diff --git a/src/cli/upgrade.go b/src/cli/upgrade.go
index 53952588..1c7c0bff 100644
--- a/src/cli/upgrade.go
+++ b/src/cli/upgrade.go
@@ -57,6 +57,13 @@ var upgradeCmd = &cobra.Command{
 
 		version := fmt.Sprintf("v%s", build.Version)
 
+		if upgrade.IsMajorUpgrade(build.Version, latest) {
+			message := terminal.StopProgress()
+			message += fmt.Sprintf("\n🚨 major upgrade available: %s -> %s, use oh-my-posh upgrade --force to upgrade\n\n", version, latest)
+			fmt.Print(message)
+			return
+		}
+
 		if version != latest {
 			executeUpgrade(latest)
 			return
diff --git a/src/upgrade/cli.go b/src/upgrade/cli.go
index 69e20f44..2cb359b9 100644
--- a/src/upgrade/cli.go
+++ b/src/upgrade/cli.go
@@ -2,6 +2,7 @@ package upgrade
 
 import (
 	"fmt"
+	"strings"
 
 	"github.com/charmbracelet/bubbles/spinner"
 	tea "github.com/charmbracelet/bubbletea"
@@ -144,3 +145,15 @@ func Run(latest string) error {
 
 	return programModel.error
 }
+
+func IsMajorUpgrade(current, latest string) bool {
+	if len(current) == 0 {
+		return false
+	}
+
+	getMajorNumber := func(version string) string {
+		return strings.Split(version, ".")[0]
+	}
+
+	return getMajorNumber(current) != getMajorNumber(latest)
+}
diff --git a/src/upgrade/cli_test.go b/src/upgrade/cli_test.go
new file mode 100644
index 00000000..c0a0bde3
--- /dev/null
+++ b/src/upgrade/cli_test.go
@@ -0,0 +1,25 @@
+package upgrade
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+)
+
+func TestIsMajorUpgrade(t *testing.T) {
+	cases := []struct {
+		Case           string
+		Expected       bool
+		CurrentVersion string
+		LatestVersion  string
+	}{
+		{Case: "Same version", Expected: false, CurrentVersion: "v3.0.0", LatestVersion: "v3.0.0"},
+		{Case: "Breaking change", Expected: true, CurrentVersion: "v3.0.0", LatestVersion: "v4.0.0"},
+		{Case: "Empty version, mostly development build", Expected: false, LatestVersion: "v4.0.0"},
+	}
+
+	for _, tc := range cases {
+		canUpgrade := IsMajorUpgrade(tc.CurrentVersion, tc.LatestVersion)
+		assert.Equal(t, tc.Expected, canUpgrade, tc.Case)
+	}
+}