diff --git a/packages/shared/src/atomicWrite.test.ts b/packages/shared/src/atomicWrite.test.ts
index 366009f833132..3b0a99ec0d2d2 100644
--- a/packages/shared/src/atomicWrite.test.ts
+++ b/packages/shared/src/atomicWrite.test.ts
@@ -14,6 +14,36 @@ import { writeFileStringAtomically } from "./atomicWrite.ts";
 import * as HostProcess from "./HostProcess.ts";
 
 it.layer(NodeServices.layer)("writeFileStringAtomically", (it) => {
+  it.effect.each(HostProcess.Platform.defaultValue() === "linux" ? [39, 40, 41] : [])(
+    "matches native file access for a chain of %i symlinks",
+    (hops) =>
+      Effect.gen(function* () {
+        const fs = yield* FileSystem.FileSystem;
+        const path = yield* Path.Path;
+        const root = yield* fs.makeTempDirectoryScoped({ prefix: "t3-atomic-write-" });
+        const destination = path.join(root, "settings.json");
+        const first = path.join(root, "link-0");
+        yield* fs.writeFileString(destination, "before");
+        for (let index = hops - 1; index >= 0; index--) {
+          const target = index === hops - 1 ? "settings.json" : `link-${index + 1}`;
+          yield* fs.symlink(target, path.join(root, `link-${index}`));
+        }
+
+        const read = yield* Effect.exit(fs.readFileString(first));
+        const write = yield* Effect.exit(
+          writeFileStringAtomically({ filePath: first, contents: "after" }),
+        );
+
+        assert.strictEqual(Exit.isSuccess(read), hops <= 40);
+        assert.strictEqual(Exit.isSuccess(write), Exit.isSuccess(read));
+        assert.strictEqual(
+          yield* fs.readFileString(destination),
+          Exit.isSuccess(read) ? "after" : "before",
+        );
+        assert.strictEqual(yield* fs.readLink(first), "link-1");
+      }),
+  );
+
   it.effect("keeps a symlinked file linked and rewrites its destination", () =>
     Effect.gen(function* () {
       const fs = yield* FileSystem.FileSystem;
diff --git a/packages/shared/src/symlink.ts b/packages/shared/src/symlink.ts
index 2dcb9631c3862..9d71d2a687d93 100644
--- a/packages/shared/src/symlink.ts
+++ b/packages/shared/src/symlink.ts
@@ -23,7 +23,8 @@ export const resolveSymlinkTarget = Effect.fn("symlink.resolveSymlinkTarget")(fu
   const fs = yield* FileSystem.FileSystem;
   const path = yield* Path.Path;
   let current = path.resolve(filePath);
-  for (let hop = 0; hop < MAX_SYMLINK_HOPS; hop++) {
+  // The terminal file needs a probe after the last permitted link is followed.
+  for (let hop = 0; hop <= MAX_SYMLINK_HOPS; hop++) {
     const link = yield* fs.readLink(current).pipe(
       Effect.asSome,
       Effect.catchIf(isNotASymlink, () => Effect.succeedNone),