diff --git a/internal/dockeragent/agent.go b/internal/dockeragent/agent.go
index 942e4a0..ec03975 100644
--- a/internal/dockeragent/agent.go
+++ b/internal/dockeragent/agent.go
@@ -1615,8 +1615,10 @@ func (a *Agent) checkForUpdates(ctx context.Context) {
 		return
 	}
 
-	// Compare versions
-	if versionResp.Version == Version {
+	// Compare versions - normalize by stripping "v" prefix for comparison.
+	// Server returns version without prefix (e.g., "4.33.1"), but agent's
+	// Version may include it (e.g., "v4.33.1") depending on build.
+	if normalizeVersion(versionResp.Version) == normalizeVersion(Version) {
 		a.logger.Debug().Str("version", Version).Msg("Agent is up to date")
 		return
 	}
@@ -1882,3 +1884,8 @@ func (a *Agent) selfUpdate(ctx context.Context) error {
 
 	return nil
 }
+
+// normalizeVersion strips the "v" prefix from version strings for comparison.
+func normalizeVersion(version string) string {
+	return strings.TrimPrefix(strings.TrimSpace(version), "v")
+}