diff --git a/lib/util/url.ts b/lib/util/url.ts
index f13966eb..1c550307 100644
--- a/lib/util/url.ts
+++ b/lib/util/url.ts
@@ -16,7 +16,7 @@ const urlEncodePatterns = [
 ] as [RegExp, string][];
 
 // RegExp patterns to URL-decode special characters for local filesystem paths
-const urlDecodePatterns = [/%23/g, "#", /%24/g, "$", /%26/g, "&", /%2C/g, ",", /%40/g, "@"];
+const urlDecodePatterns = [/%23/g, "#", /%24/g, "$", /%26/g, "&", /%2C/g, ",", /%3F/g, "?", /%40/g, "@"];
 
 const unsafeDomainSuffixes = [".localhost", ".local", ".internal", ".intranet", ".corp", ".home", ".lan"];
 
@@ -638,16 +638,26 @@ export function toFileSystemPath(path: string | undefined, keepFileProtocol?: bo
   // Escape only the non-encoded ones so percent-encoded sequences still decode normally.
   path = path!.replace(/%(?![0-9A-Fa-f]{2})/g, "%25");
 
-  // Step 1: `decodeURI` will decode characters such as Cyrillic characters, spaces, etc.
-  path = decodeURI(path!);
-
-  // Step 2: Manually decode characters that are not decoded by `decodeURI`.
-  // This includes characters such as "#" and "?", which have special meaning in URLs,
-  // but are just normal characters in a filesystem path.
+  // Step 1: Manually decode characters that `decodeURI` intentionally leaves alone
+  // (they're URI-reserved) but are just normal characters in a filesystem path,
+  // e.g. "#" and "?". This MUST run before `decodeURI`, not after: `fromFileSystemPath`
+  // percent-escapes a literal "%" as "%25", so a real filename containing the literal
+  // text "%3F" round-trips as "%253F". If `decodeURI` runs first, "%25" -> "%" reveals
+  // a literal "%3F" substring that didn't exist in the encoded form, and this pass
+  // would then wrongly decode that revealed text a second time (%3F -> "?"), silently
+  // reading the wrong file. Running this pass first, the literal "%253F" doesn't
+  // contain the substring "%3F" (it's "%25" followed by "3F"), so it's untouched here
+  // and correctly decoded once by `decodeURI` below (%25 -> %). Each escape in the
+  // original filename is consumed exactly once, either here or by `decodeURI`, never
+  // both. Case-insensitive: percent-encoding hex digits are case-insensitive per
+  // RFC 3986 §2.1, so "%3f" must decode the same as "%3F".
   for (let i = 0; i < urlDecodePatterns.length; i += 2) {
-    path = path.replace(urlDecodePatterns[i], urlDecodePatterns[i + 1] as string);
+    path = path.replace(new RegExp((urlDecodePatterns[i] as RegExp).source, "gi"), urlDecodePatterns[i + 1] as string);
   }
 
+  // Step 2: `decodeURI` will decode characters such as Cyrillic characters, spaces, etc.
+  path = decodeURI(path!);
+
   // Step 3: If it's a "file://" URL, then format it consistently
   // or convert it to a local filesystem path
   let isFileUrl = path.toLowerCase().startsWith("file://");
diff --git a/test/specs/util/url.spec.ts b/test/specs/util/url.spec.ts
index 9563c059..68c8d18f 100644
--- a/test/specs/util/url.spec.ts
+++ b/test/specs/util/url.spec.ts
@@ -152,3 +152,53 @@ describe("Handle Linux file paths", () => {
     expect($url.toFileSystemPath("FILE:///a/random/Path/file.json")).to.equal("/a/random/Path/file.json");
   });
 });
+
+describe("Round-trip special characters in filesystem paths", () => {
+  // POSIX-only: on Windows, fromFileSystemPath prepends cwd() and normalizes
+  // separators, so these absolute-POSIX-path assertions don't hold. Mocked the
+  // same way as the "Handle Linux file paths" block above.
+  beforeAll(function (this: any) {
+    vi.spyOn(isWin, "isWindows").mockReturnValue(false);
+  });
+
+  afterAll(function (this: any) {
+    vi.restoreAllMocks();
+  });
+
+  it("should round-trip a literal question mark", () => {
+    const original = "/a/random/Path/defs?1.json";
+    const encoded = $url.fromFileSystemPath(original);
+    expect(encoded).to.equal("/a/random/Path/defs%3F1.json");
+    expect($url.toFileSystemPath(encoded)).to.equal(original);
+  });
+
+  it("should round-trip a literal hash", () => {
+    const original = "/a/random/Path/defs#1.json";
+    const encoded = $url.fromFileSystemPath(original);
+    expect(encoded).to.equal("/a/random/Path/defs%231.json");
+    expect($url.toFileSystemPath(encoded)).to.equal(original);
+  });
+
+  it("should round-trip a filename that literally contains the text '%3F' without double-decoding it", () => {
+    // Regression test (jonluca, PR review 2026-08-07): a filename whose NAME is the
+    // literal text "%3F" (percent, 3, F -- not an encoded "?") must not be silently
+    // read as the "?" sibling file. fromFileSystemPath escapes the literal "%" to
+    // "%25", producing "%253F" -- if toFileSystemPath decoded %25->% before consuming
+    // reserved escapes, the revealed "%3F" text would wrongly decode to "?" a second
+    // time. It must decode back to the exact original literal text instead.
+    const original = "/a/random/Path/defs%3F1.json";
+    const encoded = $url.fromFileSystemPath(original);
+    expect(encoded).to.equal("/a/random/Path/defs%253F1.json");
+    expect($url.toFileSystemPath(encoded)).to.equal(original);
+    // And the two filenames must remain distinguishable -- this is the actual bug:
+    // parsing the encoded literal-%3F path must NOT collapse onto the "?" sibling.
+    const questionMarkOriginal = "/a/random/Path/defs?1.json";
+    expect($url.toFileSystemPath(encoded)).to.not.equal(questionMarkOriginal);
+  });
+
+  it("should decode a lowercase %3f the same as uppercase %3F (RFC 3986 §2.1: hex digits are case-insensitive)", () => {
+    const original = "/a/random/Path/defs?1.json";
+    expect($url.toFileSystemPath("/a/random/Path/defs%3f1.json")).to.equal(original);
+    expect($url.toFileSystemPath("/a/random/Path/defs%3F1.json")).to.equal(original);
+  });
+});