diff --git a/src/runtime/shell/interpreter.rs b/src/runtime/shell/interpreter.rs
index 9ee2ebb91e77..d9f29974fc5c 100644
--- a/src/runtime/shell/interpreter.rs
+++ b/src/runtime/shell/interpreter.rs
@@ -2169,15 +2169,22 @@ pub(crate) fn shell_dup(fd: Fd) -> bun_sys::Result<Fd> {
 /// `dirfd`'s drive root, `/dev/null` maps to `NUL`, and relative paths are
 /// joined against `dirfd`'s real path. Returns a NUL-terminated slice that
 /// either borrows `buf` or is `to` itself.
+///
+/// `to` is a command operand and can be arbitrarily long. `buf` fits every
+/// path Windows can open, so a rewritten path that does not fit it gets the
+/// `ENAMETOOLONG` that `syscall` would have returned for it, naming `to`.
 #[cfg(windows)]
 fn shell_get_path<'a>(
     dirfd: Fd,
     to: &'a bun_core::ZStr,
     buf: &'a mut bun_paths::PathBuffer,
+    syscall: bun_sys::Tag,
 ) -> bun_sys::Result<&'a bun_core::ZStr> {
     if to.as_bytes() == b"/dev/null" {
         return Ok(crate::shell::shell_body::WINDOWS_DEV_NULL);
     }
+    let name_too_long =
+        || bun_sys::Error::from_code(bun_sys::E::ENAMETOOLONG, syscall).with_path(to.as_bytes());
     if bun_paths::Platform::Posix.is_absolute(to.as_bytes()) {
         let source_root_len = {
             let dirpath = bun_sys::get_fd_path(dirfd, buf).map_err(|e| e.with_fd(dirfd))?;
@@ -2188,6 +2195,9 @@ fn shell_get_path<'a>(
         // needed. Splice `to[1..]` after the root.
         let to_tail = &to.as_bytes()[1..];
         let end = source_root_len + to_tail.len();
+        if end >= buf.len() {
+            return Err(name_too_long());
+        }
         buf[source_root_len..end].copy_from_slice(to_tail);
         buf[end] = 0;
         return Ok(bun_core::ZStr::from_buf(buf.as_slice(), end));
@@ -2195,16 +2205,24 @@ fn shell_get_path<'a>(
     if bun_paths::Platform::Windows.is_absolute(to.as_bytes()) {
         return Ok(to);
     }
-    // Relative: resolve dirfd → path, then join.
-    // Note: a single-buffer join would read `dirpath` (a slice of `buf`)
-    // while writing `buf`; copy `dirpath`
-    // out first so the mutable borrow on `buf` is exclusive.
-    let dirpath = bun_sys::get_fd_path(dirfd, buf)
-        .map_err(|e| e.with_fd(dirfd))?
-        .to_vec();
-    Ok(bun_paths::resolve_path::join_z_buf::<
-        bun_paths::platform::Auto,
-    >(&mut buf[..], &[&dirpath, to.as_bytes()]))
+    // Relative: resolve dirfd → path, then join. `join_z_buf` straight into
+    // `buf` has no bounds check, so join outside it and copy the result in once
+    // its normalized length (`..` segments may have shrunk it) is known to fit.
+    let mut spill = Vec::new();
+    let joined = {
+        let dirpath = bun_sys::get_fd_path(dirfd, buf).map_err(|e| e.with_fd(dirfd))?;
+        bun_paths::resolve_path::join_spill::<bun_paths::platform::Auto>(
+            &mut spill,
+            &[dirpath, to.as_bytes()],
+        )
+    };
+    let len = joined.len();
+    if len >= buf.len() {
+        return Err(name_too_long());
+    }
+    buf[..len].copy_from_slice(joined);
+    buf[len] = 0;
+    Ok(bun_core::ZStr::from_buf(buf.as_slice(), len))
 }
 
 /// Windows: rewrite the path via `shell_get_path` then `bun_sys::stat`, tagging
@@ -2215,7 +2233,7 @@ pub(crate) fn shell_statat(dir: Fd, path_: &bun_core::ZStr) -> bun_sys::Result<b
     #[cfg(windows)]
     {
         let mut buf = bun_paths::path_buffer_pool::get();
-        let p = shell_get_path(dir, path_, &mut buf)?;
+        let p = shell_get_path(dir, path_, &mut buf, bun_sys::Tag::fstatat)?;
         return bun_sys::stat(p).map_err(|e| e.with_path(path_.as_bytes()));
     }
     #[cfg(not(windows))]
@@ -2241,7 +2259,7 @@ pub(crate) fn shell_openat(
         if flags & bun_sys::O::DIRECTORY != 0 {
             if bun_paths::Platform::Posix.is_absolute(path.as_bytes()) {
                 let mut buf = bun_paths::path_buffer_pool::get();
-                let p = shell_get_path(dir, path, &mut buf)?;
+                let p = shell_get_path(dir, path, &mut buf, bun_sys::Tag::open)?;
                 return bun_sys::open_dir_at_windows_a(
                     dir,
                     p.as_bytes(),
@@ -2270,7 +2288,7 @@ pub(crate) fn shell_openat(
             .make_lib_uv_owned_for_syscall(bun_sys::Tag::open, bun_sys::ErrorCase::CloseOnFail);
         }
         let mut buf = bun_paths::path_buffer_pool::get();
-        let p = shell_get_path(dir, path, &mut buf)?;
+        let p = shell_get_path(dir, path, &mut buf, bun_sys::Tag::open)?;
         // No `makeLibUVOwnedForSyscall` here: `bun_sys::open` on Windows
         // routes through `sys_uv` and already yields a uv-owned fd.
         return bun_sys::open(p, flags, perm);
diff --git a/test/js/bun/shell/bunshell.test.ts b/test/js/bun/shell/bunshell.test.ts
index d1e6553875e7..bed159c845f6 100644
--- a/test/js/bun/shell/bunshell.test.ts
+++ b/test/js/bun/shell/bunshell.test.ts
@@ -3240,3 +3240,70 @@ test.skipIf(isWindows)("external command resolution uses the PATH from the shell
     expect(exitCode).toBe(0);
   }
 });
+
+// On Windows the shell rewrites each file operand against the cwd it tracks
+// before opening or stat-ing it: relative names are joined onto the cwd and a
+// `/name` is put on the cwd's drive. The rewrite goes through one 98302-byte
+// path buffer, and an operand that did not fit used to be copied in unchecked
+// and take the process down. It has to fail like any other over-long name.
+// POSIX hands operands to the *at() syscalls as-is, so there is nothing to
+// rewrite there. Runs in a child process so a regression fails the test
+// instead of killing the test runner.
+test.if(isWindows)("operands longer than the path buffer fail with ENAMETOOLONG instead of crashing", async () => {
+  using dir = tempDir("shell-long-operand", { "in.txt": "content\n" });
+  const script = `
+    import { $ } from "bun";
+    $.nothrow();
+    $.cwd(process.env.SHELL_CWD);
+    const long = Buffer.alloc(100_000, "a").toString();
+    // Longer than the buffer as written, but normalizes back down to a name
+    // inside the cwd; this worked before and has to keep working.
+    const collapsing = Buffer.alloc(100_000, "a/../").toString();
+    const show = buf => buf.toString().replaceAll(long, "<long>").replaceAll(collapsing, "<collapsing>");
+    const run = async promise => {
+      const { exitCode, stdout, stderr } = await promise.quiet();
+      return { exitCode, stdout: show(stdout), stderr: show(stderr) };
+    };
+    console.log(
+      JSON.stringify({
+        cat: await run($\`cat \${long}\`),
+        redirect: await run($\`echo hi > \${long}\`),
+        isFile: await run($\`[[ -f \${long} ]]\`),
+        rootedCat: await run($\`cat \${"/" + long}\`),
+        rootedLs: await run($\`ls \${"/" + long}\`),
+        rootedMvTarget: await run($\`mv in.txt \${"/" + long}\`),
+        rootedRedirect: await run($\`echo hi > \${"/" + long}\`),
+        rootedIsDir: await run($\`[[ -d \${"/" + long} ]]\`),
+        collapsingCat: await run($\`cat \${collapsing + "in.txt"}\`),
+        collapsingIsFile: await run($\`[[ -f \${collapsing + "in.txt"} ]]\`),
+        collapsingRedirect: await run($\`echo hi > \${collapsing + "out.txt"}\`),
+      }),
+    );
+  `;
+  await using proc = Bun.spawn({
+    cmd: [bunExe(), "-e", script],
+    env: { ...bunEnv, SHELL_CWD: String(dir) },
+    stdout: "pipe",
+    stderr: "pipe",
+  });
+  const [stdout, stderr, exitCode] = await Promise.all([proc.stdout.text(), proc.stderr.text(), proc.exited]);
+  expect(stderr).toBe("");
+  const failed = (stderr: string) => ({ exitCode: 1, stdout: "", stderr });
+  const succeeded = (stdout: string) => ({ exitCode: 0, stdout, stderr: "" });
+  expect(JSON.parse(stdout)).toEqual({
+    cat: failed("cat: <long>: File name too long\n"),
+    redirect: failed("bun: File name too long: <long>"),
+    isFile: failed(""),
+    rootedCat: failed("cat: /<long>: File name too long\n"),
+    rootedLs: failed("ls: /<long>: File name too long\n"),
+    rootedMvTarget: failed("mv: /<long>: File name too long\n"),
+    rootedRedirect: failed("bun: File name too long: /<long>"),
+    rootedIsDir: failed(""),
+    collapsingCat: succeeded("content\n"),
+    collapsingIsFile: succeeded(""),
+    collapsingRedirect: succeeded(""),
+  });
+  expect(await Bun.file(join(String(dir), "in.txt")).text()).toBe("content\n");
+  expect(await Bun.file(join(String(dir), "out.txt")).text()).toBe("hi\n");
+  expect(exitCode).toBe(0);
+});