diff --git a/cfsetup.yaml b/cfsetup.yaml
index d8d80c49..e30467c1 100644
--- a/cfsetup.yaml
+++ b/cfsetup.yaml
@@ -194,6 +194,7 @@ stretch: &stretch
     builddeps:
       - *pinned_go_fips
       - build-essential
+      - gotest-to-teamcity
     post-cache:
       - export GOOS=linux
       - export GOARCH=amd64
@@ -201,7 +202,7 @@ stretch: &stretch
       # cd to a non-module directory: https://github.com/golang/go/issues/24250
       - (cd / && go get github.com/BurntSushi/go-sumtype)
       - export PATH="$HOME/go/bin:$PATH"
-      - make test
+      - make test | gotest-to-teamcity
   update-homebrew:
     builddeps:
       - openssh-client
diff --git a/cmd/cloudflared/main.go b/cmd/cloudflared/main.go
index 71495db9..0d28cbc7 100644
--- a/cmd/cloudflared/main.go
+++ b/cmd/cloudflared/main.go
@@ -2,6 +2,7 @@ package main
 
 import (
 	"fmt"
+	"math/rand"
 	"strings"
 	"time"
 
@@ -43,6 +44,7 @@ var (
 )
 
 func main() {
+	rand.Seed(time.Now().UnixNano())
 	metrics.RegisterBuildInfo(BuildTime, Version)
 	raven.SetRelease(Version)
 
diff --git a/origin/backoffhandler.go b/origin/backoffhandler.go
index e99605e1..96b3326c 100644
--- a/origin/backoffhandler.go
+++ b/origin/backoffhandler.go
@@ -2,6 +2,7 @@ package origin
 
 import (
 	"context"
+	"math/rand"
 	"time"
 )
 
@@ -30,7 +31,7 @@ type BackoffHandler struct {
 	resetDeadline time.Time
 }
 
-func (b BackoffHandler) GetBackoffDuration(ctx context.Context) (time.Duration, bool) {
+func (b BackoffHandler) GetMaxBackoffDuration(ctx context.Context) (time.Duration, bool) {
 	// Follows the same logic as Backoff, but without mutating the receiver.
 	// This select has to happen first to reflect the actual behaviour of the Backoff function.
 	select {
@@ -45,7 +46,8 @@ func (b BackoffHandler) GetBackoffDuration(ctx context.Context) (time.Duration,
 	if b.retries >= b.MaxRetries && !b.RetryForever {
 		return time.Duration(0), false
 	}
-	return time.Duration(b.GetBaseTime() * 1 << b.retries), true
+	maxTimeToWait := b.GetBaseTime() * 1 << (b.retries + 1)
+	return maxTimeToWait, true
 }
 
 // BackoffTimer returns a channel that sends the current time when the exponential backoff timeout expires.
@@ -62,7 +64,9 @@ func (b *BackoffHandler) BackoffTimer() <-chan time.Time {
 	} else {
 		b.retries++
 	}
-	return timeAfter(time.Duration(b.GetBaseTime() * 1 << (b.retries - 1)))
+	maxTimeToWait := time.Duration(b.GetBaseTime() * 1 << (b.retries))
+	timeToWait := time.Duration(rand.Int63n(maxTimeToWait.Nanoseconds()))
+	return timeAfter(timeToWait)
 }
 
 // Backoff is used to wait according to exponential backoff. Returns false if the
@@ -83,7 +87,9 @@ func (b *BackoffHandler) Backoff(ctx context.Context) bool {
 // Sets a grace period within which the the backoff timer is maintained. After the grace
 // period expires, the number of retries & backoff duration is reset.
 func (b *BackoffHandler) SetGracePeriod() {
-	b.resetDeadline = timeNow().Add(time.Duration(b.GetBaseTime() * 2 << b.retries))
+	maxTimeToWait := b.GetBaseTime() * 2 << (b.retries + 1)
+	timeToWait := time.Duration(rand.Int63n(maxTimeToWait.Nanoseconds()))
+	b.resetDeadline = timeNow().Add(timeToWait)
 }
 
 func (b BackoffHandler) GetBaseTime() time.Duration {
diff --git a/origin/backoffhandler_test.go b/origin/backoffhandler_test.go
index 6c8e4e9c..8add3f0b 100644
--- a/origin/backoffhandler_test.go
+++ b/origin/backoffhandler_test.go
@@ -40,7 +40,7 @@ func TestBackoffCancel(t *testing.T) {
 	if backoff.Backoff(ctx) {
 		t.Fatalf("backoff allowed after cancel")
 	}
-	if _, ok := backoff.GetBackoffDuration(ctx); ok {
+	if _, ok := backoff.GetMaxBackoffDuration(ctx); ok {
 		t.Fatalf("backoff allowed after cancel")
 	}
 }
@@ -69,24 +69,24 @@ func TestBackoffGracePeriod(t *testing.T) {
 	}
 }
 
-func TestGetBackoffDurationRetries(t *testing.T) {
+func TestGetMaxBackoffDurationRetries(t *testing.T) {
 	// make backoff return immediately
 	timeAfter = immediateTimeAfter
 	ctx := context.Background()
 	backoff := BackoffHandler{MaxRetries: 3}
-	if _, ok := backoff.GetBackoffDuration(ctx); !ok {
+	if _, ok := backoff.GetMaxBackoffDuration(ctx); !ok {
 		t.Fatalf("backoff failed immediately")
 	}
 	backoff.Backoff(ctx) // noop
-	if _, ok := backoff.GetBackoffDuration(ctx); !ok {
+	if _, ok := backoff.GetMaxBackoffDuration(ctx); !ok {
 		t.Fatalf("backoff failed after 1 retry")
 	}
 	backoff.Backoff(ctx) // noop
-	if _, ok := backoff.GetBackoffDuration(ctx); !ok {
+	if _, ok := backoff.GetMaxBackoffDuration(ctx); !ok {
 		t.Fatalf("backoff failed after 2 retry")
 	}
 	backoff.Backoff(ctx) // noop
-	if _, ok := backoff.GetBackoffDuration(ctx); ok {
+	if _, ok := backoff.GetMaxBackoffDuration(ctx); ok {
 		t.Fatalf("backoff allowed after 3 (max) retries")
 	}
 	if backoff.Backoff(ctx) {
@@ -94,25 +94,25 @@ func TestGetBackoffDurationRetries(t *testing.T) {
 	}
 }
 
-func TestGetBackoffDuration(t *testing.T) {
+func TestGetMaxBackoffDuration(t *testing.T) {
 	// make backoff return immediately
 	timeAfter = immediateTimeAfter
 	ctx := context.Background()
 	backoff := BackoffHandler{MaxRetries: 3}
-	if duration, ok := backoff.GetBackoffDuration(ctx); !ok || duration != time.Second {
-		t.Fatalf("backoff didn't return 1 second on first retry")
+	if duration, ok := backoff.GetMaxBackoffDuration(ctx); !ok || duration > time.Second*2 {
+		t.Fatalf("backoff (%s) didn't return < 2 seconds on first retry", duration)
 	}
 	backoff.Backoff(ctx) // noop
-	if duration, ok := backoff.GetBackoffDuration(ctx); !ok || duration != time.Second*2 {
-		t.Fatalf("backoff didn't return 2 seconds on second retry")
+	if duration, ok := backoff.GetMaxBackoffDuration(ctx); !ok || duration > time.Second*4 {
+		t.Fatalf("backoff (%s) didn't return < 4 seconds on second retry", duration)
 	}
 	backoff.Backoff(ctx) // noop
-	if duration, ok := backoff.GetBackoffDuration(ctx); !ok || duration != time.Second*4 {
-		t.Fatalf("backoff didn't return 4 seconds on third retry")
+	if duration, ok := backoff.GetMaxBackoffDuration(ctx); !ok || duration > time.Second*8 {
+		t.Fatalf("backoff (%s) didn't return < 8 seconds on third retry", duration)
 	}
 	backoff.Backoff(ctx) // noop
-	if duration, ok := backoff.GetBackoffDuration(ctx); ok || duration != 0 {
-		t.Fatalf("backoff didn't return 0 seconds on fourth retry (exceeding limit)")
+	if duration, ok := backoff.GetMaxBackoffDuration(ctx); ok || duration != 0 {
+		t.Fatalf("backoff (%s) didn't return 0 seconds on fourth retry (exceeding limit)", duration)
 	}
 }
 
@@ -121,27 +121,27 @@ func TestBackoffRetryForever(t *testing.T) {
 	timeAfter = immediateTimeAfter
 	ctx := context.Background()
 	backoff := BackoffHandler{MaxRetries: 3, RetryForever: true}
-	if duration, ok := backoff.GetBackoffDuration(ctx); !ok || duration != time.Second {
-		t.Fatalf("backoff didn't return 1 second on first retry")
+	if duration, ok := backoff.GetMaxBackoffDuration(ctx); !ok || duration > time.Second*2 {
+		t.Fatalf("backoff (%s) didn't return < 2 seconds on first retry", duration)
 	}
 	backoff.Backoff(ctx) // noop
-	if duration, ok := backoff.GetBackoffDuration(ctx); !ok || duration != time.Second*2 {
-		t.Fatalf("backoff didn't return 2 seconds on second retry")
+	if duration, ok := backoff.GetMaxBackoffDuration(ctx); !ok || duration > time.Second*4 {
+		t.Fatalf("backoff (%s) didn't return < 4 seconds on second retry", duration)
 	}
 	backoff.Backoff(ctx) // noop
-	if duration, ok := backoff.GetBackoffDuration(ctx); !ok || duration != time.Second*4 {
-		t.Fatalf("backoff didn't return 4 seconds on third retry")
+	if duration, ok := backoff.GetMaxBackoffDuration(ctx); !ok || duration > time.Second*8 {
+		t.Fatalf("backoff (%s) didn't return < 8 seconds on third retry", duration)
 	}
 	if !backoff.Backoff(ctx) {
 		t.Fatalf("backoff refused on fourth retry despire RetryForever")
 	}
-	if duration, ok := backoff.GetBackoffDuration(ctx); !ok || duration != time.Second*8 {
+	if duration, ok := backoff.GetMaxBackoffDuration(ctx); !ok || duration > time.Second*16 {
 		t.Fatalf("backoff returned %v instead of 8 seconds on fourth retry", duration)
 	}
 	if !backoff.Backoff(ctx) {
 		t.Fatalf("backoff refused on fifth retry despire RetryForever")
 	}
-	if duration, ok := backoff.GetBackoffDuration(ctx); !ok || duration != time.Second*8 {
+	if duration, ok := backoff.GetMaxBackoffDuration(ctx); !ok || duration > time.Second*16 {
 		t.Fatalf("backoff returned %v instead of 8 seconds on fifth retry", duration)
 	}
 }
diff --git a/origin/reconnect.go b/origin/reconnect.go
index 5b64f38c..c05c66e2 100644
--- a/origin/reconnect.go
+++ b/origin/reconnect.go
@@ -108,7 +108,7 @@ func (cm *reconnectCredentialManager) RefreshAuth(
 	authOutcome, err := authenticate(ctx, backoff.Retries())
 	if err != nil {
 		cm.authFail.WithLabelValues(err.Error()).Inc()
-		if _, ok := backoff.GetBackoffDuration(ctx); ok {
+		if _, ok := backoff.GetMaxBackoffDuration(ctx); ok {
 			return backoff.BackoffTimer(), nil
 		}
 		return nil, err
diff --git a/origin/reconnect_test.go b/origin/reconnect_test.go
index d3cf6dbe..9b9dfa8c 100644
--- a/origin/reconnect_test.go
+++ b/origin/reconnect_test.go
@@ -8,6 +8,7 @@ import (
 	"time"
 
 	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
 
 	tunnelpogs "github.com/cloudflare/cloudflared/tunnelrpc/pogs"
 )
@@ -28,13 +29,14 @@ func TestRefreshAuthBackoff(t *testing.T) {
 	// authentication failures should consume the backoff
 	for i := uint(0); i < backoff.MaxRetries; i++ {
 		retryChan, err := rcm.RefreshAuth(context.Background(), backoff, auth)
-		assert.NoError(t, err)
-		assert.NotNil(t, retryChan)
-		assert.Equal(t, (1<<i)*time.Second, wait)
+		require.NoError(t, err)
+		require.NotNil(t, retryChan)
+		require.Greater(t, wait.Seconds(), 0.0)
+		require.Less(t, wait.Seconds(), float64((1<<(i+1))*time.Second))
 	}
 	retryChan, err := rcm.RefreshAuth(context.Background(), backoff, auth)
-	assert.Error(t, err)
-	assert.Nil(t, retryChan)
+	require.Error(t, err)
+	require.Nil(t, retryChan)
 
 	// now we actually make contact with the remote server
 	_, _ = rcm.RefreshAuth(context.Background(), backoff, func(ctx context.Context, n int) (tunnelpogs.AuthOutcome, error) {
@@ -47,8 +49,8 @@ func TestRefreshAuthBackoff(t *testing.T) {
 		expectedGracePeriod := time.Duration(time.Second * 2 << backoff.MaxRetries)
 		return time.Now().Add(expectedGracePeriod * 2)
 	}
-	_, ok := backoff.GetBackoffDuration(context.Background())
-	assert.True(t, ok)
+	_, ok := backoff.GetMaxBackoffDuration(context.Background())
+	require.True(t, ok)
 }
 
 func TestRefreshAuthSuccess(t *testing.T) {
diff --git a/origin/tunnel.go b/origin/tunnel.go
index 260942ad..dee37261 100644
--- a/origin/tunnel.go
+++ b/origin/tunnel.go
@@ -174,11 +174,11 @@ func ServeTunnelLoop(
 
 		config.Observer.SendReconnect(connIndex)
 
-		duration, ok := protocolFallback.GetBackoffDuration(ctx)
+		duration, ok := protocolFallback.GetMaxBackoffDuration(ctx)
 		if !ok {
 			return err
 		}
-		connLog.Info().Msgf("Retrying connection in %s seconds", duration)
+		connLog.Info().Msgf("Retrying connection in up to %s seconds", duration)
 
 		select {
 		case <-ctx.Done():