diff --git a/Cargo.lock b/Cargo.lock
index 8976c485..0a11d8e9 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -107,6 +107,11 @@ dependencies = [
  "constant_time_eq 0.1.4 (registry+https://github.com/rust-lang/crates.io-index)",
 ]
 
+[[package]]
+name = "block"
+version = "0.1.6"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+
 [[package]]
 name = "byteorder"
 version = "1.3.2"
@@ -318,6 +323,15 @@ dependencies = [
  "lazy_static 1.4.0 (registry+https://github.com/rust-lang/crates.io-index)",
 ]
 
+[[package]]
+name = "dbus"
+version = "0.6.5"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+dependencies = [
+ "libc 0.2.65 (registry+https://github.com/rust-lang/crates.io-index)",
+ "libdbus-sys 0.2.1 (registry+https://github.com/rust-lang/crates.io-index)",
+]
+
 [[package]]
 name = "directories"
 version = "2.0.2"
@@ -327,6 +341,16 @@ dependencies = [
  "dirs-sys 0.3.4 (registry+https://github.com/rust-lang/crates.io-index)",
 ]
 
+[[package]]
+name = "dirs"
+version = "1.0.5"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+dependencies = [
+ "libc 0.2.65 (registry+https://github.com/rust-lang/crates.io-index)",
+ "redox_users 0.3.1 (registry+https://github.com/rust-lang/crates.io-index)",
+ "winapi 0.3.8 (registry+https://github.com/rust-lang/crates.io-index)",
+]
+
 [[package]]
 name = "dirs-sys"
 version = "0.3.4"
@@ -690,6 +714,14 @@ name = "libc"
 version = "0.2.65"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 
+[[package]]
+name = "libdbus-sys"
+version = "0.2.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+dependencies = [
+ "pkg-config 0.3.17 (registry+https://github.com/rust-lang/crates.io-index)",
+]
+
 [[package]]
 name = "lock_api"
 version = "0.3.2"
@@ -706,6 +738,25 @@ dependencies = [
  "cfg-if 0.1.10 (registry+https://github.com/rust-lang/crates.io-index)",
 ]
 
+[[package]]
+name = "mac-notification-sys"
+version = "0.3.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+dependencies = [
+ "cc 1.0.47 (registry+https://github.com/rust-lang/crates.io-index)",
+ "chrono 0.4.10 (registry+https://github.com/rust-lang/crates.io-index)",
+ "dirs 1.0.5 (registry+https://github.com/rust-lang/crates.io-index)",
+ "objc-foundation 0.1.1 (registry+https://github.com/rust-lang/crates.io-index)",
+]
+
+[[package]]
+name = "malloc_buf"
+version = "0.0.6"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+dependencies = [
+ "libc 0.2.65 (registry+https://github.com/rust-lang/crates.io-index)",
+]
+
 [[package]]
 name = "matches"
 version = "0.1.8"
@@ -849,6 +900,15 @@ dependencies = [
  "void 1.0.2 (registry+https://github.com/rust-lang/crates.io-index)",
 ]
 
+[[package]]
+name = "notify-rust"
+version = "3.6.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+dependencies = [
+ "dbus 0.6.5 (registry+https://github.com/rust-lang/crates.io-index)",
+ "mac-notification-sys 0.3.0 (registry+https://github.com/rust-lang/crates.io-index)",
+]
+
 [[package]]
 name = "num-integer"
 version = "0.1.41"
@@ -883,6 +943,32 @@ dependencies = [
  "num-traits 0.2.10 (registry+https://github.com/rust-lang/crates.io-index)",
 ]
 
+[[package]]
+name = "objc"
+version = "0.2.7"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+dependencies = [
+ "malloc_buf 0.0.6 (registry+https://github.com/rust-lang/crates.io-index)",
+]
+
+[[package]]
+name = "objc-foundation"
+version = "0.1.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+dependencies = [
+ "block 0.1.6 (registry+https://github.com/rust-lang/crates.io-index)",
+ "objc 0.2.7 (registry+https://github.com/rust-lang/crates.io-index)",
+ "objc_id 0.1.1 (registry+https://github.com/rust-lang/crates.io-index)",
+]
+
+[[package]]
+name = "objc_id"
+version = "0.1.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+dependencies = [
+ "objc 0.2.7 (registry+https://github.com/rust-lang/crates.io-index)",
+]
+
 [[package]]
 name = "openssl"
 version = "0.10.26"
@@ -1864,6 +1950,7 @@ dependencies = [
  "lazy_static 1.4.0 (registry+https://github.com/rust-lang/crates.io-index)",
  "log 0.4.8 (registry+https://github.com/rust-lang/crates.io-index)",
  "nix 0.15.0 (registry+https://github.com/rust-lang/crates.io-index)",
+ "notify-rust 3.6.3 (registry+https://github.com/rust-lang/crates.io-index)",
  "openssl-probe 0.1.2 (registry+https://github.com/rust-lang/crates.io-index)",
  "pretty_env_logger 0.3.1 (registry+https://github.com/rust-lang/crates.io-index)",
  "rust-ini 0.13.0 (registry+https://github.com/rust-lang/crates.io-index)",
@@ -2119,6 +2206,7 @@ dependencies = [
 "checksum base64 0.9.3 (registry+https://github.com/rust-lang/crates.io-index)" = "489d6c0ed21b11d038c31b6ceccca973e65d73ba3bd8ecb9a2babf5546164643"
 "checksum bitflags 1.2.1 (registry+https://github.com/rust-lang/crates.io-index)" = "cf1de2fe8c75bc145a2f577add951f8134889b4795d47466a54a5c846d691693"
 "checksum blake2b_simd 0.5.9 (registry+https://github.com/rust-lang/crates.io-index)" = "b83b7baab1e671718d78204225800d6b170e648188ac7dc992e9d6bddf87d0c0"
+"checksum block 0.1.6 (registry+https://github.com/rust-lang/crates.io-index)" = "0d8c1fef690941d3e7788d328517591fecc684c084084702d6ff1641e993699a"
 "checksum byteorder 1.3.2 (registry+https://github.com/rust-lang/crates.io-index)" = "a7c3dd8985a7111efc5c80b44e23ecdd8c007de8ade3b96595387e812b957cf5"
 "checksum bytes 0.4.12 (registry+https://github.com/rust-lang/crates.io-index)" = "206fdffcfa2df7cbe15601ef46c813fce0965eb3286db6b56c583b814b51c81c"
 "checksum bzip2 0.3.3 (registry+https://github.com/rust-lang/crates.io-index)" = "42b7c3cbf0fa9c1b82308d57191728ca0256cb821220f4e2fd410a72ade26e3b"
@@ -2142,7 +2230,9 @@ dependencies = [
 "checksum crossbeam-queue 0.1.2 (registry+https://github.com/rust-lang/crates.io-index)" = "7c979cd6cfe72335896575c6b5688da489e420d36a27a0b9eb0c73db574b4a4b"
 "checksum crossbeam-utils 0.6.6 (registry+https://github.com/rust-lang/crates.io-index)" = "04973fa96e96579258a5091af6003abde64af786b860f18622b82e026cca60e6"
 "checksum crossbeam-utils 0.7.0 (registry+https://github.com/rust-lang/crates.io-index)" = "ce446db02cdc3165b94ae73111e570793400d0794e46125cc4056c81cbb039f4"
+"checksum dbus 0.6.5 (registry+https://github.com/rust-lang/crates.io-index)" = "48b5f0f36f1eebe901b0e6bee369a77ed3396334bf3f09abd46454a576f71819"
 "checksum directories 2.0.2 (registry+https://github.com/rust-lang/crates.io-index)" = "551a778172a450d7fc12e629ca3b0428d00f6afa9a43da1b630d54604e97371c"
+"checksum dirs 1.0.5 (registry+https://github.com/rust-lang/crates.io-index)" = "3fd78930633bd1c6e35c4b42b1df7b0cbc6bc191146e512bb3bedf243fcc3901"
 "checksum dirs-sys 0.3.4 (registry+https://github.com/rust-lang/crates.io-index)" = "afa0b23de8fd801745c471deffa6e12d248f962c9fd4b4c33787b055599bde7b"
 "checksum dtoa 0.4.4 (registry+https://github.com/rust-lang/crates.io-index)" = "ea57b42383d091c85abcc2706240b94ab2a8fa1fc81c10ff23c4de06e2a90b5e"
 "checksum either 1.5.3 (registry+https://github.com/rust-lang/crates.io-index)" = "bb1f6b1ce1c140482ea30ddd3335fc0024ac7ee112895426e0a629a6c20adfe3"
@@ -2184,8 +2274,11 @@ dependencies = [
 "checksum language-tags 0.2.2 (registry+https://github.com/rust-lang/crates.io-index)" = "a91d884b6667cd606bb5a69aa0c99ba811a115fc68915e7056ec08a46e93199a"
 "checksum lazy_static 1.4.0 (registry+https://github.com/rust-lang/crates.io-index)" = "e2abad23fbc42b3700f2f279844dc832adb2b2eb069b2df918f455c4e18cc646"
 "checksum libc 0.2.65 (registry+https://github.com/rust-lang/crates.io-index)" = "1a31a0627fdf1f6a39ec0dd577e101440b7db22672c0901fe00a9a6fbb5c24e8"
+"checksum libdbus-sys 0.2.1 (registry+https://github.com/rust-lang/crates.io-index)" = "dc12a3bc971424edbbf7edaf6e5740483444db63aa8e23d3751ff12a30f306f0"
 "checksum lock_api 0.3.2 (registry+https://github.com/rust-lang/crates.io-index)" = "e57b3997725d2b60dbec1297f6c2e2957cc383db1cebd6be812163f969c7d586"
 "checksum log 0.4.8 (registry+https://github.com/rust-lang/crates.io-index)" = "14b6052be84e6b71ab17edffc2eeabf5c2c3ae1fdb464aae35ac50c67a44e1f7"
+"checksum mac-notification-sys 0.3.0 (registry+https://github.com/rust-lang/crates.io-index)" = "3dfb6b71a9a89cd38b395d994214297447e8e63b1ba5708a9a2b0b1048ceda76"
+"checksum malloc_buf 0.0.6 (registry+https://github.com/rust-lang/crates.io-index)" = "62bb907fe88d54d8d9ce32a3cceab4218ed2f6b7d35617cafe9adf84e43919cb"
 "checksum matches 0.1.8 (registry+https://github.com/rust-lang/crates.io-index)" = "7ffc5c5338469d4d3ea17d269fa8ea3512ad247247c30bd2df69e68309ed0a08"
 "checksum maybe-uninit 2.0.0 (registry+https://github.com/rust-lang/crates.io-index)" = "60302e4db3a61da70c0cb7991976248362f30319e88850c487b9b95bbf059e00"
 "checksum memchr 2.2.1 (registry+https://github.com/rust-lang/crates.io-index)" = "88579771288728879b57485cc7d6b07d648c9f0141eb955f8ab7f9d45394468e"
@@ -2201,10 +2294,14 @@ dependencies = [
 "checksum native-tls 0.2.3 (registry+https://github.com/rust-lang/crates.io-index)" = "4b2df1a4c22fd44a62147fd8f13dd0f95c9d8ca7b2610299b2a2f9cf8964274e"
 "checksum net2 0.2.33 (registry+https://github.com/rust-lang/crates.io-index)" = "42550d9fb7b6684a6d404d9fa7250c2eb2646df731d1c06afc06dcee9e1bcf88"
 "checksum nix 0.15.0 (registry+https://github.com/rust-lang/crates.io-index)" = "3b2e0b4f3320ed72aaedb9a5ac838690a8047c7b275da22711fddff4f8a14229"
+"checksum notify-rust 3.6.3 (registry+https://github.com/rust-lang/crates.io-index)" = "f8da29142be3f71b2165a6b3991c26045b674edbf04cdfc42f323094fc3e4b5a"
 "checksum num-integer 0.1.41 (registry+https://github.com/rust-lang/crates.io-index)" = "b85e541ef8255f6cf42bbfe4ef361305c6c135d10919ecc26126c4e5ae94bc09"
 "checksum num-traits 0.2.10 (registry+https://github.com/rust-lang/crates.io-index)" = "d4c81ffc11c212fa327657cb19dd85eb7419e163b5b076bede2bdb5c974c07e4"
 "checksum num_cpus 1.11.1 (registry+https://github.com/rust-lang/crates.io-index)" = "76dac5ed2a876980778b8b85f75a71b6cbf0db0b1232ee12f826bccb00d09d72"
 "checksum number_prefix 0.2.8 (registry+https://github.com/rust-lang/crates.io-index)" = "dbf9993e59c894e3c08aa1c2712914e9e6bf1fcbfc6bef283e2183df345a4fee"
+"checksum objc 0.2.7 (registry+https://github.com/rust-lang/crates.io-index)" = "915b1b472bc21c53464d6c8461c9d3af805ba1ef837e1cac254428f4a77177b1"
+"checksum objc-foundation 0.1.1 (registry+https://github.com/rust-lang/crates.io-index)" = "1add1b659e36c9607c7aab864a76c7a4c2760cd0cd2e120f3fb8b952c7e22bf9"
+"checksum objc_id 0.1.1 (registry+https://github.com/rust-lang/crates.io-index)" = "c92d4ddb4bd7b50d730c215ff871754d0da6b2178849f8a2a2ab69712d0c073b"
 "checksum openssl 0.10.26 (registry+https://github.com/rust-lang/crates.io-index)" = "3a3cc5799d98e1088141b8e01ff760112bbd9f19d850c124500566ca6901a585"
 "checksum openssl-probe 0.1.2 (registry+https://github.com/rust-lang/crates.io-index)" = "77af24da69f9d9341038eba93a073b1fdaaa1b788221b00a69bce9e762cb32de"
 "checksum openssl-sys 0.9.53 (registry+https://github.com/rust-lang/crates.io-index)" = "465d16ae7fc0e313318f7de5cecf57b2fbe7511fd213978b457e1c96ff46736f"
diff --git a/Cargo.toml b/Cargo.toml
index 0b487876..7475a80f 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -36,6 +36,9 @@ thiserror = "1.0.9"
 anyhow = "1.0.25"
 tempfile = "3.1.0"
 
+[target.'cfg(target_os = "macos")'.dependencies]
+notify-rust = "3.6.3"
+
 [target.'cfg(unix)'.dependencies]
 nix = "0.15.0"
 
diff --git a/src/main.rs b/src/main.rs
index ad744e51..37ec0950 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -33,6 +33,7 @@ where
     F: Fn() -> Result<()>,
     M: Into<Cow<'a, str>> + Debug,
 {
+    let key = key.into();
     debug!("Step {:?}", key);
 
     loop {
@@ -51,7 +52,7 @@ where
                 }
 
                 let should_ask = interrupted || !no_retry;
-                let should_retry = should_ask && should_retry(interrupted)?;
+                let should_retry = should_ask && should_retry(interrupted, key.as_ref())?;
 
                 if !should_retry {
                     report.push_result(Some((key, false)));
diff --git a/src/terminal.rs b/src/terminal.rs
index b912ff5b..8f28a5de 100644
--- a/src/terminal.rs
+++ b/src/terminal.rs
@@ -1,6 +1,8 @@
 use chrono::{Local, Timelike};
 use console::{style, Term};
 use lazy_static::lazy_static;
+#[cfg(target_os = "macos")]
+use notify_rust::Notification;
 use std::cmp::{max, min};
 use std::env;
 use std::io::{self, Write};
@@ -124,7 +126,8 @@ impl Terminal {
             .ok();
     }
 
-    fn should_retry(&mut self, interrupted: bool) -> Result<bool, io::Error> {
+    #[allow(unused_variables)]
+    fn should_retry(&mut self, interrupted: bool, step_name: &str) -> Result<bool, io::Error> {
         if self.width.is_none() {
             return Ok(false);
         }
@@ -132,6 +135,16 @@ impl Terminal {
         if self.set_title {
             self.term.set_title("Topgrade - Awaiting user");
         }
+
+        #[cfg(target_os = "macos")]
+        Notification::new()
+            .summary("Topgrade")
+            .body(&format!("{} failed", step_name))
+            .appname("topgrade")
+            .timeout(0)
+            .show()
+            .ok();
+
         self.term
             .write_fmt(format_args!(
                 "\n{}",
@@ -178,8 +191,8 @@ impl Default for Terminal {
     }
 }
 
-pub fn should_retry(interrupted: bool) -> Result<bool, io::Error> {
-    TERMINAL.lock().unwrap().should_retry(interrupted)
+pub fn should_retry(interrupted: bool, step_name: &str) -> Result<bool, io::Error> {
+    TERMINAL.lock().unwrap().should_retry(interrupted, step_name)
 }
 
 pub fn print_separator<P: AsRef<str>>(message: P) {