diff --git a/Cargo.lock b/Cargo.lock
index e586778e..09e1b822 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -224,15 +224,6 @@ version = "0.8.21"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "d0a5c400df2834b80a4c3327b3aad3a4c4cd4de0629063962b03235697506a28"
 
-[[package]]
-name = "daemonize"
-version = "0.5.0"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "ab8bfdaacb3c887a54d41bdf48d3af8873b3f5566469f8ba21b92057509f116e"
-dependencies = [
- "libc",
-]
-
 [[package]]
 name = "either"
 version = "1.15.0"
@@ -522,7 +513,6 @@ dependencies = [
  "byteorder",
  "clap",
  "crossbeam-channel",
- "daemonize",
  "lazy_static",
  "libc",
  "libproc",
diff --git a/libshpool/Cargo.toml b/libshpool/Cargo.toml
index a9dc10ff..2aa63e55 100644
--- a/libshpool/Cargo.toml
+++ b/libshpool/Cargo.toml
@@ -43,7 +43,6 @@ tempfile = "3" # RAII tmp files
 strip-ansi-escapes = "0.2.0" # cleaning up strings for pager display
 notify = { version = "7", features = ["crossbeam-channel"] }  # watch config file for updates
 libproc = "0.14.8" # sniffing shells by examining the subprocess
-daemonize = "0.5" # autodaemonization
 parking_lot = { version = "0.12", features = ["arc_lock"] } # faster more featureful sync primitives
 shpool-protocol = { version = "0.4.0", path = "../shpool-protocol" } # client-server protocol
 
diff --git a/libshpool/src/daemon/mod.rs b/libshpool/src/daemon/mod.rs
index 7b52ec71..fe43588b 100644
--- a/libshpool/src/daemon/mod.rs
+++ b/libshpool/src/daemon/mod.rs
@@ -17,7 +17,7 @@ use std::{env, os::unix::net::UnixListener, path::PathBuf};
 use anyhow::Context;
 use tracing::{info, instrument};
 
-use crate::{config, consts, hooks};
+use crate::{config, consts, daemonize, hooks};
 
 mod etc_environment;
 mod exit_notify;
@@ -43,7 +43,7 @@ pub fn run(
     >,
     socket: PathBuf,
 ) -> anyhow::Result<()> {
-    if let Ok(daemonize) = env::var(consts::AUTODAEMONIZE_VAR) {
+    let pid_guard = if let Ok(daemonize) = env::var(consts::AUTODAEMONIZE_VAR) {
         if daemonize == "true" {
             // Safety: this is executing before we have forked any threads,
             // so we are still in single-threaded mode, therefore it is safe
@@ -55,9 +55,15 @@ pub fn run(
             let pid_file = socket.with_file_name("daemonized-shpool.pid");
 
             info!("daemonizing with pid_file={:?}", pid_file);
-            daemonize::Daemonize::new().pid_file(pid_file).start().context("daemonizing")?;
+            // Safety: we are calling this before having forked any threads,
+            // which is sufficient to meet the safety requirements for fork().
+            Some(unsafe { daemonize::daemonize(pid_file) }.context("daemonizing")?)
+        } else {
+            None
         }
-    }
+    } else {
+        None
+    };
 
     info!("\n\n======================== STARTING DAEMON ============================\n\n");
 
@@ -82,7 +88,13 @@ pub fn run(
         }
     };
     // spawn the signal handler thread in the background
-    signals::Handler::new(cleanup_socket.clone()).spawn()?;
+    signals::Handler::new(
+        vec![cleanup_socket.clone(), pid_guard.as_ref().map(|g| g.path().clone())]
+            .into_iter()
+            .flatten()
+            .collect(),
+    )
+    .spawn()?;
 
     server::Server::serve(server, listener)?;
 
diff --git a/libshpool/src/daemon/signals.rs b/libshpool/src/daemon/signals.rs
index 3359883d..3bd21633 100644
--- a/libshpool/src/daemon/signals.rs
+++ b/libshpool/src/daemon/signals.rs
@@ -23,11 +23,11 @@ use signal_hook::{consts::TERM_SIGNALS, flag, iterator::Signals};
 use tracing::{error, info};
 
 pub struct Handler {
-    sock: Option<PathBuf>,
+    cleanup_paths: Vec<PathBuf>,
 }
 impl Handler {
-    pub fn new(sock: Option<PathBuf>) -> Self {
-        Handler { sock }
+    pub fn new(cleanup_paths: Vec<PathBuf>) -> Self {
+        Handler { cleanup_paths }
     }
 
     pub fn spawn(self) -> anyhow::Result<()> {
@@ -58,8 +58,8 @@ impl Handler {
                 assert!(TERM_SIGNALS.contains(&signal));
 
                 info!("term sig handler: cleaning up socket");
-                if let Some(sock) = self.sock {
-                    if let Err(e) = std::fs::remove_file(sock).context("cleaning up socket") {
+                for path in self.cleanup_paths.into_iter() {
+                    if let Err(e) = std::fs::remove_file(path).context("cleaning up socket") {
                         error!("error cleaning up socket file: {}", e);
                     }
                 }
diff --git a/libshpool/src/daemonize.rs b/libshpool/src/daemonize.rs
index 867aa5a6..a3c666c4 100644
--- a/libshpool/src/daemonize.rs
+++ b/libshpool/src/daemonize.rs
@@ -12,16 +12,32 @@
 // See the License for the specific language governing permissions and
 // limitations under the License.
 
-use std::{ffi::OsStr, os::unix::net::UnixStream, path::Path, process, thread, time::Duration};
+use std::{
+    ffi::OsStr,
+    fs,
+    io::{Seek, SeekFrom, Write},
+    os::unix::net::UnixStream,
+    path::{Path, PathBuf},
+    process, thread,
+    time::Duration,
+};
 
 use crate::{config, consts, Args};
 
 use anyhow::{anyhow, Context};
-use tracing::info;
+use nix::{
+    fcntl,
+    fcntl::FlockArg,
+    sys::{wait, wait::WaitStatus},
+    unistd,
+    unistd::ForkResult,
+};
+use tracing::{error, info};
 
 /// Check if we can connect to the control socket, and if we
-/// can't, fork the daemon in the background.
-pub fn maybe_fork_daemon<B, P>(
+/// can't, launch the daemon in the background. This should be
+/// called by client subcommands like `shpool attach` or `shpool list`
+pub fn maybe_launch_daemon<B, P>(
     config_manager: &config::Manager,
     args: &Args,
     shpool_bin: B,
@@ -106,3 +122,132 @@ where
 
     Err(anyhow!("daemonizing: launched daemon, but control socket never came up"))
 }
+
+pub struct PidFileGuard {
+    p: PathBuf,
+}
+
+impl PidFileGuard {
+    pub fn path(&self) -> &PathBuf {
+        &self.p
+    }
+}
+
+impl std::ops::Drop for PidFileGuard {
+    fn drop(&mut self) {
+        if let Err(e) = std::fs::remove_file(&self.p) {
+            error!("cleaning up pid file: {:?}", e);
+        }
+    }
+}
+
+/// Perform the traditional daemonization double-fork setsid dance.
+/// This should be called from within `shpool daemon` to detach it
+/// from the launching shell.
+///
+/// Safety: see nix::unistd::fork for preconditions.
+pub unsafe fn daemonize(pid_path: PathBuf) -> anyhow::Result<PidFileGuard> {
+    let old_mask = nix::sys::stat::umask(nix::sys::stat::Mode::empty());
+    info!("set empty umask (old mask: {:?}", old_mask);
+
+    // `cd /` in order to avoid holding open the directory the user
+    // happened to launch `shpool attach` in so that we don't block
+    // deletes of that directory the whole time that the daemon
+    // sticks around.
+    std::env::set_current_dir("/").context("cding to root")?;
+
+    // Fork and become the child in order to stop being the process group
+    // leader. We need to avoid being the process group leader in order
+    // to call setsid().
+    //
+    // Safety: the caller has ensured fork preconditions are met, which
+    // meet the become_child preconditions.
+    unsafe { become_child(true) }.context("first fork")?;
+
+    let sid = unistd::setsid().context("creating new session")?;
+    info!("while daemonizing setsid() = {}", sid);
+
+    let pid_file = fs::OpenOptions::new()
+        .read(true)
+        .write(true)
+        .create(true)
+        .truncate(false)
+        .open(&pid_path)
+        .context("opening pid file")?;
+    let mut pid_file = match fcntl::Flock::lock(pid_file, FlockArg::LockExclusiveNonblock) {
+        Ok(l) => l,
+        Err((_, errno)) if errno == nix::errno::Errno::EWOULDBLOCK => {
+            return Err(anyhow!("another daemon is already running"));
+        }
+        Err((_, errno)) => {
+            return Err(anyhow!("locking pid file: {:?}", errno));
+        }
+    };
+
+    // Safety: the caller has ensured fork preconditions are met, which
+    // meet the become_child preconditions.
+    unsafe { become_child(false) }.context("second fork")?;
+
+    // Actually write the pid file contents only now that we are in
+    // the grandchild and have our final pid.
+    pid_file.set_len(0).context("truncating pid file")?;
+    pid_file.seek(SeekFrom::Start(0)).context("seeking to start of pid file")?;
+    writeln!(*pid_file, "{}", std::process::id()).context("writing pid")?;
+
+    redirect_std_fds_to_null()?;
+
+    Ok(PidFileGuard { p: pid_path })
+}
+
+fn redirect_std_fds_to_null() -> anyhow::Result<()> {
+    // Safety: path is a valid null terminated string, O_RDWR is a valid flag.
+    let nullfd = unsafe { libc::open(b"/dev/null\0" as *const [u8; 10] as _, libc::O_RDWR) };
+    if nullfd == -1 {
+        return Err(anyhow!("opening /dev/null: {}", nix::errno::Errno::last()));
+    }
+    // Safety: nullfd is valid and newfd need not be open for saftey
+    let fd = unsafe { libc::dup2(nullfd, libc::STDIN_FILENO) };
+    if fd == -1 {
+        return Err(anyhow!("redirecting stdin to /dev/null: {}", nix::errno::Errno::last()));
+    }
+    // Safety: nullfd is valid and newfd need not be open for saftey
+    let fd = unsafe { libc::dup2(nullfd, libc::STDOUT_FILENO) };
+    if fd == -1 {
+        return Err(anyhow!("redirecting stdout to /dev/null: {}", nix::errno::Errno::last()));
+    }
+    // Safety: nullfd is valid and newfd need not be open for saftey
+    let fd = unsafe { libc::dup2(nullfd, libc::STDERR_FILENO) };
+    if fd == -1 {
+        return Err(anyhow!("redirecting stderr to /dev/null: {}", nix::errno::Errno::last()));
+    }
+
+    Ok(())
+}
+
+/// fork() and exit from the parent, so the only running process
+/// is the child process. If `wait_child` is true, rather than
+/// exiting immediately, the parent will wait for the child proc
+/// to exit and exit with its exit code. In the double-fork dance,
+/// we want to do this the first time so we propagate the error
+/// in case of a crash in the intermediate proc.
+///
+/// Safety: see nix::unistd::fork for preconditions.
+unsafe fn become_child(wait_child: bool) -> anyhow::Result<()> {
+    // Safety: since the caller has me the fork preconditions, this is
+    // safe.
+    match unsafe { unistd::fork() }.context("forking for daemonization")? {
+        ForkResult::Parent { child } => {
+            if wait_child {
+                match wait::waitpid(child, None).context("waiting for child")? {
+                    WaitStatus::Exited(_, status) => std::process::exit(status),
+                    WaitStatus::Signaled(_, _, _) => std::process::exit(1),
+                    _ => {}
+                }
+            } else {
+                std::process::exit(0);
+            }
+        }
+        ForkResult::Child => {}
+    }
+    Ok(())
+}
diff --git a/libshpool/src/lib.rs b/libshpool/src/lib.rs
index aad548d6..72b06817 100644
--- a/libshpool/src/lib.rs
+++ b/libshpool/src/lib.rs
@@ -327,7 +327,18 @@ impl<'writer> tracing_subscriber::fmt::MakeWriter<'writer> for LogWriterBuilder
 
 /// Run the shpool tool with the given arguments. If hooks is provided,
 /// inject the callbacks into the daemon.
-pub fn run(args: Args, hooks: Option<Box<dyn hooks::Hooks + Send + Sync>>) -> anyhow::Result<()> {
+///
+/// # Safety
+///
+/// Callers MUST NOT call this routine after forking a thread.
+/// internally shpool will double-fork to daemonize, and doing so with
+/// multiple threads running is unsafe. Really this only applies when
+/// consts::AUTODAEMONIZE_VAR is set to true in the environment, but
+/// we still need to mark this entrypoint unsafe to be sound.
+pub unsafe fn run(
+    args: Args,
+    hooks: Option<Box<dyn hooks::Hooks + Send + Sync>>,
+) -> anyhow::Result<()> {
     match (&args.command, env::var(consts::SENTINEL_FLAG_VAR).as_deref()) {
         (Commands::Daemon, Ok("prompt")) => {
             println!("{}", consts::PROMPT_SENTINEL);
@@ -401,7 +412,7 @@ pub fn run(args: Args, hooks: Option<Box<dyn hooks::Hooks + Send + Sync>>) -> an
     if !config_manager.get().nodaemonize.unwrap_or(false) || args.daemonize {
         let arg0 = env::args().next().ok_or(anyhow!("arg0 missing"))?;
         if !args.no_daemonize && !matches!(args.command, Commands::Daemon) {
-            daemonize::maybe_fork_daemon(&config_manager, &args, arg0, &socket)?;
+            daemonize::maybe_launch_daemon(&config_manager, &args, arg0, &socket)?;
         }
     }
 
diff --git a/shpool/src/main.rs b/shpool/src/main.rs
index e7f221d2..f3e0f03c 100644
--- a/shpool/src/main.rs
+++ b/shpool/src/main.rs
@@ -27,5 +27,6 @@ fn main() -> anyhow::Result<()> {
         return Ok(());
     }
 
-    libshpool::run(args, None)
+    // Safety: there is only a single thread running.
+    unsafe { libshpool::run(args, None) }
 }
diff --git a/shpool/tests/attach.rs b/shpool/tests/attach.rs
index 302d6c78..131f6c9b 100644
--- a/shpool/tests/attach.rs
+++ b/shpool/tests/attach.rs
@@ -5,7 +5,6 @@ use std::{
     fs,
     io::BufRead,
     io::{Read, Write},
-    path::PathBuf,
     process::{Command, Stdio},
     thread, time,
 };
@@ -1549,55 +1548,6 @@ fn fresh_shell_does_not_have_prompt_setup_code() -> anyhow::Result<()> {
     Ok(())
 }
 
-#[test]
-#[timeout(30000)]
-fn autodaemonize() -> anyhow::Result<()> {
-    let tmp_dir = tmpdir::Dir::new("/tmp/shpool-test")?;
-    eprintln!("testing autodaemonization in {:?}", tmp_dir.path());
-
-    let mut socket_path = PathBuf::from(tmp_dir.path());
-    socket_path.push("control.sock");
-
-    let mut log_file = PathBuf::from(tmp_dir.path());
-    log_file.push("attach.log");
-
-    // we have to manually spawn the child because the whole point is that there
-    // isn't a daemon yet so we can't use the attach method.
-    let mut child = Command::new(support::shpool_bin()?)
-        .stdout(Stdio::piped())
-        .stderr(Stdio::piped())
-        .arg("--daemonize")
-        .arg("--socket")
-        .arg(socket_path)
-        .arg("--log-file")
-        .arg(log_file)
-        .arg("--config-file")
-        .arg(support::testdata_file("norc.toml"))
-        .arg("attach")
-        .arg("sh1")
-        .spawn()
-        .context("spawning attach process")?;
-
-    // After half a second, the daemon should have spanwed
-    std::thread::sleep(time::Duration::from_millis(500));
-    child.kill().context("killing child")?;
-
-    let mut stdout = child.stdout.take().context("missing stdout")?;
-    let mut stdout_str = String::from("");
-    stdout.read_to_string(&mut stdout_str).context("slurping stdout")?;
-    let stdout_re = Regex::new(".*prompt>.*")?;
-    assert!(stdout_re.is_match(&stdout_str));
-
-    // best effort attempt to clean up after ourselves
-    Command::new("pkill")
-        .arg("-f")
-        .arg("shpool-test-autodaemonize")
-        .output()
-        .context("running cleanup process")?;
-
-    Ok(())
-}
-
 #[test]
 #[timeout(30000)]
 fn config_tmp_default_dir() -> anyhow::Result<()> {
diff --git a/shpool/tests/daemon.rs b/shpool/tests/daemon.rs
index 79ee2f1d..01ba1c3b 100644
--- a/shpool/tests/daemon.rs
+++ b/shpool/tests/daemon.rs
@@ -5,7 +5,7 @@ use std::{
         net::{UnixListener, UnixStream},
         process::CommandExt as _,
     },
-    path,
+    path::{self, PathBuf},
     process::{Command, Stdio},
     time,
 };
@@ -344,3 +344,128 @@ fn allows_dynamic_log_adjustments() -> anyhow::Result<()> {
 
     Ok(())
 }
+
+#[test]
+#[timeout(30000)]
+fn autodaemonize() -> anyhow::Result<()> {
+    let tmp_dir = tmpdir::Dir::new("/tmp/shpool-test")?;
+    eprintln!("testing autodaemonization in {:?}", tmp_dir.path());
+
+    let mut socket_path = PathBuf::from(tmp_dir.path());
+    socket_path.push("control.sock");
+
+    let mut log_file = PathBuf::from(tmp_dir.path());
+    log_file.push("attach.log");
+
+    // we have to manually spawn the child because the whole point is that there
+    // isn't a daemon yet so we can't use the attach method.
+    let mut child = Command::new(support::shpool_bin()?)
+        .stdout(Stdio::piped())
+        .stderr(Stdio::piped())
+        .arg("--daemonize")
+        .arg("--socket")
+        .arg(socket_path)
+        .arg("--log-file")
+        .arg(log_file)
+        .arg("--config-file")
+        .arg(support::testdata_file("norc.toml"))
+        .arg("attach")
+        .arg("sh1")
+        .spawn()
+        .context("spawning attach process")?;
+
+    // After half a second, the daemon should have spanwed
+    std::thread::sleep(time::Duration::from_millis(500));
+    child.kill().context("killing child")?;
+
+    let mut stdout = child.stdout.take().context("missing stdout")?;
+    let mut stdout_str = String::from("");
+    stdout.read_to_string(&mut stdout_str).context("slurping stdout")?;
+    let stdout_re = Regex::new(".*prompt>.*")?;
+    assert!(stdout_re.is_match(&stdout_str));
+
+    // best effort attempt to clean up after ourselves
+    Command::new("pkill")
+        .arg("-f")
+        .arg("shpool-test-autodaemonize")
+        .output()
+        .context("running cleanup process")?;
+
+    Ok(())
+}
+
+#[test]
+#[timeout(30000)]
+fn daemonize_cwd_cleanup() -> anyhow::Result<()> {
+    let launch_dir = tmpdir::Dir::new("/tmp/shpool-test-launch")?;
+    let daemon_dir = tmpdir::Dir::new("/tmp/shpool-test-daemon")?;
+
+    let socket_path = daemon_dir.path().join("shpool.socket");
+    let log_file = daemon_dir.path().join("shpool.log");
+
+    // Launch from launch_dir
+    let out = Command::new(support::shpool_bin()?)
+        .current_dir(launch_dir.path())
+        .arg("--daemonize")
+        .arg("--socket")
+        .arg(&socket_path)
+        .arg("--log-file")
+        .arg(&log_file)
+        .arg("--config-file")
+        .arg(support::testdata_file("norc.toml"))
+        .arg("list")
+        .output()
+        .context("running shpool list --daemonize")?;
+
+    assert!(out.status.success(), "shpool list should succeed");
+
+    // Give it a moment just in case
+    std::thread::sleep(time::Duration::from_millis(100));
+
+    // Explicitly try to remove the launch directory.
+    // If the daemon didn't cd /, this might fail because the directory is busy.
+    let rm_res = std::fs::remove_dir_all(launch_dir.path());
+
+    // Best-effort cleanup of the background daemon spawned by --daemonize.
+    Command::new("pkill").arg("-f").arg(socket_path.to_string_lossy().as_ref()).output().ok();
+
+    rm_res.context("removing launch directory")?;
+
+    Ok(())
+}
+
+#[test]
+#[timeout(30000)]
+fn daemonize_pid_file_exists() -> anyhow::Result<()> {
+    let tmp_dir = tmpdir::Dir::new("/tmp/shpool-test-pid")?;
+    let socket_path = tmp_dir.path().join("shpool.socket");
+    let log_file = tmp_dir.path().join("shpool.log");
+    let pid_file = tmp_dir.path().join("daemonized-shpool.pid");
+
+    // Launch daemon via autodaemonize
+    let out = Command::new(support::shpool_bin()?)
+        .arg("--daemonize")
+        .arg("--socket")
+        .arg(&socket_path)
+        .arg("--log-file")
+        .arg(&log_file)
+        .arg("--config-file")
+        .arg(support::testdata_file("norc.toml"))
+        .arg("list")
+        .output()
+        .context("running shpool list --daemonize")?;
+
+    assert!(out.status.success(), "shpool list should succeed");
+
+    // Give it a moment to spawn
+    std::thread::sleep(time::Duration::from_millis(500));
+
+    let pid_exists = pid_file.exists();
+
+    // Cleanup
+    Command::new("pkill").arg("-f").arg(socket_path.to_string_lossy().as_ref()).output().ok();
+
+    assert!(pid_exists, "pid file should exist while daemon is running");
+
+    Ok(())
+}
diff --git a/shpool/tests/support/daemon.rs b/shpool/tests/support/daemon.rs
index 102761b2..3f932d35 100644
--- a/shpool/tests/support/daemon.rs
+++ b/shpool/tests/support/daemon.rs
@@ -239,7 +239,9 @@ impl Proc {
 
         // spawn the daemon in a thread
         thread::spawn(move || {
-            if let Err(err) = libshpool::run(args, Some(hooks_recorder)) {
+            // Safety: we do not have consts::AUTODAEMONIZE_VAR set in the
+            // environment, so libshpool::run will not fork.
+            if let Err(err) = unsafe { libshpool::run(args, Some(hooks_recorder)) } {
                 eprintln!("shpool proc exited with err: {err:?}");
             }
         });