diff --git a/src/CMakeLists.txt b/src/CMakeLists.txt
index 8c2af2c3..e14f7345 100644
--- a/src/CMakeLists.txt
+++ b/src/CMakeLists.txt
@@ -61,6 +61,9 @@ add_executable(tomato
 	./tox_dht_cap_histo.hpp
 	./tox_dht_cap_histo.cpp
 
+	./tox_friend_faux_offline_messaging.hpp
+	./tox_friend_faux_offline_messaging.cpp
+
 	./chat_gui4.hpp
 	./chat_gui4.cpp
 )
diff --git a/src/chat_gui4.cpp b/src/chat_gui4.cpp
index eaccac33..c91783a1 100644
--- a/src/chat_gui4.cpp
+++ b/src/chat_gui4.cpp
@@ -96,13 +96,21 @@ const void* clipboard_callback(void* userdata, const char* mime_type, size_t* si
 }
 
 void ChatGui4::setClipboardData(std::vector<std::string> mime_types, std::shared_ptr<std::vector<uint8_t>>&& data) {
-	std::vector<const char*> tmp_mimetype_list;
-	for (const auto& mime_type : mime_types) {
-		tmp_mimetype_list.push_back(mime_type.data());
+	if (!static_cast<bool>(data)) {
+		std::cerr << "CG error: tried to set clipboard with empty shp\n";
+		return;
 	}
 
+	if (data->empty()) {
+		std::cerr << "CG error: tried to set clipboard with empty data\n";
+		return;
+	}
+
+	std::vector<const char*> tmp_mimetype_list;
+
 	std::lock_guard lg{_set_clipboard_data_mutex};
 	for (const auto& mime_type : mime_types) {
+		tmp_mimetype_list.push_back(mime_type.data());
 		_set_clipboard_data[mime_type] = data;
 	}
 
diff --git a/src/main_screen.cpp b/src/main_screen.cpp
index f5eb477d..d68c5e1b 100644
--- a/src/main_screen.cpp
+++ b/src/main_screen.cpp
@@ -16,6 +16,7 @@ MainScreen::MainScreen(SDL_Renderer* renderer_, std::string save_path, std::stri
 	tcm(cr, tc, tc),
 	tmm(rmm, cr, tcm, tc, tc),
 	ttm(rmm, cr, tcm, tc, tc),
+	tffom(cr, rmm, tcm, tc, tc),
 	mmil(rmm),
 	tam(rmm, cr, conf),
 	sdlrtu(renderer_),
@@ -241,6 +242,8 @@ Screen* MainScreen::tick(float time_delta, bool& quit) {
 
 	tcm.iterate(time_delta); // compute
 
+	const float fo_interval = tffom.tick(time_delta);
+
 	tam.iterate(); // compute
 
 	const float pm_interval = pm.tick(time_delta); // compute
@@ -253,6 +256,10 @@ Screen* MainScreen::tick(float time_delta, bool& quit) {
 		tc.toxIterationInterval()/1000.f,
 		pm_interval
 	);
+	_min_tick_interval = std::min<float>(
+		_min_tick_interval,
+		fo_interval
+	);
 
 	switch (_compute_perf_mode) {
 		// normal 1ms lower bound
diff --git a/src/main_screen.hpp b/src/main_screen.hpp
index 84facd66..8dfaf7cc 100644
--- a/src/main_screen.hpp
+++ b/src/main_screen.hpp
@@ -25,6 +25,7 @@
 #include "./settings_window.hpp"
 #include "./tox_ui_utils.hpp"
 #include "./tox_dht_cap_histo.hpp"
+#include "./tox_friend_faux_offline_messaging.hpp"
 
 #include <string>
 #include <iostream>
@@ -52,6 +53,7 @@ struct MainScreen final : public Screen {
 	ToxContactModel2 tcm;
 	ToxMessageManager tmm;
 	ToxTransferManager ttm;
+	ToxFriendFauxOfflineMessaging tffom;
 
 	MediaMetaInfoLoader mmil;
 	ToxAvatarManager tam;
diff --git a/src/tox_friend_faux_offline_messaging.cpp b/src/tox_friend_faux_offline_messaging.cpp
new file mode 100644
index 00000000..ca93336d
--- /dev/null
+++ b/src/tox_friend_faux_offline_messaging.cpp
@@ -0,0 +1,188 @@
+#include "./tox_friend_faux_offline_messaging.hpp"
+
+#include <solanaceae/toxcore/tox_interface.hpp>
+
+#include <solanaceae/contact/components.hpp>
+#include <solanaceae/tox_contacts/components.hpp>
+#include <solanaceae/message3/components.hpp>
+#include <solanaceae/tox_messages/components.hpp>
+
+#include <limits>
+#include <cstdint>
+
+namespace Message::Components {
+	struct LastSendAttempt {
+		uint64_t ts {0};
+	};
+} // Message::Components
+
+namespace Contact::Components {
+	struct NextSendAttempt {
+		uint64_t ts {0};
+	};
+} // Contact::Components
+
+ToxFriendFauxOfflineMessaging::ToxFriendFauxOfflineMessaging(
+	Contact3Registry& cr,
+	RegistryMessageModel& rmm,
+	ToxContactModel2& tcm,
+	ToxI& t,
+	ToxEventProviderI& tep
+) : _cr(cr), _rmm(rmm), _tcm(tcm), _t(t), _tep(tep) {
+}
+
+float ToxFriendFauxOfflineMessaging::tick(float time_delta) {
+	// hard limit interval to once per minute
+	_interval_timer += time_delta;
+	if (_interval_timer < 1.f * 60.f) {
+		return std::max(60.f - _interval_timer, 0.001f); // TODO: min next timer
+	}
+	_interval_timer = 0.f;
+
+	const uint64_t ts_now = Message::getTimeMS();
+
+	// check ALL
+	// for each online tox friend
+	uint64_t min_next_attempt_ts {std::numeric_limits<uint64_t>::max()};
+	_cr.view<Contact::Components::ToxFriendEphemeral, Contact::Components::ConnectionState>()
+	.each([this, &min_next_attempt_ts, ts_now](const Contact3 c, const auto& tfe, const auto& cs) {
+		if (cs.state == Contact::Components::ConnectionState::disconnected) {
+			// cleanup
+			if (_cr.all_of<Contact::Components::NextSendAttempt>(c)) {
+				_cr.remove<Contact::Components::NextSendAttempt>(c);
+			}
+		} else {
+			if (!_cr.all_of<Contact::Components::NextSendAttempt>(c)) {
+				const auto& nsa = _cr.emplace<Contact::Components::NextSendAttempt>(c, ts_now + uint64_t(_delay_after_cc*1000)); // wait before first message is sent
+				min_next_attempt_ts = std::min(min_next_attempt_ts, nsa.ts);
+			} else {
+				auto& next_attempt = _cr.get<Contact::Components::NextSendAttempt>(c).ts;
+
+				if (doFriendMessageCheck(c, tfe)) {
+					next_attempt = ts_now + uint64_t(_delay_inbetween*1000);
+				}
+
+				min_next_attempt_ts = std::min(min_next_attempt_ts, next_attempt);
+			}
+		}
+	});
+
+	if (min_next_attempt_ts <= ts_now) {
+		// we (probably) sent this iterate
+		_interval_timer = 60.f - 0.1f; // TODO: ugly magic
+		return 0.1f;
+	} else if (min_next_attempt_ts == std::numeric_limits<uint64_t>::max()) {
+		// nothing to sync or all offline that need syncing
+		return 60.f; // TODO: ugly magic
+	} else {
+		// TODO: ugly magic
+		return _interval_timer = 60.f - std::min(60.f, (min_next_attempt_ts - ts_now) / 1000.f);
+	}
+}
+
+bool ToxFriendFauxOfflineMessaging::doFriendMessageCheck(const Contact3 c, const Contact::Components::ToxFriendEphemeral& tfe) {
+	// walk all messages and check if
+	// unacked message
+	// timeouts for exising unacked messages expired (send)
+
+	auto* mr = static_cast<const RegistryMessageModel&>(_rmm).get(c);
+	if (mr == nullptr) {
+		// no messages
+		return false;
+	}
+
+	const uint64_t ts_now = Message::getTimeMS();
+
+	// filter for unconfirmed messages
+
+	// we assume sorted
+	// ("reverse" iteration <.<)
+	auto msg_view = mr->view<Message::Components::Timestamp>();
+	// we search for the oldest, not too recently sent, unconfirmed message
+	for (auto it = msg_view.rbegin(), view_end = msg_view.rend(); it != view_end; it++) {
+		const Message3 msg = *it;
+
+		// require
+		if (!mr->all_of<
+				Message::Components::MessageText, // text only for now
+				Message::Components::ContactTo
+			>(msg)
+		) {
+			continue; // skip
+		}
+
+		// exclude
+		if (mr->any_of<
+				Message::Components::Remote::TimestampReceived // this acts like a tag, which is wrong in groups
+			>(msg)
+		) {
+			continue; // skip
+		}
+
+		uint64_t msg_ts = msg_view.get<Message::Components::Timestamp>(msg).ts;
+		if (mr->all_of<Message::Components::TimestampWritten>(msg)) {
+			msg_ts = mr->get<Message::Components::TimestampWritten>(msg).ts;
+		}
+		if (mr->all_of<Message::Components::LastSendAttempt>(msg)) {
+			const auto lsa = mr->get<Message::Components::LastSendAttempt>(msg).ts;
+			if (lsa > msg_ts) {
+				msg_ts = lsa;
+			}
+		}
+
+		if (ts_now < (msg_ts + uint64_t(_delay_retry * 1000))) {
+			// not time yet
+			continue;
+		}
+
+		// it is time
+		const auto [msg_id, _] = _t.toxFriendSendMessage(
+			tfe.friend_number,
+			(
+				mr->all_of<Message::Components::TagMessageIsAction>(msg)
+					? Tox_Message_Type::TOX_MESSAGE_TYPE_ACTION
+					: Tox_Message_Type::TOX_MESSAGE_TYPE_NORMAL
+			),
+			mr->get<Message::Components::MessageText>(msg).text
+		);
+
+		// TODO: this is ugly
+		mr->emplace_or_replace<Message::Components::LastSendAttempt>(msg, ts_now);
+
+		if (msg_id.has_value()) {
+			// tmm will pick this up for us
+			mr->emplace_or_replace<Message::Components::ToxFriendMessageID>(msg, msg_id.value());
+		} // else error
+
+		// we sent our message, no point further iterating
+		return true;
+	}
+
+	// TODO: somehow cleanup lsa
+
+	return false;
+}
+
+bool ToxFriendFauxOfflineMessaging::onToxEvent(const Tox_Event_Friend_Connection_Status* e) {
+	const auto friend_number = tox_event_friend_connection_status_get_friend_number(e);
+	const auto friend_status = tox_event_friend_connection_status_get_connection_status(e);
+
+	if (friend_status == Tox_Connection::TOX_CONNECTION_NONE) {
+		return false; // skip
+		// maybe cleanup?
+	}
+
+	auto c = _tcm.getContactFriend(friend_number);
+	if (!static_cast<bool>(c) || !c.all_of<Contact::Components::ToxFriendEphemeral, Contact::Components::ConnectionState>()) {
+		// UH error??
+		return false;
+	}
+
+	_cr.emplace_or_replace<Contact::Components::NextSendAttempt>(c, Message::getTimeMS() + uint64_t(_delay_after_cc*1000)); // wait before first message is sent
+
+	// TODO: ugly magic
+	_interval_timer = 60.f - 0.1f;
+
+	return false;
+}
+
diff --git a/src/tox_friend_faux_offline_messaging.hpp b/src/tox_friend_faux_offline_messaging.hpp
new file mode 100644
index 00000000..4829216d
--- /dev/null
+++ b/src/tox_friend_faux_offline_messaging.hpp
@@ -0,0 +1,50 @@
+#pragma once
+
+#include <solanaceae/toxcore/tox_event_interface.hpp>
+#include <solanaceae/tox_contacts/tox_contact_model2.hpp>
+#include <solanaceae/contact/contact_model3.hpp>
+#include <solanaceae/message3/registry_message_model.hpp>
+
+// fwd
+struct ToxI;
+namespace Contact::Components {
+	struct ToxFriendEphemeral;
+}
+
+// resends unconfirmed messages.
+// timers get reset on connection changes, and send order is preserved.
+class ToxFriendFauxOfflineMessaging : public ToxEventI {
+	Contact3Registry& _cr;
+	RegistryMessageModel& _rmm;
+	ToxContactModel2& _tcm;
+	ToxI& _t;
+	ToxEventProviderI& _tep;
+
+	float _interval_timer{0.f};
+
+	// TODO: increase timer?
+	const float _delay_after_cc {4.5f};
+	const float _delay_inbetween {0.3f};
+	const float _delay_retry {10.f}; // retry sending after 10s
+
+	public:
+		ToxFriendFauxOfflineMessaging(
+			Contact3Registry& cr,
+			RegistryMessageModel& rmm,
+			ToxContactModel2& tcm,
+			ToxI& t,
+			ToxEventProviderI& tep
+		);
+
+		float tick(float time_delta);
+
+	private:
+		// only called for online friends
+		// returns true if a message was sent
+		// dont call this too often
+		bool doFriendMessageCheck(const Contact3 c, const Contact::Components::ToxFriendEphemeral& tfe);
+
+	protected:
+		bool onToxEvent(const Tox_Event_Friend_Connection_Status* e) override;
+};
+