diff --git a/ctfcli/cli/media.py b/ctfcli/cli/media.py
index 7dc14ec..4363b31 100644
--- a/ctfcli/cli/media.py
+++ b/ctfcli/cli/media.py
@@ -4,6 +4,8 @@
 
 from ctfcli.core.api import API
 from ctfcli.core.config import Config
+from ctfcli.core.media import Media
+from ctfcli.utils.hashing import hash_file
 
 
 class MediaCommand:
@@ -17,23 +19,57 @@ def add(self, path):
 
         filename = os.path.basename(path)
         location = f"media/{filename}"
-        file_payload = {
-            "type": "page",
-            "location": location,
-        }
-
-        with open(path, mode="rb") as file_handle:
-            # Specifically use data= here to send multipart/form-data
-            r = api.post("/api/v1/files", files={"file": (filename, file_handle)}, data=file_payload)
-            r.raise_for_status()
-            resp = r.json()
-            server_location = resp["data"][0]["location"]
+        server_location = Media.upload(api, path, location)
 
         config.config.set("media", location, f"/files/{server_location}")
 
         with open(config.config_path, "w+") as f:
             config.write(f)
 
+    def sync(self):
+        """Sync all local media files in the media folder to the remote instance"""
+        config = Config()
+        if config.config.has_section("media") is False:
+            config.config.add_section("media")
+
+        media_path = config.project_path / "media"
+        if not media_path.is_dir():
+            click.secho(f"Could not locate media folder '{media_path}'", fg="red")
+            return 1
+
+        api = API()
+
+        r = api.get("/api/v1/files?type=page")
+        r.raise_for_status()
+        remote_files = {f"/files/{f['location']}": f for f in r.json()["data"]}
+
+        for local_file in sorted(media_path.rglob("*")):
+            if not local_file.is_file() or local_file.name.startswith("."):
+                continue
+
+            location = f"media/{local_file.relative_to(media_path).as_posix()}"
+            remote_file = remote_files.get(config["media"].get(location))
+
+            if remote_file:
+                with open(local_file, mode="rb") as file_handle:
+                    local_sha1sum = hash_file(file_handle)
+
+                if remote_file.get("sha1sum") == local_sha1sum:
+                    click.secho(f"Skipping unchanged media '{location}'", fg="yellow")
+                    continue
+
+                r = api.delete(f"/api/v1/files/{remote_file['id']}")
+                r.raise_for_status()
+
+            server_location = Media.upload(api, local_file, location)
+            config.config.set("media", location, f"/files/{server_location}")
+            click.secho(f"Synced media '{location}'", fg="green")
+
+        with open(config.config_path, "w+") as f:
+            config.write(f)
+
+        return 0
+
     def rm(self, path):
         """Remove local media file from remote server and local config"""
         config = Config()
diff --git a/ctfcli/core/media.py b/ctfcli/core/media.py
index cf77150..0a745b2 100644
--- a/ctfcli/core/media.py
+++ b/ctfcli/core/media.py
@@ -1,9 +1,25 @@
+import os
+
 from ctfcli.core.config import Config
 from ctfcli.core.exceptions import ProjectNotInitialized
 from ctfcli.utils.tools import safe_format
 
 
 class Media:
+    @staticmethod
+    def upload(api, path, location: str) -> str:
+        file_payload = {
+            "type": "page",
+            "location": location,
+        }
+
+        with open(path, mode="rb") as file_handle:
+            # Specifically use data= here to send multipart/form-data
+            r = api.post("/api/v1/files", files={"file": (os.path.basename(path), file_handle)}, data=file_payload)
+            r.raise_for_status()
+            resp = r.json()
+            return resp["data"][0]["location"]
+
     @staticmethod
     def replace_placeholders(content: str) -> str:
         config = Config()