diff --git a/rust/headless-client/src/ipc_service.rs b/rust/headless-client/src/ipc_service.rs
index 27ea8eb71..45b7ffccf 100644
--- a/rust/headless-client/src/ipc_service.rs
+++ b/rust/headless-client/src/ipc_service.rs
@@ -101,7 +101,6 @@ pub enum ClientMsg {
         release: String,
         account_slug: Option<String>,
     },
-    StopTelemetry,
 }
 
 /// Messages that end up in the GUI, either forwarded from connlib or from the IPC service.
@@ -182,12 +181,20 @@ fn run_debug_ipc_service(cli: Cli) -> Result<()> {
         .build()?;
     let _guard = rt.enter();
     let mut signals = signals::Terminate::new()?;
+    let mut telemetry = Telemetry::default();
 
     rt.block_on(ipc_listen(
         cli.common.dns_control,
         &log_filter_reloader,
         &mut signals,
+        &mut telemetry,
     ))
+    .inspect(|_| rt.block_on(telemetry.stop()))
+    .inspect_err(|e| {
+        tracing::error!(error = anyhow_dyn_err(e), "IPC service failed");
+
+        rt.block_on(telemetry.stop_on_crash())
+    })
 }
 
 #[cfg(not(debug_assertions))]
@@ -242,6 +249,7 @@ async fn ipc_listen(
     dns_control_method: DnsControlMethod,
     log_filter_reloader: &LogFilterReloader,
     signals: &mut signals::Terminate,
+    telemetry: &mut Telemetry,
 ) -> Result<()> {
     // Create the device ID and IPC service config dir if needed
     // This also gives the GUI a safe place to put the log filter config
@@ -249,7 +257,6 @@ async fn ipc_listen(
         .context("Failed to read / create device ID")?
         .id;
 
-    let mut telemetry = Telemetry::default();
     telemetry.set_firezone_id(firezone_id);
 
     let mut server = IpcServer::new(ServiceId::Prod).await?;
@@ -259,7 +266,7 @@ async fn ipc_listen(
             &mut server,
             &mut dns_controller,
             log_filter_reloader,
-            &mut telemetry,
+            telemetry,
         ));
         let Some(handler) = poll_fn(|cx| {
             if let Poll::Ready(()) = signals.poll_recv(cx) {
@@ -564,9 +571,6 @@ impl<'a> Handler<'a> {
                     self.telemetry.set_account_slug(account_slug);
                 }
             }
-            ClientMsg::StopTelemetry => {
-                self.telemetry.stop().await;
-            }
         }
         Ok(())
     }
diff --git a/rust/headless-client/src/ipc_service/linux.rs b/rust/headless-client/src/ipc_service/linux.rs
index 3d26ce6c9..7263e5c85 100644
--- a/rust/headless-client/src/ipc_service/linux.rs
+++ b/rust/headless-client/src/ipc_service/linux.rs
@@ -1,6 +1,8 @@
 use super::CliCommon;
 use crate::signals;
 use anyhow::{bail, Result};
+use firezone_logging::anyhow_dyn_err;
+use firezone_telemetry::Telemetry;
 
 /// Cross-platform entry point for systemd / Windows services
 ///
@@ -15,12 +17,20 @@ pub(crate) fn run_ipc_service(cli: CliCommon) -> Result<()> {
         .build()?;
     let _guard = rt.enter();
     let mut signals = signals::Terminate::new()?;
+    let mut telemetry = Telemetry::default();
 
     rt.block_on(super::ipc_listen(
         cli.dns_control,
         &log_filter_reloader,
         &mut signals,
+        &mut telemetry,
     ))
+    .inspect(|_| rt.block_on(telemetry.stop()))
+    .inspect_err(|e| {
+        tracing::error!(error = anyhow_dyn_err(e), "IPC service failed");
+
+        rt.block_on(telemetry.stop_on_crash())
+    })
 }
 
 /// Returns true if the IPC service can run properly
diff --git a/rust/headless-client/src/ipc_service/windows.rs b/rust/headless-client/src/ipc_service/windows.rs
index faf210cef..cd2bbd32f 100644
--- a/rust/headless-client/src/ipc_service/windows.rs
+++ b/rust/headless-client/src/ipc_service/windows.rs
@@ -2,6 +2,7 @@ use crate::CliCommon;
 use anyhow::{bail, Context as _, Result};
 use firezone_bin_shared::platform::DnsControlMethod;
 use firezone_logging::anyhow_dyn_err;
+use firezone_telemetry::Telemetry;
 use futures::future::{self, Either};
 use std::{
     ffi::{c_void, OsString},
@@ -209,13 +210,23 @@ fn fallible_service_run(
         process_id: None,
     })?;
 
+    let mut telemetry = Telemetry::default();
+
     // Add new features in `service_run_async` if possible.
     // We don't want to bail out of `fallible_service_run` and forget to tell
     // Windows that we're shutting down.
-    let result = rt.block_on(service_run_async(&log_filter_reloader, shutdown_rx));
-    if let Err(error) = &result {
-        tracing::error!(error = anyhow_dyn_err(error));
-    }
+    let result = rt
+        .block_on(service_run_async(
+            &log_filter_reloader,
+            &mut telemetry,
+            shutdown_rx,
+        ))
+        .inspect(|_| rt.block_on(telemetry.stop()))
+        .inspect_err(|e| {
+            tracing::error!(error = anyhow_dyn_err(e), "IPC service failed");
+
+            rt.block_on(telemetry.stop_on_crash())
+        });
 
     // Drop the logging handle so it flushes the logs before we let Windows kill our process.
     // There is no obvious and elegant way to do this, since the logging and `ServiceState`
@@ -254,6 +265,7 @@ fn fallible_service_run(
 /// Logging must already be set up before calling this.
 async fn service_run_async(
     log_filter_reloader: &crate::LogFilterReloader,
+    telemetry: &mut Telemetry,
     mut shutdown_rx: mpsc::Receiver<()>,
 ) -> Result<()> {
     // Useless - Windows will never send us Ctrl+C when running as a service
@@ -262,7 +274,8 @@ async fn service_run_async(
     let listen_fut = pin!(super::ipc_listen(
         DnsControlMethod::Nrpt,
         log_filter_reloader,
-        &mut signals
+        &mut signals,
+        telemetry
     ));
     match future::select(listen_fut, pin!(shutdown_rx.recv())).await {
         Either::Left((Err(error), _)) => Err(error).context("`ipc_listen` threw an error"),