diff --git a/pkg/util/iptables/iptables.go b/pkg/util/iptables/iptables.go
index a1424c590f9..a4766a793fb 100644
--- a/pkg/util/iptables/iptables.go
+++ b/pkg/util/iptables/iptables.go
@@ -502,16 +502,22 @@ const (
 // Monitor is part of Interface
 func (runner *runner) Monitor(canary Chain, tables []Table, reloadFunc func(), interval time.Duration, stopCh <-chan struct{}) {
 	for {
-		for _, table := range tables {
-			if _, err := runner.EnsureChain(table, canary); err != nil {
-				klog.Warningf("Could not set up iptables canary %s/%s: %v", string(table), string(canary), err)
-				return
+		_ = utilwait.PollImmediateUntil(interval, func() (bool, error) {
+			for _, table := range tables {
+				if _, err := runner.EnsureChain(table, canary); err != nil {
+					klog.Warningf("Could not set up iptables canary %s/%s: %v", string(table), string(canary), err)
+					return false, nil
+				}
 			}
-		}
+			return true, nil
+		}, stopCh)
 
 		// Poll until stopCh is closed or iptables is flushed
 		err := utilwait.PollUntil(interval, func() (bool, error) {
-			if runner.chainExists(tables[0], canary) {
+			if exists, err := runner.chainExists(tables[0], canary); exists {
+				return false, nil
+			} else if isResourceError(err) {
+				klog.Warningf("Could not check for iptables canary %s/%s: %v", string(tables[0]), string(canary), err)
 				return false, nil
 			}
 			klog.V(2).Infof("iptables canary %s/%s deleted", string(tables[0]), string(canary))
@@ -520,7 +526,7 @@ func (runner *runner) Monitor(canary Chain, tables []Table, reloadFunc func(), i
 			// so we don't start reloading too soon.
 			err := utilwait.PollImmediate(iptablesFlushPollTime, iptablesFlushTimeout, func() (bool, error) {
 				for i := 1; i < len(tables); i++ {
-					if runner.chainExists(tables[i], canary) {
+					if exists, err := runner.chainExists(tables[i], canary); exists || isResourceError(err) {
 						return false, nil
 					}
 				}
@@ -547,14 +553,14 @@ func (runner *runner) Monitor(canary Chain, tables []Table, reloadFunc func(), i
 
 // chainExists is used internally by Monitor; none of the public Interface methods can be
 // used to distinguish "chain exists" from "chain does not exist" with no side effects
-func (runner *runner) chainExists(table Table, chain Chain) bool {
+func (runner *runner) chainExists(table Table, chain Chain) (bool, error) {
 	fullArgs := makeFullArgs(table, chain)
 
 	runner.mu.Lock()
 	defer runner.mu.Unlock()
 
 	_, err := runner.run(opListChain, fullArgs)
-	return err == nil
+	return err == nil, err
 }
 
 type operation string
@@ -691,3 +697,16 @@ func IsNotFoundError(err error) bool {
 	}
 	return false
 }
+
+const iptablesStatusResourceProblem = 4
+
+// isResourceError returns true if the error indicates that iptables ran into a "resource
+// problem" and was unable to attempt the request. In particular, this will be true if it
+// times out trying to get the iptables lock.
+func isResourceError(err error) bool {
+	if ee, isExitError := err.(utilexec.ExitError); isExitError {
+		return ee.ExitStatus() == iptablesStatusResourceProblem
+	} else {
+		return false
+	}
+}
diff --git a/pkg/util/iptables/monitor_test.go b/pkg/util/iptables/monitor_test.go
index 0a0cc875d6a..7f4d4176dc8 100644
--- a/pkg/util/iptables/monitor_test.go
+++ b/pkg/util/iptables/monitor_test.go
@@ -41,6 +41,9 @@ type monitorFakeExec struct {
 	sync.Mutex
 
 	tables map[string]sets.String
+
+	block      bool
+	wasBlocked bool
 }
 
 func newMonitorFakeExec() *monitorFakeExec {
@@ -51,6 +54,22 @@ func newMonitorFakeExec() *monitorFakeExec {
 	return &monitorFakeExec{tables: tables}
 }
 
+func (mfe *monitorFakeExec) blockIPTables(block bool) {
+	mfe.Lock()
+	defer mfe.Unlock()
+
+	mfe.block = block
+}
+
+func (mfe *monitorFakeExec) getWasBlocked() bool {
+	mfe.Lock()
+	defer mfe.Unlock()
+
+	wasBlocked := mfe.wasBlocked
+	mfe.wasBlocked = false
+	return wasBlocked
+}
+
 func (mfe *monitorFakeExec) Command(cmd string, args ...string) exec.Cmd {
 	return &monitorFakeCmd{mfe: mfe, cmd: cmd, args: args}
 }
@@ -96,6 +115,12 @@ func (mfc *monitorFakeCmd) CombinedOutput() ([]byte, error) {
 		return []byte{}, fmt.Errorf("no such table %q", tableName)
 	}
 
+	// For ease-of-testing reasons, blockIPTables blocks create and list, but not delete
+	if mfc.mfe.block && op != opDeleteChain {
+		mfc.mfe.wasBlocked = true
+		return []byte{}, exec.CodeExitError{Code: 4, Err: fmt.Errorf("could not get xtables.lock, etc")}
+	}
+
 	switch op {
 	case opCreateChain:
 		if !table.Has(chainName) {
@@ -199,8 +224,17 @@ func TestIPTablesMonitor(t *testing.T) {
 		t.Errorf("got unexpected number of reloads after partial flush: %v", err)
 	}
 
-	// If we delete the last chain, it should reload now
+	// Now ensure that "iptables -L" will get an error about the xtables.lock, and
+	// delete the last chain. The monitor should not reload, because it can't actually
+	// tell if the chain was deleted or not.
+	mfe.blockIPTables(true)
 	ipt.DeleteChain(TableNAT, canary)
+	if err := waitForBlocked(mfe); err != nil {
+		t.Errorf("failed waiting for monitor to be blocked from monitoring: %v", err)
+	}
+
+	// After unblocking the monitor, it should now reload
+	mfe.blockIPTables(false)
 
 	if err := waitForReloads(&reloads, 2); err != nil {
 		t.Errorf("got unexpected number of reloads after slow flush: %v", err)
@@ -213,11 +247,40 @@ func TestIPTablesMonitor(t *testing.T) {
 	close(stopCh)
 
 	if err := waitForNoReload(&reloads, 2); err != nil {
-		t.Errorf("got unexpected number of reloads after partial flush: %v", err)
+		t.Errorf("got unexpected number of reloads after stop: %v", err)
 	}
 	if !ensureNoChains(mfe) {
 		t.Errorf("canaries still exist after stopping monitor")
 	}
+
+	// If we create a new monitor while the iptables lock is held, it will
+	// retry creating canaries until it succeeds
+
+	stopCh = make(chan struct{})
+	_ = mfe.getWasBlocked()
+	mfe.blockIPTables(true)
+	go ipt.Monitor(canary, tables, func() {
+		if !ensureNoChains(mfe) {
+			t.Errorf("reload called while canaries still exist")
+		}
+		atomic.AddUint32(&reloads, 1)
+	}, 100*time.Millisecond, stopCh)
+
+	// Monitor should not have created canaries yet
+	if !ensureNoChains(mfe) {
+		t.Errorf("canary created while iptables blocked")
+	}
+
+	if err := waitForBlocked(mfe); err != nil {
+		t.Errorf("failed waiting for monitor to fail creating canaries: %v", err)
+	}
+
+	mfe.blockIPTables(false)
+	if err := waitForChains(mfe, canary, tables); err != nil {
+		t.Errorf("failed to create iptables canaries: %v", err)
+	}
+
+	close(stopCh)
 }
 
 func waitForChains(mfe *monitorFakeExec, canary Chain, tables []Table) error {
@@ -266,3 +329,10 @@ func waitForNoReload(reloads *uint32, expected uint32) error {
 	}
 	return nil
 }
+
+func waitForBlocked(mfe *monitorFakeExec) error {
+	return utilwait.PollImmediate(100*time.Millisecond, time.Second, func() (bool, error) {
+		blocked := mfe.getWasBlocked()
+		return blocked, nil
+	})
+}