diff --git a/routes.go b/routes.go
index bab35ea8..f1fbb995 100644
--- a/routes.go
+++ b/routes.go
@@ -106,13 +106,36 @@ func (h *Headscale) DisableRoute(id uint64) error {
 		return err
 	}
 
-	route.Enabled = false
-	route.IsPrimary = false
-	err = h.db.Save(route).Error
+	// Tailscale requires both IPv4 and IPv6 exit routes to
+	// be enabled at the same time, as per
+	// https://github.com/juanfont/headscale/issues/804#issuecomment-1399314002
+	if !route.isExitRoute() {
+		route.Enabled = false
+		route.IsPrimary = false
+		err = h.db.Save(route).Error
+		if err != nil {
+			return err
+		}
+
+		return h.handlePrimarySubnetFailover()
+	}
+
+	routes, err := h.GetMachineRoutes(&route.Machine)
 	if err != nil {
 		return err
 	}
 
+	for i := range routes {
+		if routes[i].isExitRoute() {
+			routes[i].Enabled = false
+			routes[i].IsPrimary = false
+			err = h.db.Save(&routes[i]).Error
+			if err != nil {
+				return err
+			}
+		}
+	}
+
 	return h.handlePrimarySubnetFailover()
 }
 
@@ -122,7 +145,30 @@ func (h *Headscale) DeleteRoute(id uint64) error {
 		return err
 	}
 
-	if err := h.db.Unscoped().Delete(&route).Error; err != nil {
+	// Tailscale requires both IPv4 and IPv6 exit routes to
+	// be enabled at the same time, as per
+	// https://github.com/juanfont/headscale/issues/804#issuecomment-1399314002
+	if !route.isExitRoute() {
+		if err := h.db.Unscoped().Delete(&route).Error; err != nil {
+			return err
+		}
+
+		return h.handlePrimarySubnetFailover()
+	}
+
+	routes, err := h.GetMachineRoutes(&route.Machine)
+	if err != nil {
+		return err
+	}
+
+	routesToDelete := []Route{}
+	for _, r := range routes {
+		if r.isExitRoute() {
+			routesToDelete = append(routesToDelete, r)
+		}
+	}
+
+	if err := h.db.Unscoped().Delete(&routesToDelete).Error; err != nil {
 		return err
 	}
 
diff --git a/routes_test.go b/routes_test.go
index b67b3ee9..e2d056b7 100644
--- a/routes_test.go
+++ b/routes_test.go
@@ -457,6 +457,37 @@ func (s *Suite) TestAllowedIPRoutes(c *check.C) {
 
 	c.Assert(foundExitNodeV4, check.Equals, true)
 	c.Assert(foundExitNodeV6, check.Equals, true)
+
+	// Now we disable only one of the exit routes
+	// and we see if both are disabled
+	var exitRouteV4 Route
+	for _, route := range routes {
+		if route.isExitRoute() && netip.Prefix(route.Prefix) == prefixExitNodeV4 {
+			exitRouteV4 = route
+
+			break
+		}
+	}
+
+	err = app.DisableRoute(uint64(exitRouteV4.ID))
+	c.Assert(err, check.IsNil)
+
+	enabledRoutes1, err = app.GetEnabledRoutes(&machine1)
+	c.Assert(err, check.IsNil)
+	c.Assert(len(enabledRoutes1), check.Equals, 1)
+
+	// and now we delete only one of the exit routes
+	// and we check if both are deleted
+	routes, err = app.GetMachineRoutes(&machine1)
+	c.Assert(err, check.IsNil)
+	c.Assert(len(routes), check.Equals, 4)
+
+	err = app.DeleteRoute(uint64(exitRouteV4.ID))
+	c.Assert(err, check.IsNil)
+
+	routes, err = app.GetMachineRoutes(&machine1)
+	c.Assert(err, check.IsNil)
+	c.Assert(len(routes), check.Equals, 2)
 }
 
 func (s *Suite) TestDeleteRoutes(c *check.C) {