this post was submitted on 02 Apr 2026
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I’m guessing it’s one of two things:
It could be two shortcuts to outlook. One might actually be Outlook classic.
Another issue could be a dreaded dual mailbox scenario that occurs when an hybrid on-premises user account gets a mailbox in exchange online before their on-prem account has its attributes created. It’s annoying to deal with and fix.
I’m curious as to what the issue is and how they fix it. I would assume that latency and bandwidth are a big problem and they have WAN acceleration going on, which can cause some apps to bug out.
I actually helped Riberbed identify and fix a bug with Exchange optimization that took 4 years to fix. The tech I worked with for about a year when we identified it called me up 3 years later to tell me himself that they fixed and closed it.
Judging by the two Outlooks installed on my cooperate machine I'm guessing Outlook and Outlook (classic) are the two installed... Though they could have "Outlook for Windows" installed too as I see it offering it to me via the Windows store.