diff --git a/src/net/tools/naive/naive_connection.cc b/src/net/tools/naive/naive_connection.cc
index f814f778e1..cae3b73692 100644
--- a/src/net/tools/naive/naive_connection.cc
+++ b/src/net/tools/naive/naive_connection.cc
@@ -211,10 +211,16 @@ int NaiveConnection::DoConnectServer() {
     if (rv == 0) {
       IPEndPoint ipe;
       if (ipe.FromSockAddr(dst.addr, dst.addr_len)) {
-        origin = HostPortPair::FromIPEndPoint(ipe);
-        auto name = resolver_->FindNameByAddress(ipe.address());
+        const auto& addr = ipe.address();
+        auto name = resolver_->FindNameByAddress(addr);
         if (!name.empty()) {
           origin.set_host(name);
+        } else if (!resolver_->IsInResolvedRange(addr)) {
+          origin = HostPortPair::FromIPEndPoint(ipe);
+        } else {
+          LOG(ERROR) << "Connection " << id_ << " to unresolved name for "
+                     << addr.ToString();
+          return ERR_ADDRESS_INVALID;
         }
       }
     }
diff --git a/src/net/tools/naive/redirect_resolver.cc b/src/net/tools/naive/redirect_resolver.cc
index 2ab85db625..939e163870 100644
--- a/src/net/tools/naive/redirect_resolver.cc
+++ b/src/net/tools/naive/redirect_resolver.cc
@@ -20,6 +20,12 @@
 
 namespace {
 constexpr int kUdpReadBufferSize = 1024;
+constexpr int kResolutionTtl = 60;
+constexpr int kResolutionRecycleTime = 60 * 5;
+
+std::string PackedIPv4ToString(uint32_t addr) {
+  return net::IPAddress(addr >> 24, addr >> 16, addr >> 8, addr).ToString();
+}
 }  // namespace
 
 namespace net {
@@ -133,6 +139,9 @@ int RedirectResolver::HandleReadResult(int result) {
         // Too few available addresses. Overwrites old one.
         auto res_it = by_addr->second;
 
+        LOG(INFO) << "Overwrite " << res_it->name << " "
+                  << PackedIPv4ToString(res_it->addr) << " with " << name << " "
+                  << PackedIPv4ToString(addr);
         resolution_by_name_.erase(res_it->by_name);
         resolutions_.erase(res_it);
         resolutions_.emplace_back();
@@ -146,6 +155,7 @@ int RedirectResolver::HandleReadResult(int result) {
         res_it->by_name = by_name;
         res_it->by_addr = by_addr;
       } else {
+        LOG(INFO) << "Add " << name << " " << PackedIPv4ToString(addr);
         resolutions_.emplace_back();
         auto res_it = std::prev(resolutions_.end());
 
@@ -161,8 +171,10 @@ int RedirectResolver::HandleReadResult(int result) {
         auto now = base::TimeTicks::Now();
         for (auto it = resolutions_.begin();
              it != resolutions_.end() &&
-             (now - it->time).InSeconds() > 60 * 5;) {
+             (now - it->time).InSeconds() > kResolutionRecycleTime;) {
           auto next = std::next(it);
+          LOG(INFO) << "Drop " << it->name << " "
+                    << PackedIPv4ToString(it->addr);
           resolution_by_name_.erase(it->by_name);
           resolution_by_addr_.erase(it->by_addr);
           resolutions_.erase(it);
@@ -175,7 +187,7 @@ int RedirectResolver::HandleReadResult(int result) {
     record.name = name;
     record.type = dns_protocol::kTypeA;
     record.klass = dns_protocol::kClassIN;
-    record.ttl = 60;
+    record.ttl = kResolutionTtl;
     uint32_t addr = by_name->second->addr;
     record.SetOwnedRdata(IPAddressToPackedString(
         IPAddress(addr >> 24, addr >> 16, addr >> 8, addr)));
@@ -208,6 +220,12 @@ int RedirectResolver::HandleReadResult(int result) {
       base::BindOnce(&RedirectResolver::OnSend, base::Unretained(this)));
 }
 
+bool RedirectResolver::IsInResolvedRange(const IPAddress& address) const {
+  if (!address.IsIPv4())
+    return false;
+  return IPAddressMatchesPrefix(address, range_, prefix_);
+}
+
 std::string RedirectResolver::FindNameByAddress(
     const IPAddress& address) const {
   if (!address.IsIPv4())
diff --git a/src/net/tools/naive/redirect_resolver.h b/src/net/tools/naive/redirect_resolver.h
index 9c91c67cf6..c8551ac5bd 100644
--- a/src/net/tools/naive/redirect_resolver.h
+++ b/src/net/tools/naive/redirect_resolver.h
@@ -41,6 +41,7 @@ class RedirectResolver {
                    size_t prefix);
   ~RedirectResolver();
 
+  bool IsInResolvedRange(const IPAddress& address) const;
   std::string FindNameByAddress(const IPAddress& address) const;
 
  private: