diff --git a/CHANGELOG.md b/CHANGELOG.md
index 5d6d708012..9f5a13c384 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -10,6 +10,7 @@
 
 - (snapshots) Update `snapshots download` to use the new archive endpoint, triggering the archive build and polling until it is ready before downloading ([#3344](https://github.com/getsentry/sentry-cli/pull/3344))
 - (snapshots) Show a clear "project was renamed" error instead of a cryptic JSON parse failure when uploading to a renamed project slug ([#3341](https://github.com/getsentry/sentry-cli/pull/3341))
+- Fix update nagger never showing when a newer version is available ([#3347](https://github.com/getsentry/sentry-cli/issues/3347))
 
 ## 3.5.1
 
diff --git a/src/utils/update.rs b/src/utils/update.rs
index 60aab0bc38..14f787f436 100644
--- a/src/utils/update.rs
+++ b/src/utils/update.rs
@@ -109,7 +109,7 @@ impl LastUpdateCheck {
             if let Some(ref release_v) = self.last_fetched_version;
             if let Some(ref check_v) = self.last_check_version;
             then {
-                Version::parse(release_v.as_str()).unwrap() < Version::parse(VERSION).unwrap() &&
+                Version::parse(VERSION).unwrap() < Version::parse(release_v.as_str()).unwrap() &&
                 check_v.as_str() == VERSION
             } else {
                 false