diff --git a/cli/tools/upgrade.rs b/cli/tools/upgrade.rs
index eaead9ff61..787dc05dbc 100644
--- a/cli/tools/upgrade.rs
+++ b/cli/tools/upgrade.rs
@@ -164,15 +164,22 @@ pub fn check_for_upgrades(cache_dir: PathBuf) {
     });
   }
 
-  // Print a message if an update is available, unless:
-  //   * stderr is not a tty
-  //   * we're already running the 'deno upgrade' command.
+  // Print a message if an update is available
   if let Some(upgrade_version) = update_checker.should_prompt() {
-    if atty::is(atty::Stream::Stderr) {
-      eprint!(
-        "{} ",
-        colors::green(format!("Deno {upgrade_version} has been released."))
-      );
+    if log::log_enabled!(log::Level::Info) && atty::is(atty::Stream::Stderr) {
+      if version::is_canary() {
+        eprint!(
+          "{} ",
+          colors::green("A new canary release of Deno is available.")
+        );
+      } else {
+        eprint!(
+          "{} {} → {} ",
+          colors::green("A new release of Deno is available:"),
+          colors::cyan(version::deno()),
+          colors::cyan(upgrade_version)
+        );
+      }
       eprintln!(
         "{}",
         colors::italic_gray("Run `deno upgrade` to install it.")