diff --git a/tools/chatgui/transport/chat_core.c b/tools/chatgui/transport/chat_core.c
index 0b3a240b..607df578 100644
--- a/tools/chatgui/transport/chat_core.c
+++ b/tools/chatgui/transport/chat_core.c
@@ -727,14 +727,18 @@ void chat_core_connect_auto(uint64_t node_id,
                             void (*cb)(int result, uint64_t node_id, void* arg),
                             void* arg,
                             void** out_state) {
-    if (!g_cc.initialized || !g_cc.inst || !cb) return;
+    if (!g_cc.initialized || !g_cc.inst || !cb) {
+        DEBUG_INFO(DEBUG_CATEGORY_DEBUG, "%s: auto_connect FAIL (not initialized) node=0x%016llx init=%d inst=%p cb=%p",
+                   CC_ID, (unsigned long long)node_id, g_cc.initialized, (void*)g_cc.inst, (void*)cb);
+        return;
+    }
     if (out_state) *out_state = NULL;
 
     struct ETCP_SOCKET* best_socket = g_cc.inst->etcp_sockets;
     while (best_socket && best_socket->local_addr.ss_family != AF_INET) best_socket = best_socket->next;
     if (!best_socket) {
-        DEBUG_ERROR(DEBUG_CATEGORY_CONNECTIVITY, "%s: auto_connect no AF_INET socket for node 0x%016llx",
-                    CC_ID, (unsigned long long)node_id);
+        DEBUG_INFO(DEBUG_CATEGORY_DEBUG, "%s: auto_connect FAIL (no AF_INET socket) node=0x%016llx sockets=%p",
+                   CC_ID, (unsigned long long)node_id, (void*)g_cc.inst->etcp_sockets);
         cb(CC_ERR_INTERNAL, node_id, arg);
         return;
     }
@@ -753,8 +757,8 @@ void chat_core_connect_auto(uint64_t node_id,
         sqlite3_finalize(st);
     }
     if (pubkey[0] == 0 && pubkey[1] == 0) {
-        DEBUG_ERROR(DEBUG_CATEGORY_CONNECTIVITY, "%s: auto_connect no pubkey for node 0x%016llx",
-                    CC_ID, (unsigned long long)node_id);
+        DEBUG_INFO(DEBUG_CATEGORY_DEBUG, "%s: auto_connect FAIL (no pubkey in DB) node=0x%016llx",
+                   CC_ID, (unsigned long long)node_id);
         cb(CC_ERR_NOT_FOUND, node_id, arg);
         return;
     }
@@ -787,13 +791,14 @@ void chat_core_connect_auto(uint64_t node_id,
       }
       addr_count = uniq; }
     if (addr_count == 0) {
-        DEBUG_DEBUG(DEBUG_CATEGORY_DEBUG, "%s: auto_connect no IPv4 addrs yet for node 0x%016llx (BGP not synced?)", CC_ID, (unsigned long long)node_id);
+        DEBUG_INFO(DEBUG_CATEGORY_DEBUG, "%s: auto_connect FAIL (no IPv4 addrs in DB) node=0x%016llx (BGP not synced?)",
+                   CC_ID, (unsigned long long)node_id);
         cb(CC_ERR_NO_ADDRESSES, node_id, arg);
         return;
     }
 
     struct ca_state* pst = u_calloc(1, sizeof(struct ca_state));
-    if (!pst) { cb(CC_ERR_INTERNAL, node_id, arg); return; }
+    if (!pst) { DEBUG_INFO(DEBUG_CATEGORY_DEBUG, "%s: auto_connect FAIL (alloc ca_state) node=0x%016llx", CC_ID, (unsigned long long)node_id); cb(CC_ERR_INTERNAL, node_id, arg); return; }
     pst->inst = g_cc.inst;
     pst->addr_count = addr_count;
     pst->pending_count = addr_count;
@@ -804,7 +809,7 @@ void chat_core_connect_auto(uint64_t node_id,
     pst->conns = u_calloc(addr_count, sizeof(struct ETCP_CONN*));
     pst->timers = u_calloc(addr_count, sizeof(void*));
     pst->ctxs   = u_calloc(addr_count, sizeof(struct ca_ctx*));
-    if (!pst->conns || !pst->timers || !pst->ctxs) { ca_cleanup(pst); cb(CC_ERR_INTERNAL, node_id, arg); return; }
+    if (!pst->conns || !pst->timers || !pst->ctxs) { DEBUG_INFO(DEBUG_CATEGORY_DEBUG, "%s: auto_connect FAIL (alloc arrays) node=0x%016llx", CC_ID, (unsigned long long)node_id); ca_cleanup(pst); cb(CC_ERR_INTERNAL, node_id, arg); return; }
 
     for (int i = 0; i < addr_count; i++) {
         struct sockaddr_in sin;
@@ -847,7 +852,8 @@ void chat_core_connect_auto(uint64_t node_id,
     if (out_state) *out_state = pst;
 
     if (pst->pending_count <= 0 && !pst->delivered) {
-        DEBUG_ERROR(DEBUG_CATEGORY_CONNECTIVITY, "%s: auto_connect all %d attempts failed to start", CC_ID, addr_count);
+        DEBUG_INFO(DEBUG_CATEGORY_DEBUG, "%s: auto_connect FAIL (all %d attempts failed to start) node=0x%016llx",
+                   CC_ID, addr_count, (unsigned long long)node_id);
         if (out_state) *out_state = NULL;
         cb(CC_ERR_UNREACHABLE, node_id, arg);
         ca_cleanup(pst);
diff --git a/tools/chatgui/transport/chat_sync.c b/tools/chatgui/transport/chat_sync.c
index 3ac53304..41e388b0 100644
--- a/tools/chatgui/transport/chat_sync.c
+++ b/tools/chatgui/transport/chat_sync.c
@@ -180,6 +180,7 @@ static void ac_fill(struct auto_connect* ac) {
         f->created_tb = get_time_tb();
         chat_core_connect_auto(nid, ac_result_cb, f, &f->ca_state);
         if (!f->ca_state) {
+            DEBUG_INFO(DEBUG_CATEGORY_DEBUG, "%s: flight to 0x%016llx FAIL (ca_state=NULL, sync fail in chat_core_connect_auto)", AC_ID, (unsigned long long)nid);
             f->node_id = 0; f->created_tb = 0;
             continue;
         }