diff --git a/README.md b/README.md
index c4733ea..81c2bf5 100644
--- a/README.md
+++ b/README.md
@@ -45,6 +45,7 @@ Check out the **[contributing wiki](https://github.com/pion/webrtc/wiki/Contribu
 * [Zizheng Tai](https://github.com/ZizhengTai)
 * [Aaron France](https://github.com/AeroNotix)
 * [Chao Yuan](https://github.com/yuanchao0310)
+* [Jason Maldonis](https://github.com/jjmaldonis)
 
 ### License
 MIT License - see [LICENSE](LICENSE) for full text
diff --git a/agent.go b/agent.go
index dfa0876..6b87693 100644
--- a/agent.go
+++ b/agent.go
@@ -51,8 +51,8 @@ const (
 	// the number of bytes that can be buffered before we start to error
 	maxBufferSize = 1000 * 1000 // 1MB
 
-	// the number of outbound binding requests we cache
-	maxPendingBindingRequests = 50
+	// wait time before binding requests can be deleted
+	maxBindingRequestTimeout = 500 * time.Millisecond
 )
 
 var (
@@ -60,6 +60,7 @@ var (
 )
 
 type bindingRequest struct {
+	timestamp      time.Time
 	transactionID  [stun.TransactionIDSize]byte
 	destination    net.Addr
 	isUseCandidate bool
@@ -338,7 +339,7 @@ func NewAgent(config *AgentConfig) (*Agent, error) {
 		connectionState:        ConnectionStateNew,
 		localCandidates:        make(map[NetworkType][]Candidate),
 		remoteCandidates:       make(map[NetworkType][]Candidate),
-		pendingBindingRequests: make([]bindingRequest, 0, maxPendingBindingRequests),
+		pendingBindingRequests: make([]bindingRequest, 0),
 		checklist:              make([]*candidatePair, 0),
 		urls:                   config.Urls,
 		networkTypes:           config.NetworkTypes,
@@ -953,17 +954,12 @@ func (a *Agent) findRemoteCandidate(networkType NetworkType, addr net.Addr) Cand
 func (a *Agent) sendBindingRequest(m *stun.Message, local, remote Candidate) {
 	a.log.Tracef("ping STUN from %s to %s\n", local.String(), remote.String())
 
-	if overflow := len(a.pendingBindingRequests) - (maxPendingBindingRequests - 1); overflow > 0 {
-		a.log.Debugf("Discarded %d pending binding requests, pendingBindingRequests is full", overflow)
-		a.pendingBindingRequests = a.pendingBindingRequests[overflow:]
-	}
-
-	useCandidate := m.Contains(stun.AttrUseCandidate)
-
+	a.invalidatePendingBindingRequests(time.Now())
 	a.pendingBindingRequests = append(a.pendingBindingRequests, bindingRequest{
+		timestamp:      time.Now(),
 		transactionID:  m.TransactionID,
 		destination:    remote.addr(),
-		isUseCandidate: useCandidate,
+		isUseCandidate: m.Contains(stun.AttrUseCandidate),
 	})
 
 	a.sendSTUN(m, local, remote)
@@ -985,9 +981,32 @@ func (a *Agent) sendBindingSuccess(m *stun.Message, local, remote Candidate) {
 	}
 }
 
+/* Removes pending binding requests that are over maxBindingRequestTimeout old
+
+   Let HTO be the transaction timeout, which SHOULD be 2*RTT if
+   RTT is known or 500 ms otherwise.
+   https://tools.ietf.org/html/rfc8445#appendix-B.1
+*/
+func (a *Agent) invalidatePendingBindingRequests(filterTime time.Time) {
+	initialSize := len(a.pendingBindingRequests)
+
+	temp := a.pendingBindingRequests[:0]
+	for _, bindingRequest := range a.pendingBindingRequests {
+		if filterTime.Sub(bindingRequest.timestamp) < maxBindingRequestTimeout {
+			temp = append(temp, bindingRequest)
+		}
+	}
+
+	a.pendingBindingRequests = temp
+	if bindRequestsRemoved := initialSize - len(a.pendingBindingRequests); bindRequestsRemoved > 0 {
+		a.log.Tracef("Discarded %d binding requests because they expired", bindRequestsRemoved)
+	}
+}
+
 // Assert that the passed TransactionID is in our pendingBindingRequests and returns the destination
 // If the bindingRequest was valid remove it from our pending cache
 func (a *Agent) handleInboundBindingSuccess(id [stun.TransactionIDSize]byte) (bool, *bindingRequest) {
+	a.invalidatePendingBindingRequests(time.Now())
 	for i := range a.pendingBindingRequests {
 		if a.pendingBindingRequests[i].transactionID == id {
 			validBindingRequest := a.pendingBindingRequests[i]
diff --git a/agent_test.go b/agent_test.go
index 6f7e524..5a1b7ea 100644
--- a/agent_test.go
+++ b/agent_test.go
@@ -10,6 +10,7 @@ import (
 	"github.com/pion/stun"
 	"github.com/pion/transport/test"
 	"github.com/pion/transport/vnet"
+	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 )
 
@@ -325,7 +326,7 @@ func TestHandlePeerReflexive(t *testing.T) {
 			tID := [stun.TransactionIDSize]byte{}
 			copy(tID[:], []byte("ABC"))
 			a.pendingBindingRequests = []bindingRequest{
-				{tID, &net.UDPAddr{}, false},
+				{time.Now(), tID, &net.UDPAddr{}, false},
 			}
 
 			hostConfig := CandidateHostConfig{
@@ -551,6 +552,7 @@ func TestInboundValidity(t *testing.T) {
 		if len(a.remoteCandidates) == 1 {
 			t.Fatal("Binding with invalid MessageIntegrity was able to create prflx candidate")
 		}
+
 	})
 
 	t.Run("Invalid Binding success responses should be discarded", func(t *testing.T) {
@@ -1200,3 +1202,27 @@ func TestInitExtIPMapping(t *testing.T) {
 		t.Fatalf("Unexpected error: %v", err)
 	}
 }
+
+func TestBindingRequestTimeout(t *testing.T) {
+	const expectedRemovalCount = 2
+
+	a, err := NewAgent(&AgentConfig{})
+	assert.NoError(t, err)
+
+	now := time.Now()
+	a.pendingBindingRequests = append(a.pendingBindingRequests, bindingRequest{
+		timestamp: now,
+	})
+	a.pendingBindingRequests = append(a.pendingBindingRequests, bindingRequest{
+		timestamp: now.Add(-25 * time.Millisecond),
+	})
+	a.pendingBindingRequests = append(a.pendingBindingRequests, bindingRequest{
+		timestamp: now.Add(-750 * time.Millisecond),
+	})
+	a.pendingBindingRequests = append(a.pendingBindingRequests, bindingRequest{
+		timestamp: now.Add(-75 * time.Hour),
+	})
+
+	a.invalidatePendingBindingRequests(now)
+	assert.Equal(t, len(a.pendingBindingRequests), expectedRemovalCount, "Binding invalidation due to timeout did not remove the correct number of binding requests")
+}