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So rackspace deprecated cram_md5 recently and to my unpleasant surprise, my webapp, using exim4 as an MTA on debian squeeze, has to be reconfigured to use ssl to connect to the rackspace smarthost (e.g. the secure.emailsrvr.com 465 being used to relay mail). This is not pretty, as trying to get exim to send via smtp over SSL seems to be a very unforgiving process, mainly because of the continuous guessing which exact setting is causing rejection.

Is there any easy way to test authentication as if I was exim? Or test which authentication methods exim is using while it tries to connect to the rackspace smarthost?

Currently, I can't even be sure that exim itself isn't still trying to use cram_md5 as it still lists that as a potential authenticator: sudo exim -bV ... Authenticators: cram_md5 plaintext ...

So how do I move from cram_md5 auth or plaintext auth to plaintext over ssl?

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