diff --git a/src/api/InfluxDB.cpp b/src/api/InfluxDB.cpp
index ee3a8a20..163b8c0d 100644
--- a/src/api/InfluxDB.cpp
+++ b/src/api/InfluxDB.cpp
@@ -282,6 +282,41 @@ void vz::api::InfluxDB::send() {
 	const int duplicates = channel()->duplicates();
 	const int duplicates_ms = duplicates * 1000;
 
+	// Snapshot _last_timestamp and _lastReadingSent before the build loop so we
+	// can roll back on send failure.  The loop advances both fields as it runs,
+	// but the HTTP send has not happened yet.  If the send fails, buf->undelete()
+	// restores the buffer items but without rolling back these fields the readings
+	// would be permanently skipped on every subsequent attempt.
+	//
+	// Three cases must be handled correctly:
+	//   A) duplicates=0          — only _last_timestamp matters
+	//   B) duplicates>0, _lastReadingSent was nullptr before loop
+	//                            — loop may allocate it; must free and null on rollback
+	//   C) duplicates>0, _lastReadingSent was already set before loop
+	//                            — must restore its value, not just the pointer
+	const int64_t snapshot_last_timestamp = _last_timestamp;
+	Reading *snapshot_lastReadingSent = nullptr;
+	if (_lastReadingSent) {
+		snapshot_lastReadingSent = new Reading(*_lastReadingSent);
+	}
+
+	auto rollback_state = [&]() {
+		_last_timestamp = snapshot_last_timestamp;
+		if (snapshot_lastReadingSent) {
+			// Case C: _lastReadingSent existed before — restore its value
+			if (!_lastReadingSent)
+				_lastReadingSent = new Reading(*snapshot_lastReadingSent);
+			else
+				*_lastReadingSent = *snapshot_lastReadingSent;
+	} else {
+			// Cases A & B: _lastReadingSent was nullptr before the loop.
+			// If the loop allocated it, free it now so the next send()
+			// call starts fresh and doesn't compare against a stale reading.
+		delete _lastReadingSent;
+			_lastReadingSent = nullptr;
+		}
+	};
+
 	// build request body from buffer contents
 	buf->lock();
 	for (it = buf->begin(); it != buf->end(); it++) {
@@ -393,6 +428,9 @@ void vz::api::InfluxDB::send() {
 			buf->clean(); // delete the stuff we just sent to InfluxDB from the buffer
 		} else {
 			buf->undelete(); // failure to insert, so dont delete the buffer
+			rollback_state(); // restore _last_timestamp and _lastReadingSent so all
+			                  // buffered readings are retried on next send() call
+
 			if (curl_code != CURLE_OK) {
 				print(log_error, "CURL Error: %s", channel()->name(),
 					  curl_easy_strerror(curl_code));
@@ -402,11 +440,21 @@ void vz::api::InfluxDB::send() {
 				print(log_error, "InfluxDB response was %s", channel()->name(),
 					  _response->get_response().c_str());
 			}
+			if (buf->size() > 30) {
+				print(log_error, "InfluxDB buffer contains %i undelivered readings",
+				      channel()->name(), buf->size());
+			}
 		}
 	} else { // there is nothing to send
 		print(log_info, "Nothing to send to InfluxDB api", channel()->name());
 	}
 
+	// Free the snapshot in all code paths.
+	// In the failure+Case C path rollback_state() restored _lastReadingSent from it,
+	// but snapshot_lastReadingSent itself is a separate allocation that must always
+	// be freed here.
+	delete snapshot_lastReadingSent;
+
 	if (curlSessionProvider) {
 		// release our curl session
 		curlSessionProvider->return_session(_host + channel()->uuid(), _api.curl);