diff --git a/go.sum b/go.sum
index 0d2227f7..951bc44e 100644
--- a/go.sum
+++ b/go.sum
@@ -11,6 +11,7 @@ github.com/google/go-cmp v0.4.0 h1:xsAVV57WRhGj6kEIi8ReJzQlHHqcBYCElAvkovg3B/4=
 github.com/google/go-cmp v0.4.0/go.mod h1:v8dTdLbMG2kIc/vJvl+f65V22dbkXbowE6jgT/gNBxE=
 github.com/minio/highwayhash v1.0.0 h1:iMSDhgUILCr0TNm8LWlSjF8N0ZIj2qbO8WHp6Q/J2BA=
 github.com/minio/highwayhash v1.0.0/go.mod h1:xQboMTeM9nY9v/LlAOxFctujiv5+Aq2hR5dxBpaMbdc=
+github.com/nats-io/jwt v0.3.2 h1:+RB5hMpXUUA2dfxuhBTEkMOrYmM+gKIZYS1KjSostMI=
 github.com/nats-io/jwt v0.3.2/go.mod h1:/euKqTS1ZD+zzjYrY7pseZrTtWQSjujC7xjPc8wL6eU=
 github.com/nats-io/jwt v0.3.3-0.20200519195258-f2bf5ce574c7 h1:RnGotxlghqR5D2KDAu4TyuLqyjuylOsJiAFhXvMvQIc=
 github.com/nats-io/jwt v0.3.3-0.20200519195258-f2bf5ce574c7/go.mod h1:n3cvmLfBfnpV4JJRN7lRYCyZnw48ksGsbThGXEk4w9M=
diff --git a/server/jwt.go b/server/jwt.go
index d9d0c916..029a5e46 100644
--- a/server/jwt.go
+++ b/server/jwt.go
@@ -105,6 +105,24 @@ func validateTrustedOperators(o *Options) error {
 			return fmt.Errorf("system_account in config and operator JWT must be identical")
 		}
 	}
+	srvMajor, srvMinor, srvUpdate, _ := jwt.ParseServerVersion(strings.Split(VERSION, "-")[0])
+	for _, opc := range o.TrustedOperators {
+		if major, minor, update, err := jwt.ParseServerVersion(opc.AssertServerVersion); err != nil {
+			return fmt.Errorf("operator %s expects version %s got error instead: %s",
+				opc.Subject, opc.AssertServerVersion, err)
+		} else if major > srvMajor {
+			return fmt.Errorf("operator %s expected major version %d > server major version %d",
+				opc.Subject, major, srvMajor)
+		} else if srvMajor > major {
+		} else if minor > srvMinor {
+			return fmt.Errorf("operator %s expected minor version %d > server minor version %d",
+				opc.Subject, minor, srvMinor)
+		} else if srvMinor > minor {
+		} else if update > srvUpdate {
+			return fmt.Errorf("operator %s expected update version %d > server update version %d",
+				opc.Subject, update, srvUpdate)
+		}
+	}
 	// If we have operators, fill in the trusted keys.
 	// FIXME(dlc) - We had TrustedKeys before TrustedOperators. The jwt.OperatorClaims
 	// has a DidSign(). Use that longer term. For now we can expand in place.
diff --git a/server/opts_test.go b/server/opts_test.go
index f1355826..913a01c5 100644
--- a/server/opts_test.go
+++ b/server/opts_test.go
@@ -2664,3 +2664,51 @@ func TestReadOperatorJWTSystemAccountMismatch(t *testing.T) {
 		t.Fatalf("Received unexpected error %s", err)
 	}
 }
+
+const operatorJwtAssertVersion_1_2_3 = `
+	listen: "127.0.0.1:-1"
+	// Operator "TESTOP"
+	operator: eyJ0eXAiOiJqd3QiLCJhbGciOiJlZDI1NTE5LW5rZXkifQ.eyJqdGkiOiJYWFhGNEREQTdRSEtCSU5MUlBSNTZPUFFTUjc0RFdLSjZCQkZWN1BSVEpMNUtDUUdCUFhBIiwiaWF0IjoxNTkwNTI4NTI1LCJpc3MiOiJPRDRYSkwyM0haSlozTzZKQ0FGUTZSVk9ZR0JZWUtGU0tIRlJFWkRaUEJGN1I0SlpQSTVWNzNLTSIsInN1YiI6Ik9ENFhKTDIzSFpKWjNPNkpDQUZRNlJWT1lHQllZS0ZTS0hGUkVaRFpQQkY3UjRKWlBJNVY3M0tNIiwibmF0cyI6eyJhc3NlcnRfc2VydmVyX3ZlcnNpb24iOiIxLjIuMyIsInR5cGUiOiJvcGVyYXRvciIsInZlcnNpb24iOjJ9fQ.ERRsFUekK7W5tZbeYlkLlwU3AGMpZTtlh5jKIj2rWoLnoWLlWcjXYD4uKdaT-tNGbsahiQZV82C5_K89BCWODA
+	resolver: MEMORY
+	resolver_preload: {
+	}
+`
+
+func TestReadOperatorAssertVersion(t *testing.T) {
+	confFileName := createConfFile(t, []byte(operatorJwtAssertVersion_1_2_3))
+	defer os.Remove(confFileName)
+	opts, err := ProcessConfigFile(confFileName)
+	if err != nil {
+		t.Fatalf("Received unexpected error %s", err)
+	}
+	s, err := NewServer(opts)
+	if err != nil {
+		t.Fatalf("Received unexpected error %s", err)
+	}
+	s.Shutdown()
+}
+
+const operatorJwtAssertVersion_10_20_30 = `
+	listen: "127.0.0.1:-1"
+	// Operator "TESTOP"
+	operator: eyJ0eXAiOiJqd3QiLCJhbGciOiJlZDI1NTE5LW5rZXkifQ.eyJqdGkiOiJJRjNXQkFENk9JWE5HTzRWUFkzQ0hTS1ZMUDJXT0ZLQkZPR0RMUFRHSERVR0hRV1BUVlNRIiwiaWF0IjoxNTkwNTI4NTI1LCJpc3MiOiJPQ0laQUFVN0dDNkREU0QyTk1VQU9VQ0JRS09SQlNEQUxPSVBNRDRSVEM0SUhCRUZQRVE0TjZERSIsInN1YiI6Ik9DSVpBQVU3R0M2RERTRDJOTVVBT1VDQlFLT1JCU0RBTE9JUE1ENFJUQzRJSEJFRlBFUTRONkRFIiwibmF0cyI6eyJhc3NlcnRfc2VydmVyX3ZlcnNpb24iOiIxMC4yMC4zMCIsInR5cGUiOiJvcGVyYXRvciIsInZlcnNpb24iOjJ9fQ.bGFUCQIa2D5GjluEbXYJQGZnsM_O1r46b_xq2AUp4cEYGqCqvBAJZp9coBTgXL-4MPjyoPZSj2RglC1yUy9aDQ
+	resolver: MEMORY
+	resolver_preload: {
+	}
+`
+
+func TestReadOperatorAssertVersionFail(t *testing.T) {
+	confFileName := createConfFile(t, []byte(operatorJwtAssertVersion_10_20_30))
+	defer os.Remove(confFileName)
+	opts, err := ProcessConfigFile(confFileName)
+	if err != nil {
+		t.Fatalf("Received unexpected error %s", err)
+	}
+	s, err := NewServer(opts)
+	if err == nil {
+		s.Shutdown()
+		t.Fatalf("Received no error")
+	} else if !strings.Contains(err.Error(), "expected major version 10 > server major version") {
+		t.Fatal("expected different error got: ", err)
+	}
+}