I opened a case with Microsoft. They connected to my computer and had me 2 hours going back and forth doing tests (they were very polite, and tried to help).
Their suggestions are the same above. That didn't help. However, they thought that my profile having too many rules (+100) might have something to do.
Offline I cleaned up my rules, deleting a lot of rules that I had disabled (~20 rules). That fixed the issue.
It seems that some rule was corrupted, or my total rules count didn't allow Exchange to add the rule for the automatic reply. In any case, my situation is resolved.
This is a great question, since we recently migrated to Office 365 from an on-prem Exchange server.
For us, what caused us to question this is the 49.5 GB of mailbox space -- and the desire to get rid of offline archives. I mean, really, if you don't need to archive, do you really want a cached mailbox that's nearly 50 GB in size? Heck no!
Not to mention whatever you archive is outside the control of IT. If a user loses it, and it hasn't been backed up, it's GONE.
For us, we also wanted the flexibility to be able to have all the laptop users access some cached data so they can easily work while on a plane or otherwise offline.
Our answer applies to Outlook 2013 users:
When setting up the user account in Outlook 2013, you get to choose how much data you want to cache based on a timeline. In the Server Settings =>> Offline Settings select "Use Cached Exchange Mode" and pick how many months (up to six in our case) that you want to cache locally. For us, the magic number was two months.
One extra benefit with Outlook 2013: the cached file is said to be 40% smaller than the cached files created in earlier versions. Now I can have a 50 GB mailbox, avoid the pain of missing archive files -- and still offer the convenience for travelling workers to be able to work offline if they want to. I say that's a good deal!
BTW, if they're not showing the image in this post, try going to
Best Answer
You will have to change the default email retention for deleted items in Office 365. Not a long time ago, it was 30 days by default, but Microsoft decided to change it to something like "Keep Forever".
https://blogs.office.com/2015/02/20/extended-email-retention-deleted-items-office-365/