diff --git a/wgengine/magicsock/relaymanager.go b/wgengine/magicsock/relaymanager.go
index fd3f19dfb..2b636dc57 100644
--- a/wgengine/magicsock/relaymanager.go
+++ b/wgengine/magicsock/relaymanager.go
@@ -112,12 +112,21 @@ type relayEndpointHandshakeWorkDoneEvent struct {
 	latency          time.Duration  // only relevant if pongReceivedFrom.IsValid()
 }
 
-// activeWorkRunLoop returns true if there is outstanding allocation or
-// handshaking work, otherwise it returns false.
-func (r *relayManager) activeWorkRunLoop() bool {
+// hasActiveWorkRunLoop returns true if there is outstanding allocation or
+// handshaking work for any endpoint, otherwise it returns false.
+func (r *relayManager) hasActiveWorkRunLoop() bool {
 	return len(r.allocWorkByEndpoint) > 0 || len(r.handshakeWorkByEndpointByServerDisco) > 0
 }
 
+// hasActiveWorkForEndpointRunLoop returns true if there is outstanding
+// allocation or handshaking work for the provided endpoint, otherwise it
+// returns false.
+func (r *relayManager) hasActiveWorkForEndpointRunLoop(ep *endpoint) bool {
+	_, handshakeWork := r.handshakeWorkByEndpointByServerDisco[ep]
+	_, allocWork := r.allocWorkByEndpoint[ep]
+	return handshakeWork || allocWork
+}
+
 // runLoop is a form of event loop. It ensures exclusive access to most of
 // [relayManager] state.
 func (r *relayManager) runLoop() {
@@ -128,9 +137,10 @@ func (r *relayManager) runLoop() {
 	for {
 		select {
 		case ep := <-r.allocateHandshakeCh:
-			r.stopWorkRunLoop(ep, stopHandshakeWorkOnlyKnownServers)
-			r.allocateAllServersRunLoop(ep)
-			if !r.activeWorkRunLoop() {
+			if !r.hasActiveWorkForEndpointRunLoop(ep) {
+				r.allocateAllServersRunLoop(ep)
+			}
+			if !r.hasActiveWorkRunLoop() {
 				return
 			}
 		case done := <-r.allocateWorkDoneCh:
@@ -141,27 +151,27 @@ func (r *relayManager) runLoop() {
 				// overwrite pre-existing keys.
 				delete(r.allocWorkByEndpoint, done.work.ep)
 			}
-			if !r.activeWorkRunLoop() {
+			if !r.hasActiveWorkRunLoop() {
 				return
 			}
 		case ep := <-r.cancelWorkCh:
-			r.stopWorkRunLoop(ep, stopHandshakeWorkAllServers)
-			if !r.activeWorkRunLoop() {
+			r.stopWorkRunLoop(ep)
+			if !r.hasActiveWorkRunLoop() {
 				return
 			}
 		case newServerEndpoint := <-r.newServerEndpointCh:
 			r.handleNewServerEndpointRunLoop(newServerEndpoint)
-			if !r.activeWorkRunLoop() {
+			if !r.hasActiveWorkRunLoop() {
 				return
 			}
 		case done := <-r.handshakeWorkDoneCh:
 			r.handleHandshakeWorkDoneRunLoop(done)
-			if !r.activeWorkRunLoop() {
+			if !r.hasActiveWorkRunLoop() {
 				return
 			}
 		case discoMsgEvent := <-r.rxHandshakeDiscoMsgCh:
 			r.handleRxHandshakeDiscoMsgRunLoop(discoMsgEvent)
-			if !r.activeWorkRunLoop() {
+			if !r.hasActiveWorkRunLoop() {
 				return
 			}
 		}
@@ -317,8 +327,8 @@ func relayManagerInputEvent[T any](r *relayManager, ctx context.Context, eventCh
 }
 
 // allocateAndHandshakeAllServers kicks off allocation and handshaking of relay
-// endpoints for 'ep' on all known relay servers, canceling any existing
-// in-progress work.
+// endpoints for 'ep' on all known relay servers if there is no outstanding
+// work.
 func (r *relayManager) allocateAndHandshakeAllServers(ep *endpoint) {
 	relayManagerInputEvent(r, nil, &r.allocateHandshakeCh, ep)
 }
@@ -328,18 +338,9 @@ func (r *relayManager) stopWork(ep *endpoint) {
 	relayManagerInputEvent(r, nil, &r.cancelWorkCh, ep)
 }
 
-// stopHandshakeWorkFilter represents filters for handshake work cancellation
-type stopHandshakeWorkFilter bool
-
-const (
-	stopHandshakeWorkAllServers       stopHandshakeWorkFilter = false
-	stopHandshakeWorkOnlyKnownServers                         = true
-)
-
 // stopWorkRunLoop cancels & clears outstanding allocation and handshaking
-// work for 'ep'. Handshake work cancellation is subject to the filter supplied
-// in 'f'.
-func (r *relayManager) stopWorkRunLoop(ep *endpoint, f stopHandshakeWorkFilter) {
+// work for 'ep'.
+func (r *relayManager) stopWorkRunLoop(ep *endpoint) {
 	allocWork, ok := r.allocWorkByEndpoint[ep]
 	if ok {
 		allocWork.cancel()
@@ -348,13 +349,10 @@ func (r *relayManager) stopWorkRunLoop(ep *endpoint, f stopHandshakeWorkFilter)
 	}
 	byServerDisco, ok := r.handshakeWorkByEndpointByServerDisco[ep]
 	if ok {
-		for disco, handshakeWork := range byServerDisco {
-			_, knownServer := r.serversByDisco[disco]
-			if knownServer || f == stopHandshakeWorkAllServers {
-				handshakeWork.cancel()
-				done := <-handshakeWork.doneCh
-				r.handleHandshakeWorkDoneRunLoop(done)
-			}
+		for _, handshakeWork := range byServerDisco {
+			handshakeWork.cancel()
+			done := <-handshakeWork.doneCh
+			r.handleHandshakeWorkDoneRunLoop(done)
 		}
 	}
 }