diff --git a/dreadnode/main.py b/dreadnode/main.py
index d3773e70..ea3169a8 100644
--- a/dreadnode/main.py
+++ b/dreadnode/main.py
@@ -7,7 +7,7 @@
 from dataclasses import dataclass
 from datetime import datetime, timezone
 from pathlib import Path
-from urllib.parse import urljoin
+from urllib.parse import urljoin, urlparse, urlunparse
 
 import coolname  # type: ignore [import-untyped]
 import logfire
@@ -205,6 +205,16 @@ def initialize(self) -> None:
                 category=DreadnodeConfigWarning,
             )
 
+        if self.server:
+            parsed_url = urlparse(self.server)
+            if not parsed_url.scheme:
+                netloc = parsed_url.path.split("/")[0]
+                path = "/".join(parsed_url.path.split("/")[1:])
+                parsed_new = parsed_url._replace(
+                    scheme="https", netloc=netloc, path=f"/{path}" if path else ""
+                )
+                self.server = urlunparse(parsed_new)
+
         if self.local_dir is not False:
             config = FileExportConfig(
                 base_path=self.local_dir,