new file mode 100644
index 000000000000..37af005091b5
--- /dev/null
+++ b/fixtures/workers-with-assets/public/about/[boop].html
@@ -0,0 +1 @@
+<p>[boop].html</p>
diff --git a/fixtures/workers-with-assets/tests/index.test.ts b/fixtures/workers-with-assets/tests/index.test.ts
index 1c620282574b..a6de8dfa13e8 100644
--- a/fixtures/workers-with-assets/tests/index.test.ts
+++ b/fixtures/workers-with-assets/tests/index.test.ts
@@ -119,12 +119,29 @@ describe("[Workers + Assets] dynamic site", () => {
 	});
 
 	it("should work with encoded path names", async ({ expect }) => {
-		let response = await fetch(
-			`http://${ip}:${port}/about/%5Bf%C3%BCnky%5D.txt`
-		);
+		let response = await fetch(`http://${ip}:${port}/about/[fünky].txt`);
 		let text = await response.text();
 		expect(response.status).toBe(200);
+		expect(response.url).toBe(
+			`http://${ip}:${port}/about/%5Bf%C3%BCnky%5D.txt`
+		);
 		expect(text).toContain(`This should work.`);
+
+		response = await fetch(`http://${ip}:${port}/about/[boop]`);
+		text = await response.text();
+		expect(response.status).toBe(200);
+		expect(response.url).toBe(`http://${ip}:${port}/about/%5Bboop%5D`);
+		expect(text).toContain(`[boop].html`);
+
+		response = await fetch(`http://${ip}:${port}/about/%5Bboop%5D`);
+		text = await response.text();
+		expect(response.status).toBe(200);
+		expect(text).toContain(`[boop].html`);
+
+		response = await fetch(`http://${ip}:${port}/about/%255Bboop%255D`);
+		text = await response.text();
+		expect(response.status).toBe(200);
+		expect(text).toContain(`%5Bboop%5D.html`);
 	});
 
 	it("should forward all request types to the user Worker if there are *not* assets on that route", async ({
diff --git a/packages/miniflare/src/plugins/assets/index.ts b/packages/miniflare/src/plugins/assets/index.ts
index e3a868f67bce..0f28394ef768 100644
--- a/packages/miniflare/src/plugins/assets/index.ts
+++ b/packages/miniflare/src/plugins/assets/index.ts
@@ -3,12 +3,12 @@ import fs from "node:fs/promises";
 import path from "node:path";
 import {
 	CONTENT_HASH_OFFSET,
-	encodeFilePath,
 	ENTRY_SIZE,
 	getContentType,
 	HEADER_SIZE,
 	MAX_ASSET_COUNT,
 	MAX_ASSET_SIZE,
+	normalizeFilePath,
 	PATH_HASH_OFFSET,
 	PATH_HASH_SIZE,
 } from "@cloudflare/workers-shared";
@@ -239,10 +239,9 @@ const walk = async (dir: string) => {
 				 */
 
 				const [pathHash, contentHash] = await Promise.all([
-					hashPath(encodeFilePath(relativeFilepath, path.sep)),
-					hashPath(
-						encodeFilePath(filepath, path.sep) + filestat.mtimeMs.toString()
-					),
+					hashPath(normalizeFilePath(relativeFilepath)),
+					// used absolute filepath here so that changes to the enclosing asset folder will be registered
+					hashPath(filepath + filestat.mtimeMs.toString()),
 				]);
 				manifest.push({
 					pathHash,
diff --git a/packages/miniflare/src/workers/assets/assets-kv.worker.ts b/packages/miniflare/src/workers/assets/assets-kv.worker.ts
index f90fdcd74074..9bd584cb0003 100644
--- a/packages/miniflare/src/workers/assets/assets-kv.worker.ts
+++ b/packages/miniflare/src/workers/assets/assets-kv.worker.ts
@@ -26,7 +26,14 @@ export default <ExportedHandler<Env>>{
 		const { filePath, contentType } = entry;
 		const blobsService = env[SharedBindings.MAYBE_SERVICE_BLOBS];
 		const response = await blobsService.fetch(
-			new URL(filePath, "http://placeholder")
+			new URL(
+				// somewhere in blobservice I think this is being decoded again
+				filePath
+					.split("/")
+					.map((x) => encodeURIComponent(x))
+					.join("/"),
+				"http://placeholder"
+			)
 		);
 		const newResponse = new Response(response.body, response);
 		// ensure the runtime will return the metadata we need
diff --git a/packages/workers-shared/asset-worker/src/handler.ts b/packages/workers-shared/asset-worker/src/handler.ts
index a873f72b8a59..111279afa2ba 100644
--- a/packages/workers-shared/asset-worker/src/handler.ts
+++ b/packages/workers-shared/asset-worker/src/handler.ts
@@ -18,7 +18,9 @@ export const handleRequest = async (
 ) => {
 	const { pathname, search } = new URL(request.url);
 
-	const intent = await getIntent(pathname, configuration, exists);
+	const decodedPathname = decodePath(pathname);
+	const intent = await getIntent(decodedPathname, configuration, exists);
+
 	if (!intent) {
 		return new NotFoundResponse();
 	}
@@ -30,15 +32,24 @@ export const handleRequest = async (
 	if (!["GET", "HEAD"].includes(method)) {
 		return new MethodNotAllowedResponse();
 	}
-	if (intent.redirect) {
-		return new TemporaryRedirectResponse(intent.redirect + search);
+
+	const decodedDestination = intent.redirect ?? decodedPathname;
+	const encodedDestination = encodePath(decodedDestination);
+
+	/**
+	 * The canonical path we serve an asset at is the decoded and re-encoded version.
+	 * Thus we need to redirect if that is different from the decoded version.
+	 * We combine this with other redirects (e.g. for html_handling) to avoid multiple redirects.
+	 */
+	if (encodedDestination !== pathname || intent.redirect) {
+		return new TemporaryRedirectResponse(encodedDestination + search);
 	}
+
 	if (!intent.asset) {
 		return new InternalServerErrorResponse(new Error("Unknown action"));
 	}
 
 	const asset = await getByETag(intent.asset.eTag);
-
 	const headers = getHeaders(intent.asset.eTag, asset.contentType, request);
 
 	const strongETag = `"${intent.asset.eTag}"`;
@@ -114,7 +125,10 @@ const htmlHandlingAutoTrailingSlash = async (
 	if (pathname.endsWith("/index")) {
 		if (exactETag) {
 			// there's a binary /index file
-			return { asset: { eTag: exactETag, status: 200 }, redirect: null };
+			return {
+				asset: { eTag: exactETag, status: 200 },
+				redirect: null,
+			};
 		} else {
 			if (
 				(redirectResult = await safeRedirect(
@@ -167,7 +181,10 @@ const htmlHandlingAutoTrailingSlash = async (
 	} else if (pathname.endsWith("/")) {
 		if ((eTagResult = await exists(`${pathname}index.html`))) {
 			// /foo/index.html exists so serve at /foo/
-			return { asset: { eTag: eTagResult, status: 200 }, redirect: null };
+			return {
+				asset: { eTag: eTagResult, status: 200 },
+				redirect: null,
+			};
 		} else if (
 			(redirectResult = await safeRedirect(
 				`${pathname.slice(0, -"/".length)}.html`,
@@ -208,10 +225,16 @@ const htmlHandlingAutoTrailingSlash = async (
 
 	if (exactETag) {
 		// there's a binary /foo file
-		return { asset: { eTag: exactETag, status: 200 }, redirect: null };
+		return {
+			asset: { eTag: exactETag, status: 200 },
+			redirect: null,
+		};
 	} else if ((eTagResult = await exists(`${pathname}.html`))) {
 		// foo.html exists so serve at /foo
-		return { asset: { eTag: eTagResult, status: 200 }, redirect: null };
+		return {
+			asset: { eTag: eTagResult, status: 200 },
+			redirect: null,
+		};
 	} else if (
 		(redirectResult = await safeRedirect(
 			`${pathname}/index.html`,
@@ -240,7 +263,10 @@ const htmlHandlingForceTrailingSlash = async (
 	if (pathname.endsWith("/index")) {
 		if (exactETag) {
 			// there's a binary /index file
-			return { asset: { eTag: exactETag, status: 200 }, redirect: null };
+			return {
+				asset: { eTag: exactETag, status: 200 },
+				redirect: null,
+			};
 		} else {
 			if (
 				(redirectResult = await safeRedirect(
@@ -293,12 +319,18 @@ const htmlHandlingForceTrailingSlash = async (
 	} else if (pathname.endsWith("/")) {
 		if ((eTagResult = await exists(`${pathname}index.html`))) {
 			// /foo/index.html exists so serve at /foo/
-			return { asset: { eTag: eTagResult, status: 200 }, redirect: null };
+			return {
+				asset: { eTag: eTagResult, status: 200 },
+				redirect: null,
+			};
 		} else if (
 			(eTagResult = await exists(`${pathname.slice(0, -"/".length)}.html`))
 		) {
 			// /foo.html exists so serve at /foo/
-			return { asset: { eTag: eTagResult, status: 200 }, redirect: null };
+			return {
+				asset: { eTag: eTagResult, status: 200 },
+				redirect: null,
+			};
 		}
 	} else if (pathname.endsWith(".html")) {
 		if (
@@ -314,7 +346,10 @@ const htmlHandlingForceTrailingSlash = async (
 			return redirectResult;
 		} else if (exactETag) {
 			// there's both /foo.html and /foo/index.html so we serve /foo.html at /foo.html only
-			return { asset: { eTag: exactETag, status: 200 }, redirect: null };
+			return {
+				asset: { eTag: exactETag, status: 200 },
+				redirect: null,
+			};
 		} else if (
 			(redirectResult = await safeRedirect(
 				`${pathname.slice(0, -".html".length)}/index.html`,
@@ -331,7 +366,10 @@ const htmlHandlingForceTrailingSlash = async (
 
 	if (exactETag) {
 		// there's a binary /foo file
-		return { asset: { eTag: exactETag, status: 200 }, redirect: null };
+		return {
+			asset: { eTag: exactETag, status: 200 },
+			redirect: null,
+		};
 	} else if (
 		(redirectResult = await safeRedirect(
 			`${pathname}.html`,
@@ -371,7 +409,10 @@ const htmlHandlingDropTrailingSlash = async (
 	if (pathname.endsWith("/index")) {
 		if (exactETag) {
 			// there's a binary /index file
-			return { asset: { eTag: exactETag, status: 200 }, redirect: null };
+			return {
+				asset: { eTag: exactETag, status: 200 },
+				redirect: null,
+			};
 		} else {
 			if (pathname === "/index") {
 				if (
@@ -436,7 +477,10 @@ const htmlHandlingDropTrailingSlash = async (
 			return redirectResult;
 		} else if (exactETag) {
 			// there's both /foo.html and /foo/index.html so we serve /foo/index.html at /foo/index.html only
-			return { asset: { eTag: exactETag, status: 200 }, redirect: null };
+			return {
+				asset: { eTag: exactETag, status: 200 },
+				redirect: null,
+			};
 		} else if (
 			(redirectResult = await safeRedirect(
 				`${pathname.slice(0, -"/index.html".length)}.html`,
@@ -453,7 +497,10 @@ const htmlHandlingDropTrailingSlash = async (
 		if (pathname === "/") {
 			if ((eTagResult = await exists("/index.html"))) {
 				// /index.html exists so serve at /
-				return { asset: { eTag: eTagResult, status: 200 }, redirect: null };
+				return {
+					asset: { eTag: eTagResult, status: 200 },
+					redirect: null,
+				};
 			}
 		} else if (
 			(redirectResult = await safeRedirect(
@@ -506,13 +553,22 @@ const htmlHandlingDropTrailingSlash = async (
 
 	if (exactETag) {
 		// there's a binary /foo file
-		return { asset: { eTag: exactETag, status: 200 }, redirect: null };
+		return {
+			asset: { eTag: exactETag, status: 200 },
+			redirect: null,
+		};
 	} else if ((eTagResult = await exists(`${pathname}.html`))) {
 		// /foo.html exists so serve at /foo
-		return { asset: { eTag: eTagResult, status: 200 }, redirect: null };
+		return {
+			asset: { eTag: eTagResult, status: 200 },
+			redirect: null,
+		};
 	} else if ((eTagResult = await exists(`${pathname}/index.html`))) {
 		// /foo/index.html exists so serve at /foo
-		return { asset: { eTag: eTagResult, status: 200 }, redirect: null };
+		return {
+			asset: { eTag: eTagResult, status: 200 },
+			redirect: null,
+		};
 	}
 
 	return notFound(pathname, configuration, exists);
@@ -525,7 +581,10 @@ const htmlHandlingNone = async (
 ): Promise<Intent> => {
 	const exactETag = await exists(pathname);
 	if (exactETag) {
-		return { asset: { eTag: exactETag, status: 200 }, redirect: null };
+		return {
+			asset: { eTag: exactETag, status: 200 },
+			redirect: null,
+		};
 	} else {
 		return notFound(pathname, configuration, exists);
 	}
@@ -540,7 +599,10 @@ const notFound = async (
 		case "single-page-application": {
 			const eTag = await exists("/index.html");
 			if (eTag) {
-				return { asset: { eTag, status: 200 }, redirect: null };
+				return {
+					asset: { eTag, status: 200 },
+					redirect: null,
+				};
 			}
 			return null;
 		}
@@ -550,7 +612,10 @@ const notFound = async (
 				cwd = cwd.slice(0, cwd.lastIndexOf("/"));
 				const eTag = await exists(`${cwd}/404.html`);
 				if (eTag) {
-					return { asset: { eTag, status: 404 }, redirect: null };
+					return {
+						asset: { eTag, status: 404 },
+						redirect: null,
+					};
 				}
 			}
 			return null;
@@ -575,6 +640,7 @@ const safeRedirect = async (
 
 	if (!(await exists(destination))) {
 		const intent = await getIntent(destination, configuration, exists, true);
+		// return only if the eTag matches - i.e. not the 404 case
 		if (intent?.asset && intent.asset.eTag === (await exists(file))) {
 			return {
 				asset: null,
@@ -585,3 +651,44 @@ const safeRedirect = async (
 
 	return null;
 };
+/**
+ *
+ * +===========================================+===========+======================+
+ * |              character type               |  fetch()  | encodeURIComponent() |
+ * +===========================================+===========+======================+
+ * | unreserved ASCII e.g. a-z                 | unchanged | unchanged            |
+ * +-------------------------------------------+-----------+----------------------+
+ * | reserved (sometimes encoded)			   | unchanged | encoded			  |
+ * | e.g. [ ] @ $ ! ' ( ) * + , ; = : ? # & %  |           |                      |
+ * +-------------------------------------------+-----------+----------------------+
+ * | non-ASCII e.g. ü. and space               | encoded   | encoded              |
+ * +-------------------------------------------+-----------+----------------------+
+ *
+ * 1. Decode incoming path to handle non-ASCII characters or optionally encoded characters (e.g. square brackets)
+ * 2. Match decoded path to manifest
+ * 3. Re-encode the path and redirect if the re-encoded path is different from the original path
+ *
+ * If the user uploads a file that is already URL-encoded, that is accessible only at the (double) encoded path.
+ * e.g. /%5Bboop%5D.html is served at /%255Bboop%255D only
+ *
+ * */
+
+/**
+ * Decode all incoming paths to ensure that we can handle paths with non-ASCII characters.
+ */
+export const decodePath = (pathname: string) => {
+	return pathname
+		.split("/")
+		.map((x) => decodeURIComponent(x))
+		.join("/");
+};
+/**
+ * Use the encoded path as the canonical path for sometimes-encoded characters
+ * e.g. /[boop] -> /%5Bboop%5D 307
+ */
+const encodePath = (pathname: string) => {
+	return pathname
+		.split("/")
+		.map((x) => encodeURIComponent(x))
+		.join("/");
+};
diff --git a/packages/workers-shared/asset-worker/src/index.ts b/packages/workers-shared/asset-worker/src/index.ts
index b30f51b04ce0..3330fa2a702d 100644
--- a/packages/workers-shared/asset-worker/src/index.ts
+++ b/packages/workers-shared/asset-worker/src/index.ts
@@ -2,7 +2,7 @@ import { WorkerEntrypoint } from "cloudflare:workers";
 import { setupSentry } from "../../utils/sentry";
 import { AssetsManifest } from "./assets-manifest";
 import { applyConfigurationDefaults } from "./configuration";
-import { getIntent, handleRequest } from "./handler";
+import { decodePath, getIntent, handleRequest } from "./handler";
 import {
 	InternalServerErrorResponse,
 	MethodNotAllowedResponse,
@@ -75,8 +75,9 @@ export default class extends WorkerEntrypoint<Env> {
 	async unstable_canFetch(request: Request): Promise<boolean | Response> {
 		const url = new URL(request.url);
 		const method = request.method.toUpperCase();
+		const decodedPathname = decodePath(url.pathname);
 		const intent = await getIntent(
-			url.pathname,
+			decodedPathname,
 			{
 				...applyConfigurationDefaults(this.env.CONFIG),
 				not_found_handling: "none",
diff --git a/packages/workers-shared/utils/helpers.ts b/packages/workers-shared/utils/helpers.ts
index 7bd560658dc5..d986fb52c9d0 100644
--- a/packages/workers-shared/utils/helpers.ts
+++ b/packages/workers-shared/utils/helpers.ts
@@ -1,20 +1,12 @@
+import { isAbsolute, sep } from "node:path";
 import { getType } from "mime";
 
-/** normalises sep for windows, and encodes each segment */
-export const encodeFilePath = (filePath: string, sep: string) => {
-	const encodedPath = filePath
-		.split(sep)
-		.map((segment) => encodeURIComponent(segment))
-		.join("/");
-	return "/" + encodedPath;
-};
-
-/** reverses encodeFilePath for accessing from file system */
-export const decodeFilePath = (filePath: string, sep: string) => {
-	return filePath
-		.split("/")
-		.map((segment) => decodeURIComponent(segment))
-		.join(sep);
+/** normalises sep for windows and prefix with `/` */
+export const normalizeFilePath = (relativeFilepath: string) => {
+	if (isAbsolute(relativeFilepath)) {
+		throw new Error(`Expected relative path`);
+	}
+	return "/" + relativeFilepath.split(sep).join("/");
 };
 
 export const getContentType = (absFilePath: string) => {
diff --git a/packages/workers-shared/utils/tsconfig.json b/packages/workers-shared/utils/tsconfig.json
index 965b1378614d..33c65059b33a 100644
--- a/packages/workers-shared/utils/tsconfig.json
+++ b/packages/workers-shared/utils/tsconfig.json
@@ -4,7 +4,7 @@
 		"lib": ["es2021"],
 		"module": "NodeNext",
 		"moduleResolution": "nodenext",
-		"types": ["@cloudflare/workers-types/experimental"],
+		"types": ["@cloudflare/workers-types/experimental", "@types/node"],
 		"noEmit": true,
 		"isolatedModules": true,
 		"allowSyntheticDefaultImports": true,
diff --git a/packages/wrangler/src/__tests__/deploy.test.ts b/packages/wrangler/src/__tests__/deploy.test.ts
index b586daf1e336..da9f8b92fce1 100644
--- a/packages/wrangler/src/__tests__/deploy.test.ts
+++ b/packages/wrangler/src/__tests__/deploy.test.ts
@@ -4427,11 +4427,11 @@ addEventListener('fetch', event => {});`
 			expect(manifestBodies.length).toBe(1);
 			expect(manifestBodies[0]).toEqual({
 				manifest: {
-					"/b%C3%A9%C3%ABp/boo%5Ep.txt": {
+					"/béëp/boo^p.txt": {
 						hash: "ff5016e92f039aa743a4ff7abb3180fa",
 						size: 17,
 					},
-					"/boop/file%231.txt": {
+					"/boop/file#1.txt": {
 						hash: "7574a8cd3094a050388ac9663af1c1d6",
 						size: 17,
 					},
diff --git a/packages/wrangler/src/experimental-assets.ts b/packages/wrangler/src/experimental-assets.ts
index eecc51ce5a15..cc4bd1412b1a 100644
--- a/packages/wrangler/src/experimental-assets.ts
+++ b/packages/wrangler/src/experimental-assets.ts
@@ -3,11 +3,10 @@ import { existsSync } from "node:fs";
 import { readdir, readFile, stat } from "node:fs/promises";
 import * as path from "node:path";
 import {
-	decodeFilePath,
-	encodeFilePath,
 	getContentType,
 	MAX_ASSET_COUNT,
 	MAX_ASSET_SIZE,
+	normalizeFilePath,
 } from "@cloudflare/workers-shared";
 import chalk from "chalk";
 import PQueue from "p-queue";
@@ -101,10 +100,7 @@ export const syncExperimentalAssets = async (
 			}
 			// just logging file uploads at the moment...
 			// unsure how to log deletion vs unchanged file ignored/if we want to log this
-			assetLogCount = logAssetUpload(
-				`+ ${decodeFilePath(manifestEntry[0], path.sep)}`,
-				assetLogCount
-			);
+			assetLogCount = logAssetUpload(`+ ${manifestEntry[0]}`, assetLogCount);
 			return manifestEntry;
 		});
 	});
@@ -123,8 +119,7 @@ export const syncExperimentalAssets = async (
 			// This is so we don't run out of memory trying to upload the files.
 			const payload = new FormData();
 			for (const manifestEntry of bucket) {
-				const decodedFilePath = decodeFilePath(manifestEntry[0], path.sep);
-				const absFilePath = path.join(assetDirectory, decodedFilePath);
+				const absFilePath = path.join(assetDirectory, manifestEntry[0]);
 				payload.append(
 					manifestEntry[1].hash,
 					new File(
@@ -268,7 +263,7 @@ export const buildAssetManifest = async (dir: string) => {
 							`Ensure all assets in your assets directory "${dir}" conform with the Workers maximum size requirement.`
 					);
 				}
-				manifest[encodeFilePath(relativeFilepath, path.sep)] = {
+				manifest[normalizeFilePath(relativeFilepath)] = {
 					hash: hashFile(filepath),
 					size: filestat.size,
 				};
diff --git a/pnpm-lock.yaml b/pnpm-lock.yaml
index 4b70f4ab449d..031639717fa3 100644
--- a/pnpm-lock.yaml
+++ b/pnpm-lock.yaml
@@ -6,6 +6,12 @@ settings:
 
 catalogs:
   default:
+    '@vitest/runner':
+      specifier: ~2.1.1
+      version: 2.1.1
+    '@vitest/snapshot':
+      specifier: ~2.1.1
+      version: 2.1.1
     vitest:
       specifier: ~2.1.1
       version: 2.1.1