diff --git a/update/types.go b/update/types.go
index a6fd721e..be3eb479 100644
--- a/update/types.go
+++ b/update/types.go
@@ -82,7 +82,7 @@ func IsOutdated(current, latest string) bool {
 		// fallback to naive comparison
 		return current != latest
 	}
-	return latestVer.GreaterThan(currentVer)
+	return currentVer.LessThan(latestVer)
 }
 
 // IsDevReleaseOutdated returns true if installed tool (dev version) is outdated
diff --git a/update/types_test.go b/update/types_test.go
new file mode 100644
index 00000000..a686f10c
--- /dev/null
+++ b/update/types_test.go
@@ -0,0 +1,63 @@
+package updateutils
+
+import (
+	"fmt"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+)
+
+func TestIsOutdated(t *testing.T) {
+	tests := []struct {
+		current  string
+		latest   string
+		expected bool
+	}{
+		{
+			current:  "1.0.0",
+			latest:   "1.1.0",
+			expected: true,
+		},
+		{
+			current:  "1.0.0",
+			latest:   "1.0.0",
+			expected: false,
+		},
+		{
+			current:  "1.1.0",
+			latest:   "1.0.0",
+			expected: false,
+		},
+		{
+			current:  "1.0.0-dev",
+			latest:   "1.0.0",
+			expected: true,
+		},
+		{
+			current:  "invalid",
+			latest:   "1.0.0",
+			expected: true,
+		},
+		{
+			current:  "invalid1",
+			latest:   "invalid2",
+			expected: true,
+		},
+		{
+			current:  "1.0.0-alpha",
+			latest:   "1.0.0",
+			expected: true,
+		},
+		{
+			current:  "1.0.0-alpha",
+			latest:   "1.0.0-beta",
+			expected: true,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(fmt.Sprintf("current: %v, latest: %v", tt.current, tt.latest), func(t *testing.T) {
+			assert.Equal(t, tt.expected, IsOutdated(tt.current, tt.latest), "version comparison failed")
+		})
+	}
+}