diff --git a/bot/interfaces.go b/bot/interfaces.go
index fb27f94..5c11eb6 100644
--- a/bot/interfaces.go
+++ b/bot/interfaces.go
@@ -3,8 +3,10 @@
 package bot
 
 import (
+	"github.com/gabriel-vasile/mimetype"
 	"net/http"
 	"regexp"
+	"strings"
 
 	"github.com/jmoiron/sqlx"
 
@@ -50,6 +52,28 @@ type EmbedAuthor struct {
 	IconURL string
 }
 
+type File struct {
+	Description string
+	Data        []byte
+	mime        *mimetype.MIME
+}
+
+func (f File) Mime() *mimetype.MIME {
+	if f.mime == nil {
+		f.mime = mimetype.Detect(f.Data)
+	}
+	return f.mime
+}
+
+func (f File) ContentType() string {
+	return f.Mime().String()
+}
+
+func (f File) FileName() string {
+	ext := f.Mime().Extension()
+	return strings.ReplaceAll(f.Description, " ", "-") + ext
+}
+
 type ImageAttachment struct {
 	URL    string
 	AltTxt string
diff --git a/connectors/discord/discord.go b/connectors/discord/discord.go
index 930a4c8..6e5109a 100644
--- a/connectors/discord/discord.go
+++ b/connectors/discord/discord.go
@@ -1,6 +1,7 @@
 package discord
 
 import (
+	"bytes"
 	"errors"
 	"fmt"
 	"net/http"
@@ -111,6 +112,7 @@ func (d *Discord) sendMessage(channel, message string, meMessage bool, args ...a
 	}
 
 	embeds := []*discordgo.MessageEmbed{}
+	files := []*discordgo.File{}
 
 	for _, arg := range args {
 		switch a := arg.(type) {
@@ -130,17 +132,23 @@ func (d *Discord) sendMessage(channel, message string, meMessage bool, args ...a
 				Height: a.Height,
 			}
 			embeds = append(embeds, embed)
+		case bot.File:
+			files = append(files, &discordgo.File{
+				Name:        a.FileName(),
+				ContentType: a.ContentType(),
+				Reader:      bytes.NewBuffer(a.Data),
+			})
 		}
 	}
 
 	data := &discordgo.MessageSend{
 		Content: message,
 		Embeds:  embeds,
+		Files:   files,
 	}
 
 	log.Debug().
 		Interface("data", data).
-		Interface("args", args).
 		Msg("sending message")
 
 	st, err := d.client.ChannelMessageSendComplex(channel, data)
diff --git a/plugins/meme/meme.go b/plugins/meme/meme.go
index 5865cc2..707da1f 100644
--- a/plugins/meme/meme.go
+++ b/plugins/meme/meme.go
@@ -4,6 +4,7 @@ import (
 	"bytes"
 	"encoding/json"
 	"fmt"
+	"github.com/google/uuid"
 	"image"
 	"image/color"
 	"image/draw"
@@ -209,7 +210,7 @@ func (p *MemePlugin) sendMeme(c bot.Connector, channel, channelName, msgID strin
 
 	encodedSpec, _ := json.Marshal(spec)
 
-	w, h, err := p.checkMeme(imgURL)
+	_, _, err = p.checkMeme(imgURL)
 	if err != nil {
 		msg := fmt.Sprintf("Hey %v, I couldn't download that image you asked for.", from.Name)
 		p.bot.Send(c, bot.Ephemeral, channel, from.ID, msg)
@@ -222,12 +223,18 @@ func (p *MemePlugin) sendMeme(c bot.Connector, channel, channelName, msgID strin
 	q.Add("spec", string(encodedSpec))
 	u.RawQuery = q.Encode()
 
+	img, err := p.genMeme(spec)
+	if err != nil {
+		msg := fmt.Sprintf("Hey %v, I couldn't download that image you asked for.", from.Name)
+		p.bot.Send(c, bot.Ephemeral, channel, from.ID, msg)
+		return
+	}
+
 	log.Debug().Msgf("image is at %s", u.String())
-	_, err = p.bot.Send(c, bot.Message, channel, "", bot.ImageAttachment{
-		URL:    u.String(),
-		AltTxt: fmt.Sprintf("%s: %s", from.Name, message),
-		Width:  w,
-		Height: h,
+	p.bot.Send(c, bot.Message, channel, fmt.Sprintf("%s sent a meme:", from.Name))
+	_, err = p.bot.Send(c, bot.Message, channel, "", bot.File{
+		Description: uuid.NewString(),
+		Data:        img,
 	})
 
 	if err == nil && msgID != "" {