diff --git a/internal/notify/email.go b/internal/notify/email.go
index 4606d73..e645eef 100644
--- a/internal/notify/email.go
+++ b/internal/notify/email.go
@@ -18,8 +18,11 @@ import (
 
 	"github.com/moov-io/ach"
 	"github.com/moov-io/achgateway/internal/service"
+	"github.com/moov-io/base/telemetry"
 
 	gomail "github.com/ory/mail/v3"
+	"go.opentelemetry.io/otel/attribute"
+	"go.opentelemetry.io/otel/trace"
 )
 
 type Email struct {
@@ -94,20 +97,20 @@ func setupGoMailClient(cfg *service.Email) (*gomail.Dialer, error) {
 	}, nil
 }
 
-func (mailer *Email) Info(msg *Message) error {
+func (mailer *Email) Info(ctx context.Context, msg *Message) error {
 	contents, err := marshalEmail(mailer.cfg, msg)
 	if err != nil {
 		return err
 	}
-	return sendEmail(mailer.cfg, mailer.dialer, msg.Filename, contents)
+	return sendEmail(ctx, mailer.cfg, mailer.dialer, msg.Filename, contents)
 }
 
-func (mailer *Email) Critical(msg *Message) error {
+func (mailer *Email) Critical(ctx context.Context, msg *Message) error {
 	contents, err := marshalEmail(mailer.cfg, msg)
 	if err != nil {
 		return err
 	}
-	return sendEmail(mailer.cfg, mailer.dialer, msg.Filename, contents)
+	return sendEmail(ctx, mailer.cfg, mailer.dialer, msg.Filename, contents)
 }
 
 func marshalEmail(cfg *service.Email, msg *Message) (string, error) {
@@ -136,7 +139,12 @@ func marshalEmail(cfg *service.Email, msg *Message) (string, error) {
 	return buf.String(), nil
 }
 
-func sendEmail(cfg *service.Email, dialer *gomail.Dialer, filename, body string) error {
+func sendEmail(ctx context.Context, cfg *service.Email, dialer *gomail.Dialer, filename, body string) error {
+	_, span := telemetry.StartSpan(ctx, "notify-send-email", trace.WithAttributes(
+		attribute.String("achgateway.filename", filename),
+	))
+	defer span.End()
+
 	m := gomail.NewMessage()
 	m.SetHeader("From", cfg.From)
 	m.SetHeader("To", cfg.To...)
@@ -150,6 +158,8 @@ func sendEmail(cfg *service.Email, dialer *gomail.Dialer, filename, body string)
 
 	var outErr error
 	for tries := 1; tries <= maxRetries; tries++ {
+		span.AddEvent(fmt.Sprintf("attempt-%d", tries))
+
 		outErr = dialer.DialAndSend(context.Background(), m)
 		if outErr != nil {
 			if strings.Contains(outErr.Error(), "i/o timeout") {
diff --git a/internal/notify/email_test.go b/internal/notify/email_test.go
index bc647f5..9db808b 100644
--- a/internal/notify/email_test.go
+++ b/internal/notify/email_test.go
@@ -5,6 +5,7 @@
 package notify
 
 import (
+	"context"
 	"fmt"
 	"path/filepath"
 	"strings"
@@ -45,7 +46,8 @@ func TestEmailSend(t *testing.T) {
 	body, err := marshalEmail(cfg, msg)
 	require.NoError(t, err)
 
-	if err := sendEmail(cfg, dialer, msg.Filename, body); err != nil {
+	ctx := context.Background()
+	if err := sendEmail(ctx, cfg, dialer, msg.Filename, body); err != nil {
 		t.Fatal(err)
 	}
 
diff --git a/internal/notify/kafka.go b/internal/notify/kafka.go
index 7f80b97..3eac2f2 100644
--- a/internal/notify/kafka.go
+++ b/internal/notify/kafka.go
@@ -41,14 +41,14 @@ type event struct {
 	UploadStatus uploadStatus `json:"uploadStatus"`
 }
 
-func (s *Kafka) Info(msg *Message) error {
+func (s *Kafka) Info(ctx context.Context, msg *Message) error {
 	event := marshalKafkaMessage(success, msg)
-	return s.send(event)
+	return s.send(ctx, event)
 }
 
-func (s *Kafka) Critical(msg *Message) error {
+func (s *Kafka) Critical(ctx context.Context, msg *Message) error {
 	event := marshalKafkaMessage(failed, msg)
-	return s.send(event)
+	return s.send(ctx, event)
 }
 
 func marshalKafkaMessage(status uploadStatus, msg *Message) event {
@@ -67,7 +67,7 @@ func marshalKafkaMessage(status uploadStatus, msg *Message) event {
 	}
 }
 
-func (s *Kafka) send(evt event) error {
+func (s *Kafka) send(ctx context.Context, evt event) error {
 	bs, err := compliance.Protect(s.cfg.Transform, models.Event{
 		Type:  "",
 		Event: evt,
@@ -76,7 +76,7 @@ func (s *Kafka) send(evt event) error {
 		return fmt.Errorf("unable to protect notifer kafka event: %v", err)
 	}
 
-	return s.publisher.Send(context.Background(), &pubsub.Message{
+	return s.publisher.Send(ctx, &pubsub.Message{
 		Body: bs,
 	})
 }
diff --git a/internal/notify/mock_sender.go b/internal/notify/mock_sender.go
index 604a12b..2e355fd 100644
--- a/internal/notify/mock_sender.go
+++ b/internal/notify/mock_sender.go
@@ -1,5 +1,7 @@
 package notify
 
+import "context"
+
 type MockSender struct {
 	infoCalled     bool
 	criticalCalled bool
@@ -7,13 +9,13 @@ type MockSender struct {
 	msg            *Message
 }
 
-func (s *MockSender) Info(msg *Message) error {
+func (s *MockSender) Info(_ context.Context, msg *Message) error {
 	s.infoCalled = true
 	s.msg = msg
 	return s.Err
 }
 
-func (s *MockSender) Critical(msg *Message) error {
+func (s *MockSender) Critical(_ context.Context, msg *Message) error {
 	s.criticalCalled = true
 	s.msg = msg
 	return s.Err
diff --git a/internal/notify/multi.go b/internal/notify/multi.go
index c144f0c..849d94f 100644
--- a/internal/notify/multi.go
+++ b/internal/notify/multi.go
@@ -80,11 +80,11 @@ func (ms *MultiSender) senderTypes() string {
 	return strings.Join(out, ", ")
 }
 
-func (ms *MultiSender) Info(msg *Message) error {
+func (ms *MultiSender) Info(ctx context.Context, msg *Message) error {
 	var firstError error
 	for i := range ms.senders {
-		err := ms.retry(func() error {
-			return ms.senders[i].Info(msg)
+		err := ms.retry(ctx, func() error {
+			return ms.senders[i].Info(ctx, msg)
 		})
 		if err != nil {
 			ms.logger.Logf("multi-sender: Info %T: %v", ms.senders[i], err)
@@ -99,11 +99,11 @@ func (ms *MultiSender) Info(msg *Message) error {
 	return firstError
 }
 
-func (ms *MultiSender) Critical(msg *Message) error {
+func (ms *MultiSender) Critical(ctx context.Context, msg *Message) error {
 	var firstError error
 	for i := range ms.senders {
-		err := ms.retry(func() error {
-			return ms.senders[i].Critical(msg)
+		err := ms.retry(ctx, func() error {
+			return ms.senders[i].Critical(ctx, msg)
 		})
 		if err != nil {
 			ms.logger.Logf("multi-sender: Critical %T: %v", ms.senders[i], err)
@@ -118,13 +118,12 @@ func (ms *MultiSender) Critical(msg *Message) error {
 	return firstError
 }
 
-func (ms *MultiSender) retry(f func() error) error {
+func (ms *MultiSender) retry(ctx context.Context, f func() error) error {
 	if ms.retryConfig != nil {
 		backoff, err := setupBackoff(ms.retryConfig)
 		if err != nil {
 			return fmt.Errorf("retry: %v", err)
 		}
-		ctx := context.Background()
 		return retry.Do(ctx, backoff, func(ctx context.Context) error {
 			return isRetryableError(f())
 		})
diff --git a/internal/notify/multi_test.go b/internal/notify/multi_test.go
index 894b0fa..e5076d4 100644
--- a/internal/notify/multi_test.go
+++ b/internal/notify/multi_test.go
@@ -5,6 +5,7 @@
 package notify
 
 import (
+	"context"
 	"errors"
 	"testing"
 	"time"
@@ -25,13 +26,14 @@ func TestMultiSender(t *testing.T) {
 
 	msg := &Message{Direction: Upload}
 
-	require.NoError(t, sender.Info(msg))
-	require.NoError(t, sender.Critical(msg))
+	ctx := context.Background()
+	require.NoError(t, sender.Info(ctx, msg))
+	require.NoError(t, sender.Critical(ctx, msg))
 
 	sender.senders = append(sender.senders, &MockSender{})
 
-	require.NoError(t, sender.Info(msg))
-	require.NoError(t, sender.Critical(msg))
+	require.NoError(t, sender.Info(ctx, msg))
+	require.NoError(t, sender.Critical(ctx, msg))
 }
 
 func TestMultiSenderErr(t *testing.T) {
@@ -44,10 +46,11 @@ func TestMultiSenderErr(t *testing.T) {
 		},
 	}
 
+	ctx := context.Background()
 	msg := &Message{Direction: Upload}
 
-	require.Equal(t, sender.Info(msg), sendErr)
-	require.Equal(t, sender.Critical(msg), sendErr)
+	require.Equal(t, sender.Info(ctx, msg), sendErr)
+	require.Equal(t, sender.Critical(ctx, msg), sendErr)
 }
 
 func TestMulti__Retry(t *testing.T) {
diff --git a/internal/notify/notify.go b/internal/notify/notify.go
index 2584f9e..70b8673 100644
--- a/internal/notify/notify.go
+++ b/internal/notify/notify.go
@@ -5,6 +5,8 @@
 package notify
 
 import (
+	"context"
+
 	"github.com/moov-io/ach"
 )
 
@@ -26,6 +28,6 @@ type Message struct {
 }
 
 type Sender interface {
-	Info(msg *Message) error
-	Critical(msg *Message) error
+	Info(ctx context.Context, msg *Message) error
+	Critical(ctx context.Context, msg *Message) error
 }
diff --git a/internal/notify/pagerduty.go b/internal/notify/pagerduty.go
index 537f71e..10edde2 100644
--- a/internal/notify/pagerduty.go
+++ b/internal/notify/pagerduty.go
@@ -10,8 +10,11 @@ import (
 	"fmt"
 
 	"github.com/moov-io/achgateway/internal/service"
+	"github.com/moov-io/base/telemetry"
 
 	"github.com/PagerDuty/go-pagerduty"
+	"go.opentelemetry.io/otel/attribute"
+	"go.opentelemetry.io/otel/trace"
 )
 
 type PagerDuty struct {
@@ -50,12 +53,12 @@ func (pd *PagerDuty) Ping() error {
 	return nil
 }
 
-func (pd *PagerDuty) Info(msg *Message) error {
+func (pd *PagerDuty) Info(_ context.Context, msg *Message) error {
 	// Skip sending Info notifications, PagerDuty is setup for critical alerts
 	return nil
 }
 
-func (pd *PagerDuty) Critical(msg *Message) error {
+func (pd *PagerDuty) Critical(ctx context.Context, msg *Message) error {
 	opts := &pagerduty.CreateIncidentOptions{
 		Type:  "incident",
 		Title: fmt.Sprintf("ERROR during file %s", msg.Direction),
@@ -72,11 +75,15 @@ func (pd *PagerDuty) Critical(msg *Message) error {
 		// Downloads don't have to such a high priority
 		opts.Urgency = "low"
 	}
-	return pd.createIncident(opts)
+	return pd.createIncident(ctx, opts)
 }
 
-func (pd *PagerDuty) createIncident(opts *pagerduty.CreateIncidentOptions) error {
-	ctx := context.Background()
+func (pd *PagerDuty) createIncident(ctx context.Context, opts *pagerduty.CreateIncidentOptions) error {
+	_, span := telemetry.StartSpan(ctx, "notify-trigger-pagerduty", trace.WithAttributes(
+		attribute.String("achgateway.error", opts.Title),
+	))
+	defer span.End()
+
 	_, err := pd.client.CreateIncidentWithContext(ctx, pd.from, opts)
 	return err
 }
diff --git a/internal/notify/pagerduty_test.go b/internal/notify/pagerduty_test.go
index cbd6b09..ce8bfe1 100644
--- a/internal/notify/pagerduty_test.go
+++ b/internal/notify/pagerduty_test.go
@@ -5,11 +5,13 @@
 package notify
 
 import (
+	"context"
 	"os"
 	"testing"
 
 	"github.com/moov-io/ach"
 	"github.com/moov-io/achgateway/internal/service"
+
 	"github.com/stretchr/testify/require"
 )
 
@@ -40,8 +42,9 @@ func TestPagerDuty(t *testing.T) {
 	}
 
 	file := ach.NewFile()
+	ctx := context.Background()
 
-	if err := pd.Info(&Message{
+	if err := pd.Info(ctx, &Message{
 		Direction: Download,
 		Filename:  "20200529-140002-1.ach",
 		File:      file,
@@ -49,7 +52,7 @@ func TestPagerDuty(t *testing.T) {
 		t.Fatal(err)
 	}
 
-	if err := pd.Critical(&Message{
+	if err := pd.Critical(ctx, &Message{
 		Direction: Upload,
 		Filename:  "20200529-140002-2.ach",
 		File:      file,
diff --git a/internal/notify/slack.go b/internal/notify/slack.go
index 358a54e..4e4f3b3 100644
--- a/internal/notify/slack.go
+++ b/internal/notify/slack.go
@@ -6,6 +6,7 @@ package notify
 
 import (
 	"bytes"
+	"context"
 	"encoding/json"
 	"fmt"
 	"net/http"
@@ -14,6 +15,10 @@ import (
 
 	"github.com/moov-io/achgateway"
 	"github.com/moov-io/achgateway/internal/service"
+	"github.com/moov-io/base/telemetry"
+
+	"go.opentelemetry.io/otel/attribute"
+	"go.opentelemetry.io/otel/trace"
 )
 
 type Slack struct {
@@ -40,14 +45,14 @@ const (
 	failed  = uploadStatus("FAILED")
 )
 
-func (s *Slack) Info(msg *Message) error {
+func (s *Slack) Info(ctx context.Context, msg *Message) error {
 	slackMsg := marshalSlackMessage(success, msg)
-	return s.send(slackMsg)
+	return s.send(ctx, slackMsg)
 }
 
-func (s *Slack) Critical(msg *Message) error {
+func (s *Slack) Critical(ctx context.Context, msg *Message) error {
 	slackMsg := marshalSlackMessage(failed, msg)
-	return s.send(slackMsg)
+	return s.send(ctx, slackMsg)
 }
 
 func marshalSlackMessage(status uploadStatus, msg *Message) string {
@@ -77,7 +82,12 @@ type webhook struct {
 	Text string `json:"text"`
 }
 
-func (s *Slack) send(msg string) error {
+func (s *Slack) send(ctx context.Context, msg string) error {
+	_, span := telemetry.StartSpan(ctx, "notify-send-slack", trace.WithAttributes(
+		attribute.String("achgateway.message", msg),
+	))
+	defer span.End()
+
 	var body bytes.Buffer
 	err := json.NewEncoder(&body).Encode(&webhook{
 		Text: msg,
@@ -86,7 +96,7 @@ func (s *Slack) send(msg string) error {
 		return err
 	}
 
-	req, err := http.NewRequest("POST", s.webhookURL, &body)
+	req, err := http.NewRequestWithContext(ctx, "POST", s.webhookURL, &body)
 	if err != nil {
 		return err
 	}
diff --git a/internal/notify/slack_test.go b/internal/notify/slack_test.go
index 2164319..8a923aa 100644
--- a/internal/notify/slack_test.go
+++ b/internal/notify/slack_test.go
@@ -6,6 +6,7 @@ package notify
 
 import (
 	"bytes"
+	"context"
 	"io"
 	"net/http"
 	"net/http/httptest"
@@ -14,9 +15,8 @@ import (
 	"github.com/moov-io/ach"
 	"github.com/moov-io/achgateway/internal/service"
 
-	"github.com/stretchr/testify/require"
-
 	"github.com/gorilla/mux"
+	"github.com/stretchr/testify/require"
 )
 
 func TestSlack(t *testing.T) {
@@ -44,12 +44,13 @@ func TestSlack(t *testing.T) {
 		Filename:  "20200529-152259.ach",
 		File:      ach.NewFile(),
 	}
+	ctx := context.Background()
 
-	if err := slack.Info(msg); err != nil {
+	if err := slack.Info(ctx, msg); err != nil {
 		t.Fatal(err)
 	}
 
-	if err := slack.Critical(msg); err != nil {
+	if err := slack.Critical(ctx, msg); err != nil {
 		t.Fatal(err)
 	}
 }
diff --git a/internal/pipeline/aggregate.go b/internal/pipeline/aggregate.go
index c841511..362787a 100644
--- a/internal/pipeline/aggregate.go
+++ b/internal/pipeline/aggregate.go
@@ -350,11 +350,11 @@ func (xfagg *aggregator) notifyAfterUpload(ctx context.Context, filename string,
 	}
 
 	if uploadErr != nil {
-		if err := notifier.Critical(msg); err != nil {
+		if err := notifier.Critical(ctx, msg); err != nil {
 			return fmt.Errorf("problem sending critical notification for file=%s: %v", filename, err)
 		}
 	} else {
-		if err := notifier.Info(msg); err != nil {
+		if err := notifier.Info(ctx, msg); err != nil {
 			return fmt.Errorf("problem sending info notification for file=%s: %v", filename, err)
 		}
 	}
@@ -378,6 +378,11 @@ func (xfagg *aggregator) notifyAboutHoliday(day *schedule.Day) {
 		return
 	}
 
+	ctx, span := telemetry.StartSpan(context.Background(), "notify-about-holiday", trace.WithAttributes(
+		attribute.String("achgateway.holiday", day.Holiday.Name),
+	))
+	defer span.End()
+
 	if uploadAgent.Notifications != nil {
 		slackConfigs := xfagg.shard.Notifications.FindSlacks(uploadAgent.Notifications.Slack)
 		for i := range slackConfigs {
@@ -387,7 +392,7 @@ func (xfagg *aggregator) notifyAboutHoliday(day *schedule.Day) {
 				continue
 			}
 
-			err = ss.Info(&notify.Message{
+			err = ss.Info(ctx, &notify.Message{
 				Contents: formatHolidayMessage(day),
 			})
 			if err != nil {