We have a hybrid Exchange environment, but all user mailboxes have been migrated to Exchange Online. The only on-premises Exchange Server SE instance is retained for management.
A random selection of users receives this error in classic Outlook when trying to configure automatic replies: "Your automatic reply settings cannot be displayed because the server is currently unavailable. Try again later."
Automatic replies work normally in Outlook on the web. EWS is enabled, mailbox rules are not oversized or corrupted, and autodiscover and EWS both point to Exchange Online. Comparing Outlook's Test E-mail AutoConfiguration results between working and affected users shows the same URLs resolving correctly.
Clearing Office credentials, removing cached autodiscover files, changing related policy settings, and recreating the Outlook profile have not helped. The only reliable fix so far is deleting the affected user's entire Windows profile, which creates additional issues and is not practical to do at scale. Has anyone found a less disruptive fix?
3 Answers
Since automatic replies work in Outlook on the web, this looks more like a client-side Office identity or Windows profile cache problem than an Exchange or EWS issue. Signing out of Office, removing stale Office credentials from Credential Manager, and authenticating again can help. It is also worth comparing the full Test E-mail AutoConfiguration output with a working user, not just the final URLs.
The fact that only a few users are also having trouble signing in or sending mail suggests the issue may involve the local Office/WAM identity state rather than mailbox configuration. I would compare the affected users’ Windows sign-in and Office activation state with a working user, then test whether recreating only the Windows identity and Office cache is possible instead of deleting the whole profile.
Before rebuilding the entire Windows profile, try deleting the cached autodiscover data under the user’s local Outlook folders, including the hidden XML files in the Outlook and Outlook16 directories. There is also policy that can disable cached autodiscover lookups. This can sometimes clear stale endpoint information without touching the rest of the profile.
I deleted the Outlook cache folders and applied the policy change, but the affected users still get the same error.

That was my initial suspicion too, but clearing the credentials did not change anything. The autodiscover tests also match the working users and resolve to Exchange Online.