diff --git a/src/runtime/shell/builtin/mkdir.rs b/src/runtime/shell/builtin/mkdir.rs
index a4695d61c6b2..829711d08dbf 100644
--- a/src/runtime/shell/builtin/mkdir.rs
+++ b/src/runtime/shell/builtin/mkdir.rs
@@ -298,6 +298,7 @@ impl ShellMkdirTask {
         use bun_paths::{Platform, platform, resolve_path};
         // We have to give an absolute path to our mkdir implementation for it
         // to work with cwd.
+        let mut spill = Vec::new();
         let filepath: &bun_core::ZStr = if Platform::AUTO.is_absolute(&this.filepath) {
             // Owned `Vec<u8>`; ensure NUL-terminated.
             if this.filepath.last() != Some(&0) {
@@ -305,9 +306,22 @@ impl ShellMkdirTask {
             }
             bun_core::ZStr::from_buf(&this.filepath, this.filepath.len() - 1)
         } else {
-            resolve_path::join_z::<platform::Auto>(&[&this.cwd_path, &this.filepath])
+            resolve_path::join_z_spill::<platform::Auto>(
+                &mut spill,
+                &[&this.cwd_path, &this.filepath],
+            )
         };
 
+        // `NodeFS` expects the `Valid::path_string_length` bound its JS callers
+        // enforce; past it, `PathLike::slice_z` yields "" and mkdir reports ENOENT.
+        if filepath.len() >= bun_paths::MAX_PATH_BYTES {
+            this.err = Some(
+                bun_sys::Error::from_code(bun_sys::E::ENAMETOOLONG, bun_sys::Tag::mkdir)
+                    .with_path(filepath.as_bytes()),
+            );
+            return;
+        }
+
         let mut node_fs = NodeFS::default();
         let args = fs_args::Mkdir {
             path: PathLike::String(bun_ptr::cow_slice::CowSlice::init_unchecked(
diff --git a/src/runtime/shell/builtin/touch.rs b/src/runtime/shell/builtin/touch.rs
index 95ae1398deee..c4ef56c0ff31 100644
--- a/src/runtime/shell/builtin/touch.rs
+++ b/src/runtime/shell/builtin/touch.rs
@@ -265,15 +265,17 @@ impl ShellTouchTask {
     pub(crate) fn run_from_thread_pool(this: &mut ShellTouchTask) {
         use bun_paths::resolve_path::{self, Platform, platform};
         use bun_sys::FdExt as _;
-        // We have to give an absolute path.
-        let mut buf = bun_paths::PathBuffer::uninit();
+        // We have to give an absolute path. An operand that does not fit the
+        // path buffer is still passed on whole, so the OS reports ENAMETOOLONG
+        // for it like for any other operand.
+        let mut spill = Vec::new();
         let filepath: &bun_core::ZStr = if Platform::AUTO.is_absolute(&this.filepath) {
-            // Re-terminate into the path buffer (`filepath` is the bare argv
-            // bytes without the trailing NUL).
-            resolve_path::join_z_buf::<platform::Auto>(buf.as_mut_slice(), &[&this.filepath])
+            // Re-terminate (`filepath` is the bare argv bytes without the
+            // trailing NUL).
+            resolve_path::join_z_spill::<platform::Auto>(&mut spill, &[&this.filepath])
         } else {
-            resolve_path::join_z_buf::<platform::Auto>(
-                buf.as_mut_slice(),
+            resolve_path::join_z_spill::<platform::Auto>(
+                &mut spill,
                 &[&this.cwd_path, &this.filepath],
             )
         };
diff --git a/test/js/bun/shell/commands/mkdir.test.ts b/test/js/bun/shell/commands/mkdir.test.ts
new file mode 100644
index 000000000000..8fd48977b24e
--- /dev/null
+++ b/test/js/bun/shell/commands/mkdir.test.ts
@@ -0,0 +1,77 @@
+import { expect, test } from "bun:test";
+import { bunEnv, bunExe, isWindows, tempDir } from "harness";
+import { join } from "node:path";
+
+// A relative operand was joined onto the cwd in a fixed 4096-byte buffer, so an
+// operand longer than that crashed the process, and an operand longer than a
+// PathBuffer (however it was spelled) was handed to the fs layer as "" and
+// reported as ENOENT. Runs in a child process so a crash shows up as a failed
+// assertion rather than taking the test runner down with it.
+test("operands longer than the path buffers are reported, not a crash", async () => {
+  using dir = tempDir("mkdir-long-operand", {});
+  const fixture = /* ts */ `
+    import { $ } from "bun";
+    import { existsSync } from "node:fs";
+    $.nothrow();
+    const dir = process.argv[1];
+    const long = Buffer.alloc(5000, "a").toString();
+    // Past the path buffer on every platform, Windows included.
+    const huge = Buffer.alloc(100_000, "h").toString();
+    // Longer than the buffers as written, but normalizes down to one component.
+    const dotSlashes = Buffer.alloc(6000, "./").toString();
+    const run = async (...args: string[]) => {
+      const { exitCode, stderr } = await $\`mkdir \${args}\`.quiet();
+      return { exitCode, stderr: stderr.toString() };
+    };
+    console.log(JSON.stringify({
+      cwd: process.cwd(),
+      relative: await run(long),
+      absolute: await run(dir + "/" + long),
+      parents: await run("-p", long),
+      huge: await run(huge),
+      mixed: { ...(await run(long, "short")), shortCreated: existsSync(dir + "/short") },
+      dotSlashes: { ...(await run(dotSlashes + "normalized")), created: existsSync(dir + "/normalized") },
+      absoluteDotSlashes: {
+        ...(await run(dir + "/" + dotSlashes + "as-written")),
+        created: existsSync(dir + "/as-written"),
+      },
+    }));
+  `;
+  await using proc = Bun.spawn({
+    cmd: [bunExe(), "-e", fixture, String(dir)],
+    env: bunEnv,
+    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 { cwd, ...results } = JSON.parse(stdout);
+
+  const long = Buffer.alloc(5000, "a").toString();
+  const huge = Buffer.alloc(100_000, "h").toString();
+  const dotSlashes = Buffer.alloc(6000, "./").toString();
+  // mkdir reports the path it operated on: a relative operand joined onto the
+  // cwd, an absolute one as written.
+  const tooLong = (path: string) => `mkdir: ${path}: File name too long\n`;
+  // 5000 bytes fits Windows' much larger path buffer, so there the OS picks
+  // the error; what matters is that each operand fails on its own.
+  const failed = (path: string) =>
+    isWindows ? { exitCode: 1, stderr: expect.stringMatching(/^mkdir: /) } : { exitCode: 1, stderr: tooLong(path) };
+  expect(results).toEqual({
+    relative: failed(join(cwd, long)),
+    absolute: failed(`${dir}/${long}`),
+    parents: failed(join(cwd, long)),
+    huge: { exitCode: 1, stderr: tooLong(join(cwd, huge)) },
+    mixed: { ...failed(join(cwd, long)), shortCreated: true },
+    dotSlashes: { exitCode: 0, stderr: "", created: true },
+    // An absolute operand is not normalized (`..` through a symlink means
+    // something else to the kernel), so like the kernel and coreutils, mkdir
+    // bounds it as written. On Windows it fits the much larger buffer and the
+    // fs layer normalizes it while converting it to a wide path, so it works.
+    absoluteDotSlashes: isWindows
+      ? { exitCode: 0, stderr: "", created: true }
+      : { ...failed(`${dir}/${dotSlashes}as-written`), created: false },
+  });
+  expect(exitCode).toBe(0);
+});
diff --git a/test/js/bun/shell/commands/touch.test.ts b/test/js/bun/shell/commands/touch.test.ts
new file mode 100644
index 000000000000..8c5e69391006
--- /dev/null
+++ b/test/js/bun/shell/commands/touch.test.ts
@@ -0,0 +1,63 @@
+import { expect, test } from "bun:test";
+import { bunEnv, bunExe, isWindows, tempDir } from "harness";
+import { join } from "node:path";
+
+// Every operand, absolute or not, was joined into a fixed-size path buffer, so
+// an operand longer than that crashed the process. Runs in a child process so a
+// crash shows up as a failed assertion rather than taking the test runner down
+// with it.
+test("operands longer than the path buffer are reported, not a crash", async () => {
+  using dir = tempDir("touch-long-operand", {});
+  const fixture = /* ts */ `
+    import { $ } from "bun";
+    import { existsSync } from "node:fs";
+    $.nothrow();
+    const dir = process.argv[1];
+    const long = Buffer.alloc(5000, "a").toString();
+    // Past the path buffer on every platform, Windows included.
+    const huge = Buffer.alloc(100_000, "h").toString();
+    // Longer than the buffer as written, but normalizes down to one component.
+    const dotSlashes = Buffer.alloc(6000, "./").toString() + "normalized";
+    const run = async (...args: string[]) => {
+      const { exitCode, stderr } = await $\`touch \${args}\`.quiet();
+      return { exitCode, stderr: stderr.toString() };
+    };
+    console.log(JSON.stringify({
+      cwd: process.cwd(),
+      relative: await run(long),
+      absolute: await run(dir + "/" + long),
+      huge: await run(huge),
+      mixed: { ...(await run(long, "short")), shortCreated: existsSync(dir + "/short") },
+      dotSlashes: { ...(await run(dotSlashes)), created: existsSync(dir + "/normalized") },
+    }));
+  `;
+  await using proc = Bun.spawn({
+    cmd: [bunExe(), "-e", fixture, String(dir)],
+    env: bunEnv,
+    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 { cwd, ...results } = JSON.parse(stdout);
+
+  const long = Buffer.alloc(5000, "a").toString();
+  const huge = Buffer.alloc(100_000, "h").toString();
+  // The over-long path is passed to the OS whole, and touch reports the path
+  // it operated on: a relative operand joined onto the cwd. Which errno
+  // Windows picks for it is up to the OS; what matters is that each operand
+  // fails on its own.
+  const failed = (path: string) =>
+    isWindows
+      ? { exitCode: 1, stderr: expect.stringMatching(/^touch: /) }
+      : { exitCode: 1, stderr: `touch: ${path}: File name too long\n` };
+  expect(results).toEqual({
+    relative: failed(join(cwd, long)),
+    absolute: failed(`${dir}/${long}`),
+    huge: failed(join(cwd, huge)),
+    mixed: { ...failed(join(cwd, long)), shortCreated: true },
+    dotSlashes: { exitCode: 0, stderr: "", created: true },
+  });
+  expect(exitCode).toBe(0);
+});