diff --git a/src/openvpn/forward.c b/src/openvpn/forward.c
index ae0512fc..f44f473f 100644
--- a/src/openvpn/forward.c
+++ b/src/openvpn/forward.c
@@ -405,12 +405,16 @@ send_control_channel_string(struct context *c, const char *str, int msglevel)
 static void
 check_add_routes_action(struct context *c, const bool errors)
 {
-    do_route(&c->options, c->c1.route_list, c->c1.route_ipv6_list,
-             c->c1.tuntap, c->plugins, c->c2.es, &c->net_ctx);
+    bool route_status = do_route(&c->options, c->c1.route_list, c->c1.route_ipv6_list,
+                                 c->c1.tuntap, c->plugins, c->c2.es, &c->net_ctx);
+
+    int flags = (errors ? ISC_ERRORS : 0);
+    flags |= (!route_status ? ISC_ROUTE_ERRORS : 0);
+
     update_time();
     event_timeout_clear(&c->c2.route_wakeup);
     event_timeout_clear(&c->c2.route_wakeup_expire);
-    initialization_sequence_completed(c, errors ? ISC_ERRORS : 0); /* client/p2p --route-delay was defined */
+    initialization_sequence_completed(c, flags); /* client/p2p --route-delay was defined */
 }
 
 static void
diff --git a/src/openvpn/init.c b/src/openvpn/init.c
index fc1943bc..6715e2d2 100644
--- a/src/openvpn/init.c
+++ b/src/openvpn/init.c
@@ -1648,6 +1648,15 @@ initialization_sequence_completed(struct context *c, const unsigned int flags)
         {
             detail = "ERROR";
         }
+        /* Flag route error only on platforms where trivial "already exists" errors
+         * are filtered out. Currently this is the case on Windows or if usng netlink.
+         */
+#if defined(_WIN32) || defined(ENABLE_SITNL)
+        else if (flags & ISC_ROUTE_ERRORS)
+        {
+            detail = "ROUTE_ERROR";
+        }
+#endif
 
         CLEAR(local);
         actual = &get_link_socket_info(c)->lsa->actual;
@@ -1697,7 +1706,7 @@ initialization_sequence_completed(struct context *c, const unsigned int flags)
  * Possibly add routes and/or call route-up script
  * based on options.
  */
-void
+bool
 do_route(const struct options *options,
          struct route_list *route_list,
          struct route_ipv6_list *route_ipv6_list,
@@ -1706,10 +1715,11 @@ do_route(const struct options *options,
          struct env_set *es,
          openvpn_net_ctx_t *ctx)
 {
+    bool ret = true;
     if (!options->route_noexec && ( route_list || route_ipv6_list ) )
     {
-        add_routes(route_list, route_ipv6_list, tt, ROUTE_OPTION_FLAGS(options),
-                   es, ctx);
+        ret = add_routes(route_list, route_ipv6_list, tt, ROUTE_OPTION_FLAGS(options),
+                         es, ctx);
         setenv_int(es, "redirect_gateway", route_did_redirect_default_gateway(route_list));
     }
 #ifdef ENABLE_MANAGEMENT
@@ -1748,6 +1758,7 @@ do_route(const struct options *options,
         show_adapters(D_SHOW_NET|M_NOPREFIX);
     }
 #endif
+    return ret;
 }
 
 /*
@@ -1798,10 +1809,11 @@ can_preserve_tun(struct tuntap *tt)
 }
 
 static bool
-do_open_tun(struct context *c)
+do_open_tun(struct context *c, int *error_flags)
 {
     struct gc_arena gc = gc_new();
     bool ret = false;
+    *error_flags = 0;
 
     if (!can_preserve_tun(c->c1.tuntap))
     {
@@ -1868,8 +1880,9 @@ do_open_tun(struct context *c)
         if (route_order() == ROUTE_BEFORE_TUN)
         {
             /* Ignore route_delay, would cause ROUTE_BEFORE_TUN to be ignored */
-            do_route(&c->options, c->c1.route_list, c->c1.route_ipv6_list,
-                     c->c1.tuntap, c->plugins, c->c2.es, &c->net_ctx);
+            bool status = do_route(&c->options, c->c1.route_list, c->c1.route_ipv6_list,
+                                   c->c1.tuntap, c->plugins, c->c2.es, &c->net_ctx);
+            *error_flags |= (status ? 0 : ISC_ROUTE_ERRORS);
         }
 #ifdef TARGET_ANDROID
         /* Store the old fd inside the fd so open_tun can use it */
@@ -1930,8 +1943,9 @@ do_open_tun(struct context *c)
         /* possibly add routes */
         if ((route_order() == ROUTE_AFTER_TUN) && (!c->options.route_delay_defined))
         {
-            do_route(&c->options, c->c1.route_list, c->c1.route_ipv6_list,
-                     c->c1.tuntap, c->plugins, c->c2.es, &c->net_ctx);
+            int status = do_route(&c->options, c->c1.route_list, c->c1.route_ipv6_list,
+                                  c->c1.tuntap, c->plugins, c->c2.es, &c->net_ctx);
+            *error_flags |= (status ? 0 : ISC_ROUTE_ERRORS);
         }
 
         ret = true;
@@ -2227,6 +2241,7 @@ do_deferred_options_part2(struct context *c)
 bool
 do_up(struct context *c, bool pulled_options, unsigned int option_types_found)
 {
+    int error_flags = 0;
     if (!c->c2.do_up_ran)
     {
         reset_coarse_timers(c);
@@ -2243,7 +2258,7 @@ do_up(struct context *c, bool pulled_options, unsigned int option_types_found)
         /* if --up-delay specified, open tun, do ifconfig, and run up script now */
         if (c->options.up_delay || PULL_DEFINED(&c->options))
         {
-            c->c2.did_open_tun = do_open_tun(c);
+            c->c2.did_open_tun = do_open_tun(c, &error_flags);
             update_time();
 
             /*
@@ -2272,7 +2287,7 @@ do_up(struct context *c, bool pulled_options, unsigned int option_types_found)
                 else
                 {
                     management_sleep(1);
-                    c->c2.did_open_tun = do_open_tun(c);
+                    c->c2.did_open_tun = do_open_tun(c, &error_flags);
                     update_time();
                 }
             }
@@ -2345,12 +2360,12 @@ do_up(struct context *c, bool pulled_options, unsigned int option_types_found)
             }
             else
             {
-                initialization_sequence_completed(c, 0); /* client/p2p --route-delay undefined */
+                initialization_sequence_completed(c, error_flags); /* client/p2p --route-delay undefined */
             }
         }
         else if (c->options.mode == MODE_POINT_TO_POINT)
         {
-            initialization_sequence_completed(c, 0); /* client/p2p restart with --persist-tun */
+            initialization_sequence_completed(c, error_flags); /* client/p2p restart with --persist-tun */
         }
 
         c->c2.do_up_ran = true;
@@ -4481,7 +4496,8 @@ init_instance(struct context *c, const struct env_set *env, const unsigned int f
      * open tun/tap device, ifconfig, run up script, etc. */
     if (!(options->up_delay || PULL_DEFINED(options)) && (c->mode == CM_P2P || c->mode == CM_TOP))
     {
-        c->c2.did_open_tun = do_open_tun(c);
+        int error_flags = 0;
+        c->c2.did_open_tun = do_open_tun(c, &error_flags);
     }
 
     c->c2.frame_initial = c->c2.frame;
diff --git a/src/openvpn/init.h b/src/openvpn/init.h
index d0fb6ea1..2315b3ca 100644
--- a/src/openvpn/init.h
+++ b/src/openvpn/init.h
@@ -71,12 +71,9 @@ void init_instance(struct context *c, const struct env_set *env, const unsigned
  */
 void init_query_passwords(const struct context *c);
 
-void do_route(const struct options *options,
-              struct route_list *route_list,
-              struct route_ipv6_list *route_ipv6_list,
-              const struct tuntap *tt,
-              const struct plugin_list *plugins,
-              struct env_set *es,
+bool do_route(const struct options *options, struct route_list *route_list,
+              struct route_ipv6_list *route_ipv6_list, const struct tuntap *tt,
+              const struct plugin_list *plugins, struct env_set *es,
               openvpn_net_ctx_t *ctx);
 
 void close_instance(struct context *c);
@@ -116,6 +113,7 @@ void free_context_buffers(struct context_buffers *b);
 
 #define ISC_ERRORS (1<<0)
 #define ISC_SERVER (1<<1)
+#define ISC_ROUTE_ERRORS (1<<2)
 void initialization_sequence_completed(struct context *c, const unsigned int flags);
 
 #ifdef ENABLE_MANAGEMENT
diff --git a/src/openvpn/route.c b/src/openvpn/route.c
index 0d4aeaaf..99f948ba 100644
--- a/src/openvpn/route.c
+++ b/src/openvpn/route.c
@@ -907,7 +907,7 @@ init_route_ipv6_list(struct route_ipv6_list *rl6,
     return ret;
 }
 
-static void
+static bool
 add_route3(in_addr_t network,
            in_addr_t netmask,
            in_addr_t gateway,
@@ -923,7 +923,7 @@ add_route3(in_addr_t network,
     r.network = network;
     r.netmask = netmask;
     r.gateway = gateway;
-    add_route(&r, tt, flags, rgi, es, ctx);
+    return add_route(&r, tt, flags, rgi, es, ctx);
 }
 
 static void
@@ -945,7 +945,7 @@ del_route3(in_addr_t network,
     delete_route(&r, tt, flags, rgi, es, ctx);
 }
 
-static void
+static bool
 add_bypass_routes(struct route_bypass *rb,
                   in_addr_t gateway,
                   const struct tuntap *tt,
@@ -954,21 +954,16 @@ add_bypass_routes(struct route_bypass *rb,
                   const struct env_set *es,
                   openvpn_net_ctx_t *ctx)
 {
-    int i;
-    for (i = 0; i < rb->n_bypass; ++i)
+    int ret = true;
+    for (int i = 0; i < rb->n_bypass; ++i)
     {
         if (rb->bypass[i])
         {
-            add_route3(rb->bypass[i],
-                       IPV4_NETMASK_HOST,
-                       gateway,
-                       tt,
-                       flags | ROUTE_REF_GW,
-                       rgi,
-                       es,
-                       ctx);
+            ret = add_route3(rb->bypass[i], IPV4_NETMASK_HOST, gateway, tt,
+                             flags | ROUTE_REF_GW, rgi, es, ctx) && ret;
         }
     }
+    return ret;
 }
 
 static void
@@ -997,12 +992,13 @@ del_bypass_routes(struct route_bypass *rb,
     }
 }
 
-static void
+static bool
 redirect_default_route_to_vpn(struct route_list *rl, const struct tuntap *tt,
                               unsigned int flags, const struct env_set *es,
                               openvpn_net_ctx_t *ctx)
 {
     const char err[] = "NOTE: unable to redirect IPv4 default gateway --";
+    bool ret = true;
 
     if (rl && rl->flags & RG_ENABLE)
     {
@@ -1011,6 +1007,7 @@ redirect_default_route_to_vpn(struct route_list *rl, const struct tuntap *tt,
         if (!(rl->spec.flags & RTSA_REMOTE_ENDPOINT) && (rl->flags & RG_REROUTE_GW))
         {
             msg(M_WARN, "%s VPN gateway parameter (--route-gateway or --ifconfig) is missing", err);
+            ret = false;
         }
         /*
          * check if a default route is defined, unless:
@@ -1021,6 +1018,7 @@ redirect_default_route_to_vpn(struct route_list *rl, const struct tuntap *tt,
                  && (rl->spec.flags & RTSA_REMOTE_HOST))
         {
             msg(M_WARN, "%s Cannot read current default gateway from system", err);
+            ret = false;
         }
         else
         {
@@ -1047,14 +1045,9 @@ redirect_default_route_to_vpn(struct route_list *rl, const struct tuntap *tt,
                 if ((rl->spec.flags & RTSA_REMOTE_HOST)
                     && rl->spec.remote_host != IPV4_INVALID_ADDR)
                 {
-                    add_route3(rl->spec.remote_host,
-                               IPV4_NETMASK_HOST,
-                               rl->rgi.gateway.addr,
-                               tt,
-                               flags | ROUTE_REF_GW,
-                               &rl->rgi,
-                               es,
-                               ctx);
+                    ret = add_route3(rl->spec.remote_host, IPV4_NETMASK_HOST,
+                                     rl->rgi.gateway.addr, tt, flags | ROUTE_REF_GW,
+                                     &rl->rgi, es, ctx);
                     rl->iflags |= RL_DID_LOCAL;
                 }
                 else
@@ -1065,32 +1058,20 @@ redirect_default_route_to_vpn(struct route_list *rl, const struct tuntap *tt,
 #endif /* ifndef TARGET_ANDROID */
 
             /* route DHCP/DNS server traffic through original default gateway */
-            add_bypass_routes(&rl->spec.bypass, rl->rgi.gateway.addr, tt, flags,
-                              &rl->rgi, es, ctx);
+            ret = add_bypass_routes(&rl->spec.bypass, rl->rgi.gateway.addr, tt, flags,
+                                    &rl->rgi, es, ctx);
 
             if (rl->flags & RG_REROUTE_GW)
             {
                 if (rl->flags & RG_DEF1)
                 {
                     /* add new default route (1st component) */
-                    add_route3(0x00000000,
-                               0x80000000,
-                               rl->spec.remote_endpoint,
-                               tt,
-                               flags,
-                               &rl->rgi,
-                               es,
-                               ctx);
+                    ret = add_route3(0x00000000, 0x80000000, rl->spec.remote_endpoint,
+                                     tt, flags, &rl->rgi, es, ctx) && ret;
 
                     /* add new default route (2nd component) */
-                    add_route3(0x80000000,
-                               0x80000000,
-                               rl->spec.remote_endpoint,
-                               tt,
-                               flags,
-                               &rl->rgi,
-                               es,
-                               ctx);
+                    ret = add_route3(0x80000000, 0x80000000, rl->spec.remote_endpoint,
+                                     tt, flags, &rl->rgi, es, ctx) && ret;
                 }
                 else
                 {
@@ -1103,14 +1084,8 @@ redirect_default_route_to_vpn(struct route_list *rl, const struct tuntap *tt,
                     }
 
                     /* add new default route */
-                    add_route3(0,
-                               0,
-                               rl->spec.remote_endpoint,
-                               tt,
-                               flags,
-                               &rl->rgi,
-                               es,
-                               ctx);
+                    ret = add_route3(0, 0, rl->spec.remote_endpoint, tt,
+                                     flags, &rl->rgi, es, ctx) && ret;
                 }
             }
 
@@ -1118,6 +1093,7 @@ redirect_default_route_to_vpn(struct route_list *rl, const struct tuntap *tt,
             rl->iflags |= RL_DID_REDIRECT_DEFAULT_GATEWAY;
         }
     }
+    return ret;
 }
 
 static void
@@ -1194,12 +1170,12 @@ undo_redirect_default_route_to_vpn(struct route_list *rl,
     }
 }
 
-void
+bool
 add_routes(struct route_list *rl, struct route_ipv6_list *rl6,
            const struct tuntap *tt, unsigned int flags,
            const struct env_set *es, openvpn_net_ctx_t *ctx)
 {
-    redirect_default_route_to_vpn(rl, tt, flags, es, ctx);
+    bool ret = redirect_default_route_to_vpn(rl, tt, flags, es, ctx);
     if (rl && !(rl->iflags & RL_ROUTES_ADDED) )
     {
         struct route_ipv4 *r;
@@ -1232,7 +1208,7 @@ add_routes(struct route_list *rl, struct route_ipv6_list *rl6,
             {
                 delete_route(r, tt, flags, &rl->rgi, es, ctx);
             }
-            add_route(r, tt, flags, &rl->rgi, es, ctx);
+            ret = add_route(r, tt, flags, &rl->rgi, es, ctx) && ret;
         }
         rl->iflags |= RL_ROUTES_ADDED;
     }
@@ -1254,10 +1230,11 @@ add_routes(struct route_list *rl, struct route_ipv6_list *rl6,
             {
                 delete_route_ipv6(r, tt, flags, es, ctx);
             }
-            add_route_ipv6(r, tt, flags, es, ctx);
+            ret = add_route_ipv6(r, tt, flags, es, ctx) && ret;
         }
         rl6->iflags |= RL_ROUTES_ADDED;
     }
+    return ret;
 }
 
 void
@@ -1569,7 +1546,7 @@ is_on_link(const int is_local_route, const unsigned int flags, const struct rout
     return rgi && (is_local_route == LR_MATCH || ((flags & ROUTE_REF_GW) && (rgi->flags & RGI_ON_LINK)));
 }
 
-void
+bool
 add_route(struct route_ipv4 *r,
           const struct tuntap *tt,
           unsigned int flags,
@@ -1582,7 +1559,7 @@ add_route(struct route_ipv4 *r,
 
     if (!(r->flags & RT_DEFINED))
     {
-        return;
+        return true; /* no error */
     }
 
     struct argv argv = argv_new();
@@ -1635,7 +1612,7 @@ add_route(struct route_ipv4 *r,
     {
         openvpn_snprintf(out, sizeof(out), "%s %s %s", network, netmask, gateway);
     }
-    management_android_control(management, "ROUTE", out);
+    status = management_android_control(management, "ROUTE", out);
 
 #elif defined (_WIN32)
     {
@@ -1845,6 +1822,8 @@ done:
     gc_free(&gc);
     /* release resources potentially allocated during route setup */
     net_ctx_reset(ctx);
+
+    return (status != 0);
 }
 
 
@@ -1871,7 +1850,7 @@ route_ipv6_clear_host_bits( struct route_ipv6 *r6 )
     }
 }
 
-void
+bool
 add_route_ipv6(struct route_ipv6 *r6, const struct tuntap *tt,
                unsigned int flags, const struct env_set *es,
                openvpn_net_ctx_t *ctx)
@@ -1882,7 +1861,7 @@ add_route_ipv6(struct route_ipv6 *r6, const struct tuntap *tt,
 
     if (!(r6->flags & RT_DEFINED) )
     {
-        return;
+        return true; /* no error */
     }
 
     struct argv argv = argv_new();
@@ -1972,7 +1951,7 @@ add_route_ipv6(struct route_ipv6 *r6, const struct tuntap *tt,
 
     openvpn_snprintf(out, sizeof(out), "%s/%d %s", network, r6->netbits, device);
 
-    management_android_control(management, "ROUTE6", out);
+    status = management_android_control(management, "ROUTE6", out);
 
 #elif defined (_WIN32)
 
@@ -2092,6 +2071,8 @@ done:
     gc_free(&gc);
     /* release resources potentially allocated during route setup */
     net_ctx_reset(ctx);
+
+    return (status != 0);
 }
 
 static void
diff --git a/src/openvpn/route.h b/src/openvpn/route.h
index 74ecd343..1c940a9b 100644
--- a/src/openvpn/route.h
+++ b/src/openvpn/route.h
@@ -259,15 +259,12 @@ void copy_route_ipv6_option_list(struct route_ipv6_option_list *dest,
 
 void route_ipv6_clear_host_bits( struct route_ipv6 *r6 );
 
-void add_route_ipv6(struct route_ipv6 *r, const struct tuntap *tt, unsigned int flags, const struct env_set *es, openvpn_net_ctx_t *ctx);
+bool add_route_ipv6(struct route_ipv6 *r, const struct tuntap *tt, unsigned int flags, const struct env_set *es, openvpn_net_ctx_t *ctx);
 
 void delete_route_ipv6(const struct route_ipv6 *r, const struct tuntap *tt, unsigned int flags, const struct env_set *es, openvpn_net_ctx_t *ctx);
 
-void add_route(struct route_ipv4 *r,
-               const struct tuntap *tt,
-               unsigned int flags,
-               const struct route_gateway_info *rgi,
-               const struct env_set *es,
+bool add_route(struct route_ipv4 *r, const struct tuntap *tt, unsigned int flags,
+               const struct route_gateway_info *rgi, const struct env_set *es,
                openvpn_net_ctx_t *ctx);
 
 void add_route_to_option_list(struct route_option_list *l,
@@ -301,12 +298,9 @@ void route_list_add_vpn_gateway(struct route_list *rl,
                                 struct env_set *es,
                                 const in_addr_t addr);
 
-void add_routes(struct route_list *rl,
-                struct route_ipv6_list *rl6,
-                const struct tuntap *tt,
-                unsigned int flags,
-                const struct env_set *es,
-                openvpn_net_ctx_t *ctx);
+bool add_routes(struct route_list *rl, struct route_ipv6_list *rl6,
+                const struct tuntap *tt, unsigned int flags,
+                const struct env_set *es, openvpn_net_ctx_t *ctx);
 
 void delete_routes(struct route_list *rl,
                    struct route_ipv6_list *rl6,