diff --git a/src/ripple/app/main/Application.cpp b/src/ripple/app/main/Application.cpp
index be0a7b46a..20427107b 100644
--- a/src/ripple/app/main/Application.cpp
+++ b/src/ripple/app/main/Application.cpp
@@ -1527,7 +1527,7 @@ ApplicationImp::setup(boost::program_options::variables_map const& cmdline)
         reportingETL_->start();
 
     // Datagram monitor if applicable
-    if (!config_->standalone() && config_->DATAGRAM_MONITOR != "")
+    if (!config_->standalone() && !config_->DATAGRAM_MONITOR.empty())
     {
         datagram_monitor_ = std::make_unique<DatagramMonitor>(*this);
         if (datagram_monitor_)
diff --git a/src/ripple/app/misc/DatagramMonitor.h b/src/ripple/app/misc/DatagramMonitor.h
index ba6ce0213..033090581 100644
--- a/src/ripple/app/misc/DatagramMonitor.h
+++ b/src/ripple/app/misc/DatagramMonitor.h
@@ -996,15 +996,24 @@ private:
     void
     monitorThread()
     {
-        auto endpoint = parseEndpoint(app_.config().DATAGRAM_MONITOR);
-        int sock = createSocket(endpoint);
+        std::vector<std::pair<EndpointInfo, int>> endpoints;
+
+        for (auto const& epStr : app_.config().DATAGRAM_MONITOR)
+        {
+            auto endpoint = parseEndpoint(epStr);
+            endpoints.push_back(
+                std::make_pair(endpoint, createSocket(endpoint)));
+        }
 
         while (running_)
         {
             try
             {
                 auto info = generateServerInfo();
-                sendPacket(sock, endpoint, info);
+                for (auto const& ep : endpoints)
+                {
+                    sendPacket(ep.second, ep.first, info);
+                }
                 std::this_thread::sleep_for(std::chrono::seconds(1));
             }
             catch (const std::exception& e)
@@ -1015,7 +1024,10 @@ private:
             }
         }
 
-        close(sock);
+        for (auto const& ep : endpoints)
+        {
+            close(ep.second);
+        }
     }
 
 public:
diff --git a/src/ripple/core/Config.h b/src/ripple/core/Config.h
index 5d9977770..3e2c3c81a 100644
--- a/src/ripple/core/Config.h
+++ b/src/ripple/core/Config.h
@@ -155,7 +155,7 @@ public:
     std::map<std::string, PublicKey>
         IMPORT_VL_KEYS;  // hex string -> class PublicKey (for caching purposes)
 
-    std::string DATAGRAM_MONITOR;
+    std::vector<std::string> DATAGRAM_MONITOR;
 
     enum StartUpType {
         FRESH,
diff --git a/src/ripple/core/impl/Config.cpp b/src/ripple/core/impl/Config.cpp
index 656993752..7673d16ec 100644
--- a/src/ripple/core/impl/Config.cpp
+++ b/src/ripple/core/impl/Config.cpp
@@ -510,11 +510,10 @@ Config::loadFromString(std::string const& fileContents)
             NETWORK_ID = beast::lexicalCastThrow<uint32_t>(strTemp);
     }
 
-    if (getSingleSection(secConfig, SECTION_DATAGRAM_MONITOR, strTemp, j_))
+    if (auto s = getIniFileSection(secConfig, SECTION_DATAGRAM_MONITOR))
     {
-        std::vector<std::string> vecTemp{strTemp};
-        replaceColons(vecTemp);
-        DATAGRAM_MONITOR = vecTemp[0];
+        DATAGRAM_MONITOR = *s;
+        replaceColons(DATAGRAM_MONITOR);
     }
 
     if (getSingleSection(secConfig, SECTION_PEER_PRIVATE, strTemp, j_))