diff --git a/server/gateway.go b/server/gateway.go
index 1629998c..e41de23d 100644
--- a/server/gateway.go
+++ b/server/gateway.go
@@ -679,7 +679,7 @@ func (s *Server) solicitGateway(cfg *gatewayCfg, firstConnect bool) {
 				s.gateway.Lock()
 				// We could have just accepted an inbound for this remote gateway.
 				// So if there is an inbound, let's try again to connect.
-				if len(s.gateway.in) > 0 {
+				if s.gateway.hasInbound(cfg.Name) {
 					s.gateway.Unlock()
 					continue
 				}
@@ -697,6 +697,20 @@ func (s *Server) solicitGateway(cfg *gatewayCfg, firstConnect bool) {
 	}
 }
 
+// Returns true if there is an inbound for the given `name`.
+// Lock held on entry.
+func (g *srvGateway) hasInbound(name string) bool {
+	for _, ig := range g.in {
+		ig.mu.Lock()
+		igname := ig.gw.name
+		ig.mu.Unlock()
+		if igname == name {
+			return true
+		}
+	}
+	return false
+}
+
 // Called when a gateway connection is either accepted or solicited.
 // If accepted, the gateway is marked as inbound.
 // If solicited, the gateway is marked as outbound.
diff --git a/server/gateway_test.go b/server/gateway_test.go
index fd0eeeb8..c634df28 100644
--- a/server/gateway_test.go
+++ b/server/gateway_test.go
@@ -1290,6 +1290,81 @@ func TestGatewayImplicitReconnectRace(t *testing.T) {
 	waitForInboundGateways(t, sa2, 1, 2*time.Second)
 }
 
+type gwReconnAttemptLogger struct {
+	DummyLogger
+	errCh chan string
+}
+
+func (l *gwReconnAttemptLogger) Errorf(format string, v ...interface{}) {
+	msg := fmt.Sprintf(format, v...)
+	if strings.Contains(msg, `Error connecting to implicit gateway "A"`) {
+		select {
+		case l.errCh <- msg:
+		default:
+		}
+	}
+}
+
+func TestGatewayImplicitReconnectHonorConnectRetries(t *testing.T) {
+	ob := testDefaultOptionsForGateway("B")
+	ob.ReconnectErrorReports = 1
+	ob.Gateway.ConnectRetries = 2
+	sb := runGatewayServer(ob)
+	defer sb.Shutdown()
+
+	l := &gwReconnAttemptLogger{errCh: make(chan string, 3)}
+	sb.SetLogger(l, true, false)
+
+	oa := testGatewayOptionsFromToWithServers(t, "A", "B", sb)
+	sa := runGatewayServer(oa)
+	defer sa.Shutdown()
+
+	// Wait for the proper connections
+	waitForOutboundGateways(t, sa, 1, time.Second)
+	waitForOutboundGateways(t, sb, 1, time.Second)
+	waitForInboundGateways(t, sa, 1, time.Second)
+	waitForInboundGateways(t, sb, 1, time.Second)
+
+	// Now have C connect to B.
+	oc := testGatewayOptionsFromToWithServers(t, "C", "B", sb)
+	sc := runGatewayServer(oc)
+	defer sc.Shutdown()
+
+	// Wait for the proper connections
+	waitForOutboundGateways(t, sa, 2, time.Second)
+	waitForOutboundGateways(t, sb, 2, time.Second)
+	waitForOutboundGateways(t, sc, 2, time.Second)
+	waitForInboundGateways(t, sa, 2, time.Second)
+	waitForInboundGateways(t, sb, 2, time.Second)
+	waitForInboundGateways(t, sc, 2, time.Second)
+
+	// Shutdown sa now...
+	sa.Shutdown()
+
+	// B will try to reconnect to A 3 times (we stop after attempts > ConnectRetries)
+	timeout := time.NewTimer(time.Second)
+	for i := 0; i < 3; i++ {
+		select {
+		case <-l.errCh:
+			// OK
+		case <-timeout.C:
+			t.Fatal("Did not get debug trace about reconnect")
+		}
+	}
+	// If we get 1 more, we have an issue!
+	select {
+	case e := <-l.errCh:
+		t.Fatalf("Should not have attempted to reconnect: %q", e)
+	case <-time.After(250 * time.Millisecond):
+		// OK!
+	}
+
+	waitForOutboundGateways(t, sb, 1, 2*time.Second)
+	waitForInboundGateways(t, sb, 1, 2*time.Second)
+	waitForOutboundGateways(t, sc, 1, 2*time.Second)
+	waitForInboundGateways(t, sc, 1, 2*time.Second)
+}
+
 func TestGatewayURLsFromClusterSentInINFO(t *testing.T) {
 	o2 := testDefaultOptionsForGateway("B")
 	s2 := runGatewayServer(o2)