diff --git a/bridge/discord/discord.go b/bridge/discord/discord.go
index 1ae655bf..84171fa5 100644
--- a/bridge/discord/discord.go
+++ b/bridge/discord/discord.go
@@ -237,8 +237,10 @@ func (b *Bdiscord) Send(msg config.Message) (string, error) {
 				}
 			}
 		}
+
 		// skip empty messages
-		if msg.Text == "" {
+		if msg.Text == "" && (msg.Extra == nil || len(msg.Extra["file"]) == 0) {
+			b.Log.Debugf("Skipping empty message %#v", msg)
 			return "", nil
 		}
 
@@ -261,16 +263,16 @@ func (b *Bdiscord) Send(msg config.Message) (string, error) {
 				return "", err
 			}
 		}
-		msg, err := b.webhookExecute(
-			wID,
-			wToken,
-			true,
-			&discordgo.WebhookParams{
-				Content:   msg.Text,
-				Username:  msg.Username,
-				AvatarURL: msg.Avatar,
-			})
-		return msg.ID, err
+		b.Log.Debugf("Processing webhook sending for message %#v", msg)
+		msg, err := b.webhookSend(&msg, wID, wToken)
+		if err != nil {
+			b.Log.Errorf("Could not broadcast via webook for message %#v: %s", msg, err)
+			return "", err
+		}
+		if msg == nil {
+			return "", nil
+		}
+		return msg.ID, nil
 	}
 
 	b.Log.Debugf("Broadcasting using token (API)")
@@ -312,7 +314,7 @@ func (b *Bdiscord) Send(msg config.Message) (string, error) {
 	if err != nil {
 		return "", err
 	}
-	return res.ID, err
+	return res.ID, nil
 }
 
 // useWebhook returns true if we have a webhook defined somewhere
@@ -376,3 +378,57 @@ func (b *Bdiscord) handleUploadFile(msg *config.Message, channelID string) (stri
 	}
 	return "", nil
 }
+
+// webhookSend send one or more message via webhook, taking care of file
+// uploads (from slack, telegram or mattermost).
+// Returns messageID and error.
+func (b *Bdiscord) webhookSend(msg *config.Message, webhookID, token string) (*discordgo.Message, error) {
+	var (
+		res *discordgo.Message
+		err error
+	)
+
+	// WebhookParams can have either `Content` or `File`.
+
+	// We can't send empty messages.
+	if msg.Text != "" {
+		res, err = b.c.WebhookExecute(
+			webhookID,
+			token,
+			true,
+			&discordgo.WebhookParams{
+				Content:   msg.Text,
+				Username:  msg.Username,
+				AvatarURL: msg.Avatar,
+			},
+		)
+		if err != nil {
+			b.Log.Errorf("Could not send text (%s) for message %#v: %s", msg.Text, msg, err)
+		}
+	}
+
+	if msg.Extra != nil {
+		for _, f := range msg.Extra["file"] {
+			fi := f.(config.FileInfo)
+			file := discordgo.File{
+				Name:        fi.Name,
+				ContentType: "",
+				Reader:      bytes.NewReader(*fi.Data),
+			}
+			_, e2 := b.c.WebhookExecute(
+				webhookID,
+				token,
+				false,
+				&discordgo.WebhookParams{
+					Username:  msg.Username,
+					AvatarURL: msg.Avatar,
+					File:      &file,
+				},
+			)
+			if e2 != nil {
+				b.Log.Errorf("Could not send file %#v for message %#v: %s", file, msg, e2)
+			}
+		}
+	}
+	return res, err
+}
diff --git a/bridge/discord/helpers.go b/bridge/discord/helpers.go
index 58676842..1447c530 100644
--- a/bridge/discord/helpers.go
+++ b/bridge/discord/helpers.go
@@ -1,7 +1,6 @@
 package bdiscord
 
 import (
-	"encoding/json"
 	"errors"
 	"regexp"
 	"strings"
@@ -236,26 +235,3 @@ func enumerateUsernames(s string) []string {
 	}
 	return usernames
 }
-
-// webhookExecute executes a webhook.
-// webhookID: The ID of a webhook.
-// token    : The auth token for the webhook
-// wait	    : Waits for server confirmation of message send and ensures that the return struct is populated (it is nil otherwise)
-func (b *Bdiscord) webhookExecute(webhookID, token string, wait bool, data *discordgo.WebhookParams) (st *discordgo.Message, err error) {
-	uri := discordgo.EndpointWebhookToken(webhookID, token)
-
-	if wait {
-		uri += "?wait=true"
-	}
-	response, err := b.c.RequestWithBucketID("POST", uri, data, discordgo.EndpointWebhookToken("", ""))
-	if !wait || err != nil {
-		return nil, err
-	}
-
-	err = json.Unmarshal(response, &st)
-	if err != nil {
-		return nil, discordgo.ErrJSONUnmarshal
-	}
-
-	return st, nil
-}
diff --git a/go.mod b/go.mod
index c380835c..080ff55c 100644
--- a/go.mod
+++ b/go.mod
@@ -7,6 +7,7 @@ require (
 	github.com/Philipp15b/go-steam v1.0.1-0.20180818081528-681bd9573329
 	github.com/Rhymen/go-whatsapp v0.0.3-0.20190729104911-5c79b2cf277a
 	github.com/bwmarrin/discordgo v0.19.0
+	// github.com/bwmarrin/discordgo v0.19.0
 	github.com/d5/tengo v1.24.1
 	github.com/dfordsoft/golib v0.0.0-20180902042739-76ee6ab99bec
 	github.com/fsnotify/fsnotify v1.4.7