diff --git a/src/net/p2p/managerbase.cpp b/src/net/p2p/managerbase.cpp
index f65cc876..303499b5 100644
--- a/src/net/p2p/managerbase.cpp
+++ b/src/net/p2p/managerbase.cpp
@@ -264,14 +264,16 @@ namespace P2P {
       LOGDEBUG("Peer " + toString(nodeId) + " is a discovery node, cannot send request");
       return nullptr;
     }
+    // Track the request
+    auto request = std::make_shared<Request>(message->command(), message->id(), session->hostNodeId(), message);
+    insertRequest(request);
+    // If message was never sent, then no request has been made. Fail and return.
     if (!session->write(message)) {
-      // If message was never sent, then no request has been made. Fail and return.
+      // We know the latest insert went into the active bucket, so we can just remove it.
+      std::unique_lock lock(this->requestsMutex_);
+      requests_[activeRequests_].erase(message->id());
       return nullptr;
     }
-    // Message was sent, so create a pending request entry and insert it in the active bucket.
-    // If the active bucket is full, clear the old bucket and make it the new active bucket.
-    auto request = std::make_shared<Request>(message->command(), message->id(), session->hostNodeId(), message);
-    insertRequest(request);
     return request;
   }
 
@@ -731,16 +733,17 @@ namespace P2P {
     std::make_shared<Session>(std::move(socket), ConnectionType::INBOUND, *this)->run();
   }
 
-  void ManagerBase::insertRequest(const std::shared_ptr<Request>& request) {
+  void ManagerBase::insertRequest(std::shared_ptr<Request> request) {
     // The previous logic would silently overwrite the previous entry in case of an (improbable)
     // request ID collision; this logic is retained here, since lookups will be directed to the
     // active bucket first (so a colliding entry that is in the older bucket is shadowed anyway).
     std::unique_lock lock(this->requestsMutex_);
-    requests_[activeRequests_][request->id()] = request;
     if (requests_[activeRequests_].size() >= REQUEST_BUCKET_SIZE_LIMIT) {
       activeRequests_ = 1 - activeRequests_;
       requests_[activeRequests_].clear();
     }
+    // Make sure the latest insertion always ended up in what is the current active bucket
+    requests_[activeRequests_][request->id()] = std::move(request);
   }
 
   void ManagerBase::handleRequestAnswer(const NodeID& nodeId, const std::shared_ptr<const Message>& message) {
diff --git a/src/net/p2p/managerbase.h b/src/net/p2p/managerbase.h
index b1d12d38..b1f08cdb 100644
--- a/src/net/p2p/managerbase.h
+++ b/src/net/p2p/managerbase.h
@@ -11,7 +11,7 @@ See the LICENSE.txt file in the project root for more information.
 /// Size of a sync-requests active bucket, in items (requests); there are two buckets.
 /// This needs to be large enough to hold the maximum number of requests that can be conceivable generated
 /// in the maximum time period that it takes to answer a request.
-#define REQUEST_BUCKET_SIZE_LIMIT 100000
+#define REQUEST_BUCKET_SIZE_LIMIT 100'000
 
 #include "discovery.h"
 #include "session.h" // encoding.h -> utils/options.h
@@ -147,7 +147,7 @@ namespace P2P {
        * Insert a new request into requests_.
        * @param request The newly created request to be tracked by requests_.
        */
-      void insertRequest(const std::shared_ptr<Request>& request);
+      void insertRequest(std::shared_ptr<Request> request);
 
       /**
        * Handles a message that is a generic answer to a synchronous generic remote request.