diff --git a/CHANGELOG.md b/CHANGELOG.md
index 08745581205..60003ffc014 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -44,6 +44,7 @@ This project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0.htm
 - `traceIDRatioSampler` (given by `TraceIDRatioBased(float64)`) now uses the rightmost bits for sampling decisions,
   fixing random sampling when using ID generators like `xray.IDGenerator`
   and increasing parity with other language implementations. (#3557)
+- The OTLP exporter for traces and metrics will print the final retryable error message when attempts to retry time out. (#3514)
 - The instrument kind names in `go.opentelemetry.io/otel/sdk/metric` are updated to match the API. (#3562)
   - `InstrumentKindSyncCounter` is renamed to `InstrumentKindCounter`
   - `InstrumentKindSyncUpDownCounter` is renamed to `InstrumentKindUpDownCounter`
diff --git a/exporters/otlp/internal/retry/retry.go b/exporters/otlp/internal/retry/retry.go
index 3d43f7aea97..2d14d248336 100644
--- a/exporters/otlp/internal/retry/retry.go
+++ b/exporters/otlp/internal/retry/retry.go
@@ -119,8 +119,8 @@ func (c Config) RequestFunc(evaluate EvaluateFunc) RequestFunc {
 				delay = throttle
 			}
 
-			if err := waitFunc(ctx, delay); err != nil {
-				return err
+			if ctxErr := waitFunc(ctx, delay); ctxErr != nil {
+				return fmt.Errorf("%w: %s", ctxErr, err)
 			}
 		}
 	}
@@ -129,6 +129,9 @@ func (c Config) RequestFunc(evaluate EvaluateFunc) RequestFunc {
 // Allow override for testing.
 var waitFunc = wait
 
+// wait takes the caller's context, and the amount of time to wait.  It will
+// return nil if the timer fires before or at the same time as the context's
+// deadline.  This indicates that the call can be retried.
 func wait(ctx context.Context, delay time.Duration) error {
 	timer := time.NewTimer(delay)
 	defer timer.Stop()
diff --git a/exporters/otlp/internal/retry/retry_test.go b/exporters/otlp/internal/retry/retry_test.go
index 2b2f92e69c9..61f84e8350d 100644
--- a/exporters/otlp/internal/retry/retry_test.go
+++ b/exporters/otlp/internal/retry/retry_test.go
@@ -32,19 +32,16 @@ func TestWait(t *testing.T) {
 		expected error
 	}{
 		{
-			ctx:      context.Background(),
-			delay:    time.Duration(0),
-			expected: nil,
+			ctx:   context.Background(),
+			delay: time.Duration(0),
 		},
 		{
-			ctx:      context.Background(),
-			delay:    time.Duration(1),
-			expected: nil,
+			ctx:   context.Background(),
+			delay: time.Duration(1),
 		},
 		{
-			ctx:      context.Background(),
-			delay:    time.Duration(-1),
-			expected: nil,
+			ctx:   context.Background(),
+			delay: time.Duration(-1),
 		},
 		{
 			ctx: func() context.Context {
@@ -59,7 +56,12 @@ func TestWait(t *testing.T) {
 	}
 
 	for _, test := range tests {
-		assert.Equal(t, test.expected, wait(test.ctx, test.delay))
+		err := wait(test.ctx, test.delay)
+		if test.expected == nil {
+			assert.NoError(t, err)
+		} else {
+			assert.ErrorIs(t, err, test.expected)
+		}
 	}
 }
 
@@ -133,7 +135,7 @@ func TestBackoffRetry(t *testing.T) {
 	origWait := waitFunc
 	var done bool
 	waitFunc = func(_ context.Context, d time.Duration) error {
-		delta := math.Ceil(float64(delay)*backoff.DefaultRandomizationFactor) - float64(delay)
+		delta := math.Ceil(float64(delay) * backoff.DefaultRandomizationFactor)
 		assert.InDelta(t, delay, d, delta, "retry not backoffed")
 		// Try twice to ensure call is attempted again after delay.
 		if done {
@@ -150,6 +152,31 @@ func TestBackoffRetry(t *testing.T) {
 	}), assert.AnError)
 }
 
+func TestBackoffRetryCanceledContext(t *testing.T) {
+	ev := func(error) (bool, time.Duration) { return true, 0 }
+
+	delay := time.Millisecond
+	reqFunc := Config{
+		Enabled:         true,
+		InitialInterval: delay,
+		MaxInterval:     delay,
+		// Never stop retrying.
+		MaxElapsedTime: 10 * time.Millisecond,
+	}.RequestFunc(ev)
+
+	ctx, cancel := context.WithCancel(context.Background())
+	count := 0
+	cancel()
+	err := reqFunc(ctx, func(context.Context) error {
+		count++
+		return assert.AnError
+	})
+
+	assert.ErrorIs(t, err, context.Canceled)
+	assert.Contains(t, err.Error(), assert.AnError.Error())
+	assert.Equal(t, 1, count)
+}
+
 func TestThrottledRetryGreaterThanMaxElapsedTime(t *testing.T) {
 	// Ensure the throttle delay is used by making longer than backoff delay.
 	tDelay, bDelay := time.Hour, time.Nanosecond