diff --git a/src/artifacts/apple/DylibResolutionReader.ts b/src/artifacts/apple/DylibResolutionReader.ts
index 426467122b..ca0c9a7448 100644
--- a/src/artifacts/apple/DylibResolutionReader.ts
+++ b/src/artifacts/apple/DylibResolutionReader.ts
@@ -17,6 +17,10 @@ import {
 import { ArtifactReaderFailure } from "../ArtifactReader.js";
 import { DirectoryArtifactReader } from "../DirectoryArtifactReader.js";
 import { DyldSharedCache } from "./DyldSharedCacheReader.js";
+import {
+  filesystemDyldLinkTarget,
+  filesystemDyldLookupPath,
+} from "./FilesystemDyldPaths.js";
 import { hasMachoMagic, readMachoImage } from "./MachoLoadCommandReader.js";
 
 const HASH_CHUNK_BYTES = 1024 * 1024;
@@ -63,11 +67,14 @@ class FilesystemTreeView implements DylibTreeView {
 
   async #readEntry(path: string): Promise<DylibTreeEntry | undefined> {
     cancelled(this.signal);
-    const absolute = join(this.root, path);
+    const absolute = filesystemDyldLookupPath(this.root, path);
     try {
       const metadata = await lstat(absolute);
       if (metadata.isSymbolicLink())
-        return { kind: "symlink", target: await readlink(absolute) };
+        return {
+          kind: "symlink",
+          target: filesystemDyldLinkTarget(await readlink(absolute)),
+        };
       if (metadata.isDirectory()) return { kind: "directory" };
       return metadata.isFile() ? { kind: "file" } : undefined;
     } catch (cause: unknown) {
diff --git a/src/artifacts/apple/FilesystemDyldPaths.test.ts b/src/artifacts/apple/FilesystemDyldPaths.test.ts
new file mode 100644
index 0000000000..cee68e6da7
--- /dev/null
+++ b/src/artifacts/apple/FilesystemDyldPaths.test.ts
@@ -0,0 +1,53 @@
+import { expect, it } from "vitest";
+import { resolveTreePath } from "../../domain/apple/dyldPaths.js";
+import type { DylibTreeEntry } from "../../domain/apple/dylibResolution.js";
+import {
+  filesystemDyldLinkTarget,
+  filesystemDyldLookupPath,
+} from "./FilesystemDyldPaths.js";
+
+it("normalizes Windows relative links before containment checks without probing an escaped path", async () => {
+  const requested: string[] = [];
+  const result = await resolveTreePath(
+    {
+      entry: async (path: string): Promise<DylibTreeEntry | undefined> => {
+        requested.push(path);
+        return path === "link"
+          ? {
+              kind: "symlink",
+              target: filesystemDyldLinkTarget("..\\outside.dylib", "win32"),
+            }
+          : undefined;
+      },
+      image: async () => ({ status: "not-mach-o" }),
+    },
+    "link",
+  );
+  expect(result).toEqual({ kind: "escapes" });
+  expect(requested).toEqual(["link"]);
+});
+
+it("keeps POSIX backslash bytes and preserves Windows dot segments for segment-wise traversal", () => {
+  expect(filesystemDyldLinkTarget("..\\outside.dylib", "darwin")).toBe(
+    "..\\outside.dylib",
+  );
+  expect(filesystemDyldLinkTarget("nested\\..\\target", "win32")).toBe(
+    "nested/../target",
+  );
+  expect(filesystemDyldLinkTarget("C:\\outside", "win32")).toBe("/C:/outside");
+  expect(filesystemDyldLinkTarget("C:/literal-posix-directory", "darwin")).toBe(
+    "C:/literal-posix-directory",
+  );
+  expect(() => filesystemDyldLinkTarget("C:drive-relative", "win32")).toThrow(
+    "Windows drive working directory",
+  );
+});
+
+it("does not let Windows reinterpret a literal backslash-bearing loader name as traversal", () => {
+  expect(() =>
+    filesystemDyldLookupPath("C:\\root", "..\\outside.dylib", "win32"),
+  ).toThrow("cannot be represented on Windows");
+  expect(
+    filesystemDyldLookupPath("/root", "literal\\name.dylib", "darwin"),
+  ).toBe("/root/literal\\name.dylib");
+});
diff --git a/src/artifacts/apple/FilesystemDyldPaths.ts b/src/artifacts/apple/FilesystemDyldPaths.ts
new file mode 100644
index 0000000000..bff0d2b37b
--- /dev/null
+++ b/src/artifacts/apple/FilesystemDyldPaths.ts
@@ -0,0 +1,39 @@
+import { posix, win32 } from "node:path";
+import { ArtifactReaderFailure } from "../ArtifactReader.js";
+
+/**
+ * Convert host filesystem separators into the tree view's POSIX traversal
+ * namespace. Dot segments stay intact so they apply after symlink expansion;
+ * POSIX backslash filename bytes are never reinterpreted as separators.
+ */
+export const filesystemDyldLinkTarget = (
+  reported: string,
+  platform: NodeJS.Platform = process.platform,
+): string => {
+  if (platform !== "win32") return reported;
+  const portable = reported.replaceAll("\\", "/");
+  if (win32.isAbsolute(reported))
+    return portable.startsWith("/") ? portable : `/${portable}`;
+  if (/^[A-Za-z]:/u.test(reported))
+    throw new ArtifactReaderFailure(
+      "unavailable",
+      `Drive-relative symlink target depends on a Windows drive working directory: ${reported}`,
+    );
+  return portable;
+};
+
+/** Map a portable lookup to the host without allowing extra native separators to escape it. */
+export const filesystemDyldLookupPath = (
+  root: string,
+  lookup: string,
+  platform: NodeJS.Platform = process.platform,
+): string => {
+  if (platform === "win32" && lookup.includes("\\"))
+    throw new ArtifactReaderFailure(
+      "unavailable",
+      `Literal backslashes in a POSIX dyld lookup cannot be represented on Windows: ${lookup}. Analyze this tree on a POSIX host.`,
+    );
+  return platform === "win32"
+    ? win32.join(root, lookup)
+    : posix.join(root, lookup);
+};
diff --git a/src/domain/apple/dyldPaths.ts b/src/domain/apple/dyldPaths.ts
index ce0c69785c..d1a4b45bbd 100644
--- a/src/domain/apple/dyldPaths.ts
+++ b/src/domain/apple/dyldPaths.ts
@@ -37,13 +37,8 @@ export const resolveTreePath = async (
     if (entry.kind === "symlink") {
       hops += 1;
       if (hops > MAX_SYMLINK_HOPS) return { kind: "absent" };
-      if (
-        entry.target.startsWith("/") ||
-        /^[a-zA-Z]:[\\/]/u.test(entry.target) ||
-        entry.target.startsWith("\\\\") ||
-        entry.target.startsWith("//")
-      )
-        return { kind: "escapes" };
+      // Tree providers convert host link syntax to this POSIX namespace.
+      if (entry.target.startsWith("/")) return { kind: "escapes" };
       pending.unshift(...segmentsOf(entry.target));
       continue;
     }