It is a well documented fact that _autodiscover._tcp SRV record in the userdomain.com DNS zone is needed for the proper autodiscover work in Outlook (and also Offline Address Book download in cached mode and Out of Office Assistant setup).
In addition autodiscover.userdomain.com A (or CNAME) record might be needed as well.
Usually _autodiscover._tcp.userdomain.com SRV record is enough for configuration to work properly, but it seems like autodiscover.userdomain.com is being queried first and if that query fails, it queries _autodiscover._tcp.userdomain.com: I had an instance that the userdomain.com zone did not have autodiscover A record and even though other zones with similar configuration worked fine, the particular one users had problems with autodiscover.
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