diff --git a/bookwyrm/models/activitypub_mixin.py b/bookwyrm/models/activitypub_mixin.py
index 5e52576aa..d8103c9c3 100644
--- a/bookwyrm/models/activitypub_mixin.py
+++ b/bookwyrm/models/activitypub_mixin.py
@@ -529,7 +529,7 @@ async def async_broadcast(recipients: List[str], sender, data: str):
 
 
 async def sign_and_send(
-    session: aiohttp.ClientSession, sender, data: str, destination: str
+    session: aiohttp.ClientSession, sender, data: str, destination: str, **kwargs
 ):
     """Sign the messages and send them in an asynchronous bundle"""
     now = http_date()
@@ -539,11 +539,14 @@ async def sign_and_send(
         raise ValueError("No private key found for sender")
 
     digest = make_digest(data)
+    signature = make_signature(
+        "post", sender, destination, now, digest, kwargs.get("use_legacy_key")
+    )
 
     headers = {
         "Date": now,
         "Digest": digest,
-        "Signature": make_signature("post", sender, destination, now, digest, False),
+        "Signature": signature,
         "Content-Type": "application/activity+json; charset=utf-8",
         "User-Agent": USER_AGENT,
     }
@@ -554,21 +557,15 @@ async def sign_and_send(
                 logger.exception(
                     "Failed to send broadcast to %s: %s", destination, response.reason
                 )
-                logger.info("Trying again with legacy keyId")
-                # try with incorrect keyId to enable communication with legacy Bookwyrm servers
-                legacy_signature = make_signature(
-                    "post", sender, destination, now, digest, True
-                )
-                headers["Signature"] = legacy_signature
-                async with session.post(
-                    destination, data=data, headers=headers
-                ) as response:
-                    if not response.ok:
-                        logger.exception(
-                            "Failed to send broadcast with legacy keyId to %s: %s",
-                            destination,
-                            response.reason,
+                if kwargs.get("use_legacy_key") is not True:
+                    # try with incorrect keyId to enable communication with legacy Bookwyrm servers
+                    logger.info("Trying again with legacy keyId header value")
+
+                    asyncio.ensure_future(
+                        sign_and_send(
+                            session, sender, data, destination, use_legacy_key=True
                         )
+                    )
 
             return response
     except asyncio.TimeoutError: