diff --git a/tests/assets/small.webm b/tests/assets/small.webm
new file mode 100644
index 0000000..da946da
Binary files /dev/null and b/tests/assets/small.webm differ
diff --git a/tests/test_console.py b/tests/test_console.py
index 9c46b86..3b58d18 100644
--- a/tests/test_console.py
+++ b/tests/test_console.py
@@ -292,7 +292,6 @@ def test_reblogged_by(mock_get, monkeypatch, capsys):
 def test_upload(mock_post, capsys):
     mock_post.return_value = MockResponse({
         'id': 123,
-        'url': 'https://bigfish.software/123/456',
         'preview_url': 'https://bigfish.software/789/012',
         'url': 'https://bigfish.software/345/678',
         'type': 'image',
@@ -300,10 +299,10 @@ def test_upload(mock_post, capsys):
 
     console.run_command(app, user, 'upload', [__file__])
 
-    mock_post.call_count == 1
+    assert mock_post.call_count == 1
 
     args, kwargs = http.post.call_args
-    assert args == (app, user, '/api/v1/media')
+    assert args == (app, user, '/api/v2/media')
     assert isinstance(kwargs['files']['file'], io.BufferedReader)
 
     out, err = capsys.readouterr()
diff --git a/tests/test_integration.py b/tests/test_integration.py
index 1471960..ba254cc 100644
--- a/tests/test_integration.py
+++ b/tests/test_integration.py
@@ -207,6 +207,39 @@ def test_post_language(app, user, run):
     assert status["language"] == "zh"
 
 
+def test_media_thumbnail(app, user, run):
+    assets_dir = path.realpath(path.join(path.dirname(__file__), "assets"))
+
+    video_path = path.join(assets_dir, "small.webm")
+    thumbnail_path = path.join(assets_dir, "test1.png")
+
+    out = run(
+        "post",
+        "--media", video_path,
+        "--thumbnail", thumbnail_path,
+        "--description", "foo",
+        "some text"
+    )
+
+    status_id = _posted_status_id(out)
+    status = api.fetch_status(app, user, status_id)
+    [media] = status["media_attachments"]
+
+    assert media["description"] == "foo"
+    assert media["type"] == "video"
+    assert media["url"].endswith(".mp4")
+    assert media["preview_url"].endswith(".png")
+
+    # Video properties
+    assert media["meta"]["original"]["duration"] == 5.58
+    assert media["meta"]["original"]["height"] == 320
+    assert media["meta"]["original"]["width"] == 560
+
+    # Thumbnail properties
+    assert media["meta"]["small"]["height"] == 50
+    assert media["meta"]["small"]["width"] == 50
+
+
 def test_media_attachments(app, user, run):
     assets_dir = path.realpath(path.join(path.dirname(__file__), "assets"))
 
diff --git a/toot/api.py b/toot/api.py
index 2c8edb3..910b3b5 100644
--- a/toot/api.py
+++ b/toot/api.py
@@ -1,12 +1,14 @@
+import mimetypes
+from os import path
 import re
 import uuid
 
-from typing import List
+from typing import BinaryIO, List, Optional
 from urllib.parse import urlparse, urlencode, quote
 
-from toot import http, CLIENT_NAME, CLIENT_WEBSITE
-from toot.exceptions import AuthenticationError
-from toot.utils import str_bool, str_bool_nullable
+from toot import App, User, http, CLIENT_NAME, CLIENT_WEBSITE
+from toot.exceptions import AuthenticationError, ConsoleError
+from toot.utils import drop_empty_values, str_bool, str_bool_nullable
 
 SCOPES = 'read write follow'
 
@@ -85,10 +87,9 @@ def update_account(
     Update account credentials
     https://docs.joinmastodon.org/methods/accounts/#update_credentials
     """
-    files = {"avatar": avatar, "header": header}
-    files = {k: v for k, v in files.items() if v is not None}
+    files = drop_empty_values({"avatar": avatar, "header": header})
 
-    data = {
+    data = drop_empty_values({
         "bot": str_bool_nullable(bot),
         "discoverable": str_bool_nullable(discoverable),
         "display_name": display_name,
@@ -97,8 +98,7 @@ def update_account(
         "source[language]": language,
         "source[privacy]": privacy,
         "source[sensitive]": str_bool_nullable(sensitive),
-    }
-    data = {k: v for k, v in data.items() if v is not None}
+    })
 
     return http.patch(app, user, "/api/v1/accounts/update_credentials", files=files, data=data)
 
@@ -182,7 +182,9 @@ def post_status(
     # if the request is retried.
     headers = {"Idempotency-Key": uuid.uuid4().hex}
 
-    json = {
+    # Strip keys for which value is None
+    # Sending null values doesn't bother Mastodon, but it breaks Pleroma
+    json = drop_empty_values({
         'status': status,
         'media_ids': media_ids,
         'visibility': visibility,
@@ -192,11 +194,7 @@ def post_status(
         'scheduled_at': scheduled_at,
         'content_type': content_type,
         'spoiler_text': spoiler_text
-    }
-
-    # Strip keys for which value is None
-    # Sending null values doesn't bother Mastodon, but it breaks Pleroma
-    json = {k: v for k, v in json.items() if v is not None}
+    })
 
     return http.post(app, user, '/api/v1/statuses', json=json, headers=headers).json()
 
@@ -351,11 +349,44 @@ def anon_tag_timeline_generator(instance, hashtag, local=False, limit=20):
     return _anon_timeline_generator(instance, path, params)
 
 
-def upload_media(app, user, file, description=None):
-    return http.post(app, user, '/api/v1/media',
-        data={'description': description},
-        files={'file': file}
-    ).json()
+def get_media(app: App, user: User, id: str):
+    return http.get(app, user, f"/api/v1/media/{id}").json()
+
+
+def upload_media(
+    app: App,
+    user: User,
+    media: BinaryIO,
+    description: Optional[str] = None,
+    thumbnail: Optional[BinaryIO] = None,
+):
+    data = drop_empty_values({"description": description})
+
+    # NB: Documentation says that "file" should provide a mime-type which we
+    # don't do currently, but it works.
+    files = drop_empty_values({
+        "file": media,
+        "thumbnail": _add_mime_type(thumbnail)
+    })
+
+    return http.post(app, user, "/api/v2/media", data=data, files=files).json()
+
+
+def _add_mime_type(file):
+    if file is None:
+        return None
+
+    # TODO: mimetypes uses the file extension to guess the mime type which is
+    # not always good enough (e.g. files without extension). python-magic could
+    # be used instead but it requires adding it as a dependency.
+    mime_type = mimetypes.guess_type(file.name)
+
+    if not mime_type:
+        raise ConsoleError(f"Unable guess mime type of '{file.name}'. "
+                           "Ensure the file has the desired extension.")
+
+    filename = path.basename(file.name)
+    return (filename, file, mime_type)
 
 
 def search(app, user, query, resolve=False, type=None):
diff --git a/toot/commands.py b/toot/commands.py
index 9941e23..e21f5b3 100644
--- a/toot/commands.py
+++ b/toot/commands.py
@@ -2,6 +2,7 @@ import sys
 import platform
 
 from datetime import datetime, timedelta, timezone
+from time import sleep, time
 from toot import api, config, __version__
 from toot.auth import login_interactive, login_browser_interactive, create_app_interactive
 from toot.exceptions import ApiError, ConsoleError
@@ -142,19 +143,54 @@ def _get_scheduled_at(scheduled_at, scheduled_in):
 
 
 def _upload_media(app, user, args):
-    # Match media to corresponding description and upload
+    # Match media to corresponding description and thumbnail
     media = args.media or []
     descriptions = args.description or []
+    thumbnails = args.thumbnail or []
     uploaded_media = []
 
     for idx, file in enumerate(media):
         description = descriptions[idx].strip() if idx < len(descriptions) else None
-        result = _do_upload(app, user, file, description)
+        thumbnail = thumbnails[idx] if idx < len(thumbnails) else None
+        result = _do_upload(app, user, file, description, thumbnail)
         uploaded_media.append(result)
 
+    _wait_until_all_processed(app, user, uploaded_media)
+
     return [m["id"] for m in uploaded_media]
 
 
+def _wait_until_all_processed(app, user, uploaded_media):
+    """
+    Media is uploaded asynchronously, and cannot be attached until the server
+    has finished processing it. This function waits for that to happen.
+
+    Once media is processed, it will have the URL populated.
+    """
+    if all(m["url"] for m in uploaded_media):
+        return
+
+    # Timeout after waiting 1 minute
+    start_time = time()
+    timeout = 60
+
+    print_out("<dim>Waiting for media to finish processing...</dim>")
+    for media in uploaded_media:
+        _wait_until_processed(app, user, media, start_time, timeout)
+
+
+def _wait_until_processed(app, user, media, start_time, timeout):
+    if media["url"]:
+        return
+
+    media = api.get_media(app, user, media["id"])
+    while not media["url"]:
+        sleep(1)
+        if time() > start_time + timeout:
+            raise ConsoleError(f"Media not processed by server after {timeout} seconds. Aborting.")
+        media = api.get_media(app, user, media["id"])
+
+
 def delete(app, user, args):
     api.delete_status(app, user, args.status_id)
     print_out("<green>✓ Status deleted</green>")
@@ -297,7 +333,7 @@ def activate(app, user, args):
 
 
 def upload(app, user, args):
-    response = _do_upload(app, user, args.file, args.description)
+    response = _do_upload(app, user, args.file, args.description, None)
 
     msg = "Successfully uploaded media ID <yellow>{}</yellow>, type '<yellow>{}</yellow>'"
 
@@ -312,9 +348,9 @@ def search(app, user, args):
     print_search_results(response)
 
 
-def _do_upload(app, user, file, description):
+def _do_upload(app, user, file, description, thumbnail):
     print_out("Uploading media: <green>{}</green>".format(file.name))
-    return api.upload_media(app, user, file, description=description)
+    return api.upload_media(app, user, file, description=description, thumbnail=thumbnail)
 
 
 def _find_account(app, user, account_name):
diff --git a/toot/console.py b/toot/console.py
index f1f6994..ae98c6c 100644
--- a/toot/console.py
+++ b/toot/console.py
@@ -482,6 +482,12 @@ POST_COMMANDS = [
                 "help": "plain-text description of the media for accessibility "
                         "purposes, one per attached media"
             }),
+            (["--thumbnail"], {
+                "action": "append",
+                "type": FileType("rb"),
+                "help": "path to an image file to serve as media thumbnail, "
+                        "one per attached media"
+            }),
             visibility_arg,
             (["-s", "--sensitive"], {
                 "action": 'store_true',
diff --git a/toot/utils/__init__.py b/toot/utils/__init__.py
index 73ab6af..8a39fd2 100644
--- a/toot/utils/__init__.py
+++ b/toot/utils/__init__.py
@@ -7,6 +7,7 @@ import unicodedata
 import warnings
 
 from bs4 import BeautifulSoup
+from typing import Dict
 
 from toot.exceptions import ConsoleError
 
@@ -154,3 +155,8 @@ def _use_existing_tmp_file(tmp_path) -> bool:
         return char == "o"
 
     return False
+
+
+def drop_empty_values(data: Dict) -> Dict:
+    """Remove keys whose values are null"""
+    return {k: v for k, v in data.items() if v is not None}