diff --git a/activitypub.c b/activitypub.c
index a8a570c..514bf5d 100644
--- a/activitypub.c
+++ b/activitypub.c
@@ -1798,7 +1798,7 @@ void process_user_queue_item(snac *snac, xs_dict *q_item)
             if (inbox != NULL) {
                 /* add to the set and, if it's not there, send message */
                 if (xs_set_add(&inboxes, inbox) == 1)
-                    enqueue_output(snac, msg, inbox, 0);
+                    enqueue_output(snac, msg, inbox, 0, 0);
             }
             else
                 snac_log(snac, xs_fmt("cannot find inbox for %s", actor));
@@ -1812,7 +1812,7 @@ void process_user_queue_item(snac *snac, xs_dict *q_item)
             p = shibx;
             while (xs_list_iter(&p, &inbox)) {
                 if (xs_set_add(&inboxes, inbox) == 1)
-                    enqueue_output(snac, msg, inbox, 0);
+                    enqueue_output(snac, msg, inbox, 0, 0);
             }
         }
 
@@ -1896,6 +1896,7 @@ void process_queue_item(xs_dict *q_item)
         xs_str *seckey = xs_dict_get(q_item, "seckey");
         xs_dict *msg   = xs_dict_get(q_item, "message");
         int retries    = xs_number_get(xs_dict_get(q_item, "retries"));
+        int p_status   = xs_number_get(xs_dict_get(q_item, "p_status"));
         xs *payload    = NULL;
         int p_size     = 0;
 
@@ -1909,8 +1910,9 @@ void process_queue_item(xs_dict *q_item)
             return;
         }
 
-        /* deliver */
-        status = send_to_inbox_raw(keyid, seckey, inbox, msg, &payload, &p_size, retries == 0 ? 3 : 8);
+        /* deliver (if previous error status was a timeout, try now longer) */
+        status = send_to_inbox_raw(keyid, seckey, inbox, msg,
+                    &payload, &p_size, p_status == 599 ? 20 : 3);
 
         if (payload) {
             if (p_size > 64) {
@@ -1934,6 +1936,11 @@ void process_queue_item(xs_dict *q_item)
         if (!valid_status(status)) {
             retries++;
 
+            /* if it's not the first time it fails with a timeout,
+               penalize the server by skipping one retry */
+            if (p_status == status && status == 499)
+                retries++;
+
             /* error sending; requeue? */
             if (status == 400 || status == 404 || status == 410 || status < 0)
                 /* explicit error: discard */
@@ -1943,7 +1950,7 @@ void process_queue_item(xs_dict *q_item)
                 srv_log(xs_fmt("output message: giving up %s %d", inbox, status));
             else {
                 /* requeue */
-                enqueue_output_raw(keyid, seckey, msg, inbox, retries);
+                enqueue_output_raw(keyid, seckey, msg, inbox, retries, status);
                 srv_log(xs_fmt("output message: requeue %s #%d", inbox, retries));
             }
         }
diff --git a/data.c b/data.c
index 3b22114..cf4d39b 100644
--- a/data.c
+++ b/data.c
@@ -2041,13 +2041,16 @@ void enqueue_input(snac *snac, const xs_dict *msg, const xs_dict *req, int retri
 
 
 void enqueue_output_raw(const char *keyid, const char *seckey,
-                        xs_dict *msg, xs_str *inbox, int retries)
+                        xs_dict *msg, xs_str *inbox, int retries, int p_status)
 /* enqueues an output message to an inbox */
 {
     xs *qmsg   = _new_qmsg("output", msg, retries);
     char *ntid = xs_dict_get(qmsg, "ntid");
     xs *fn     = xs_fmt("%s/queue/%s.json", srv_basedir, ntid);
 
+    xs *ns = xs_number_new(p_status);
+    qmsg = xs_dict_append(qmsg, "p_status", ns);
+
     qmsg = xs_dict_append(qmsg, "inbox",  inbox);
     qmsg = xs_dict_append(qmsg, "keyid",  keyid);
     qmsg = xs_dict_append(qmsg, "seckey", seckey);
@@ -2062,7 +2065,7 @@ void enqueue_output_raw(const char *keyid, const char *seckey,
 }
 
 
-void enqueue_output(snac *snac, xs_dict *msg, xs_str *inbox, int retries)
+void enqueue_output(snac *snac, xs_dict *msg, xs_str *inbox, int retries, int p_status)
 /* enqueues an output message to an inbox */
 {
     if (xs_startswith(inbox, snac->actor)) {
@@ -2072,7 +2075,7 @@ void enqueue_output(snac *snac, xs_dict *msg, xs_str *inbox, int retries)
 
     char *seckey = xs_dict_get(snac->key, "secret");
 
-    enqueue_output_raw(snac->actor, seckey, msg, inbox, retries);
+    enqueue_output_raw(snac->actor, seckey, msg, inbox, retries, p_status);
 }
 
 
@@ -2082,7 +2085,7 @@ void enqueue_output_by_actor(snac *snac, xs_dict *msg, const xs_str *actor, int
     xs *inbox = get_actor_inbox(snac, actor);
 
     if (!xs_is_null(inbox))
-        enqueue_output(snac, msg, inbox, retries);
+        enqueue_output(snac, msg, inbox, retries, 0);
     else
         snac_log(snac, xs_fmt("enqueue_output_by_actor cannot get inbox %s", actor));
 }
diff --git a/snac.h b/snac.h
index 9800bb5..7cf3d7e 100644
--- a/snac.h
+++ b/snac.h
@@ -178,8 +178,8 @@ int instance_unblock(const char *instance);
 
 void enqueue_input(snac *snac, const xs_dict *msg, const xs_dict *req, int retries);
 void enqueue_output_raw(const char *keyid, const char *seckey,
-                        xs_dict *msg, xs_str *inbox, int retries);
-void enqueue_output(snac *snac, xs_dict *msg, xs_str *inbox, int retries);
+                        xs_dict *msg, xs_str *inbox, int retries, int p_status);
+void enqueue_output(snac *snac, xs_dict *msg, xs_str *inbox, int retries, int p_status);
 void enqueue_output_by_actor(snac *snac, xs_dict *msg, const xs_str *actor, int retries);
 void enqueue_email(xs_str *msg, int retries);
 void enqueue_telegram(const xs_str *msg, const char *bot, const char *chat_id);