diff --git a/pkg/v1/remote/write.go b/pkg/v1/remote/write.go
index fb3dd7974..7b9f31e19 100644
--- a/pkg/v1/remote/write.go
+++ b/pkg/v1/remote/write.go
@@ -337,16 +337,29 @@ func (r *progressReader) Close() error { return r.rc.Close() }
 // streamBlob streams the contents of the blob to the specified location.
 // On failure, this will return an error.  On success, this will return the location
 // header indicating how to commit the streamed blob.
-func (w *writer) streamBlob(ctx context.Context, blob io.ReadCloser, streamLocation string) (commitLocation string, rerr error) {
+func (w *writer) streamBlob(ctx context.Context, layer v1.Layer, streamLocation string) (commitLocation string, rerr error) {
 	reset := func() {}
 	defer func() {
 		if rerr != nil {
 			reset()
 		}
 	}()
+	blob, err := layer.Compressed()
+	if err != nil {
+		return "", err
+	}
+
+	getBody := layer.Compressed
 	if w.updates != nil {
 		var count int64
 		blob = &progressReader{rc: blob, updates: w.updates, lastUpdate: w.lastUpdate, count: &count}
+		getBody = func() (io.ReadCloser, error) {
+			blob, err := layer.Compressed()
+			if err != nil {
+				return nil, err
+			}
+			return &progressReader{rc: blob, updates: w.updates, lastUpdate: w.lastUpdate, count: &count}, nil
+		}
 		reset = func() {
 			atomic.AddInt64(&w.lastUpdate.Complete, -count)
 			w.updates <- *w.lastUpdate
@@ -357,6 +370,10 @@ func (w *writer) streamBlob(ctx context.Context, blob io.ReadCloser, streamLocat
 	if err != nil {
 		return "", err
 	}
+	if _, ok := layer.(*stream.Layer); !ok {
+		// We can't retry streaming layers.
+		req.GetBody = getBody
+	}
 	req.Header.Set("Content-Type", "application/octet-stream")
 
 	resp, err := w.client.Do(req.WithContext(ctx))
@@ -467,11 +484,7 @@ func (w *writer) uploadOne(ctx context.Context, l v1.Layer) error {
 			ctx = redact.NewContext(ctx, "omitting binary blobs from logs")
 		}
 
-		blob, err := l.Compressed()
-		if err != nil {
-			return err
-		}
-		location, err = w.streamBlob(ctx, blob, location)
+		location, err = w.streamBlob(ctx, l, location)
 		if err != nil {
 			return err
 		}
diff --git a/pkg/v1/remote/write_test.go b/pkg/v1/remote/write_test.go
index 3d031c1a8..092465e9c 100644
--- a/pkg/v1/remote/write_test.go
+++ b/pkg/v1/remote/write_test.go
@@ -586,12 +586,8 @@ func TestStreamBlob(t *testing.T) {
 	if err != nil {
 		t.Fatalf("ConfigLayer: %v", err)
 	}
-	blob, err := l.Compressed()
-	if err != nil {
-		t.Fatalf("layer.Compressed: %v", err)
-	}
 
-	commitLocation, err := w.streamBlob(context.Background(), blob, streamLocation.String())
+	commitLocation, err := w.streamBlob(context.Background(), l, streamLocation.String())
 	if err != nil {
 		t.Errorf("streamBlob() = %v", err)
 	}
@@ -638,12 +634,8 @@ func TestStreamLayer(t *testing.T) {
 
 	streamLocation := w.url(expectedPath)
 	sl := stream.NewLayer(newBlob())
-	blob, err := sl.Compressed()
-	if err != nil {
-		t.Fatalf("layer.Compressed: %v", err)
-	}
 
-	commitLocation, err := w.streamBlob(context.Background(), blob, streamLocation.String())
+	commitLocation, err := w.streamBlob(context.Background(), sl, streamLocation.String())
 	if err != nil {
 		t.Errorf("streamBlob: %v", err)
 	}