diff --git a/src/server/campaignd/server.cpp b/src/server/campaignd/server.cpp
index 3ffe26645774..71450f85ef07 100644
--- a/src/server/campaignd/server.cpp
+++ b/src/server/campaignd/server.cpp
@@ -1149,16 +1149,11 @@ void server::handle_request_campaign(const server::request& req)
 		}
 
 		LOG_CS << req << "Sending add-on '" << name << "' version: " << to << " size: " << full_pack_size / 1024 << " KiB\n";
-		if(auto sock = utils::get_if<socket_ptr>(&req.sock)) {
+		utils::visit([this, &req, &full_pack_path](auto&& socket) {
 			boost::system::error_code ec;
-			coro_send_file(*sock, full_pack_path, req.yield[ec]);
-			if(check_error(ec, *sock)) return;
-		} else {
-			// FIXME: need to decide what to do about sending addons over TLS.
-			// sendfile is low level api so either drop TLS for this part
-			// or don't use sendfile at all.
-			ERR_CS << "Not sending addon over TLS yet\n";
-		}
+			coro_send_file(socket, full_pack_path, req.yield[ec]);
+			if(check_error(ec, socket)) return;
+		}, req.sock);
 	}
 
 	// Clients doing upgrades or some other specific thing shouldn't bump
@@ -1210,13 +1205,11 @@ void server::handle_request_campaign_hash(const server::request& req)
 		}
 
 		LOG_CS << req << "Sending add-on hash index for '" << req.cfg["name"] << "' size: " << file_size / 1024 << " KiB\n";
-		if(auto sock = utils::get_if<socket_ptr>(&req.sock)) {
+		utils::visit([this, &path, &req](auto&& socket) {
 			boost::system::error_code ec;
-			coro_send_file(*sock, path, req.yield[ec]);
-			if(check_error(ec, *sock)) return;
-		} else {
-			ERR_CS << "No sendfile over TLS\n";
-		}
+			coro_send_file(socket, path, req.yield[ec]);
+			if(check_error(ec, socket)) return;
+		}, req.sock);
 	}
 }
 
diff --git a/src/server/common/server_base.cpp b/src/server/common/server_base.cpp
index 98e14c203719..0881dab399e0 100644
--- a/src/server/common/server_base.cpp
+++ b/src/server/common/server_base.cpp
@@ -309,10 +309,38 @@ template<class SocketPtr> void server_base::coro_send_doc(SocketPtr socket, simp
 template void server_base::coro_send_doc<socket_ptr>(socket_ptr socket, simple_wml::document& doc, boost::asio::yield_context yield);
 template void server_base::coro_send_doc<tls_socket_ptr>(tls_socket_ptr socket, simple_wml::document& doc, boost::asio::yield_context yield);
 
+template<class SocketPtr> void coro_send_file_userspace(SocketPtr socket, const std::string& filename, boost::asio::yield_context yield)
+{
+	std::size_t filesize { std::size_t(filesystem::file_size(filename)) };
+	union DataSize
+	{
+		uint32_t size;
+		char buf[4];
+	} data_size {};
+	data_size.size = htonl(filesize);
+
+	async_write(*socket, boost::asio::buffer(data_size.buf), yield);
+
+	auto ifs { filesystem::istream_file(filename) };
+	ifs->seekg(0);
+	while(ifs->good()) {
+		char buf[16384];
+		ifs->read(buf, sizeof(buf));
+		async_write(*socket, boost::asio::buffer(buf, ifs->gcount()), yield);
+	}
+}
+
 #ifdef HAVE_SENDFILE
 
 template<class SocketPtr> void server_base::coro_send_file(SocketPtr socket, const std::string& filename, boost::asio::yield_context yield)
 {
+	// We fallback to userspace if using TLS socket because sendfile is not aware of TLS state
+	// TODO: keep in mind possibility of using KTLS instead. This seem to be available only in openssl3 branch for now
+	if constexpr (utils::decayed_is_same<tls_socket_ptr, decltype(socket)>) {
+		coro_send_file_userspace(socket, filename, yield);
+		return;
+	} else {
+
 	std::size_t filesize { std::size_t(filesystem::file_size(filename)) };
 	int in_file { open(filename.c_str(), O_RDONLY) };
 	off_t offset { 0 };
@@ -364,12 +392,17 @@ template<class SocketPtr> void server_base::coro_send_file(SocketPtr socket, con
 
 		// Loop around to try calling sendfile again.
 	}
+	}
 }
 
 #elif defined(_WIN32)
 
 template<class SocketPtr> void server_base::coro_send_file(SocketPtr socket, const std::string& filename, boost::asio::yield_context yield)
 {
+	if constexpr (utils::decayed_is_same<tls_socket_ptr, decltype(socket)>) {
+		coro_send_file_userspace(socket, filename, yield);
+		return;
+	} else {
 
 	OVERLAPPED overlap;
 	std::vector<boost::asio::const_buffer> buffers;
@@ -425,19 +458,20 @@ template<class SocketPtr> void server_base::coro_send_file(SocketPtr socket, con
 			throw std::runtime_error("TransmitFile failed");
 		}
 	}
+	}
 }
 
 #else
 
 template<class SocketPtr> void server_base::coro_send_file(SocketPtr socket, const std::string& filename, boost::asio::yield_context yield)
 {
-// TODO: Implement this for systems without sendfile()
-	assert(false && "Not implemented yet");
+	coro_send_file_userspace(socket, filename, yield);
 }
 
 #endif
 
 template void server_base::coro_send_file<socket_ptr>(socket_ptr socket, const std::string& filename, boost::asio::yield_context yield);
+template void server_base::coro_send_file<tls_socket_ptr>(tls_socket_ptr socket, const std::string& filename, boost::asio::yield_context yield);
 
 template<class SocketPtr> std::unique_ptr<simple_wml::document> server_base::coro_receive_doc(SocketPtr socket, boost::asio::yield_context yield)
 {