diff --git a/server/fleet/operating_systems.go b/server/fleet/operating_systems.go
index 91c9a1ead7..dda49c63f2 100644
--- a/server/fleet/operating_systems.go
+++ b/server/fleet/operating_systems.go
@@ -2,8 +2,9 @@ package fleet
 
 import (
 	"fmt"
-	"strconv"
 	"strings"
+
+	"github.com/Masterminds/semver"
 )
 
 // OperatingSystem is an operating system uniquely identified according to its name and version.
@@ -32,6 +33,8 @@ func (os OperatingSystem) IsWindows() bool {
 	return strings.ToLower(os.Platform) == "windows"
 }
 
+var macOSNudgeLastVersion = semver.MustParse("14")
+
 // RequiresNudge returns whether the target platform is darwin and
 // below version 14. Starting at macOS 14 nudge is no longer required,
 // as the mechanism to notify users about updates is built in.
@@ -40,12 +43,12 @@ func (os *OperatingSystem) RequiresNudge() (bool, error) {
 		return false, nil
 	}
 
-	versionFloat, err := strconv.ParseFloat(os.Version, 32)
+	version, err := semver.NewVersion(os.Version)
 	if err != nil {
 		return false, fmt.Errorf("parsing macos version \"%s\": %w", os.Version, err)
 	}
 
-	if float32(versionFloat) < 14 {
+	if version.LessThan(macOSNudgeLastVersion) {
 		return true, nil
 	}
 
diff --git a/server/fleet/operating_systems_test.go b/server/fleet/operating_systems_test.go
index 3f737297b2..9fc35e686c 100644
--- a/server/fleet/operating_systems_test.go
+++ b/server/fleet/operating_systems_test.go
@@ -33,10 +33,10 @@ func TestOperatingSystemRequiresNudge(t *testing.T) {
 		{platform: "chrome", version: "12.1"},
 		{platform: "chrome", version: "15"},
 		{platform: "darwin", parseError: true},
-		{platform: "darwin", version: "12.0", requiresNudge: true},
+		{platform: "darwin", version: "12.0.9", requiresNudge: true},
 		{platform: "darwin", version: "11", requiresNudge: true},
 		{platform: "darwin", version: "14.0"},
-		{platform: "darwin", version: "14.3"},
+		{platform: "darwin", version: "14.3.2"},
 		{platform: "windows"},
 		{platform: "windows", version: "12.2"},
 		{platform: "windows", version: "15.4"},