diff --git a/internal/event/context.go b/internal/event/context.go
index fa20e8c53c..bef6c3668a 100644
--- a/internal/event/context.go
+++ b/internal/event/context.go
@@ -368,7 +368,7 @@ func newSendCtx(ctx context.Context) (context.Context, context.CancelFunc) {
 	switch {
 	case ctx == nil:
 		return context.Background(), nil
-	case ctx.Err() == context.Canceled:
+	case ctx.Err() == context.Canceled || ctx.Err() == context.DeadlineExceeded:
 		sendCtx, sendCancel = context.WithTimeout(context.Background(), cancelledSendTimeout)
 		info, ok := RequestInfoFromContext(ctx)
 		if ok {
diff --git a/internal/event/context_unexported_test.go b/internal/event/context_unexported_test.go
index 48ccdd77d7..338dcdd131 100644
--- a/internal/event/context_unexported_test.go
+++ b/internal/event/context_unexported_test.go
@@ -6,6 +6,7 @@ package event
 import (
 	"context"
 	"testing"
+	"time"
 
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
@@ -44,6 +45,28 @@ func Test_newSendCtx(t *testing.T) {
 			}(),
 			wantCancel: true,
 		},
+		{
+			name: "deadline-exceeded-with-info",
+			ctx: func() context.Context {
+				var err error
+				ctx, cancel := context.WithDeadline(context.Background(), time.Now().Add(-1*time.Millisecond))
+				defer cancel()
+				ctx, err = NewRequestInfoContext(ctx, testInfo)
+				require.NoError(t, err)
+				return ctx
+			}(),
+			wantCancel: true,
+			wantInfo:   true,
+		},
+		{
+			name: "deadline-exceeded-no-info",
+			ctx: func() context.Context {
+				ctx, cancel := context.WithDeadline(context.Background(), time.Now().Add(-1*time.Millisecond))
+				defer cancel()
+				return ctx
+			}(),
+			wantCancel: true,
+		},
 		{
 			name:     "no-info",
 			ctx:      context.Background(),