diff --git a/src/addrman.h b/src/addrman.h
--- a/src/addrman.h
+++ b/src/addrman.h
@@ -180,6 +180,10 @@
 //! the maximum number of tried addr collisions to store
 #define ADDRMAN_SET_TRIED_COLLISION_SIZE 10
 
+//! the maximum time we'll spend trying to resolve a tried table collision, in
+//! seconds (40 minutes)
+static const int64_t ADDRMAN_TEST_WINDOW = 40 * 60;
+
 /**
  * Stochastical (IP) address manager
  */
diff --git a/src/addrman.cpp b/src/addrman.cpp
--- a/src/addrman.cpp
+++ b/src/addrman.cpp
@@ -266,9 +266,15 @@
 
     // Will moving this address into tried evict another entry?
     if (test_before_evict && (vvTried[tried_bucket][tried_bucket_pos] != -1)) {
+        // Output the entry we'd be colliding with, for debugging purposes
+        auto colliding_entry =
+            mapInfo.find(vvTried[tried_bucket][tried_bucket_pos]);
         LogPrint(BCLog::ADDRMAN,
-                 "Collision inserting element into tried table, moving %s to "
-                 "m_tried_collisions=%d\n",
+                 "Collision inserting element into tried table (%s), moving %s "
+                 "to m_tried_collisions=%d\n",
+                 colliding_entry != mapInfo.end()
+                     ? colliding_entry->second.ToString()
+                     : "",
                  addr.ToString(), m_tried_collisions.size());
         if (m_tried_collisions.size() < ADDRMAN_SET_TRIED_COLLISION_SIZE) {
             m_tried_collisions.insert(nId);
@@ -658,14 +664,25 @@
                     // Give address at least 60 seconds to successfully connect
                     if (GetAdjustedTime() - info_old.nLastTry > 60) {
                         LogPrint(BCLog::ADDRMAN,
-                                 "Swapping %s for %s in tried table\n",
-                                 info_new.ToString(), info_old.ToString());
+                                 "Replacing %s with %s in tried table\n",
+                                 info_old.ToString(), info_new.ToString());
 
                         // Replaces an existing address already in the tried
                         // table with the new address
                         Good_(info_new, false, GetAdjustedTime());
                         erase_collision = true;
                     }
+                } else if (GetAdjustedTime() - info_new.nLastSuccess >
+                           ADDRMAN_TEST_WINDOW) {
+                    // If the collision hasn't resolved in some reasonable
+                    // amount of time, just evict the old entry -- we must not
+                    // be able to connect to it for some reason.
+                    LogPrint(BCLog::ADDRMAN,
+                             "Unable to test; replacing %s with %s in tried "
+                             "table anyway\n",
+                             info_old.ToString(), info_new.ToString());
+                    Good_(info_new, false, GetAdjustedTime());
+                    erase_collision = true;
                 }
             } else {
                 // Collision is not actually a collision anymore
diff --git a/src/net.cpp b/src/net.cpp
--- a/src/net.cpp
+++ b/src/net.cpp
@@ -1931,9 +1931,14 @@
                 addr = addrman.Select(fFeeler);
             }
 
-            // if we selected an invalid address, restart
-            if (!addr.IsValid() || setConnected.count(addr.GetGroup()) ||
-                IsLocal(addr)) {
+            // Require outbound connections, other than feelers, to be to
+            // distinct network groups
+            if (!fFeeler && setConnected.count(addr.GetGroup())) {
+                break;
+            }
+
+            // if we selected an invalid or local address, restart
+            if (!addr.IsValid() || IsLocal(addr)) {
                 break;
             }