diff --git a/src/install/bin.zig b/src/install/bin.zig
index 9d0a5e4e0c..1ac5d14789 100644
--- a/src/install/bin.zig
+++ b/src/install/bin.zig
@@ -720,9 +720,15 @@ pub const Bin = extern struct {
             defer bunx_file.close();
 
             const rel_target = path.relativeBufZ(this.rel_buf, path.dirname(abs_dest, .auto), abs_target);
-            bun.assertWithLocation(strings.hasPrefixComptime(rel_target, "..\\"), @src());
 
-            const rel_target_w = strings.toWPathNormalized(&target_buf, rel_target["..\\".len..]);
+            // For Windows shims, we need a path relative to node_modules, not relative to .bin
+            // Most cases will start with "..\\" to go up from .bin, but edge cases may differ
+            const rel_target_for_shim = if (strings.hasPrefixComptime(rel_target, "..\\"))
+                rel_target["..\\".len..]
+            else
+                rel_target;
+
+            const rel_target_w = strings.toWPathNormalized(&target_buf, rel_target_for_shim);
 
             const shebang = shebang: {
                 const first_content_chunk = contents: {
diff --git a/test/regression/issue/23414.test.ts b/test/regression/issue/23414.test.ts
new file mode 100644
index 0000000000..b864b4dcf7
--- /dev/null
+++ b/test/regression/issue/23414.test.ts
@@ -0,0 +1,44 @@
+// https://github.com/oven-sh/bun/issues/23414
+// Bun crashes when trying to install packages with bin links on Windows
+// This was caused by an overly strict assertion that expected all relative paths
+// to start with "..\\" when linking bins, but edge cases exist where this isn't true.
+
+import { expect, test } from "bun:test";
+import { bunEnv, bunExe, isWindows, tempDir } from "harness";
+
+test("bin linking should not crash with assertion failure on Windows", async () => {
+  if (!isWindows) {
+    // This test is Windows-specific, skip on other platforms
+    return;
+  }
+
+  using dir = tempDir("bin-linking-test", {
+    "package.json": JSON.stringify({
+      name: "test-package",
+      version: "1.0.0",
+      dependencies: {
+        "cowsay": "1.6.0",
+      },
+    }),
+  });
+
+  await using proc = Bun.spawn({
+    cmd: [bunExe(), "install"],
+    env: bunEnv,
+    cwd: String(dir),
+    stderr: "pipe",
+    stdout: "pipe",
+  });
+
+  const [stdout, stderr, exitCode] = await Promise.all([proc.stdout.text(), proc.stderr.text(), proc.exited]);
+
+  // The main fix is that this should not panic with:
+  // "panic: Internal assertion failure at install/bin.zig:723:83"
+  expect(stderr).not.toContain("panic");
+  expect(stderr).not.toContain("assertion failure");
+  expect(stderr).not.toContain("bin.zig:723");
+
+  // Verify the install completed successfully
+  expect(exitCode).toBe(0);
+  expect(stderr).toContain("package installed");
+});