Merge pull request #2045 from wpaulino/fix-broken-commitment-test-vectors
[rust-lightning] / lightning / src / ln / outbound_payment.rs
index 77ef8d910f4fa68db19085c95595ce8b811683b5..6ede956b7d52df3a035d0fd308d505bcf2650bc5 100644 (file)
@@ -15,16 +15,21 @@ use bitcoin::secp256k1::{self, Secp256k1, SecretKey};
 
 use crate::chain::keysinterface::{EntropySource, NodeSigner, Recipient};
 use crate::ln::{PaymentHash, PaymentPreimage, PaymentSecret};
-use crate::ln::channelmanager::{HTLCSource, IDEMPOTENCY_TIMEOUT_TICKS, PaymentId};
-use crate::ln::msgs::DecodeError;
+use crate::ln::channelmanager::{ChannelDetails, HTLCSource, IDEMPOTENCY_TIMEOUT_TICKS, PaymentId};
 use crate::ln::onion_utils::HTLCFailReason;
-use crate::routing::router::{PaymentParameters, Route, RouteHop, RouteParameters, RoutePath};
+use crate::routing::router::{InFlightHtlcs, PaymentParameters, Route, RouteHop, RouteParameters, RoutePath, Router};
 use crate::util::errors::APIError;
 use crate::util::events;
 use crate::util::logger::Logger;
+use crate::util::time::Time;
+#[cfg(all(not(feature = "no-std"), test))]
+use crate::util::time::tests::SinceEpoch;
+use crate::util::ser::ReadableArgs;
 
 use core::cmp;
+use core::fmt::{self, Display, Formatter};
 use core::ops::Deref;
+
 use crate::prelude::*;
 use crate::sync::Mutex;
 
@@ -35,9 +40,13 @@ pub(crate) enum PendingOutboundPayment {
                session_privs: HashSet<[u8; 32]>,
        },
        Retryable {
+               retry_strategy: Option<Retry>,
+               attempts: PaymentAttempts,
+               payment_params: Option<PaymentParameters>,
                session_privs: HashSet<[u8; 32]>,
                payment_hash: PaymentHash,
                payment_secret: Option<PaymentSecret>,
+               keysend_preimage: Option<PaymentPreimage>,
                pending_amt_msat: u64,
                /// Used to track the fee paid. Only present if the payment was serialized on 0.0.103+.
                pending_fee_msat: Option<u64>,
@@ -54,13 +63,8 @@ pub(crate) enum PendingOutboundPayment {
                payment_hash: Option<PaymentHash>,
                timer_ticks_without_htlcs: u8,
        },
-       /// When a payer gives up trying to retry a payment, they inform us, letting us generate a
-       /// `PaymentFailed` event when all HTLCs have irrevocably failed. This avoids a number of race
-       /// conditions in MPP-aware payment retriers (1), where the possibility of multiple
-       /// `PaymentPathFailed` events with `all_paths_failed` can be pending at once, confusing a
-       /// downstream event handler as to when a payment has actually failed.
-       ///
-       /// (1) https://github.com/lightningdevkit/rust-lightning/issues/1164
+       /// When we've decided to give up retrying a payment, we mark it as abandoned so we can eventually
+       /// generate a `PaymentFailed` event when all HTLCs have irrevocably failed.
        Abandoned {
                session_privs: HashSet<[u8; 32]>,
                payment_hash: PaymentHash,
@@ -68,6 +72,38 @@ pub(crate) enum PendingOutboundPayment {
 }
 
 impl PendingOutboundPayment {
+       fn increment_attempts(&mut self) {
+               if let PendingOutboundPayment::Retryable { attempts, .. } = self {
+                       attempts.count += 1;
+               }
+       }
+       fn is_auto_retryable_now(&self) -> bool {
+               match self {
+                       PendingOutboundPayment::Retryable {
+                               retry_strategy: Some(strategy), attempts, payment_params: Some(_), ..
+                       } => {
+                               strategy.is_retryable_now(&attempts)
+                       },
+                       _ => false,
+               }
+       }
+       fn is_retryable_now(&self) -> bool {
+               match self {
+                       PendingOutboundPayment::Retryable { retry_strategy: None, .. } => {
+                               // We're handling retries manually, we can always retry.
+                               true
+                       },
+                       PendingOutboundPayment::Retryable { retry_strategy: Some(strategy), attempts, .. } => {
+                               strategy.is_retryable_now(&attempts)
+                       },
+                       _ => false,
+               }
+       }
+       pub fn insert_previously_failed_scid(&mut self, scid: u64) {
+               if let PendingOutboundPayment::Retryable { payment_params: Some(params), .. } = self {
+                       params.previously_failed_channels.push(scid);
+               }
+       }
        pub(super) fn is_fulfilled(&self) -> bool {
                match self {
                        PendingOutboundPayment::Fulfilled { .. } => true,
@@ -114,13 +150,13 @@ impl PendingOutboundPayment {
                let our_payment_hash;
                core::mem::swap(&mut session_privs, match self {
                        PendingOutboundPayment::Legacy { .. } |
-                               PendingOutboundPayment::Fulfilled { .. } =>
+                       PendingOutboundPayment::Fulfilled { .. } =>
                                return Err(()),
-                               PendingOutboundPayment::Retryable { session_privs, payment_hash, .. } |
-                                       PendingOutboundPayment::Abandoned { session_privs, payment_hash, .. } => {
-                                               our_payment_hash = *payment_hash;
-                                               session_privs
-                                       },
+                       PendingOutboundPayment::Retryable { session_privs, payment_hash, .. } |
+                       PendingOutboundPayment::Abandoned { session_privs, payment_hash, .. } => {
+                               our_payment_hash = *payment_hash;
+                               session_privs
+                       },
                });
                *self = PendingOutboundPayment::Abandoned { session_privs, payment_hash: our_payment_hash };
                Ok(())
@@ -182,9 +218,127 @@ impl PendingOutboundPayment {
        }
 }
 
-/// If a payment fails to send, it can be in one of several states. This enum is returned as the
-/// Err() type describing which state the payment is in, see the description of individual enum
-/// states for more.
+/// Strategies available to retry payment path failures.
+#[derive(Clone, Copy, Debug, Eq, Hash, PartialEq)]
+pub enum Retry {
+       /// Max number of attempts to retry payment.
+       ///
+       /// Each attempt may be multiple HTLCs along multiple paths if the router decides to split up a
+       /// retry, and may retry multiple failed HTLCs at once if they failed around the same time and
+       /// were retried along a route from a single call to [`Router::find_route_with_id`].
+       Attempts(usize),
+       #[cfg(not(feature = "no-std"))]
+       /// Time elapsed before abandoning retries for a payment. At least one attempt at payment is made;
+       /// see [`PaymentParameters::expiry_time`] to avoid any attempt at payment after a specific time.
+       ///
+       /// [`PaymentParameters::expiry_time`]: crate::routing::router::PaymentParameters::expiry_time
+       Timeout(core::time::Duration),
+}
+
+impl Retry {
+       pub(crate) fn is_retryable_now(&self, attempts: &PaymentAttempts) -> bool {
+               match (self, attempts) {
+                       (Retry::Attempts(max_retry_count), PaymentAttempts { count, .. }) => {
+                               max_retry_count > count
+                       },
+                       #[cfg(all(not(feature = "no-std"), not(test)))]
+                       (Retry::Timeout(max_duration), PaymentAttempts { first_attempted_at, .. }) =>
+                               *max_duration >= std::time::Instant::now().duration_since(*first_attempted_at),
+                       #[cfg(all(not(feature = "no-std"), test))]
+                       (Retry::Timeout(max_duration), PaymentAttempts { first_attempted_at, .. }) =>
+                               *max_duration >= SinceEpoch::now().duration_since(*first_attempted_at),
+               }
+       }
+}
+
+#[cfg(feature = "std")]
+pub(super) fn has_expired(route_params: &RouteParameters) -> bool {
+       if let Some(expiry_time) = route_params.payment_params.expiry_time {
+               if let Ok(elapsed) = std::time::SystemTime::UNIX_EPOCH.elapsed() {
+                       return elapsed > core::time::Duration::from_secs(expiry_time)
+               }
+       }
+       false
+}
+
+pub(crate) type PaymentAttempts = PaymentAttemptsUsingTime<ConfiguredTime>;
+
+/// Storing minimal payment attempts information required for determining if a outbound payment can
+/// be retried.
+pub(crate) struct PaymentAttemptsUsingTime<T: Time> {
+       /// This count will be incremented only after the result of the attempt is known. When it's 0,
+       /// it means the result of the first attempt is not known yet.
+       pub(crate) count: usize,
+       /// This field is only used when retry is `Retry::Timeout` which is only build with feature std
+       #[cfg(not(feature = "no-std"))]
+       first_attempted_at: T,
+       #[cfg(feature = "no-std")]
+       phantom: core::marker::PhantomData<T>,
+
+}
+
+#[cfg(not(any(feature = "no-std", test)))]
+type ConfiguredTime = std::time::Instant;
+#[cfg(feature = "no-std")]
+type ConfiguredTime = crate::util::time::Eternity;
+#[cfg(all(not(feature = "no-std"), test))]
+type ConfiguredTime = SinceEpoch;
+
+impl<T: Time> PaymentAttemptsUsingTime<T> {
+       pub(crate) fn new() -> Self {
+               PaymentAttemptsUsingTime {
+                       count: 0,
+                       #[cfg(not(feature = "no-std"))]
+                       first_attempted_at: T::now(),
+                       #[cfg(feature = "no-std")]
+                       phantom: core::marker::PhantomData,
+               }
+       }
+}
+
+impl<T: Time> Display for PaymentAttemptsUsingTime<T> {
+       fn fmt(&self, f: &mut Formatter) -> Result<(), fmt::Error> {
+               #[cfg(feature = "no-std")]
+               return write!(f, "attempts: {}", self.count);
+               #[cfg(not(feature = "no-std"))]
+               return write!(
+                       f,
+                       "attempts: {}, duration: {}s",
+                       self.count,
+                       T::now().duration_since(self.first_attempted_at).as_secs()
+               );
+       }
+}
+
+/// Indicates an immediate error on [`ChannelManager::send_payment_with_retry`]. Further errors
+/// may be surfaced later via [`Event::PaymentPathFailed`] and [`Event::PaymentFailed`].
+///
+/// [`ChannelManager::send_payment_with_retry`]: crate::ln::channelmanager::ChannelManager::send_payment_with_retry
+/// [`Event::PaymentPathFailed`]: crate::util::events::Event::PaymentPathFailed
+/// [`Event::PaymentFailed`]: crate::util::events::Event::PaymentFailed
+#[derive(Clone, Debug)]
+pub enum RetryableSendFailure {
+       /// The provided [`PaymentParameters::expiry_time`] indicated that the payment has expired. Note
+       /// that this error is *not* caused by [`Retry::Timeout`].
+       ///
+       /// [`PaymentParameters::expiry_time`]: crate::routing::router::PaymentParameters::expiry_time
+       PaymentExpired,
+       /// We were unable to find a route to the destination.
+       RouteNotFound,
+       /// Indicates that a payment for the provided [`PaymentId`] is already in-flight and has not
+       /// yet completed (i.e. generated an [`Event::PaymentSent`] or [`Event::PaymentFailed`]).
+       ///
+       /// [`PaymentId`]: crate::ln::channelmanager::PaymentId
+       /// [`Event::PaymentSent`]: crate::util::events::Event::PaymentSent
+       /// [`Event::PaymentFailed`]: crate::util::events::Event::PaymentFailed
+       DuplicatePayment,
+}
+
+/// If a payment fails to send with [`ChannelManager::send_payment`], it can be in one of several
+/// states. This enum is returned as the Err() type describing which state the payment is in, see
+/// the description of individual enum states for more.
+///
+/// [`ChannelManager::send_payment`]: crate::ln::channelmanager::ChannelManager::send_payment
 #[derive(Clone, Debug)]
 pub enum PaymentSendFailure {
        /// A parameter which was passed to send_payment was invalid, preventing us from attempting to
@@ -192,68 +346,58 @@ pub enum PaymentSendFailure {
        ///
        /// You can freely resend the payment in full (with the parameter error fixed).
        ///
-       /// Because the payment failed outright, no payment tracking is done, you do not need to call
-       /// [`ChannelManager::abandon_payment`] and [`ChannelManager::retry_payment`] will *not* work
-       /// for this payment.
+       /// Because the payment failed outright, no payment tracking is done and no
+       /// [`Event::PaymentPathFailed`] or [`Event::PaymentFailed`] events will be generated.
        ///
-       /// [`ChannelManager::abandon_payment`]: crate::ln::channelmanager::ChannelManager::abandon_payment
-       /// [`ChannelManager::retry_payment`]: crate::ln::channelmanager::ChannelManager::retry_payment
+       /// [`Event::PaymentPathFailed`]: crate::util::events::Event::PaymentPathFailed
+       /// [`Event::PaymentFailed`]: crate::util::events::Event::PaymentFailed
        ParameterError(APIError),
        /// A parameter in a single path which was passed to send_payment was invalid, preventing us
        /// from attempting to send the payment at all.
        ///
        /// You can freely resend the payment in full (with the parameter error fixed).
        ///
+       /// Because the payment failed outright, no payment tracking is done and no
+       /// [`Event::PaymentPathFailed`] or [`Event::PaymentFailed`] events will be generated.
+       ///
        /// The results here are ordered the same as the paths in the route object which was passed to
        /// send_payment.
        ///
-       /// Because the payment failed outright, no payment tracking is done, you do not need to call
-       /// [`ChannelManager::abandon_payment`] and [`ChannelManager::retry_payment`] will *not* work
-       /// for this payment.
-       ///
-       /// [`ChannelManager::abandon_payment`]: crate::ln::channelmanager::ChannelManager::abandon_payment
-       /// [`ChannelManager::retry_payment`]: crate::ln::channelmanager::ChannelManager::retry_payment
+       /// [`Event::PaymentPathFailed`]: crate::util::events::Event::PaymentPathFailed
+       /// [`Event::PaymentFailed`]: crate::util::events::Event::PaymentFailed
        PathParameterError(Vec<Result<(), APIError>>),
        /// All paths which were attempted failed to send, with no channel state change taking place.
        /// You can freely resend the payment in full (though you probably want to do so over different
        /// paths than the ones selected).
        ///
-       /// Because the payment failed outright, no payment tracking is done, you do not need to call
-       /// [`ChannelManager::abandon_payment`] and [`ChannelManager::retry_payment`] will *not* work
-       /// for this payment.
+       /// Because the payment failed outright, no payment tracking is done and no
+       /// [`Event::PaymentPathFailed`] or [`Event::PaymentFailed`] events will be generated.
        ///
-       /// [`ChannelManager::abandon_payment`]: crate::ln::channelmanager::ChannelManager::abandon_payment
-       /// [`ChannelManager::retry_payment`]: crate::ln::channelmanager::ChannelManager::retry_payment
+       /// [`Event::PaymentPathFailed`]: crate::util::events::Event::PaymentPathFailed
+       /// [`Event::PaymentFailed`]: crate::util::events::Event::PaymentFailed
        AllFailedResendSafe(Vec<APIError>),
        /// Indicates that a payment for the provided [`PaymentId`] is already in-flight and has not
-       /// yet completed (i.e. generated an [`Event::PaymentSent`]) or been abandoned (via
-       /// [`ChannelManager::abandon_payment`]).
+       /// yet completed (i.e. generated an [`Event::PaymentSent`] or [`Event::PaymentFailed`]).
        ///
        /// [`PaymentId`]: crate::ln::channelmanager::PaymentId
        /// [`Event::PaymentSent`]: crate::util::events::Event::PaymentSent
-       /// [`ChannelManager::abandon_payment`]: crate::ln::channelmanager::ChannelManager::abandon_payment
+       /// [`Event::PaymentFailed`]: crate::util::events::Event::PaymentFailed
        DuplicatePayment,
-       /// Some paths which were attempted failed to send, though possibly not all. At least some
-       /// paths have irrevocably committed to the HTLC and retrying the payment in full would result
-       /// in over-/re-payment.
+       /// Some paths that were attempted failed to send, though some paths may have succeeded. At least
+       /// some paths have irrevocably committed to the HTLC.
        ///
-       /// The results here are ordered the same as the paths in the route object which was passed to
-       /// send_payment, and any `Err`s which are not [`APIError::MonitorUpdateInProgress`] can be
-       /// safely retried via [`ChannelManager::retry_payment`].
+       /// The results here are ordered the same as the paths in the route object that was passed to
+       /// send_payment.
        ///
-       /// Any entries which contain `Err(APIError::MonitorUpdateInprogress)` or `Ok(())` MUST NOT be
-       /// retried as they will result in over-/re-payment. These HTLCs all either successfully sent
-       /// (in the case of `Ok(())`) or will send once a [`MonitorEvent::Completed`] is provided for
-       /// the next-hop channel with the latest update_id.
+       /// Any entries that contain `Err(APIError::MonitorUpdateInprogress)` will send once a
+       /// [`MonitorEvent::Completed`] is provided for the next-hop channel with the latest update_id.
        ///
-       /// [`ChannelManager::retry_payment`]: crate::ln::channelmanager::ChannelManager::retry_payment
        /// [`MonitorEvent::Completed`]: crate::chain::channelmonitor::MonitorEvent::Completed
        PartialFailure {
-               /// The errors themselves, in the same order as the route hops.
+               /// The errors themselves, in the same order as the paths from the route.
                results: Vec<Result<(), APIError>>,
                /// If some paths failed without irrevocably committing to the new HTLC(s), this will
-               /// contain a [`RouteParameters`] object which can be used to calculate a new route that
-               /// will pay all remaining unpaid balance.
+               /// contain a [`RouteParameters`] object for the failing paths.
                failed_paths_retry: Option<RouteParameters>,
                /// The payment id for the payment, which is now at least partially pending.
                payment_id: PaymentId,
@@ -262,15 +406,38 @@ pub enum PaymentSendFailure {
 
 pub(super) struct OutboundPayments {
        pub(super) pending_outbound_payments: Mutex<HashMap<PaymentId, PendingOutboundPayment>>,
+       pub(super) retry_lock: Mutex<()>,
 }
 
 impl OutboundPayments {
        pub(super) fn new() -> Self {
                Self {
-                       pending_outbound_payments: Mutex::new(HashMap::new())
+                       pending_outbound_payments: Mutex::new(HashMap::new()),
+                       retry_lock: Mutex::new(()),
                }
        }
 
+       pub(super) fn send_payment<R: Deref, ES: Deref, NS: Deref, IH, SP, L: Deref>(
+               &self, payment_hash: PaymentHash, payment_secret: &Option<PaymentSecret>, payment_id: PaymentId,
+               retry_strategy: Retry, route_params: RouteParameters, router: &R,
+               first_hops: Vec<ChannelDetails>, compute_inflight_htlcs: IH, entropy_source: &ES,
+               node_signer: &NS, best_block_height: u32, logger: &L,
+               pending_events: &Mutex<Vec<events::Event>>, send_payment_along_path: SP,
+       ) -> Result<(), RetryableSendFailure>
+       where
+               R::Target: Router,
+               ES::Target: EntropySource,
+               NS::Target: NodeSigner,
+               L::Target: Logger,
+               IH: Fn() -> InFlightHtlcs,
+               SP: Fn(&Vec<RouteHop>, &PaymentHash, &Option<PaymentSecret>, u64, u32, PaymentId,
+                       &Option<PaymentPreimage>, [u8; 32]) -> Result<(), APIError>,
+       {
+               self.send_payment_internal(payment_id, payment_hash, payment_secret, None, retry_strategy,
+                       route_params, router, first_hops, &compute_inflight_htlcs, entropy_source, node_signer,
+                       best_block_height, logger, pending_events, &send_payment_along_path)
+       }
+
        pub(super) fn send_payment_with_route<ES: Deref, NS: Deref, F>(
                &self, route: &Route, payment_hash: PaymentHash, payment_secret: &Option<PaymentSecret>,
                payment_id: PaymentId, entropy_source: &ES, node_signer: &NS, best_block_height: u32,
@@ -279,104 +446,359 @@ impl OutboundPayments {
        where
                ES::Target: EntropySource,
                NS::Target: NodeSigner,
-               F: Fn(&Vec<RouteHop>, &Option<PaymentParameters>, &PaymentHash, &Option<PaymentSecret>, u64,
-                  u32, PaymentId, &Option<PaymentPreimage>, [u8; 32]) -> Result<(), APIError>
+               F: Fn(&Vec<RouteHop>, &PaymentHash, &Option<PaymentSecret>, u64, u32, PaymentId,
+                       &Option<PaymentPreimage>, [u8; 32]) -> Result<(), APIError>
        {
-               let onion_session_privs = self.add_new_pending_payment(payment_hash, *payment_secret, payment_id, route, entropy_source, best_block_height)?;
-               self.send_payment_internal(route, payment_hash, payment_secret, None, payment_id, None, onion_session_privs, node_signer, best_block_height, send_payment_along_path)
+               let onion_session_privs = self.add_new_pending_payment(payment_hash, *payment_secret, payment_id, None, route, None, None, entropy_source, best_block_height)?;
+               self.pay_route_internal(route, payment_hash, payment_secret, None, payment_id, None,
+                       onion_session_privs, node_signer, best_block_height, &send_payment_along_path)
+                       .map_err(|e| { self.remove_outbound_if_all_failed(payment_id, &e); e })
        }
 
-       pub(super) fn send_spontaneous_payment<ES: Deref, NS: Deref, F>(
+       pub(super) fn send_spontaneous_payment<R: Deref, ES: Deref, NS: Deref, IH, SP, L: Deref>(
+               &self, payment_preimage: Option<PaymentPreimage>, payment_id: PaymentId,
+               retry_strategy: Retry, route_params: RouteParameters, router: &R,
+               first_hops: Vec<ChannelDetails>, inflight_htlcs: IH, entropy_source: &ES,
+               node_signer: &NS, best_block_height: u32, logger: &L,
+               pending_events: &Mutex<Vec<events::Event>>, send_payment_along_path: SP
+       ) -> Result<PaymentHash, RetryableSendFailure>
+       where
+               R::Target: Router,
+               ES::Target: EntropySource,
+               NS::Target: NodeSigner,
+               L::Target: Logger,
+               IH: Fn() -> InFlightHtlcs,
+               SP: Fn(&Vec<RouteHop>, &PaymentHash, &Option<PaymentSecret>, u64, u32, PaymentId,
+                       &Option<PaymentPreimage>, [u8; 32]) -> Result<(), APIError>,
+       {
+               let preimage = payment_preimage
+                       .unwrap_or_else(|| PaymentPreimage(entropy_source.get_secure_random_bytes()));
+               let payment_hash = PaymentHash(Sha256::hash(&preimage.0).into_inner());
+               self.send_payment_internal(payment_id, payment_hash, &None, Some(preimage), retry_strategy,
+                       route_params, router, first_hops, inflight_htlcs, entropy_source, node_signer,
+                       best_block_height, logger, pending_events, send_payment_along_path)
+                       .map(|()| payment_hash)
+       }
+
+       pub(super) fn send_spontaneous_payment_with_route<ES: Deref, NS: Deref, F>(
                &self, route: &Route, payment_preimage: Option<PaymentPreimage>, payment_id: PaymentId,
                entropy_source: &ES, node_signer: &NS, best_block_height: u32, send_payment_along_path: F
        ) -> Result<PaymentHash, PaymentSendFailure>
        where
                ES::Target: EntropySource,
                NS::Target: NodeSigner,
-               F: Fn(&Vec<RouteHop>, &Option<PaymentParameters>, &PaymentHash, &Option<PaymentSecret>, u64,
-                  u32, PaymentId, &Option<PaymentPreimage>, [u8; 32]) -> Result<(), APIError>
+               F: Fn(&Vec<RouteHop>, &PaymentHash, &Option<PaymentSecret>, u64, u32, PaymentId,
+                       &Option<PaymentPreimage>, [u8; 32]) -> Result<(), APIError>
        {
-               let preimage = match payment_preimage {
-                       Some(p) => p,
-                       None => PaymentPreimage(entropy_source.get_secure_random_bytes()),
-               };
+               let preimage = payment_preimage
+                       .unwrap_or_else(|| PaymentPreimage(entropy_source.get_secure_random_bytes()));
                let payment_hash = PaymentHash(Sha256::hash(&preimage.0).into_inner());
-               let onion_session_privs = self.add_new_pending_payment(payment_hash, None, payment_id, &route, entropy_source, best_block_height)?;
+               let onion_session_privs = self.add_new_pending_payment(payment_hash, None, payment_id, Some(preimage), &route, None, None, entropy_source, best_block_height)?;
 
-               match self.send_payment_internal(route, payment_hash, &None, Some(preimage), payment_id, None, onion_session_privs, node_signer, best_block_height, send_payment_along_path) {
+               match self.pay_route_internal(route, payment_hash, &None, Some(preimage), payment_id, None, onion_session_privs, node_signer, best_block_height, &send_payment_along_path) {
                        Ok(()) => Ok(payment_hash),
-                       Err(e) => Err(e)
+                       Err(e) => {
+                               self.remove_outbound_if_all_failed(payment_id, &e);
+                               Err(e)
+                       }
                }
        }
 
-       pub(super) fn retry_payment_with_route<ES: Deref, NS: Deref, F>(
-               &self, route: &Route, payment_id: PaymentId, entropy_source: &ES, node_signer: &NS, best_block_height: u32,
-               send_payment_along_path: F
-       ) -> Result<(), PaymentSendFailure>
+       pub(super) fn check_retry_payments<R: Deref, ES: Deref, NS: Deref, SP, IH, FH, L: Deref>(
+               &self, router: &R, first_hops: FH, inflight_htlcs: IH, entropy_source: &ES, node_signer: &NS,
+               best_block_height: u32, pending_events: &Mutex<Vec<events::Event>>, logger: &L,
+               send_payment_along_path: SP,
+       )
        where
+               R::Target: Router,
                ES::Target: EntropySource,
                NS::Target: NodeSigner,
-               F: Fn(&Vec<RouteHop>, &Option<PaymentParameters>, &PaymentHash, &Option<PaymentSecret>, u64,
-                  u32, PaymentId, &Option<PaymentPreimage>, [u8; 32]) -> Result<(), APIError>
+               SP: Fn(&Vec<RouteHop>, &PaymentHash, &Option<PaymentSecret>, u64, u32, PaymentId,
+                       &Option<PaymentPreimage>, [u8; 32]) -> Result<(), APIError>,
+               IH: Fn() -> InFlightHtlcs,
+               FH: Fn() -> Vec<ChannelDetails>,
+               L::Target: Logger,
        {
-               const RETRY_OVERFLOW_PERCENTAGE: u64 = 10;
+               let _single_thread = self.retry_lock.lock().unwrap();
+               loop {
+                       let mut outbounds = self.pending_outbound_payments.lock().unwrap();
+                       let mut retry_id_route_params = None;
+                       for (pmt_id, pmt) in outbounds.iter_mut() {
+                               if pmt.is_auto_retryable_now() {
+                                       if let PendingOutboundPayment::Retryable { pending_amt_msat, total_msat, payment_params: Some(params), payment_hash, .. } = pmt {
+                                               if pending_amt_msat < total_msat {
+                                                       retry_id_route_params = Some((*payment_hash, *pmt_id, RouteParameters {
+                                                               final_value_msat: *total_msat - *pending_amt_msat,
+                                                               payment_params: params.clone(),
+                                                       }));
+                                                       break
+                                               }
+                                       } else { debug_assert!(false); }
+                               }
+                       }
+                       core::mem::drop(outbounds);
+                       if let Some((payment_hash, payment_id, route_params)) = retry_id_route_params {
+                               self.retry_payment_internal(payment_hash, payment_id, route_params, router, first_hops(), &inflight_htlcs, entropy_source, node_signer, best_block_height, logger, pending_events, &send_payment_along_path)
+                       } else { break }
+               }
+
+               let mut outbounds = self.pending_outbound_payments.lock().unwrap();
+               outbounds.retain(|pmt_id, pmt| {
+                       let mut retain = true;
+                       if !pmt.is_auto_retryable_now() && pmt.remaining_parts() == 0 {
+                               if pmt.mark_abandoned().is_ok() {
+                                       pending_events.lock().unwrap().push(events::Event::PaymentFailed {
+                                               payment_id: *pmt_id,
+                                               payment_hash: pmt.payment_hash().expect("PendingOutboundPayments::Retryable always has a payment hash set"),
+                                       });
+                                       retain = false;
+                               }
+                       }
+                       retain
+               });
+       }
+
+       pub(super) fn needs_abandon(&self) -> bool {
+               let outbounds = self.pending_outbound_payments.lock().unwrap();
+               outbounds.iter().any(|(_, pmt)|
+                       !pmt.is_auto_retryable_now() && pmt.remaining_parts() == 0 && !pmt.is_fulfilled())
+       }
+
+       /// Errors immediately on [`RetryableSendFailure`] error conditions. Otherwise, further errors may
+       /// be surfaced asynchronously via [`Event::PaymentPathFailed`] and [`Event::PaymentFailed`].
+       ///
+       /// [`Event::PaymentPathFailed`]: crate::util::events::Event::PaymentPathFailed
+       /// [`Event::PaymentFailed`]: crate::util::events::Event::PaymentFailed
+       fn send_payment_internal<R: Deref, NS: Deref, ES: Deref, IH, SP, L: Deref>(
+               &self, payment_id: PaymentId, payment_hash: PaymentHash, payment_secret: &Option<PaymentSecret>,
+               keysend_preimage: Option<PaymentPreimage>, retry_strategy: Retry, route_params: RouteParameters,
+               router: &R, first_hops: Vec<ChannelDetails>, inflight_htlcs: IH, entropy_source: &ES,
+               node_signer: &NS, best_block_height: u32, logger: &L,
+               pending_events: &Mutex<Vec<events::Event>>, send_payment_along_path: SP,
+       ) -> Result<(), RetryableSendFailure>
+       where
+               R::Target: Router,
+               ES::Target: EntropySource,
+               NS::Target: NodeSigner,
+               L::Target: Logger,
+               IH: Fn() -> InFlightHtlcs,
+               SP: Fn(&Vec<RouteHop>, &PaymentHash, &Option<PaymentSecret>, u64, u32, PaymentId,
+                       &Option<PaymentPreimage>, [u8; 32]) -> Result<(), APIError>
+       {
+               #[cfg(feature = "std")] {
+                       if has_expired(&route_params) {
+                               return Err(RetryableSendFailure::PaymentExpired)
+                       }
+               }
+
+               let route = router.find_route_with_id(
+                       &node_signer.get_node_id(Recipient::Node).unwrap(), &route_params,
+                       Some(&first_hops.iter().collect::<Vec<_>>()), &inflight_htlcs(),
+                       payment_hash, payment_id,
+               ).map_err(|_| RetryableSendFailure::RouteNotFound)?;
+
+               let onion_session_privs = self.add_new_pending_payment(payment_hash, *payment_secret,
+                       payment_id, keysend_preimage, &route, Some(retry_strategy),
+                       Some(route_params.payment_params.clone()), entropy_source, best_block_height)
+                       .map_err(|_| RetryableSendFailure::DuplicatePayment)?;
+
+               let res = self.pay_route_internal(&route, payment_hash, payment_secret, None, payment_id, None,
+                       onion_session_privs, node_signer, best_block_height, &send_payment_along_path);
+               log_info!(logger, "Result sending payment with id {}: {:?}", log_bytes!(payment_id.0), res);
+               if let Err(e) = res {
+                       self.handle_pay_route_err(e, payment_id, payment_hash, route, route_params, router, first_hops, &inflight_htlcs, entropy_source, node_signer, best_block_height, logger, pending_events, &send_payment_along_path);
+               }
+               Ok(())
+       }
+
+       fn retry_payment_internal<R: Deref, NS: Deref, ES: Deref, IH, SP, L: Deref>(
+               &self, payment_hash: PaymentHash, payment_id: PaymentId, route_params: RouteParameters,
+               router: &R, first_hops: Vec<ChannelDetails>, inflight_htlcs: &IH, entropy_source: &ES,
+               node_signer: &NS, best_block_height: u32, logger: &L,
+               pending_events: &Mutex<Vec<events::Event>>, send_payment_along_path: &SP,
+       )
+       where
+               R::Target: Router,
+               ES::Target: EntropySource,
+               NS::Target: NodeSigner,
+               L::Target: Logger,
+               IH: Fn() -> InFlightHtlcs,
+               SP: Fn(&Vec<RouteHop>, &PaymentHash, &Option<PaymentSecret>, u64, u32, PaymentId,
+                       &Option<PaymentPreimage>, [u8; 32]) -> Result<(), APIError>
+       {
+               #[cfg(feature = "std")] {
+                       if has_expired(&route_params) {
+                               log_error!(logger, "Payment params expired on retry, abandoning payment {}", log_bytes!(payment_id.0));
+                               self.abandon_payment(payment_id, pending_events);
+                               return
+                       }
+               }
+
+               let route = match router.find_route_with_id(
+                       &node_signer.get_node_id(Recipient::Node).unwrap(), &route_params,
+                       Some(&first_hops.iter().collect::<Vec<_>>()), &inflight_htlcs(),
+                       payment_hash, payment_id,
+               ) {
+                       Ok(route) => route,
+                       Err(e) => {
+                               log_error!(logger, "Failed to find a route on retry, abandoning payment {}: {:#?}", log_bytes!(payment_id.0), e);
+                               self.abandon_payment(payment_id, pending_events);
+                               return
+                       }
+               };
                for path in route.paths.iter() {
                        if path.len() == 0 {
-                               return Err(PaymentSendFailure::ParameterError(APIError::APIMisuseError {
-                                       err: "length-0 path in route".to_string()
-                               }))
+                               log_error!(logger, "length-0 path in route");
+                               self.abandon_payment(payment_id, pending_events);
+                               return
                        }
                }
 
+               const RETRY_OVERFLOW_PERCENTAGE: u64 = 10;
                let mut onion_session_privs = Vec::with_capacity(route.paths.len());
                for _ in 0..route.paths.len() {
                        onion_session_privs.push(entropy_source.get_secure_random_bytes());
                }
 
-               let (total_msat, payment_hash, payment_secret) = {
+               macro_rules! abandon_with_entry {
+                       ($payment: expr) => {
+                               if $payment.get_mut().mark_abandoned().is_ok() && $payment.get().remaining_parts() == 0 {
+                                       pending_events.lock().unwrap().push(events::Event::PaymentFailed {
+                                               payment_id,
+                                               payment_hash,
+                                       });
+                                       $payment.remove();
+                               }
+                       }
+               }
+               let (total_msat, payment_secret, keysend_preimage) = {
                        let mut outbounds = self.pending_outbound_payments.lock().unwrap();
-                       match outbounds.get_mut(&payment_id) {
-                               Some(payment) => {
-                                       let res = match payment {
+                       match outbounds.entry(payment_id) {
+                               hash_map::Entry::Occupied(mut payment) => {
+                                       let res = match payment.get() {
                                                PendingOutboundPayment::Retryable {
-                                                       total_msat, payment_hash, payment_secret, pending_amt_msat, ..
+                                                       total_msat, keysend_preimage, payment_secret, pending_amt_msat, ..
                                                } => {
                                                        let retry_amt_msat: u64 = route.paths.iter().map(|path| path.last().unwrap().fee_msat).sum();
                                                        if retry_amt_msat + *pending_amt_msat > *total_msat * (100 + RETRY_OVERFLOW_PERCENTAGE) / 100 {
-                                                               return Err(PaymentSendFailure::ParameterError(APIError::APIMisuseError {
-                                                                       err: format!("retry_amt_msat of {} will put pending_amt_msat (currently: {}) more than 10% over total_payment_amt_msat of {}", retry_amt_msat, pending_amt_msat, total_msat).to_string()
-                                                               }))
+                                                               log_error!(logger, "retry_amt_msat of {} will put pending_amt_msat (currently: {}) more than 10% over total_payment_amt_msat of {}", retry_amt_msat, pending_amt_msat, total_msat);
+                                                               abandon_with_entry!(payment);
+                                                               return
                                                        }
-                                                       (*total_msat, *payment_hash, *payment_secret)
+                                                       (*total_msat, *payment_secret, *keysend_preimage)
                                                },
                                                PendingOutboundPayment::Legacy { .. } => {
-                                                       return Err(PaymentSendFailure::ParameterError(APIError::APIMisuseError {
-                                                               err: "Unable to retry payments that were initially sent on LDK versions prior to 0.0.102".to_string()
-                                                       }))
+                                                       log_error!(logger, "Unable to retry payments that were initially sent on LDK versions prior to 0.0.102");
+                                                       return
                                                },
                                                PendingOutboundPayment::Fulfilled { .. } => {
-                                                       return Err(PaymentSendFailure::ParameterError(APIError::APIMisuseError {
-                                                               err: "Payment already completed".to_owned()
-                                                       }));
+                                                       log_error!(logger, "Payment already completed");
+                                                       return
                                                },
                                                PendingOutboundPayment::Abandoned { .. } => {
-                                                       return Err(PaymentSendFailure::ParameterError(APIError::APIMisuseError {
-                                                               err: "Payment already abandoned (with some HTLCs still pending)".to_owned()
-                                                       }));
+                                                       log_error!(logger, "Payment already abandoned (with some HTLCs still pending)");
+                                                       return
                                                },
                                        };
+                                       if !payment.get().is_retryable_now() {
+                                               log_error!(logger, "Retries exhausted for payment id {}", log_bytes!(payment_id.0));
+                                               abandon_with_entry!(payment);
+                                               return
+                                       }
+                                       payment.get_mut().increment_attempts();
                                        for (path, session_priv_bytes) in route.paths.iter().zip(onion_session_privs.iter()) {
-                                               assert!(payment.insert(*session_priv_bytes, path));
+                                               assert!(payment.get_mut().insert(*session_priv_bytes, path));
                                        }
                                        res
                                },
-                               None =>
-                                       return Err(PaymentSendFailure::ParameterError(APIError::APIMisuseError {
-                                               err: format!("Payment with ID {} not found", log_bytes!(payment_id.0)),
-                                       })),
+                               hash_map::Entry::Vacant(_) => {
+                                       log_error!(logger, "Payment with ID {} not found", log_bytes!(payment_id.0));
+                                       return
+                               }
                        }
                };
-               self.send_payment_internal(route, payment_hash, &payment_secret, None, payment_id, Some(total_msat), onion_session_privs, node_signer, best_block_height, send_payment_along_path)
+               let res = self.pay_route_internal(&route, payment_hash, &payment_secret, keysend_preimage,
+                       payment_id, Some(total_msat), onion_session_privs, node_signer, best_block_height,
+                       &send_payment_along_path);
+               log_info!(logger, "Result retrying payment id {}: {:?}", log_bytes!(payment_id.0), res);
+               if let Err(e) = res {
+                       self.handle_pay_route_err(e, payment_id, payment_hash, route, route_params, router, first_hops, inflight_htlcs, entropy_source, node_signer, best_block_height, logger, pending_events, send_payment_along_path);
+               }
+       }
+
+       fn handle_pay_route_err<R: Deref, NS: Deref, ES: Deref, IH, SP, L: Deref>(
+               &self, err: PaymentSendFailure, payment_id: PaymentId, payment_hash: PaymentHash, route: Route,
+               mut route_params: RouteParameters, router: &R, first_hops: Vec<ChannelDetails>,
+               inflight_htlcs: &IH, entropy_source: &ES, node_signer: &NS, best_block_height: u32, logger: &L,
+               pending_events: &Mutex<Vec<events::Event>>, send_payment_along_path: &SP,
+       )
+       where
+               R::Target: Router,
+               ES::Target: EntropySource,
+               NS::Target: NodeSigner,
+               L::Target: Logger,
+               IH: Fn() -> InFlightHtlcs,
+               SP: Fn(&Vec<RouteHop>, &PaymentHash, &Option<PaymentSecret>, u64, u32, PaymentId,
+                       &Option<PaymentPreimage>, [u8; 32]) -> Result<(), APIError>
+       {
+               match err {
+                       PaymentSendFailure::AllFailedResendSafe(errs) => {
+                               Self::push_path_failed_evs_and_scids(payment_id, payment_hash, &mut route_params, route.paths, errs.into_iter().map(|e| Err(e)), pending_events);
+                               self.retry_payment_internal(payment_hash, payment_id, route_params, router, first_hops, inflight_htlcs, entropy_source, node_signer, best_block_height, logger, pending_events, send_payment_along_path);
+                       },
+                       PaymentSendFailure::PartialFailure { failed_paths_retry: Some(mut retry), results, .. } => {
+                               Self::push_path_failed_evs_and_scids(payment_id, payment_hash, &mut retry, route.paths, results.into_iter(), pending_events);
+                               // Some paths were sent, even if we failed to send the full MPP value our recipient may
+                               // misbehave and claim the funds, at which point we have to consider the payment sent, so
+                               // return `Ok()` here, ignoring any retry errors.
+                               self.retry_payment_internal(payment_hash, payment_id, retry, router, first_hops, inflight_htlcs, entropy_source, node_signer, best_block_height, logger, pending_events, send_payment_along_path);
+                       },
+                       PaymentSendFailure::PartialFailure { failed_paths_retry: None, .. } => {
+                               // This may happen if we send a payment and some paths fail, but only due to a temporary
+                               // monitor failure or the like, implying they're really in-flight, but we haven't sent the
+                               // initial HTLC-Add messages yet.
+                       },
+                       PaymentSendFailure::PathParameterError(results) => {
+                               Self::push_path_failed_evs_and_scids(payment_id, payment_hash, &mut route_params, route.paths, results.into_iter(), pending_events);
+                               self.abandon_payment(payment_id, pending_events);
+                       },
+                       PaymentSendFailure::ParameterError(e) => {
+                               log_error!(logger, "Failed to send to route due to parameter error: {:?}. Your router is buggy", e);
+                               self.abandon_payment(payment_id, pending_events);
+                       },
+                       PaymentSendFailure::DuplicatePayment => debug_assert!(false), // unreachable
+               }
+       }
+
+       fn push_path_failed_evs_and_scids<I: ExactSizeIterator + Iterator<Item = Result<(), APIError>>>(
+               payment_id: PaymentId, payment_hash: PaymentHash, route_params: &mut RouteParameters,
+               paths: Vec<Vec<RouteHop>>, path_results: I, pending_events: &Mutex<Vec<events::Event>>
+       ) {
+               let mut events = pending_events.lock().unwrap();
+               debug_assert_eq!(paths.len(), path_results.len());
+               for (path, path_res) in paths.into_iter().zip(path_results) {
+                       if let Err(e) = path_res {
+                               if let APIError::MonitorUpdateInProgress = e { continue }
+                               let mut failed_scid = None;
+                               if let APIError::ChannelUnavailable { .. } = e {
+                                       let scid = path[0].short_channel_id;
+                                       failed_scid = Some(scid);
+                                       route_params.payment_params.previously_failed_channels.push(scid);
+                               }
+                               events.push(events::Event::PaymentPathFailed {
+                                       payment_id: Some(payment_id),
+                                       payment_hash,
+                                       payment_failed_permanently: false,
+                                       failure: events::PathFailure::InitialSend { err: e },
+                                       path,
+                                       short_channel_id: failed_scid,
+                                       #[cfg(test)]
+                                       error_code: None,
+                                       #[cfg(test)]
+                                       error_data: None,
+                               });
+                       }
+               }
        }
 
        pub(super) fn send_probe<ES: Deref, NS: Deref, F>(
@@ -386,8 +808,8 @@ impl OutboundPayments {
        where
                ES::Target: EntropySource,
                NS::Target: NodeSigner,
-               F: Fn(&Vec<RouteHop>, &Option<PaymentParameters>, &PaymentHash, &Option<PaymentSecret>, u64,
-                  u32, PaymentId, &Option<PaymentPreimage>, [u8; 32]) -> Result<(), APIError>
+               F: Fn(&Vec<RouteHop>, &PaymentHash, &Option<PaymentSecret>, u64, u32, PaymentId,
+                       &Option<PaymentPreimage>, [u8; 32]) -> Result<(), APIError>
        {
                let payment_id = PaymentId(entropy_source.get_secure_random_bytes());
 
@@ -400,25 +822,29 @@ impl OutboundPayments {
                }
 
                let route = Route { paths: vec![hops], payment_params: None };
-               let onion_session_privs = self.add_new_pending_payment(payment_hash, None, payment_id, &route, entropy_source, best_block_height)?;
+               let onion_session_privs = self.add_new_pending_payment(payment_hash, None, payment_id, None, &route, None, None, entropy_source, best_block_height)?;
 
-               match self.send_payment_internal(&route, payment_hash, &None, None, payment_id, None, onion_session_privs, node_signer, best_block_height, send_payment_along_path) {
+               match self.pay_route_internal(&route, payment_hash, &None, None, payment_id, None, onion_session_privs, node_signer, best_block_height, &send_payment_along_path) {
                        Ok(()) => Ok((payment_hash, payment_id)),
-                       Err(e) => Err(e)
+                       Err(e) => {
+                               self.remove_outbound_if_all_failed(payment_id, &e);
+                               Err(e)
+                       }
                }
        }
 
        #[cfg(test)]
        pub(super) fn test_add_new_pending_payment<ES: Deref>(
                &self, payment_hash: PaymentHash, payment_secret: Option<PaymentSecret>, payment_id: PaymentId,
-               route: &Route, entropy_source: &ES, best_block_height: u32
+               route: &Route, retry_strategy: Option<Retry>, entropy_source: &ES, best_block_height: u32
        ) -> Result<Vec<[u8; 32]>, PaymentSendFailure> where ES::Target: EntropySource {
-               self.add_new_pending_payment(payment_hash, payment_secret, payment_id, route, entropy_source, best_block_height)
+               self.add_new_pending_payment(payment_hash, payment_secret, payment_id, None, route, retry_strategy, None, entropy_source, best_block_height)
        }
 
        pub(super) fn add_new_pending_payment<ES: Deref>(
                &self, payment_hash: PaymentHash, payment_secret: Option<PaymentSecret>, payment_id: PaymentId,
-               route: &Route, entropy_source: &ES, best_block_height: u32
+               keysend_preimage: Option<PaymentPreimage>, route: &Route, retry_strategy: Option<Retry>,
+               payment_params: Option<PaymentParameters>, entropy_source: &ES, best_block_height: u32
        ) -> Result<Vec<[u8; 32]>, PaymentSendFailure> where ES::Target: EntropySource {
                let mut onion_session_privs = Vec::with_capacity(route.paths.len());
                for _ in 0..route.paths.len() {
@@ -430,11 +856,15 @@ impl OutboundPayments {
                        hash_map::Entry::Occupied(_) => Err(PaymentSendFailure::DuplicatePayment),
                        hash_map::Entry::Vacant(entry) => {
                                let payment = entry.insert(PendingOutboundPayment::Retryable {
+                                       retry_strategy,
+                                       attempts: PaymentAttempts::new(),
+                                       payment_params,
                                        session_privs: HashSet::new(),
                                        pending_amt_msat: 0,
                                        pending_fee_msat: Some(0),
                                        payment_hash,
                                        payment_secret,
+                                       keysend_preimage,
                                        starting_block_height: best_block_height,
                                        total_msat: route.get_total_amount(),
                                });
@@ -448,34 +878,34 @@ impl OutboundPayments {
                }
        }
 
-       fn send_payment_internal<NS: Deref, F>(
+       fn pay_route_internal<NS: Deref, F>(
                &self, route: &Route, payment_hash: PaymentHash, payment_secret: &Option<PaymentSecret>,
                keysend_preimage: Option<PaymentPreimage>, payment_id: PaymentId, recv_value_msat: Option<u64>,
                onion_session_privs: Vec<[u8; 32]>, node_signer: &NS, best_block_height: u32,
-               send_payment_along_path: F
+               send_payment_along_path: &F
        ) -> Result<(), PaymentSendFailure>
        where
                NS::Target: NodeSigner,
-               F: Fn(&Vec<RouteHop>, &Option<PaymentParameters>, &PaymentHash, &Option<PaymentSecret>, u64,
-                  u32, PaymentId, &Option<PaymentPreimage>, [u8; 32]) -> Result<(), APIError>
+               F: Fn(&Vec<RouteHop>, &PaymentHash, &Option<PaymentSecret>, u64, u32, PaymentId,
+                       &Option<PaymentPreimage>, [u8; 32]) -> Result<(), APIError>
        {
                if route.paths.len() < 1 {
-                       return Err(PaymentSendFailure::ParameterError(APIError::InvalidRoute{err: "There must be at least one path to send over"}));
+                       return Err(PaymentSendFailure::ParameterError(APIError::InvalidRoute{err: "There must be at least one path to send over".to_owned()}));
                }
                if payment_secret.is_none() && route.paths.len() > 1 {
-                       return Err(PaymentSendFailure::ParameterError(APIError::APIMisuseError{err: "Payment secret is required for multi-path payments".to_string()}));
+                       return Err(PaymentSendFailure::ParameterError(APIError::APIMisuseError{err: "Payment secret is required for multi-path payments".to_owned()}));
                }
                let mut total_value = 0;
                let our_node_id = node_signer.get_node_id(Recipient::Node).unwrap(); // TODO no unwrap
                let mut path_errs = Vec::with_capacity(route.paths.len());
                'path_check: for path in route.paths.iter() {
                        if path.len() < 1 || path.len() > 20 {
-                               path_errs.push(Err(APIError::InvalidRoute{err: "Path didn't go anywhere/had bogus size"}));
+                               path_errs.push(Err(APIError::InvalidRoute{err: "Path didn't go anywhere/had bogus size".to_owned()}));
                                continue 'path_check;
                        }
                        for (idx, hop) in path.iter().enumerate() {
                                if idx != path.len() - 1 && hop.pubkey == our_node_id {
-                                       path_errs.push(Err(APIError::InvalidRoute{err: "Path went through us but wasn't a simple rebalance loop to us"}));
+                                       path_errs.push(Err(APIError::InvalidRoute{err: "Path went through us but wasn't a simple rebalance loop to us".to_owned()}));
                                        continue 'path_check;
                                }
                        }
@@ -494,7 +924,7 @@ impl OutboundPayments {
                let mut results = Vec::new();
                debug_assert_eq!(route.paths.len(), onion_session_privs.len());
                for (path, session_priv) in route.paths.iter().zip(onion_session_privs.into_iter()) {
-                       let mut path_res = send_payment_along_path(&path, &route.payment_params, &payment_hash, payment_secret, total_value, cur_height, payment_id, &keysend_preimage, session_priv);
+                       let mut path_res = send_payment_along_path(&path, &payment_hash, payment_secret, total_value, cur_height, payment_id, &keysend_preimage, session_priv);
                        match path_res {
                                Ok(_) => {},
                                Err(APIError::MonitorUpdateInProgress) => {
@@ -541,16 +971,11 @@ impl OutboundPayments {
                                                Some(RouteParameters {
                                                        payment_params: payment_params.clone(),
                                                        final_value_msat: pending_amt_unsent,
-                                                       final_cltv_expiry_delta: max_unsent_cltv_delta,
                                                })
                                        } else { None }
                                } else { None },
                        })
                } else if has_err {
-                       // If we failed to send any paths, we should remove the new PaymentId from the
-                       // `pending_outbound_payments` map, as the user isn't expected to `abandon_payment`.
-                       let removed = self.pending_outbound_payments.lock().unwrap().remove(&payment_id).is_some();
-                       debug_assert!(removed, "We should always have a pending payment to remove here");
                        Err(PaymentSendFailure::AllFailedResendSafe(results.drain(..).map(|r| r.unwrap_err()).collect()))
                } else {
                        Ok(())
@@ -566,12 +991,22 @@ impl OutboundPayments {
        ) -> Result<(), PaymentSendFailure>
        where
                NS::Target: NodeSigner,
-               F: Fn(&Vec<RouteHop>, &Option<PaymentParameters>, &PaymentHash, &Option<PaymentSecret>, u64,
-                  u32, PaymentId, &Option<PaymentPreimage>, [u8; 32]) -> Result<(), APIError>
+               F: Fn(&Vec<RouteHop>, &PaymentHash, &Option<PaymentSecret>, u64, u32, PaymentId,
+                       &Option<PaymentPreimage>, [u8; 32]) -> Result<(), APIError>
        {
-               self.send_payment_internal(route, payment_hash, payment_secret, keysend_preimage, payment_id,
+               self.pay_route_internal(route, payment_hash, payment_secret, keysend_preimage, payment_id,
                        recv_value_msat, onion_session_privs, node_signer, best_block_height,
-                       send_payment_along_path)
+                       &send_payment_along_path)
+                       .map_err(|e| { self.remove_outbound_if_all_failed(payment_id, &e); e })
+       }
+
+       // If we failed to send any paths, remove the new PaymentId from the `pending_outbound_payments`
+       // map as the payment is free to be resent.
+       fn remove_outbound_if_all_failed(&self, payment_id: PaymentId, err: &PaymentSendFailure) {
+               if let &PaymentSendFailure::AllFailedResendSafe(_) = err {
+                       let removed = self.pending_outbound_payments.lock().unwrap().remove(&payment_id).is_some();
+                       debug_assert!(removed, "We should always have a pending payment to remove here");
+               }
        }
 
        pub(super) fn claim_htlc<L: Deref>(
@@ -682,57 +1117,81 @@ impl OutboundPayments {
                });
        }
 
+       // Returns a bool indicating whether a PendingHTLCsForwardable event should be generated.
        pub(super) fn fail_htlc<L: Deref>(
                &self, source: &HTLCSource, payment_hash: &PaymentHash, onion_error: &HTLCFailReason,
                path: &Vec<RouteHop>, session_priv: &SecretKey, payment_id: &PaymentId,
-               payment_params: &Option<PaymentParameters>, probing_cookie_secret: [u8; 32],
-               secp_ctx: &Secp256k1<secp256k1::All>, pending_events: &Mutex<Vec<events::Event>>, logger: &L
-       ) where L::Target: Logger {
+               probing_cookie_secret: [u8; 32], secp_ctx: &Secp256k1<secp256k1::All>,
+               pending_events: &Mutex<Vec<events::Event>>, logger: &L
+       ) -> bool where L::Target: Logger {
+               #[cfg(test)]
+               let (network_update, short_channel_id, payment_retryable, onion_error_code, onion_error_data) = onion_error.decode_onion_failure(secp_ctx, logger, &source);
+               #[cfg(not(test))]
+               let (network_update, short_channel_id, payment_retryable, _, _) = onion_error.decode_onion_failure(secp_ctx, logger, &source);
+
+               let payment_is_probe = payment_is_probe(payment_hash, &payment_id, probing_cookie_secret);
                let mut session_priv_bytes = [0; 32];
                session_priv_bytes.copy_from_slice(&session_priv[..]);
                let mut outbounds = self.pending_outbound_payments.lock().unwrap();
-               let mut all_paths_failed = false;
+
+               // If any payments already need retry, there's no need to generate a redundant
+               // `PendingHTLCsForwardable`.
+               let already_awaiting_retry = outbounds.iter().any(|(_, pmt)| {
+                       let mut awaiting_retry = false;
+                       if pmt.is_auto_retryable_now() {
+                               if let PendingOutboundPayment::Retryable { pending_amt_msat, total_msat, .. } = pmt {
+                                       if pending_amt_msat < total_msat {
+                                               awaiting_retry = true;
+                                       }
+                               }
+                       }
+                       awaiting_retry
+               });
+
                let mut full_failure_ev = None;
-               if let hash_map::Entry::Occupied(mut payment) = outbounds.entry(*payment_id) {
+               let mut pending_retry_ev = false;
+               let attempts_remaining = if let hash_map::Entry::Occupied(mut payment) = outbounds.entry(*payment_id) {
                        if !payment.get_mut().remove(&session_priv_bytes, Some(&path)) {
                                log_trace!(logger, "Received duplicative fail for HTLC with payment_hash {}", log_bytes!(payment_hash.0));
-                               return
+                               return false
                        }
                        if payment.get().is_fulfilled() {
                                log_trace!(logger, "Received failure of HTLC with payment_hash {} after payment completion", log_bytes!(payment_hash.0));
-                               return
+                               return false
+                       }
+                       let mut is_retryable_now = payment.get().is_auto_retryable_now();
+                       if let Some(scid) = short_channel_id {
+                               // TODO: If we decided to blame ourselves (or one of our channels) in
+                               // process_onion_failure we should close that channel as it implies our
+                               // next-hop is needlessly blaming us!
+                               payment.get_mut().insert_previously_failed_scid(scid);
+                       }
+
+                       if payment_is_probe || !is_retryable_now || !payment_retryable {
+                               let _ = payment.get_mut().mark_abandoned(); // we'll only Err if it's a legacy payment
+                               is_retryable_now = false;
                        }
                        if payment.get().remaining_parts() == 0 {
-                               all_paths_failed = true;
                                if payment.get().abandoned() {
-                                       full_failure_ev = Some(events::Event::PaymentFailed {
-                                               payment_id: *payment_id,
-                                               payment_hash: payment.get().payment_hash().expect("PendingOutboundPayments::RetriesExceeded always has a payment hash set"),
-                                       });
+                                       if !payment_is_probe {
+                                               full_failure_ev = Some(events::Event::PaymentFailed {
+                                                       payment_id: *payment_id,
+                                                       payment_hash: payment.get().payment_hash().expect("PendingOutboundPayments::RetriesExceeded always has a payment hash set"),
+                                               });
+                                       }
                                        payment.remove();
                                }
                        }
+                       is_retryable_now
                } else {
                        log_trace!(logger, "Received duplicative fail for HTLC with payment_hash {}", log_bytes!(payment_hash.0));
-                       return
-               }
-               let mut retry = if let Some(payment_params_data) = payment_params {
-                       let path_last_hop = path.last().expect("Outbound payments must have had a valid path");
-                       Some(RouteParameters {
-                               payment_params: payment_params_data.clone(),
-                               final_value_msat: path_last_hop.fee_msat,
-                               final_cltv_expiry_delta: path_last_hop.cltv_expiry_delta,
-                       })
-               } else { None };
+                       return false
+               };
+               core::mem::drop(outbounds);
                log_trace!(logger, "Failing outbound payment HTLC with payment_hash {}", log_bytes!(payment_hash.0));
 
                let path_failure = {
-                       #[cfg(test)]
-                       let (network_update, short_channel_id, payment_retryable, onion_error_code, onion_error_data) = onion_error.decode_onion_failure(secp_ctx, logger, &source);
-                       #[cfg(not(test))]
-                       let (network_update, short_channel_id, payment_retryable, _, _) = onion_error.decode_onion_failure(secp_ctx, logger, &source);
-
-                       if payment_is_probe(payment_hash, &payment_id, probing_cookie_secret) {
+                       if payment_is_probe {
                                if !payment_retryable {
                                        events::Event::ProbeSuccessful {
                                                payment_id: *payment_id,
@@ -748,21 +1207,19 @@ impl OutboundPayments {
                                        }
                                }
                        } else {
-                               // TODO: If we decided to blame ourselves (or one of our channels) in
-                               // process_onion_failure we should close that channel as it implies our
-                               // next-hop is needlessly blaming us!
-                               if let Some(scid) = short_channel_id {
-                                       retry.as_mut().map(|r| r.payment_params.previously_failed_channels.push(scid));
+                               // If we miss abandoning the payment above, we *must* generate an event here or else the
+                               // payment will sit in our outbounds forever.
+                               if attempts_remaining && !already_awaiting_retry {
+                                       debug_assert!(full_failure_ev.is_none());
+                                       pending_retry_ev = true;
                                }
                                events::Event::PaymentPathFailed {
                                        payment_id: Some(*payment_id),
                                        payment_hash: payment_hash.clone(),
                                        payment_failed_permanently: !payment_retryable,
-                                       network_update,
-                                       all_paths_failed,
+                                       failure: events::PathFailure::OnPath { network_update },
                                        path: path.clone(),
                                        short_channel_id,
-                                       retry,
                                        #[cfg(test)]
                                        error_code: onion_error_code,
                                        #[cfg(test)]
@@ -773,15 +1230,17 @@ impl OutboundPayments {
                let mut pending_events = pending_events.lock().unwrap();
                pending_events.push(path_failure);
                if let Some(ev) = full_failure_ev { pending_events.push(ev); }
+               pending_retry_ev
        }
 
-       pub(super) fn abandon_payment(&self, payment_id: PaymentId) -> Option<events::Event> {
-               let mut failed_ev = None;
+       pub(super) fn abandon_payment(
+               &self, payment_id: PaymentId, pending_events: &Mutex<Vec<events::Event>>
+       ) {
                let mut outbounds = self.pending_outbound_payments.lock().unwrap();
                if let hash_map::Entry::Occupied(mut payment) = outbounds.entry(payment_id) {
                        if let Ok(()) = payment.get_mut().mark_abandoned() {
                                if payment.get().remaining_parts() == 0 {
-                                       failed_ev = Some(events::Event::PaymentFailed {
+                                       pending_events.lock().unwrap().push(events::Event::PaymentFailed {
                                                payment_id,
                                                payment_hash: payment.get().payment_hash().expect("PendingOutboundPayments::RetriesExceeded always has a payment hash set"),
                                        });
@@ -789,7 +1248,6 @@ impl OutboundPayments {
                                }
                        }
                }
-               failed_ev
        }
 
        #[cfg(test)]
@@ -833,13 +1291,214 @@ impl_writeable_tlv_based_enum_upgradable!(PendingOutboundPayment,
                (0, session_privs, required),
                (1, pending_fee_msat, option),
                (2, payment_hash, required),
+               // Note that while we "default" payment_param's final CLTV expiry delta to 0 we should
+               // never see it - `payment_params` was added here after the field was added/required.
+               (3, payment_params, (option: ReadableArgs, 0)),
                (4, payment_secret, option),
+               (5, keysend_preimage, option),
                (6, total_msat, required),
                (8, pending_amt_msat, required),
                (10, starting_block_height, required),
+               (not_written, retry_strategy, (static_value, None)),
+               (not_written, attempts, (static_value, PaymentAttempts::new())),
        },
        (3, Abandoned) => {
                (0, session_privs, required),
                (2, payment_hash, required),
        },
 );
+
+#[cfg(test)]
+mod tests {
+       use bitcoin::network::constants::Network;
+       use bitcoin::secp256k1::{PublicKey, Secp256k1, SecretKey};
+
+       use crate::ln::PaymentHash;
+       use crate::ln::channelmanager::PaymentId;
+       use crate::ln::features::{ChannelFeatures, NodeFeatures};
+       use crate::ln::msgs::{ErrorAction, LightningError};
+       use crate::ln::outbound_payment::{OutboundPayments, Retry, RetryableSendFailure};
+       use crate::routing::gossip::NetworkGraph;
+       use crate::routing::router::{InFlightHtlcs, PaymentParameters, Route, RouteHop, RouteParameters};
+       use crate::sync::{Arc, Mutex};
+       use crate::util::errors::APIError;
+       use crate::util::events::{Event, PathFailure};
+       use crate::util::test_utils;
+
+       #[test]
+       #[cfg(feature = "std")]
+       fn fails_paying_after_expiration() {
+               do_fails_paying_after_expiration(false);
+               do_fails_paying_after_expiration(true);
+       }
+       #[cfg(feature = "std")]
+       fn do_fails_paying_after_expiration(on_retry: bool) {
+               let outbound_payments = OutboundPayments::new();
+               let logger = test_utils::TestLogger::new();
+               let network_graph = Arc::new(NetworkGraph::new(Network::Testnet, &logger));
+               let scorer = Mutex::new(test_utils::TestScorer::new());
+               let router = test_utils::TestRouter::new(network_graph, &scorer);
+               let secp_ctx = Secp256k1::new();
+               let keys_manager = test_utils::TestKeysInterface::new(&[0; 32], Network::Testnet);
+
+               let past_expiry_time = std::time::SystemTime::UNIX_EPOCH.elapsed().unwrap().as_secs() - 2;
+               let payment_params = PaymentParameters::from_node_id(
+                               PublicKey::from_secret_key(&secp_ctx, &SecretKey::from_slice(&[42; 32]).unwrap()),
+                               0
+                       ).with_expiry_time(past_expiry_time);
+               let expired_route_params = RouteParameters {
+                       payment_params,
+                       final_value_msat: 0,
+               };
+               let pending_events = Mutex::new(Vec::new());
+               if on_retry {
+                       outbound_payments.add_new_pending_payment(PaymentHash([0; 32]), None, PaymentId([0; 32]), None,
+                       &Route { paths: vec![], payment_params: None }, Some(Retry::Attempts(1)),
+                       Some(expired_route_params.payment_params.clone()), &&keys_manager, 0).unwrap();
+                       outbound_payments.retry_payment_internal(
+                               PaymentHash([0; 32]), PaymentId([0; 32]), expired_route_params, &&router, vec![],
+                               &|| InFlightHtlcs::new(), &&keys_manager, &&keys_manager, 0, &&logger,
+                               &pending_events, &|_, _, _, _, _, _, _, _| Ok(()));
+                       let events = pending_events.lock().unwrap();
+                       assert_eq!(events.len(), 1);
+                       if let Event::PaymentFailed { .. } = events[0] { } else { panic!("Unexpected event"); }
+               } else {
+                       let err = outbound_payments.send_payment(
+                               PaymentHash([0; 32]), &None, PaymentId([0; 32]), Retry::Attempts(0), expired_route_params,
+                               &&router, vec![], || InFlightHtlcs::new(), &&keys_manager, &&keys_manager, 0, &&logger,
+                               &pending_events, |_, _, _, _, _, _, _, _| Ok(())).unwrap_err();
+                       if let RetryableSendFailure::PaymentExpired = err { } else { panic!("Unexpected error"); }
+               }
+       }
+
+       #[test]
+       fn find_route_error() {
+               do_find_route_error(false);
+               do_find_route_error(true);
+       }
+       fn do_find_route_error(on_retry: bool) {
+               let outbound_payments = OutboundPayments::new();
+               let logger = test_utils::TestLogger::new();
+               let network_graph = Arc::new(NetworkGraph::new(Network::Testnet, &logger));
+               let scorer = Mutex::new(test_utils::TestScorer::new());
+               let router = test_utils::TestRouter::new(network_graph, &scorer);
+               let secp_ctx = Secp256k1::new();
+               let keys_manager = test_utils::TestKeysInterface::new(&[0; 32], Network::Testnet);
+
+               let payment_params = PaymentParameters::from_node_id(
+                       PublicKey::from_secret_key(&secp_ctx, &SecretKey::from_slice(&[42; 32]).unwrap()), 0);
+               let route_params = RouteParameters {
+                       payment_params,
+                       final_value_msat: 0,
+               };
+               router.expect_find_route(route_params.clone(),
+                       Err(LightningError { err: String::new(), action: ErrorAction::IgnoreError }));
+
+               let pending_events = Mutex::new(Vec::new());
+               if on_retry {
+                       outbound_payments.add_new_pending_payment(PaymentHash([0; 32]), None, PaymentId([0; 32]), None,
+                               &Route { paths: vec![], payment_params: None }, Some(Retry::Attempts(1)),
+                               Some(route_params.payment_params.clone()), &&keys_manager, 0).unwrap();
+                       outbound_payments.retry_payment_internal(
+                               PaymentHash([0; 32]), PaymentId([0; 32]), route_params, &&router, vec![],
+                               &|| InFlightHtlcs::new(), &&keys_manager, &&keys_manager, 0, &&logger,
+                               &pending_events, &|_, _, _, _, _, _, _, _| Ok(()));
+                       let events = pending_events.lock().unwrap();
+                       assert_eq!(events.len(), 1);
+                       if let Event::PaymentFailed { .. } = events[0] { } else { panic!("Unexpected event"); }
+               } else {
+                       let err = outbound_payments.send_payment(
+                               PaymentHash([0; 32]), &None, PaymentId([0; 32]), Retry::Attempts(0), route_params,
+                               &&router, vec![], || InFlightHtlcs::new(), &&keys_manager, &&keys_manager, 0, &&logger,
+                               &pending_events, |_, _, _, _, _, _, _, _| Ok(())).unwrap_err();
+                       if let RetryableSendFailure::RouteNotFound = err {
+                       } else { panic!("Unexpected error"); }
+               }
+       }
+
+       #[test]
+       fn initial_send_payment_path_failed_evs() {
+               let outbound_payments = OutboundPayments::new();
+               let logger = test_utils::TestLogger::new();
+               let network_graph = Arc::new(NetworkGraph::new(Network::Testnet, &logger));
+               let scorer = Mutex::new(test_utils::TestScorer::new());
+               let router = test_utils::TestRouter::new(network_graph, &scorer);
+               let secp_ctx = Secp256k1::new();
+               let keys_manager = test_utils::TestKeysInterface::new(&[0; 32], Network::Testnet);
+
+               let sender_pk = PublicKey::from_secret_key(&secp_ctx, &SecretKey::from_slice(&[42; 32]).unwrap());
+               let receiver_pk = PublicKey::from_secret_key(&secp_ctx, &SecretKey::from_slice(&[43; 32]).unwrap());
+               let payment_params = PaymentParameters::from_node_id(sender_pk, 0);
+               let route_params = RouteParameters {
+                       payment_params: payment_params.clone(),
+                       final_value_msat: 0,
+               };
+               let failed_scid = 42;
+               let route = Route {
+                       paths: vec![vec![RouteHop {
+                               pubkey: receiver_pk,
+                               node_features: NodeFeatures::empty(),
+                               short_channel_id: failed_scid,
+                               channel_features: ChannelFeatures::empty(),
+                               fee_msat: 0,
+                               cltv_expiry_delta: 0,
+                       }]],
+                       payment_params: Some(payment_params),
+               };
+               router.expect_find_route(route_params.clone(), Ok(route.clone()));
+               let mut route_params_w_failed_scid = route_params.clone();
+               route_params_w_failed_scid.payment_params.previously_failed_channels.push(failed_scid);
+               router.expect_find_route(route_params_w_failed_scid, Ok(route.clone()));
+               router.expect_find_route(route_params.clone(), Ok(route.clone()));
+               router.expect_find_route(route_params.clone(), Ok(route.clone()));
+
+               // Ensure that a ChannelUnavailable error will result in blaming an scid in the
+               // PaymentPathFailed event.
+               let pending_events = Mutex::new(Vec::new());
+               outbound_payments.send_payment(
+                       PaymentHash([0; 32]), &None, PaymentId([0; 32]), Retry::Attempts(0), route_params.clone(),
+                       &&router, vec![], || InFlightHtlcs::new(), &&keys_manager, &&keys_manager, 0, &&logger,
+                       &pending_events,
+                       |_, _, _, _, _, _, _, _| Err(APIError::ChannelUnavailable { err: "test".to_owned() }))
+                       .unwrap();
+               let mut events = pending_events.lock().unwrap();
+               assert_eq!(events.len(), 2);
+               if let Event::PaymentPathFailed {
+                       short_channel_id,
+                       failure: PathFailure::InitialSend { err: APIError::ChannelUnavailable { .. }}, .. } = events[0]
+               {
+                       assert_eq!(short_channel_id, Some(failed_scid));
+               } else { panic!("Unexpected event"); }
+               if let Event::PaymentFailed { .. } = events[1] { } else { panic!("Unexpected event"); }
+               events.clear();
+               core::mem::drop(events);
+
+               // Ensure that a MonitorUpdateInProgress "error" will not result in a PaymentPathFailed event.
+               outbound_payments.send_payment(
+                       PaymentHash([0; 32]), &None, PaymentId([0; 32]), Retry::Attempts(0), route_params.clone(),
+                       &&router, vec![], || InFlightHtlcs::new(), &&keys_manager, &&keys_manager, 0, &&logger,
+                       &pending_events, |_, _, _, _, _, _, _, _| Err(APIError::MonitorUpdateInProgress))
+                       .unwrap();
+               {
+                       let events = pending_events.lock().unwrap();
+                       assert_eq!(events.len(), 0);
+               }
+
+               // Ensure that any other error will result in a PaymentPathFailed event but no blamed scid.
+               outbound_payments.send_payment(
+                       PaymentHash([0; 32]), &None, PaymentId([1; 32]), Retry::Attempts(0), route_params.clone(),
+                       &&router, vec![], || InFlightHtlcs::new(), &&keys_manager, &&keys_manager, 0, &&logger,
+                       &pending_events,
+                       |_, _, _, _, _, _, _, _| Err(APIError::APIMisuseError { err: "test".to_owned() }))
+                       .unwrap();
+               let events = pending_events.lock().unwrap();
+               assert_eq!(events.len(), 2);
+               if let Event::PaymentPathFailed {
+                       short_channel_id,
+                       failure: PathFailure::InitialSend { err: APIError::APIMisuseError { .. }}, .. } = events[0]
+               {
+                       assert_eq!(short_channel_id, None);
+               } else { panic!("Unexpected event"); }
+               if let Event::PaymentFailed { .. } = events[1] { } else { panic!("Unexpected event"); }
+       }
+}