diff --git a/Cargo.lock b/Cargo.lock
index ed178f1..0a32ff4 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -624,6 +624,7 @@ dependencies = [
  "serde_json",
  "serde_yaml",
  "simplelog",
+ "sysinfo",
  "tempdir",
  "thiserror",
  "widestring",
@@ -1395,9 +1396,9 @@ checksum = "830d08ce1d1d941e6b30645f1a0eb5643013d835ce3779a5fc208261dbe10f55"
 
 [[package]]
 name = "libc"
-version = "0.2.101"
+version = "0.2.126"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "3cb00336871be5ed2c8ed44b60ae9959dc5b9f08539422ed43f09e34ecaeba21"
+checksum = "349d5a591cd28b49e1d1037471617a32ddcda5731b99419008085f72d5a53836"
 
 [[package]]
 name = "libdbus-sys"
@@ -2191,6 +2192,30 @@ dependencies = [
  "rand_core 0.5.1",
 ]
 
+[[package]]
+name = "rayon"
+version = "1.5.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "bd99e5772ead8baa5215278c9b15bf92087709e9c1b2d1f97cdb5a183c933a7d"
+dependencies = [
+ "autocfg",
+ "crossbeam-deque",
+ "either",
+ "rayon-core",
+]
+
+[[package]]
+name = "rayon-core"
+version = "1.9.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "258bcdb5ac6dad48491bb2992db6b7cf74878b0384908af124823d118c99683f"
+dependencies = [
+ "crossbeam-channel",
+ "crossbeam-deque",
+ "crossbeam-utils",
+ "num_cpus",
+]
+
 [[package]]
 name = "rdrand"
 version = "0.4.0"
@@ -2607,6 +2632,21 @@ dependencies = [
  "winapi 0.3.9",
 ]
 
+[[package]]
+name = "sysinfo"
+version = "0.24.5"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "7d80929a3b477bce3a64360ca82bfb361eacce1dcb7b1fb31e8e5e181e37c212"
+dependencies = [
+ "cfg-if 1.0.0",
+ "core-foundation-sys",
+ "libc",
+ "ntapi",
+ "once_cell",
+ "rayon",
+ "winapi 0.3.9",
+]
+
 [[package]]
 name = "tempdir"
 version = "0.3.7"
diff --git a/espanso/Cargo.toml b/espanso/Cargo.toml
index 686d05b..3a8c270 100644
--- a/espanso/Cargo.toml
+++ b/espanso/Cargo.toml
@@ -56,6 +56,7 @@ colored = "2.0.0"
 tempdir = "0.3.7"
 notify = "4.0.17"
 opener = "0.5.0"
+sysinfo = "0.24.5"
 
 [target.'cfg(windows)'.dependencies]
 named_pipe = "0.4.1"
diff --git a/espanso/src/cli/service/mod.rs b/espanso/src/cli/service/mod.rs
index b9dc7fc..fe6a921 100644
--- a/espanso/src/cli/service/mod.rs
+++ b/espanso/src/cli/service/mod.rs
@@ -152,6 +152,14 @@ fn start_main(paths: &Paths, _paths_overrides: &PathsOverrides, args: &ArgMatche
   }
 
   error_eprintln!("unable to start service: timed out");
+
+  error_eprintln!(
+    "Hint: sometimes this happens because another Espanso process is left running for some reason."
+  );
+  error_eprintln!(
+    "      Please try running 'espanso restart' or manually killing all Espanso processes, then try again."
+  );
+
   SERVICE_TIMED_OUT
 }
 
diff --git a/espanso/src/cli/service/stop.rs b/espanso/src/cli/service/stop.rs
index 4a39efa..9024416 100644
--- a/espanso/src/cli/service/stop.rs
+++ b/espanso/src/cli/service/stop.rs
@@ -19,14 +19,18 @@
 
 use anyhow::{Error, Result};
 use log::error;
+use std::process::Command;
 use std::{path::Path, time::Instant};
+use sysinfo::{PidExt, ProcessExt, ProcessRefreshKind, RefreshKind, System, SystemExt};
 use thiserror::Error;
 
 use espanso_ipc::IPCClient;
 
+use crate::info_println;
 use crate::{
   ipc::{create_ipc_client_to_worker, IPCEvent},
   lock::acquire_worker_lock,
+  warn_eprintln,
 };
 
 pub fn terminate_worker(runtime_dir: &Path) -> Result<()> {
@@ -46,14 +50,18 @@ pub fn terminate_worker(runtime_dir: &Path) -> Result<()> {
     }
   }
 
-  let now = Instant::now();
-  while now.elapsed() < std::time::Duration::from_secs(3) {
-    let lock_file = acquire_worker_lock(runtime_dir);
-    if lock_file.is_some() {
-      return Ok(());
-    }
+  if wait_for_worker_to_be_stopped(runtime_dir) {
+    return Ok(());
+  }
 
-    std::thread::sleep(std::time::Duration::from_millis(200));
+  warn_eprintln!(
+    "unable to gracefully terminate espanso (timed-out), trying to force the termination..."
+  );
+
+  forcefully_terminate_espanso();
+
+  if wait_for_worker_to_be_stopped(runtime_dir) {
+    return Ok(());
   }
 
   Err(StopError::WorkerTimedOut.into())
@@ -67,3 +75,47 @@ pub enum StopError {
   #[error("ipc error: `{0}`")]
   IPCError(Error),
 }
+
+fn wait_for_worker_to_be_stopped(runtime_dir: &Path) -> bool {
+  let now = Instant::now();
+  while now.elapsed() < std::time::Duration::from_secs(3) {
+    let lock_file = acquire_worker_lock(runtime_dir);
+    if lock_file.is_some() {
+      return true;
+    }
+
+    std::thread::sleep(std::time::Duration::from_millis(200));
+  }
+
+  false
+}
+
+fn forcefully_terminate_espanso() {
+  let mut sys =
+    System::new_with_specifics(RefreshKind::new().with_processes(ProcessRefreshKind::new()));
+  sys.refresh_processes_specifics(ProcessRefreshKind::new());
+
+  let target_process_names = if cfg!(target_os = "windows") {
+    vec!["espanso.exe", "espansod.exe"]
+  } else {
+    vec!["espanso"]
+  };
+
+  let current_pid = std::process::id();
+
+  // We want to terminate all Espanso processes except this one
+  for (pid, process) in sys.processes() {
+    if target_process_names.contains(&process.name()) && pid.as_u32() != current_pid {
+      let str_pid = pid.as_u32().to_string();
+      info_println!("killing espanso process with PID: {}", str_pid);
+
+      if cfg!(target_os = "windows") {
+        let _ = Command::new("taskkill")
+          .args(&["/pid", &str_pid, "/f"])
+          .output();
+      } else {
+        let _ = Command::new("kill").args(&["-9", &str_pid]).output();
+      }
+    }
+  }
+}
diff --git a/espanso/src/main.rs b/espanso/src/main.rs
index 708cd8d..7db6bf2 100644
--- a/espanso/src/main.rs
+++ b/espanso/src/main.rs
@@ -36,6 +36,7 @@ use simplelog::{
 use crate::{
   cli::{LogMode, PathsOverrides},
   config::load_config,
+  util::log_system_info,
 };
 
 mod capabilities;
@@ -586,6 +587,7 @@ For example, specifying 'email' is equivalent to 'match/email.yml'."#))
       info!("reading configs from: {:?}", paths.config);
       info!("reading packages from: {:?}", paths.packages);
       info!("using runtime dir: {:?}", paths.runtime);
+      log_system_info();
 
       if handler.requires_config {
         let config_result =
diff --git a/espanso/src/util.rs b/espanso/src/util.rs
index 1e4a22f..42602f5 100644
--- a/espanso/src/util.rs
+++ b/espanso/src/util.rs
@@ -17,7 +17,9 @@
  * along with espanso.  If not, see <https://www.gnu.org/licenses/>.
  */
 
+use log::info;
 use std::process::Command;
+use sysinfo::{System, SystemExt};
 
 #[cfg(target_os = "windows")]
 pub fn set_command_flags(command: &mut Command) {
@@ -43,3 +45,13 @@ pub fn attach_console() {
 pub fn attach_console() {
   // Not necessary on Linux and macOS
 }
+
+pub fn log_system_info() {
+  let sys = System::new();
+  info!(
+    "system info: {} v{} - kernel: {}",
+    sys.name().unwrap_or_default(),
+    sys.os_version().unwrap_or_default(),
+    sys.kernel_version().unwrap_or_default()
+  );
+}