diff --git a/federation/entities/activitypub/entities.py b/federation/entities/activitypub/entities.py
index f355ebf..00cf521 100644
--- a/federation/entities/activitypub/entities.py
+++ b/federation/entities/activitypub/entities.py
@@ -2,11 +2,14 @@ import logging
 import uuid
 from typing import Dict
 
+import attr
+
 from federation.entities.activitypub.constants import (
     CONTEXTS_DEFAULT, CONTEXT_MANUALLY_APPROVES_FOLLOWERS, CONTEXT_SENSITIVE, CONTEXT_HASHTAG,
     CONTEXT_LD_SIGNATURES)
 from federation.entities.activitypub.enums import ActorType, ObjectType, ActivityType
 from federation.entities.activitypub.mixins import ActivitypubObjectMixin, ActivitypubActorMixin
+from federation.entities.activitypub.objects import ImageObject
 from federation.entities.base import Profile, Post, Follow, Accept
 from federation.outbound import handle_send
 from federation.types import UserType
@@ -168,5 +171,8 @@ class ActivitypubProfile(ActivitypubActorMixin, Profile):
         if self.raw_content:
             as2['summary'] = self.raw_content
         if self.image_urls.get('large'):
-            as2['icon'] = self.image_urls.get('large')
+            try:
+                as2['icon'] = attr.asdict(ImageObject(url=self.image_urls.get('large')))
+            except Exception as ex:
+                logger.warning("ActivitypubProfile.to_as2 - failed to set profile icon: %s", ex)
         return as2
diff --git a/federation/entities/activitypub/objects.py b/federation/entities/activitypub/objects.py
new file mode 100644
index 0000000..6745001
--- /dev/null
+++ b/federation/entities/activitypub/objects.py
@@ -0,0 +1,25 @@
+import attr
+
+from federation.utils.network import fetch_content_type
+
+
+@attr.s
+class ImageObject:
+    """
+    An Image object for AS2 serialization.
+    """
+    _allowed_types = (
+        "image/jpeg",
+        "image/png",
+        "image/gif",
+    )
+    url: str = attr.ib()
+    type: str = attr.ib(default="Image")
+    mediaType: str = attr.ib()
+
+    @mediaType.default
+    def cache_media_type(self):
+        content_type = fetch_content_type(self.url)
+        if content_type in self._allowed_types:
+            return content_type
+        return ""
diff --git a/federation/tests/entities/activitypub/test_entities.py b/federation/tests/entities/activitypub/test_entities.py
index e264aef..373ac25 100644
--- a/federation/tests/entities/activitypub/test_entities.py
+++ b/federation/tests/entities/activitypub/test_entities.py
@@ -79,7 +79,8 @@ class TestEntitiesConvertToAS2:
             'published': '2019-04-27T00:00:00',
         }
 
-    def test_profile_to_as2(self, activitypubprofile):
+    @patch("federation.entities.activitypub.objects.fetch_content_type", return_value="image/jpeg")
+    def test_profile_to_as2(self, mock_fetch, activitypubprofile):
         result = activitypubprofile.to_as2()
         assert result == {
             "@context": CONTEXTS_DEFAULT + [
@@ -104,7 +105,11 @@ class TestEntitiesConvertToAS2:
             "type": "Person",
             "url": "https://example.com/bob-bobertson",
             "summary": "foobar",
-            "icon": "urllarge",
+            "icon": {
+                "type": "Image",
+                "url": "urllarge",
+                "mediaType": "image/jpeg",
+            }
         }
 
 
diff --git a/federation/utils/network.py b/federation/utils/network.py
index 865a9a1..3edb7cb 100644
--- a/federation/utils/network.py
+++ b/federation/utils/network.py
@@ -3,7 +3,7 @@ import datetime
 import logging
 import re
 import socket
-from typing import Tuple
+from typing import Optional, Tuple
 
 import requests
 from ipdata import ipdata
@@ -18,6 +18,18 @@ logger = logging.getLogger("federation")
 USER_AGENT = "python/federation/%s" % __version__
 
 
+def fetch_content_type(url: str) -> Optional[str]:
+    """
+    Fetch the HEAD of the remote url to determine the content type.
+    """
+    try:
+        response = requests.head(url, headers={'user-agent': USER_AGENT}, timeout=10)
+    except RequestException as ex:
+        logger.warning("fetch_content_type - %s when fetching url %s", ex, url)
+    else:
+        return response.headers.get('Content-Type')
+
+
 def fetch_country_by_ip(ip):
     """
     Fetches country code by IP