diff --git a/content/proxy/content_writer.go b/content/proxy/content_writer.go
index 6d35ba61a..5434a1568 100644
--- a/content/proxy/content_writer.go
+++ b/content/proxy/content_writer.go
@@ -57,7 +57,7 @@ func (rw *remoteWriter) Status() (content.Status, error) {
 		Action: contentapi.WriteActionStat,
 	})
 	if err != nil {
-		return content.Status{}, errors.Wrap(err, "error getting writer status")
+		return content.Status{}, errors.Wrap(errdefs.FromGRPC(err), "error getting writer status")
 	}
 
 	return content.Status{
@@ -82,7 +82,7 @@ func (rw *remoteWriter) Write(p []byte) (n int, err error) {
 		Data:   p,
 	})
 	if err != nil {
-		return 0, err
+		return 0, errors.Wrap(errdefs.FromGRPC(err), "failed to send write")
 	}
 
 	n = int(resp.Offset - offset)
@@ -112,7 +112,7 @@ func (rw *remoteWriter) Commit(ctx context.Context, size int64, expected digest.
 		Labels:   base.Labels,
 	})
 	if err != nil {
-		return errdefs.FromGRPC(err)
+		return errors.Wrap(errdefs.FromGRPC(err), "commit failed")
 	}
 
 	if size != 0 && resp.Offset != size {
diff --git a/export.go b/export.go
index 7aac309ba..bfc25316c 100644
--- a/export.go
+++ b/export.go
@@ -22,6 +22,7 @@ import (
 
 	"github.com/containerd/containerd/images"
 	ocispec "github.com/opencontainers/image-spec/specs-go/v1"
+	"github.com/pkg/errors"
 )
 
 type exportOpts struct {
@@ -51,7 +52,7 @@ func (c *Client) Export(ctx context.Context, exporter images.Exporter, desc ocis
 	}
 	pr, pw := io.Pipe()
 	go func() {
-		pw.CloseWithError(exporter.Export(ctx, c.ContentStore(), desc, pw))
+		pw.CloseWithError(errors.Wrap(exporter.Export(ctx, c.ContentStore(), desc, pw), "export failed"))
 	}()
 	return pr, nil
 }
diff --git a/images/oci/exporter.go b/images/oci/exporter.go
index d05c22b64..bf5751e6a 100644
--- a/images/oci/exporter.go
+++ b/images/oci/exporter.go
@@ -94,7 +94,7 @@ func blobRecord(cs content.Provider, desc ocispec.Descriptor) tarRecord {
 		CopyTo: func(ctx context.Context, w io.Writer) (int64, error) {
 			r, err := cs.ReaderAt(ctx, desc)
 			if err != nil {
-				return 0, err
+				return 0, errors.Wrap(err, "failed to get reader")
 			}
 			defer r.Close()
 
@@ -103,7 +103,7 @@ func blobRecord(cs content.Provider, desc ocispec.Descriptor) tarRecord {
 
 			n, err := io.Copy(io.MultiWriter(w, dgstr.Hash()), content.NewReader(r))
 			if err != nil {
-				return 0, err
+				return 0, errors.Wrap(err, "failed to copy to tar")
 			}
 			if dgstr.Digest() != desc.Digest {
 				return 0, errors.Errorf("unexpected digest %s copied", dgstr.Digest())