diff --git a/src/core/matrix/state_res/event_auth.rs b/src/core/matrix/state_res/event_auth.rs
index 759ab5cb..bd2b9c61 100644
--- a/src/core/matrix/state_res/event_auth.rs
+++ b/src/core/matrix/state_res/event_auth.rs
@@ -5,7 +5,7 @@ use futures::{
 	future::{OptionFuture, join3},
 };
 use ruma::{
-	Int, OwnedUserId, RoomVersionId, UserId,
+	EventId, Int, OwnedUserId, RoomVersionId, UserId,
 	events::room::{
 		create::RoomCreateEventContent,
 		join_rules::{JoinRule, RoomJoinRulesEventContent},
@@ -217,8 +217,9 @@ where
 	}
 
 	/*
-	// TODO: In the past this code caused problems federating with synapse, maybe this has been
-	// resolved already. Needs testing.
+	// TODO: In the past this code was commented as it caused problems with Synapse. This is no
+	// longer the case. This needs to be implemented.
+	// See also: https://github.com/ruma/ruma/pull/2064
 	//
 	// 2. Reject if auth_events
 	// a. auth_events cannot have duplicate keys since it's a BTree
diff --git a/src/service/rooms/event_handler/call_policyserv.rs b/src/service/rooms/event_handler/call_policyserv.rs
new file mode 100644
index 00000000..4a52227d
--- /dev/null
+++ b/src/service/rooms/event_handler/call_policyserv.rs
@@ -0,0 +1,71 @@
+use conduwuit::{
+	Err, Event, PduEvent, Result, debug, implement, utils::to_canonical_object, warn,
+};
+use ruma::{
+	RoomId, ServerName,
+	api::federation::room::policy::v1::Request as PolicyRequest,
+	canonical_json::to_canonical_value,
+	events::{StateEventType, room::policy::RoomPolicyEventContent},
+};
+
+/// Returns Ok if the policy server allows the event
+#[implement(super::Service)]
+#[tracing::instrument(skip_all, level = "debug")]
+pub async fn policyserv_check(&self, pdu: &PduEvent, room_id: &RoomId) -> Result {
+	let Ok(policyserver) = self
+		.services
+		.state_accessor
+		.room_state_get_content(room_id, &StateEventType::RoomPolicy, "")
+		.await
+		.map(|c: RoomPolicyEventContent| c)
+	else {
+		return Ok(());
+	};
+
+	let via = match policyserver.via {
+		| Some(ref via) => ServerName::parse(via)?,
+		| None => {
+			debug!("No policy server configured for room {room_id}");
+			return Ok(());
+		},
+	};
+	// TODO: dont do *this*
+	let pdu_json = self.services.timeline.get_pdu_json(pdu.event_id()).await?;
+	let outgoing = self
+		.services
+		.sending
+		.convert_to_outgoing_federation_event(pdu_json)
+		.await;
+	// let s = match serde_json::to_string(outgoing.as_ref()) {
+	// 	| Ok(s) => s,
+	// 	| Err(e) => {
+	// 		warn!("Failed to convert pdu {} to outgoing federation event: {e}",
+	// pdu.event_id()); 		return Err!(Request(InvalidParam("Failed to convert PDU
+	// to outgoing event."))); 	},
+	// };
+	debug!("Checking pdu {outgoing:?} for spam with policy server {via} for room {room_id}");
+	let response = self
+		.services
+		.sending
+		.send_federation_request(via, PolicyRequest {
+			event_id: pdu.event_id().to_owned(),
+			pdu: Some(outgoing),
+		})
+		.await;
+	let response = match response {
+		| Ok(response) => response,
+		| Err(e) => {
+			warn!("Failed to contact policy server {via} for room {room_id}: {e}");
+			return Ok(());
+		},
+	};
+	if response.recommendation == "spam" {
+		warn!(
+			"Event {} in room {room_id} was marked as spam by policy server {via}",
+			pdu.event_id().to_owned()
+		);
+		return Err!(Request(Forbidden("Event was marked as spam by policy server")));
+	};
+
+	Ok(())
+}
diff --git a/src/service/rooms/event_handler/mod.rs b/src/service/rooms/event_handler/mod.rs
index 45675da8..3213db29 100644
--- a/src/service/rooms/event_handler/mod.rs
+++ b/src/service/rooms/event_handler/mod.rs
@@ -1,4 +1,5 @@
 mod acl_check;
+mod call_policyserv;
 mod fetch_and_handle_outliers;
 mod fetch_prev;
 mod fetch_state;
diff --git a/src/service/rooms/event_handler/upgrade_outlier_pdu.rs b/src/service/rooms/event_handler/upgrade_outlier_pdu.rs
index 97d3df97..2cce47a9 100644
--- a/src/service/rooms/event_handler/upgrade_outlier_pdu.rs
+++ b/src/service/rooms/event_handler/upgrade_outlier_pdu.rs
@@ -1,7 +1,7 @@
 use std::{borrow::Borrow, collections::BTreeMap, iter::once, sync::Arc, time::Instant};
 
 use conduwuit::{
-	Err, Result, debug, debug_info, err, implement,
+	Err, Event, Result, debug, debug_info, err, implement, info,
 	matrix::{EventTypeExt, PduEvent, StateKey, state_res},
 	trace,
 	utils::stream::{BroadbandExt, ReadyExt},
@@ -44,7 +44,7 @@ pub(super) async fn upgrade_outlier_to_timeline_pdu(
 		return Err!(Request(InvalidParam("Event has been soft failed")));
 	}
 
-	debug!("Upgrading to timeline pdu");
+	debug!("Upgrading pdu {} from outlier to timeline pdu", incoming_pdu.event_id);
 	let timer = Instant::now();
 	let room_version_id = get_room_version_id(create_event)?;
 
@@ -52,7 +52,7 @@ pub(super) async fn upgrade_outlier_to_timeline_pdu(
 	//     backwards extremities doing all the checks in this list starting at 1.
 	//     These are not timeline events.
 
-	debug!("Resolving state at event");
+	debug!("Resolving state at event {}", incoming_pdu.event_id);
 	let mut state_at_incoming_event = if incoming_pdu.prev_events.len() == 1 {
 		self.state_at_incoming_degree_one(&incoming_pdu).await?
 	} else {
@@ -70,7 +70,7 @@ pub(super) async fn upgrade_outlier_to_timeline_pdu(
 		state_at_incoming_event.expect("we always set this to some above");
 	let room_version = to_room_version(&room_version_id);
 
-	debug!("Performing auth check");
+	debug!("Performing auth check to upgrade {}", incoming_pdu.event_id);
 	// 11. Check the auth of the event passes based on the state of the event
 	let state_fetch_state = &state_at_incoming_event;
 	let state_fetch = |k: StateEventType, s: StateKey| async move {
@@ -80,6 +80,7 @@ pub(super) async fn upgrade_outlier_to_timeline_pdu(
 		self.services.timeline.get_pdu(event_id).await.ok()
 	};
 
+	debug!("running auth check on {}", incoming_pdu.event_id);
 	let auth_check = state_res::event_auth::auth_check(
 		&room_version,
 		&incoming_pdu,
@@ -93,7 +94,7 @@ pub(super) async fn upgrade_outlier_to_timeline_pdu(
 		return Err!(Request(Forbidden("Event has failed auth check with state at the event.")));
 	}
 
-	debug!("Gathering auth events");
+	debug!("Gathering auth events for {}", incoming_pdu.event_id);
 	let auth_events = self
 		.services
 		.state
@@ -111,6 +112,7 @@ pub(super) async fn upgrade_outlier_to_timeline_pdu(
 		ready(auth_events.get(&key).cloned())
 	};
 
+	debug!("running auth check on {} with claimed state auth", incoming_pdu.event_id);
 	let auth_check = state_res::event_auth::auth_check(
 		&room_version,
 		&incoming_pdu,
@@ -121,8 +123,8 @@ pub(super) async fn upgrade_outlier_to_timeline_pdu(
 	.map_err(|e| err!(Request(Forbidden("Auth check failed: {e:?}"))))?;
 
 	// Soft fail check before doing state res
-	debug!("Performing soft-fail check");
-	let soft_fail = match (auth_check, incoming_pdu.redacts_id(&room_version_id)) {
+	debug!("Performing soft-fail check on {}", incoming_pdu.event_id);
+	let mut soft_fail = match (auth_check, incoming_pdu.redacts_id(&room_version_id)) {
 		| (false, _) => true,
 		| (true, None) => false,
 		| (true, Some(redact_id)) =>
@@ -215,10 +217,26 @@ pub(super) async fn upgrade_outlier_to_timeline_pdu(
 			.await?;
 	}
 
+	// 14-pre. If the event is not a state event, ask the policy server about it
+	if incoming_pdu.state_key.is_none()
+		&& incoming_pdu.sender().server_name() != self.services.globals.server_name()
+	{
+		debug!("Checking policy server for event {}", incoming_pdu.event_id);
+		let policy = self.policyserv_check(&incoming_pdu, room_id);
+		if let Err(e) = policy.await {
+			warn!("Policy server check failed for event {}: {e}", incoming_pdu.event_id);
+			if !soft_fail {
+				soft_fail = true;
+			}
+		}
+		debug!("Policy server check passed for event {}", incoming_pdu.event_id);
+	}
+
 	// 14. Check if the event passes auth based on the "current state" of the room,
 	//     if not soft fail it
 	if soft_fail {
-		debug!("Soft failing event");
+		info!("Soft failing event {}", incoming_pdu.event_id);
+		// assert!(extremities.is_empty(), "soft_fail extremities empty");
 		let extremities = extremities.iter().map(Borrow::borrow);
 
 		self.services
diff --git a/src/service/rooms/timeline/mod.rs b/src/service/rooms/timeline/mod.rs
index 534d8faf..124877b3 100644
--- a/src/service/rooms/timeline/mod.rs
+++ b/src/service/rooms/timeline/mod.rs
@@ -700,6 +700,20 @@ impl Service {
 			.await
 			.saturating_add(uint!(1));
 
+		if state_key.is_none() {
+			if prev_events.is_empty() {
+				warn!("Timeline event had zero prev_events, something broke.");
+				return Err!(Request(Unknown("Timeline event had zero prev_events.")));
+			}
+			if depth.le(&uint!(2)) {
+				warn!(
+					"Had unsafe depth of {depth} in {room_id} when creating non-state event. \
+					 Bad!"
+				);
+				return Err!(Request(Unknown("Unsafe depth for non-state event.")));
+			}
+		};
+
 		let mut unsigned = unsigned.unwrap_or_default();
 
 		if let Some(state_key) = &state_key {
@@ -771,6 +785,10 @@ impl Service {
 			ready(auth_events.get(&key))
 		};
 
+		debug!(
+			"running auth check on new {} event by {} in {}",
+			pdu.kind, pdu.sender, pdu.room_id
+		);
 		let auth_check = state_res::auth_check(
 			&room_version,
 			&pdu,
@@ -975,8 +993,9 @@ impl Service {
 		state_lock: &'a RoomMutexGuard,
 	) -> Result<Option<RawPduId>>
 	where
-		Leaves: Iterator<Item = &'a EventId> + Send + 'a,
+		Leaves: Iterator<Item = &'a EventId> + Send + Clone + 'a,
 	{
+		// assert!(new_room_leaves.clone().count() > 0, "extremities are empty");
 		// We append to state before appending the pdu, so we don't have a moment in
 		// time with the pdu without it's state. This is okay because append_pdu can't
 		// fail.