diff --git a/Dockerfile b/Dockerfile
index 5d52565..67cb492 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -11,7 +11,7 @@ RUN set -e; for pkg in $(go list ./...); do \
 	done
 
 FROM alpine:edge AS resource
-RUN apk add --update bash tzdata ca-certificates
+RUN apk add --update bash tzdata ca-certificates mailcap
 COPY --from=builder /assets /opt/resource
 
 FROM resource AS tests
diff --git a/out_command.go b/out_command.go
index c5fb5eb..402e740 100644
--- a/out_command.go
+++ b/out_command.go
@@ -7,6 +7,9 @@ import (
 	"os"
 	"path/filepath"
 	"strings"
+	"mime"
+	"errors"
+	"time"
 
 	"github.com/google/go-github/github"
 )
@@ -159,9 +162,14 @@ func (c *OutCommand) fileContents(path string) (string, error) {
 }
 
 func (c *OutCommand) upload(release *github.RepositoryRelease, filePath string) error {
-	fmt.Fprintf(c.writer, "uploading %s\n", filePath)
-
 	name := filepath.Base(filePath)
+	mediaType := mime.TypeByExtension(filepath.Ext(name))
+
+	if mediaType == "" {
+		return errors.New("no mime type found for file")
+	}
+
+	fmt.Fprintf(c.writer, "uploading %s as type %s \n", name, mediaType)
 
 	var retryErr error
 	for i := 0; i < 10; i++ {
@@ -177,6 +185,8 @@ func (c *OutCommand) upload(release *github.RepositoryRelease, filePath string)
 			break
 		}
 
+		fmt.Fprintf(c.writer, "\tfailed to upload %s\n", name)
+
 		assets, err := c.github.ListReleaseAssets(*release)
 		if err != nil {
 			return err
@@ -184,6 +194,7 @@ func (c *OutCommand) upload(release *github.RepositoryRelease, filePath string)
 
 		for _, asset := range assets {
 			if asset.Name != nil && *asset.Name == name {
+				fmt.Fprintf(c.writer, "\tdeleting failed upload %s from assets\n", name)
 				err = c.github.DeleteReleaseAsset(*asset)
 				if err != nil {
 					return err
@@ -191,6 +202,8 @@ func (c *OutCommand) upload(release *github.RepositoryRelease, filePath string)
 				break
 			}
 		}
+
+		time.Sleep(2 * time.Second)
 	}
 
 	if retryErr != nil {
diff --git a/vendor/github.com/google/go-github/github/repos_releases.go b/vendor/github.com/google/go-github/github/repos_releases.go
index 5c27565..df78258 100644
--- a/vendor/github.com/google/go-github/github/repos_releases.go
+++ b/vendor/github.com/google/go-github/github/repos_releases.go
@@ -313,6 +313,8 @@ func (s *RepositoriesService) UploadReleaseAsset(ctx context.Context, owner, rep
 	}
 
 	mediaType := mime.TypeByExtension(filepath.Ext(file.Name()))
+	os.Stderr.WriteString("MediaType: " + mediaType + "\n")
+
 	req, err := s.client.NewUploadRequest(u, file, stat.Size(), mediaType)
 	if err != nil {
 		return nil, nil, err