This looks to be because guests use macaroons, which don't have an associated token_id:

Lines 357 to 364 in 34a5696

    
           ret = { 
        
               "user": user, 
        
               "is_guest": True, 
        
               "shadow_banned": False, 
        
               "token_id": None, 
        
               # all guests get the same device id 
        
               "device_id": GUEST_DEVICE_ID, 
        
           }

So when we serialize the event we don't include the transaction ID:

synapse/synapse/events/utils.py

Lines 305 to 309 in 34a5696

    
           if token_id is not None: 
        
               if token_id == getattr(e.internal_metadata, "token_id", None): 
        
                   txn_id = getattr(e.internal_metadata, "txn_id", None) 
        
                   if txn_id is not None: 
        
                       d["unsigned"]["transaction_id"] = txn_id

To fix this we may want to pass in both a user_id and token_id and changing the guard to be if user_id is not None: .... I think only a couple of places call serialize_event while specifying a token_id so it shouldn't be too invasive

	ret = {
	"user": user,
	"is_guest": True,
	"shadow_banned": False,
	"token_id": None,
	# all guests get the same device id
	"device_id": GUEST_DEVICE_ID,
	}

	if token_id is not None:
	if token_id == getattr(e.internal_metadata, "token_id", None):
	txn_id = getattr(e.internal_metadata, "txn_id", None)
	if txn_id is not None:
	d["unsigned"]["transaction_id"] = txn_id

Uh oh!

Missing transaction_id in syncs for remote-echo of messages for guests #8521

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