diff --git a/CHANGELOG.md b/CHANGELOG.md
index a6e9e87..5a0d117 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -7,6 +7,7 @@ Changelog
 * Add `toot notifications` to show notifications (thanks @dlax)
 * Add posting and replying to curses interface (thanks @Skehmatics)
 * Add `--language` option to `toot post`
+* Enable attaching upto 4 files via `--media` option on `toot post`
 
 **0.21.0 (2019-02-15)**
 
diff --git a/toot/commands.py b/toot/commands.py
index 139ce8f..3fee651 100644
--- a/toot/commands.py
+++ b/toot/commands.py
@@ -76,15 +76,18 @@ def curses(app, user, args):
 
 
 def post(app, user, args):
+    if args.media and len(args.media) > 4:
+        raise ConsoleError("Cannot attach more than 4 files.")
+
     if args.media:
-        media = _do_upload(app, user, args.media)
-        media_ids = [media['id']]
+        media = [_do_upload(app, user, file) for file in args.media]
+        media_ids = [m["id"] for m in media]
     else:
         media = None
         media_ids = None
 
     if media and not args.text:
-        args.text = media['text_url']
+        args.text = "\n".join(m['text_url'] for m in media)
 
     if not args.text:
         print_out("Write or paste your toot. Press <yellow>{}</yellow> to post it.".format(EOF_KEY))
diff --git a/toot/console.py b/toot/console.py
index ed4d31d..82c33a0 100644
--- a/toot/console.py
+++ b/toot/console.py
@@ -271,8 +271,10 @@ POST_COMMANDS = [
                 "nargs": "?",
             }),
             (["-m", "--media"], {
-                "type": FileType('rb'),
-                "help": "path to the media file to attach"
+                "action": "append",
+                "type": FileType("rb"),
+                "help": "path to the media file to attach (specify multiple "
+                        "times to attach up to 4 files)"
             }),
             (["-v", "--visibility"], {
                 "type": visibility,