diff --git a/build_library/release_util.sh b/build_library/release_util.sh
index bab54f07f6..ba4c94daaa 100644
--- a/build_library/release_util.sh
+++ b/build_library/release_util.sh
@@ -85,40 +85,50 @@ upload_packages() {
 
 make_digests() {
     local dirname=$(dirname "$1")
-    local filename=$(basename "$1")
+    local basename=$(basename "$1")
+
     cd "${dirname}"
-    info "Computing DIGESTS for ${filename}"
-    echo -n > "${filename}.DIGESTS"
-    for hash in md5 sha1 sha512; do
-        echo "# $hash HASH" | tr "a-z" "A-Z" >> "${filename}.DIGESTS"
-        ${hash}sum "${filename}" >> "${filename}.DIGESTS"
+    echo -n > "${basename}.DIGESTS"
+    for filename in "$@"; do
+        filename=$(basename "$filename")
+        info "Computing DIGESTS for ${filename}"
+        for hash in md5 sha1 sha512; do
+            echo "# $hash HASH" | tr "a-z" "A-Z" >> "${basename}.DIGESTS"
+            ${hash}sum "${filename}" >> "${basename}.DIGESTS"
+        done
     done
     cd -
 }
 
+# Upload a image along with optional supporting files
+# The image file must be the first argument
 upload_image() {
     [[ ${FLAGS_upload} -eq ${FLAGS_TRUE} ]] || return 0
     [[ -n "${BOARD}" ]] || die "board_options.sh must be sourced first"
 
-    local BUILT_IMAGE="$1"
+    local uploads=()
+    local filename
+    for filename in "$@"; do
+        if [[ ! -f "${filename}" ]]; then
+            die "File '${filename}' does not exist!"
+        fi
 
-    if [[ ! -f "${BUILT_IMAGE}" ]]; then
-        die "Image '${BUILT_IMAGE}' does not exist!"
-    fi
-
-    # Compress raw images
-    if [[ "${BUILT_IMAGE}" =~ \.(img|bin)$ ]]; then
-        info "Compressing ${BUILT_IMAGE##*/}"
-        $IMAGE_ZIPPER "${BUILT_IMAGE}"
-        BUILT_IMAGE="${BUILT_IMAGE}${IMAGE_ZIPEXT}"
-    fi
+        # Compress disk images
+        if [[ "${filename}" =~ \.(img|bin|vdi|vmdk)$ ]]; then
+            info "Compressing ${filename##*/}"
+            $IMAGE_ZIPPER -f "${filename}"
+            uploads+=( "${filename}${IMAGE_ZIPEXT}" )
+        else
+            uploads+=( "${filename}" )
+        fi
+    done
 
     # For consistency generate a .DIGESTS file similar to the one catalyst
     # produces for the SDK tarballs and up upload it too.
-    make_digests "${BUILT_IMAGE}"
+    make_digests "${uploads[@]}"
+    uploads+=( "${uploads[0]}.DIGESTS" )
 
-    local log_msg="${BUILT_IMAGE##*/}"
+    local log_msg="${1##*/}"
     local def_upload_path="${UPLOAD_ROOT}/${BOARD}/${COREOS_VERSION_STRING}"
-    upload_files "${log_msg}" "${def_upload_path}" "" \
-        "${BUILT_IMAGE}" "${BUILT_IMAGE}.DIGESTS"
+    upload_files "${log_msg}" "${def_upload_path}" "" "${uploads[@]}"
 }
diff --git a/build_library/vm_image_util.sh b/build_library/vm_image_util.sh
index 3dcf608c5d..cf0dd573f1 100644
--- a/build_library/vm_image_util.sh
+++ b/build_library/vm_image_util.sh
@@ -26,6 +26,9 @@ VM_README=
 VM_NAME=
 VM_UUID=
 
+# Contains a list of all generated files
+VM_GENERATED_FILES=()
+
 ## DEFAULT
 # If set to 1 use a hybrid GPT/MBR format instead of plain GPT
 IMG_DEFAULT_HYBRID_MBR=0
@@ -228,8 +231,9 @@ write_vm_disk() {
     fi
 
     local disk_format=$(_get_vm_opt DISK_FORMAT)
-    info "Writing $disk_format image to $(relpath "${VM_DST_IMG}")"
+    info "Writing $disk_format image $(basename "${VM_DST_IMG}")"
     _write_${disk_format}_disk "${VM_TMP_IMG}" "${VM_DST_IMG}"
+    VM_GENERATED_FILES+=( "${VM_DST_IMG}" )
 }
 
 _write_hybrid_mbr() {
@@ -319,6 +323,8 @@ qemu-system-x86_64 -curses -m ${vm_mem} -readconfig "${conf_path##*/}"
 SSH into that host with:
 ssh 127.0.0.1 -p 2222
 EOF
+
+    VM_GENERATED_FILES+=( "${conf_path}" "${VM_README}" )
 }
 
 # Generate the vmware config file
@@ -346,6 +352,7 @@ guestOS = "otherlinux"
 ethernet0.addressType = "generated"
 floppy0.present = "FALSE""
 EOF
+    VM_GENERATED_FILES+=( "${vmx_path}" )
 }
 
 # Generate a new-style (xl) Xen config file for both pvgrub and pygrub
@@ -393,6 +400,7 @@ xl console ${VM_NAME}
 Kill the vm with:
 xl destroy ${VM_NAME}
 EOF
+    VM_GENERATED_FILES+=( "${pygrub}" "${pvgrub}" "${VM_README}" )
 }
 
 vm_cleanup() {
@@ -401,6 +409,12 @@ vm_cleanup() {
 }
 
 print_readme() {
+    local filename
+    info "Files written to $(relpath "$(dirname "${VM_DST_IMG}")")"
+    for filename in "${VM_GENERATED_FILES[@]}"; do
+        info " - $(basename "${filename}")"
+    done
+
     if [[ -f "${VM_README}" ]]; then
         cat "${VM_README}"
     fi
diff --git a/image_to_vm.sh b/image_to_vm.sh
index 097cc338c4..a91f20c9f3 100755
--- a/image_to_vm.sh
+++ b/image_to_vm.sh
@@ -52,6 +52,9 @@ DEFINE_boolean prod_image "${FLAGS_FALSE}" \
 DEFINE_string to "" \
   "Destination folder for VM output file(s)"
 
+# include upload options
+. "${BUILD_LIBRARY_DIR}/release_util.sh" || exit 1
+
 # Parse command line
 FLAGS "$@" || exit 1
 eval set -- "${FLAGS_ARGV}"
@@ -116,6 +119,9 @@ write_vm_conf "${FLAGS_mem}"
 vm_cleanup
 trap - EXIT
 
+# Optionally upload all of our hard work
+upload_image "${VM_GENERATED_FILES[@]}"
+
 # Ready to set sail!
 okboat
 command_completed