Currently there is a logistical error proposed by MSC1708 which results in some homeservers unable to migrate to the new functionality proposed by MSC1711. This can happen if the delegated homeserver cannot obtain a valid TLS certificate for the domain, and an SRV record is used for backwards compatibility reasons.
Specifically, in order to be compatible with requests from both Synapse 0.34 and 1.0, servers can have both a SRV and a .well-known file, with Synapse presenting a certificate corresponding to the target of the .well-known. Synapse 0.34 is then happy because it will follow the SRV (and won't care about the incorrect certificate); Synapse 1.0 is happy because it will follow the .well-known (and will see the correct cert).
We change the order of operations to perform a .well-known lookup before falling back to resolving the SRV record. This allows for domains to delegate to other hostnames and maintains backwards compatibility with older homeservers.
More HTTP hits will be made due to the .well-known lookup being first. This is somewhat mitigated by servers caching the responses appropriately, and using connection pools where possible.